Penetration and haptenation of p‐phenylenediamine
Identifieur interne : 001699 ( Istex/Corpus ); précédent : 001698; suivant : 001700Penetration and haptenation of p‐phenylenediamine
Auteurs : Laura M. Pot ; Simone M. Scheitza ; Pieter-Jan Coenraads ; Brunhilde BlömekeSource :
- Contact Dermatitis [ 0105-1873 ] ; 2013-04.
English descriptors
Abstract
Although p‐phenylenediamine (PPD) has been recognized as an extreme sensitizer for many years, the exact mechanism of sensitization has not been elucidated yet. Penetration and the ability to bind to proteins are the first two hurdles that an allergen has to overcome to be able to sensitize. This review is an overview of studies regarding PPD penetration through skin (analogues) and studies on the amino acids that are targeted by PPD. To complete this review, the auto‐oxidation and N‐acetylation steps involved in PPD metabolism are described. In summary, under normal hair dyeing exposure conditions, <1% of the applied PPD dose penetrates the skin. The majority (>80%) of PPD that penetrates will be converted into the detoxification products monoacetyl‐PPD and diacetyl‐PPD by the N‐acetyltransferase enzymes. The small amount of PPD that does not become N‐acetylated is susceptible to auto‐oxidation reactions, yielding protein‐reactive PPD derivatives. These derivatives may bind to specific amino acids, and some of the formed adducts might be the complexes responsible for sensitization. However, true in vivo evidence is lacking, and further research to unravel the definite mechanism of sensitization is needed.
Url:
DOI: 10.1111/cod.12032
Links to Exploration step
ISTEX:E2D920629D7C2FBC62B8FB70853EA82879CAC6D0Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Penetration and haptenation of p‐phenylenediamine</title><author><name sortKey="Pot, Laura M" sort="Pot, Laura M" uniqKey="Pot L" first="Laura M." last="Pot">Laura M. Pot</name><affiliation><mods:affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</mods:affiliation></affiliation></author><author><name sortKey="Scheitza, Simone M" sort="Scheitza, Simone M" uniqKey="Scheitza S" first="Simone M." last="Scheitza">Simone M. Scheitza</name><affiliation><mods:affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</mods:affiliation></affiliation></author><author><name sortKey="Coenraads, Pieter An" sort="Coenraads, Pieter An" uniqKey="Coenraads P" first="Pieter-Jan" last="Coenraads">Pieter-Jan Coenraads</name><affiliation><mods:affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</mods:affiliation></affiliation></author><author><name sortKey="Blomeke, Brunhilde" sort="Blomeke, Brunhilde" uniqKey="Blomeke B" first="Brunhilde" last="Blömeke">Brunhilde Blömeke</name><affiliation><mods:affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: bloemeke@uni‐trier.de</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:E2D920629D7C2FBC62B8FB70853EA82879CAC6D0</idno><date when="2013" year="2013">2013</date><idno type="doi">10.1111/cod.12032</idno><idno type="url">https://api.istex.fr/document/E2D920629D7C2FBC62B8FB70853EA82879CAC6D0/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">001699</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">001699</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">Penetration and haptenation of p‐phenylenediamine</title><author><name sortKey="Pot, Laura M" sort="Pot, Laura M" uniqKey="Pot L" first="Laura M." last="Pot">Laura M. Pot</name><affiliation><mods:affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</mods:affiliation></affiliation></author><author><name sortKey="Scheitza, Simone M" sort="Scheitza, Simone M" uniqKey="Scheitza S" first="Simone M." last="Scheitza">Simone M. Scheitza</name><affiliation><mods:affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</mods:affiliation></affiliation></author><author><name sortKey="Coenraads, Pieter An" sort="Coenraads, Pieter An" uniqKey="Coenraads P" first="Pieter-Jan" last="Coenraads">Pieter-Jan Coenraads</name><affiliation><mods:affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</mods:affiliation></affiliation></author><author><name sortKey="Blomeke, Brunhilde" sort="Blomeke, Brunhilde" uniqKey="Blomeke B" first="Brunhilde" last="Blömeke">Brunhilde Blömeke</name><affiliation><mods:affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: bloemeke@uni‐trier.de</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Contact Dermatitis</title><idno type="ISSN">0105-1873</idno><idno type="eISSN">1600-0536</idno><imprint><publisher>Blackwell Publishing Ltd</publisher><pubPlace>Oxford, UK</pubPlace><date type="published" when="2013-04">2013-04</date><biblScope unit="volume">68</biblScope><biblScope unit="issue">4</biblScope><biblScope unit="page" from="193">193</biblScope><biblScope unit="page" to="207">207</biblScope></imprint><idno type="ISSN">0105-1873</idno></series><idno type="istex">E2D920629D7C2FBC62B8FB70853EA82879CAC6D0</idno><idno type="DOI">10.1111/cod.12032</idno><idno type="ArticleID">COD12032</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0105-1873</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>haptenation</term><term>penetration</term><term>protein binding</term><term>p‐phenylenediamine</term><term>sensitization</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Although p‐phenylenediamine (PPD) has been recognized as an extreme sensitizer for many years, the exact mechanism of sensitization has not been elucidated yet. Penetration and the ability to bind to proteins are the first two hurdles that an allergen has to overcome to be able to sensitize. This review is an overview of studies regarding PPD penetration through skin (analogues) and studies on the amino acids that are targeted by PPD. To complete this review, the auto‐oxidation and N‐acetylation steps involved in PPD metabolism are described. In summary, under normal hair dyeing exposure conditions, <1% of the applied PPD dose penetrates the skin. The majority (>80%) of PPD that penetrates will be converted into the detoxification products monoacetyl‐PPD and diacetyl‐PPD by the N‐acetyltransferase enzymes. The small amount of PPD that does not become N‐acetylated is susceptible to auto‐oxidation reactions, yielding protein‐reactive PPD derivatives. These derivatives may bind to specific amino acids, and some of the formed adducts might be the complexes responsible for sensitization. However, true in vivo evidence is lacking, and further research to unravel the definite mechanism of sensitization is needed.</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Laura M. Pot</name><affiliations><json:string>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</json:string></affiliations></json:item><json:item><name>Simone M. Scheitza</name><affiliations><json:string>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</json:string></affiliations></json:item><json:item><name>Pieter‐Jan Coenraads</name><affiliations><json:string>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</json:string></affiliations></json:item><json:item><name>Brunhilde Blömeke</name><affiliations><json:string>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</json:string><json:string>E-mail: bloemeke@uni‐trier.de</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>haptenation</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>penetration</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>p‐phenylenediamine</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>protein binding</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>sensitization</value></json:item></subject><articleId><json:string>COD12032</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>reviewArticle</json:string></originalGenre><abstract>Although p‐phenylenediamine (PPD) has been recognized as an extreme sensitizer for many years, the exact mechanism of sensitization has not been elucidated yet. Penetration and the ability to bind to proteins are the first two hurdles that an allergen has to overcome to be able to sensitize. This review is an overview of studies regarding PPD penetration through skin (analogues) and studies on the amino acids that are targeted by PPD. To complete this review, the auto‐oxidation and N‐acetylation steps involved in PPD metabolism are described. In summary, under normal hair dyeing exposure conditions, >1% of the applied PPD dose penetrates the skin. The majority (>80%) of PPD that penetrates will be converted into the detoxification products monoacetyl‐PPD and diacetyl‐PPD by the N‐acetyltransferase enzymes. The small amount of PPD that does not become N‐acetylated is susceptible to auto‐oxidation reactions, yielding protein‐reactive PPD derivatives. These derivatives may bind to specific amino acids, and some of the formed adducts might be the complexes responsible for sensitization. However, true in vivo evidence is lacking, and further research to unravel the definite mechanism of sensitization is needed.</abstract><qualityIndicators><score>7.196</score><pdfVersion>1.3</pdfVersion><pdfPageSize>595.276 x 782.362 pts</pdfPageSize><refBibsNative>true</refBibsNative><abstractCharCount>1225</abstractCharCount><pdfWordCount>8979</pdfWordCount><pdfCharCount>59554</pdfCharCount><pdfPageCount>15</pdfPageCount><abstractWordCount>183</abstractWordCount></qualityIndicators><title>Penetration and haptenation of p‐phenylenediamine</title><refBibs><json:item><author></author><host><volume>L262</volume><pages><last>200</last><first>169</first></pages><author></author><title>Off J Eur Union</title></host><title>Council Directive of 27 July on the approximation of the laws of Member States relating to cosmetic products (76/768/EEC).</title></json:item><json:item><host><author></author><title>U. S. Food and Drug Administration Center for Food Safety and Applied Nutrition Office of Cosmetics and Colors Fact Sheet April 18, 2001</title></host></json:item><json:item><author><json:item><name>J P Thyssen</name></json:item><json:item><name>K E Andersen</name></json:item><json:item><name>M Bruze</name></json:item></author><host><volume>60</volume><pages><last>319.</last><first>314</first></pages><author></author><title>Contact Dermatitis</title></host><title>p‐Phenylenediamine sensitization is more prevalent in central and southern European patch test centres than in Scandinavian: results from a multicentre study.</title></json:item><json:item><author><json:item><name>W Uter</name></json:item><json:item><name>H Lessmann</name></json:item><json:item><name>J Geier</name></json:item><json:item><name>A. Schnuch</name></json:item></author><host><volume>5</volume><pages><last>1001.</last><first>993</first></pages><author></author><title>J Dtsch Dermatol Ges</title></host><title>Contact allergy to hairdressing allergens in female hairdressers and clients –current data from the IVDK, 2003–2006.</title></json:item><json:item><author><json:item><name>T Rustemeyer</name></json:item><json:item><name>I M W Van Hoogstraten</name></json:item><json:item><name>B M E von Blomberg</name></json:item><json:item><name>S Gibs</name></json:item><json:item><name>R J. Scheper</name></json:item><json:item><name>J‐P Lepoittevin</name></json:item></author><host><pages><last>90.</last><first>43</first></pages><author></author><title>Contact Dermatitis</title></host><title>Mechanisms of irritant and allergic contact dermatitis.</title></json:item><json:item><author><json:item><name>J D Bos</name></json:item><json:item><name>M M. Meinardi</name></json:item></author><host><volume>9</volume><pages><last>169.</last><first>165</first></pages><author></author><title>Exp Dermatol</title></host><title>The 500 Dalton rule for the skin penetration of chemical compounds and drugs.</title></json:item><json:item><author><json:item><name>E Proksch</name></json:item><json:item><name>J M Brandner</name></json:item><json:item><name>J M. Jensen</name></json:item></author><host><volume>17</volume><pages><last>1072.</last><first>1063</first></pages><author></author><title>Exp Dermatol</title></host><title>The skin: an indispensable barrier.</title></json:item><json:item><author><json:item><name>S J Bashir</name></json:item><json:item><name>A L Chew</name></json:item><json:item><name>A Anigbogu</name></json:item><json:item><name>F Dreher</name></json:item><json:item><name>H I. Maibach</name></json:item></author><host><volume>7</volume><pages><last>48.</last><first>40</first></pages><author></author><title>Skin Res Technol</title></host><title>Physical and physiological effects of stratum corneum tape stripping.</title></json:item><json:item><author><json:item><name>F Berard</name></json:item><json:item><name>J P Marty</name></json:item><json:item><name>J F. Nicolas</name></json:item></author><host><volume>13</volume><pages><last>330.</last><first>324</first></pages><author></author><title>Eur J Dermatol</title></host><title>Allergen penetration through the skin.</title></json:item><json:item><author><json:item><name>C K Smith Pease</name></json:item><json:item><name>I R White</name></json:item><json:item><name>D A. Basketter</name></json:item></author><host><volume>27</volume><pages><last>300.</last><first>296</first></pages><author></author><title>Clin Exp Dermatol</title></host><title>Skin as a route of exposure to protein allergens.</title></json:item><json:item><author><json:item><name>K D McCarley</name></json:item><json:item><name>A L. Bunge</name></json:item></author><host><volume>90</volume><pages><last>1719.</last><first>1699</first></pages><author></author><title>J Pharm Sci</title></host><title>Pharmacokinetic models of dermal absorption.</title></json:item><json:item><author><json:item><name>C Fernandez</name></json:item><json:item><name>F Nielloud</name></json:item><json:item><name>R Fortune</name></json:item><json:item><name>L Vian</name></json:item><json:item><name>G. Marti‐Mestres</name></json:item></author><host><volume>28</volume><pages><last>63.</last><first>57</first></pages><author></author><title>J Pharm Biomed Anal</title></host><title>Benzophenone‐3: rapid prediction and evaluation using non‐invasive methods of in vivo human penetration.</title></json:item><json:item><author><json:item><name>A Pouillot</name></json:item><json:item><name>N Dayan</name></json:item><json:item><name>A S Polla</name></json:item><json:item><name>L L Polla</name></json:item><json:item><name>B S. Polla</name></json:item></author><host><volume>7</volume><pages><last>148.</last><first>143</first></pages><author></author><title>J Cosmet Dermatol</title></host><title>The stratum corneum: a double paradox.</title></json:item><json:item><author><json:item><name>H Schaefer</name></json:item><json:item><name>J. Lademann</name></json:item></author><host><volume>14</volume><pages><last>27.</last><first>23</first></pages><author></author><title>Skin Pharmacol Appl Skin Physiol</title></host><title>The role of follicular penetration. A differential view.</title></json:item><json:item><author><json:item><name>R Chourasia</name></json:item><json:item><name>S K. Jain</name></json:item></author><host><volume>10</volume><pages><last>967.</last><first>950</first></pages><author></author><title>Curr Drug Targets</title></host><title>Drug targeting through pilosebaceous route.</title></json:item><json:item><author><json:item><name>A J Lee</name></json:item><json:item><name>J R King</name></json:item><json:item><name>T G. Rogers</name></json:item></author><host><volume>13</volume><pages><last>150.</last><first>127</first></pages><author></author><title>IMA J Math Appl Med Biol</title></host><title>A multiple‐pathway model for the diffusion of drugs in skin.</title></json:item><json:item><author><json:item><name>W J Albery</name></json:item><json:item><name>J. Hadgraft</name></json:item></author><host><volume>31</volume><pages><last>147.</last><first>140</first></pages><author></author><title>J Pharm Pharmacol</title></host><title>Percutaneous absorption: in vivo experiments.</title></json:item><json:item><author><json:item><name>M K Nemanic</name></json:item><json:item><name>P M. Elias</name></json:item></author><host><volume>28</volume><pages><last>578.</last><first>573</first></pages><author></author><title>J Histochem Cytochem</title></host><title>In situ precipitation: a novel cytochemical technique for visualization of permeability pathways in mammalian stratum corneum.</title></json:item><json:item><author><json:item><name>R O Potts</name></json:item><json:item><name>M L. Francoeur</name></json:item></author><host><volume>96</volume><pages><last>499.</last><first>495</first></pages><author></author><title>J Invest Dermatol</title></host><title>The influence of stratum corneum morphology on water permeability.</title></json:item><json:item><author><json:item><name>J A Bouwstra</name></json:item><json:item><name>B A van den Bergh</name></json:item><json:item><name>M. Suhonen</name></json:item></author><host><volume>21</volume><pages><last>286.</last><first>259</first></pages><author></author><title>J Recept Signal Transduct Res</title></host><title>Topical application of drugs: mechanisms involved in chemical enhancement.</title></json:item><json:item><author><json:item><name>K C Madison</name></json:item><json:item><name>D C Swartzendruber</name></json:item><json:item><name>P W Wertz</name></json:item><json:item><name>D T. Downing</name></json:item></author><host><volume>88</volume><pages><last>718.</last><first>714</first></pages><author></author><title>J Invest Dermatol</title></host><title>Presence of intact intercellular lipid lamellae in the upper layers of the stratum corneum.</title></json:item><json:item><author><json:item><name>G K Menon</name></json:item><json:item><name>P M. Elias</name></json:item></author><host><volume>10</volume><pages><last>246.</last><first>235</first></pages><author></author><title>Skin Pharmacol</title></host><title>Morphologic basis for a pore‐pathway in mammalian stratum corneum.</title></json:item><json:item><author><json:item><name>J. Hadgraft</name></json:item></author><host><volume>58</volume><pages><last>299.</last><first>291</first></pages><author></author><title>Eur J Pharm Biopharm</title></host><title>Skin deep.</title></json:item><json:item><author><json:item><name>U Blume‐Peytavi</name></json:item><json:item><name>L Massoudy</name></json:item><json:item><name>A Patzelt</name></json:item><json:item><name>J Lademann</name></json:item><json:item><name>E Dietz</name></json:item><json:item><name>U Rasulev</name></json:item><json:item><name>N. Garcia Bartels</name></json:item></author><host><volume>76</volume><pages><last>453.</last><first>450</first></pages><author></author><title>Eur J Pharm Biopharm</title></host><title>Follicular and percutaneous penetration pathways of topically applied minoxidil foam.</title></json:item><json:item><author><json:item><name>H R Smith</name></json:item><json:item><name>D A Basketter</name></json:item><json:item><name>J P. McFadden</name></json:item></author><host><volume>27</volume><pages><last>146.</last><first>138</first></pages><author></author><title>Clin Exp Dermatol</title></host><title>Irritant dermatitis, irritancy and its role in allergic contact dermatitis.</title></json:item><json:item><author><json:item><name>M Bonneville</name></json:item><json:item><name>C Chavagnac</name></json:item><json:item><name>M Vocanson</name></json:item></author><host><volume>127</volume><pages><last>1435.</last><first>1430</first></pages><author></author><title>J Invest Dermatol</title></host><title>Skin contact irritation conditions the development and severity of allergic contact dermatitis.</title></json:item><json:item><author><json:item><name>J A. Segre</name></json:item></author><host><volume>116</volume><pages><last>1158.</last><first>1150</first></pages><author></author><title>J Clin Invest</title></host><title>Epidermal barrier formation and recovery in skin disorders.</title></json:item><json:item><author><json:item><name>A Yamamoto</name></json:item><json:item><name>S Serizawa</name></json:item><json:item><name>M Ito</name></json:item><json:item><name>Y. Sato</name></json:item></author><host><volume>283</volume><pages><last>223.</last><first>219</first></pages><author></author><title>Arch Dermatol Res</title></host><title>Stratum corneum lipid abnormalities in atopic dermatitis.</title></json:item><json:item><author><json:item><name>J P Thyssen</name></json:item><json:item><name>J D Johansen</name></json:item><json:item><name>A Linneberg</name></json:item></author><host><volume>162</volume><pages><last>1285.</last><first>1278</first></pages><author></author><title>Br J Dermatol</title></host><title>The association between null mutations in the filaggrin gene and contact sensitization to nickel and other chemicals in the general population.</title></json:item><json:item><author><json:item><name>B van Ravenzwaay</name></json:item><json:item><name>E. Leibold</name></json:item></author><host><volume>23</volume><pages><last>430.</last><first>421</first></pages><author></author><title>Hum Exp Toxicol</title></host><title>A comparison between in vitro rat and human and in vivo rat skin absorption studies.</title></json:item><json:item><author><json:item><name>F Hueber‐Becker</name></json:item><json:item><name>G J Nohynek</name></json:item><json:item><name>W J Meuling</name></json:item><json:item><name>F Benech‐Kieffer</name></json:item><json:item><name>H. Toutain</name></json:item></author><host><volume>42</volume><pages><last>1236.</last><first>1227</first></pages><author></author><title>Food Chem Toxicol</title></host><title>Human systemic exposure to a [14C]‐para‐phenylenediamine‐containing oxidative hair dye and correlation with in vitro percutaneous absorption in human or pig skin.</title></json:item><json:item><author><json:item><name>M Sznitowska</name></json:item><json:item><name>S Janicki</name></json:item><json:item><name>A. Baczek</name></json:item></author><host><volume>76</volume><pages><last>335.</last><first>327</first></pages><author></author><title>J Controlled Release</title></host><title>Studies on the effect of pH on the lipoidal route of penetration across stratum corneum.</title></json:item><json:item><author><json:item><name>A G Matoltsy</name></json:item><json:item><name>A M Downes</name></json:item><json:item><name>T M. Sweeney</name></json:item></author><host><volume>50</volume><pages><last>26.</last><first>19</first></pages><author></author><title>J Invest Dermatol</title></host><title>Studies of the epidermal water barrier. II. Investigation of the chemical nature of the water barrier.</title></json:item><json:item><author><json:item><name>Y Kawakubo</name></json:item><json:item><name>H F Merk</name></json:item><json:item><name>T A Masaoudi</name></json:item><json:item><name>S Sieben</name></json:item><json:item><name>B. Blomeke</name></json:item></author><host><volume>292</volume><pages><last>155.</last><first>150</first></pages><author></author><title>J Pharmacol Exp Ther</title></host><title>N‐Acetylation of paraphenylenediamine in human skin and keratinocytes.</title></json:item><json:item><author><json:item><name>N Goetz</name></json:item><json:item><name>P Lasserre</name></json:item><json:item><name>P Bore</name></json:item><json:item><name>G. Kalopissis</name></json:item></author><host><volume>10</volume><pages><last>73.</last><first>63</first></pages><author></author><title>Int J Cosmet Sci</title></host><title>Percutaneous absorption of p‐phenylene diamine during an actual hair dyeing procedure.</title></json:item><json:item><author><json:item><name>G J Nohynek</name></json:item><json:item><name>J A Skare</name></json:item><json:item><name>W J Meuling</name></json:item><json:item><name>D W Hein</name></json:item><json:item><name>A T De Bie</name></json:item><json:item><name>H. Toutain</name></json:item></author><host><volume>42</volume><pages><last>1891.</last><first>1885</first></pages><author></author><title>Food Chem Toxicol</title></host><title>Urinary acetylated metabolites and N‐acetyltransferase‐2 genotype in human subjects treated with a para‐phenylenediamine‐containing oxidative hair dye.</title></json:item><json:item><author><json:item><name>L J Wolfram</name></json:item><json:item><name>H I. Maibach</name></json:item></author><host><volume>277</volume><pages><last>241.</last><first>235</first></pages><author></author><title>Arch Dermatol Res</title></host><title>Percutaneous penetration of hair dyes.</title></json:item><json:item><author><json:item><name>W E Dressler</name></json:item><json:item><name>T. Appelqvist</name></json:item></author><host><volume>44</volume><pages><last>379.</last><first>371</first></pages><author></author><title>Food Chem Toxicol</title></host><title>Plasma/blood pharmacokinetics and metabolism after dermal exposure to para‐aminophenol or para‐phenylenediamine.</title></json:item><json:item><author><json:item><name>T Hu</name></json:item><json:item><name>R E Bailey</name></json:item><json:item><name>S W Morrall</name></json:item><json:item><name>M J Aardema</name></json:item><json:item><name>L A Stanley</name></json:item><json:item><name>J A. Skare</name></json:item></author><host><volume>188</volume><pages><last>129.</last><first>119</first></pages><author></author><title>Toxicol Lett</title></host><title>Dermal penetration and metabolism of p‐aminophenol and p‐phenylenediamine: application of the EpiDerm human reconstructed epidermis model.</title></json:item><json:item><author><json:item><name>C Goebel</name></json:item><json:item><name>P J Coenraads</name></json:item><json:item><name>H Rothe</name></json:item><json:item><name>G Kunze</name></json:item><json:item><name>M Kock</name></json:item><json:item><name>H Schlatter</name></json:item><json:item><name>G F Gerberick</name></json:item><json:item><name>B. Blomeke</name></json:item></author><host><volume>163</volume><pages><last>1211.</last><first>1205</first></pages><author></author><title>Br J Dermatol</title></host><title>Elicitation of the immune response to p‐phenylenediamine in allergic patients: the role of dose and exposure time.</title></json:item><json:item><author><json:item><name>W Steiling</name></json:item><json:item><name>J Kreutz</name></json:item><json:item><name>H. Hofer</name></json:item></author><host><volume>15</volume><pages><last>570.</last><first>565</first></pages><author></author><title>Toxicol In Vitro</title></host><title>Percutaneous penetration/dermal absorption of hair dyes in vitro.</title></json:item><json:item><author><json:item><name>M Kiese</name></json:item><json:item><name>E. Rauscher</name></json:item></author><host><volume>13</volume><pages><last>331.</last><first>325</first></pages><author></author><title>Toxicol Appl Pharmacol</title></host><title>The absorption of p‐toluenediamine through human skin in hair dyeing.</title></json:item><json:item><author><json:item><name>R. Hruby</name></json:item></author><host><volume>15</volume><pages><last>599.</last><first>595</first></pages><author></author><title>Food Cosmet Toxicol</title></host><title>The absorption of p‐toluenediamine by the skin of rats and dogs.</title></json:item><json:item><host><author></author><title>Opinion on Toluene‐2,5‐diamine</title></host></json:item><json:item><host><author></author><title>Opinion on p‐Phenylenediamine</title></host></json:item><json:item><author><json:item><name>J M White</name></json:item><json:item><name>D A Basketter</name></json:item><json:item><name>C K Pease</name></json:item><json:item><name>D A Sanders</name></json:item><json:item><name>J P. McFadden</name></json:item></author><host><volume>56</volume><pages><last>265.</last><first>262</first></pages><author></author><title>Contact Dermatitis</title></host><title>Intermittent exposure to low‐concentration paraphenylenediamine can be equivalent to single, higher‐dose exposure.</title></json:item><json:item><author><json:item><name>L H Jansen</name></json:item><json:item><name>M T Hojyo‐Tomoko</name></json:item><json:item><name>A M. Kligman</name></json:item></author><host><volume>90</volume><pages><last>12.</last><first>9</first></pages><author></author><title>Br J Dermatol</title></host><title>Improved fluorescence staining technique for estimating turnover of the human stratum corneum.</title></json:item><json:item><author><json:item><name>T. Platzek</name></json:item></author><host><volume>2</volume><pages><last>1183.</last><first>1169</first></pages><author></author><title>Front Biosci (Elite Ed)</title></host><title>Risk from exposure to arylamines from consumer products and hair dyes.</title></json:item><json:item><author><json:item><name>M Van Gele</name></json:item><json:item><name>B Geusens</name></json:item><json:item><name>L Brochez</name></json:item><json:item><name>R Speeckaert</name></json:item><json:item><name>J. Lambert</name></json:item></author><host><volume>8</volume><pages><last>720.</last><first>705</first></pages><author></author><title>Expert Opin Drug Deliv</title></host><title>Three‐dimensional skin models as tools for transdermal drug delivery: challenges and limitations.</title></json:item><json:item><author><json:item><name>V S Thakoersing</name></json:item><json:item><name>G S Gooris</name></json:item><json:item><name>A Mulder</name></json:item><json:item><name>M Rietveld</name></json:item><json:item><name>A El Ghalbzouri</name></json:item><json:item><name>J A. Bouwstra</name></json:item></author><host><volume>18</volume><pages><last>11</last><first>1</first></pages><author></author><title>Tissue Eng Part C Methods</title></host><title>Unraveling barrier properties of three different in‐house human skin equivalents.</title></json:item><json:item><author><json:item><name>J Bonifas</name></json:item><json:item><name>S Scheitza</name></json:item><json:item><name>J Clemens</name></json:item><json:item><name>B. Blomeke</name></json:item></author><host><volume>334</volume><pages><last>326.</last><first>318</first></pages><author></author><title>J Pharmacol Exp Ther</title></host><title>Characterization of N‐acetyltransferase 1 activity in human keratinocytes and modulation by para‐phenylenediamine.</title></json:item><json:item><author><json:item><name>R R Brancaccio</name></json:item><json:item><name>L H Brown</name></json:item><json:item><name>Y T Chang</name></json:item><json:item><name>J P Fogelman</name></json:item><json:item><name>E A Mafong</name></json:item><json:item><name>D E. Cohen</name></json:item></author><host><volume>13</volume><pages><last>18.</last><first>15</first></pages><author></author><title>Am J Contact Dermat</title></host><title>Identification and quantification of para‐phenylenediamine in a temporary black henna tattoo.</title></json:item><json:item><author><json:item><name>I J Kang</name></json:item><json:item><name>M H. Lee</name></json:item></author><host><volume>55</volume><pages><last>29.</last><first>26</first></pages><author></author><title>Contact Dermatitis</title></host><title>Quantification of para‐phenylenediamine and heavy metals in henna dye.</title></json:item><json:item><author><json:item><name>F N Marzulli</name></json:item><json:item><name>H I. Maibach</name></json:item></author><host><volume>12</volume><pages><last>227.</last><first>219</first></pages><author></author><title>Food Cosmet Toxicol</title></host><title>The use of graded concentrations in studying skin sensitizers: experimental contact sensitization in man.</title></json:item><json:item><author><json:item><name>J P Thyssen</name></json:item><json:item><name>J M White</name></json:item><json:item><name> </name></json:item></author><host><volume>59</volume><pages><last>343.</last><first>327</first></pages><author></author><title>Contact Dermatitis</title></host><title>Epidemiological data on consumer allergy to p‐phenylenediamine.</title></json:item><json:item><author><json:item><name>D W Roberts</name></json:item><json:item><name>A O. Aptula</name></json:item></author><host><volume>28</volume><pages><last>387.</last><first>377</first></pages><author></author><title>J Appl Toxicol</title></host><title>Determinants of skin sensitisation potential.</title></json:item><json:item><author><json:item><name>D W Roberts</name></json:item><json:item><name>A. Natsch</name></json:item></author><host><volume>22</volume><pages><last>603.</last><first>592</first></pages><author></author><title>Chem Res Toxicol</title></host><title>High throughput kinetic profiling approach for covalent binding to peptides: application to skin sensitization potency of Michael acceptor electrophiles.</title></json:item><json:item><author><json:item><name>I R Jowsey</name></json:item><json:item><name>D A Basketter</name></json:item><json:item><name>C Westmoreland</name></json:item><json:item><name>I. Kimber</name></json:item></author><host><volume>26</volume><pages><last>350.</last><first>341</first></pages><author></author><title>J Appl Toxicol</title></host><title>A future approach to measuring relative skin sensitising potency: a proposal.</title></json:item><json:item><author><json:item><name>I Chipinda</name></json:item><json:item><name>J M Hettick</name></json:item><json:item><name>P D. Siegel</name></json:item></author><host><volume>2011</volume><author></author><title>J Allergy (Cairo)</title></host><title>Haptenation: chemical reactivity and protein binding.</title></json:item><json:item><author><json:item><name>I Kimber</name></json:item><json:item><name>R J Dearman</name></json:item><json:item><name>D A Basketter</name></json:item><json:item><name>C A Ryan</name></json:item><json:item><name>G F. Gerberick</name></json:item></author><host><volume>47</volume><pages><last>328.</last><first>315</first></pages><author></author><title>Contact Dermatitis</title></host><title>The local lymph node assay: past, present and future.</title></json:item><json:item><author><json:item><name>G F Gerberick</name></json:item><json:item><name>J D Vassallo</name></json:item><json:item><name>R E Bailey</name></json:item><json:item><name>J G Chaney</name></json:item><json:item><name>S W Morrall</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>81</volume><pages><last>343.</last><first>332</first></pages><author></author><title>Toxicol Sci</title></host><title>Development of a peptide reactivity assay for screening contact allergens.</title></json:item><json:item><author><json:item><name>G F Gerberick</name></json:item><json:item><name>J D Vassallo</name></json:item><json:item><name>L M Foertsch</name></json:item><json:item><name>B B Price</name></json:item><json:item><name>J G Chaney</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>97</volume><pages><last>427.</last><first>417</first></pages><author></author><title>Toxicol Sci</title></host><title>Quantification of chemical peptide reactivity for screening contact allergens: a classification tree model approach.</title></json:item><json:item><author><json:item><name>K Landsteiner</name></json:item><json:item><name>J. Jacobs</name></json:item></author><host><volume>61</volume><pages><last>656.</last><first>643</first></pages><author></author><title>J Exp Med</title></host><title>Studies on the sensitization of animals with simple chemical compounds.</title></json:item><json:item><host><author></author><title>Dupuis G, Benezra C. Allergic Contact Dermatitis to Simple Chemicals. A Molecular Approach: New York, Marcel Dekker, 1982.</title></host></json:item><json:item><author><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>54</volume><pages><last>74.</last><first>73</first></pages><author></author><title>Contact Dermatitis</title></host><title>Metabolism versus chemical transformation or pro‐ versus prehaptens?</title></json:item><json:item><author><json:item><name>R J. Schmidt</name></json:item></author><host><volume>57</volume><pages><last>67.</last><first>65</first></pages><author></author><title>Contact Dermatitis</title></host><title>Free radicals and the antioxidant hypothesis of prohapten activation.</title></json:item><json:item><author><json:item><name>A O Aptula</name></json:item><json:item><name>D W Roberts</name></json:item><json:item><name>C K. Pease</name></json:item></author><host><volume>56</volume><pages><last>56.</last><first>54</first></pages><author></author><title>Contact Dermatitis</title></host><title>Haptens, prohaptens and prehaptens, or electrophiles and proelectrophiles.</title></json:item><json:item><author><json:item><name>G F Gerberick</name></json:item><json:item><name>J A Troutman</name></json:item><json:item><name>L M Foertsch</name></json:item><json:item><name>J D Vassallo</name></json:item><json:item><name>M Quijano</name></json:item><json:item><name>R L Dobson</name></json:item><json:item><name>C Goebel</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>112</volume><pages><last>174.</last><first>164</first></pages><author></author><title>Toxicol Sci</title></host><title>Investigation of peptide reactivity of pro‐hapten skin sensitizers using a peroxidase–peroxide oxidation system.</title></json:item><json:item><author><json:item><name>S R Ahlfors</name></json:item><json:item><name>O Sterner</name></json:item><json:item><name>C. Hansson</name></json:item></author><host><volume>16</volume><pages><last>68.</last><first>59</first></pages><author></author><title>Skin Pharmacol Appl Skin Physiol</title></host><title>Reactivity of contact allergenic haptens to amino acid residues in a model carrier peptide, and characterization of formed peptide–hapten adducts.</title></json:item><json:item><author><json:item><name>M Aleksic</name></json:item><json:item><name>C K Pease</name></json:item><json:item><name>D A Basketter</name></json:item><json:item><name>M Panico</name></json:item><json:item><name>H R Morris</name></json:item><json:item><name>A. Dell</name></json:item></author><host><volume>21</volume><pages><last>733.</last><first>723</first></pages><author></author><title>Toxicol In Vitro</title></host><title>Investigating protein haptenation mechanisms of skin sensitisers using human serum albumin as a model protein.</title></json:item><json:item><author><json:item><name>M Aleksic</name></json:item><json:item><name>E Thain</name></json:item><json:item><name>D Roger</name></json:item><json:item><name>O Saib</name></json:item><json:item><name>M Davies</name></json:item><json:item><name>J Li</name></json:item><json:item><name>A Aptula</name></json:item><json:item><name>R. Zazzeroni</name></json:item></author><host><volume>108</volume><pages><last>411.</last><first>401</first></pages><author></author><title>Toxicol Sci</title></host><title>Reactivity profiling: covalent modification of single nucleophile peptides for skin sensitization risk assessment.</title></json:item><json:item><author><json:item><name>J Eilstein</name></json:item><json:item><name>E Gimenez‐Arnau</name></json:item><json:item><name>D Duche</name></json:item><json:item><name>F Rousset</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>19</volume><pages><last>1256.</last><first>1248</first></pages><author></author><title>Chem Res Toxicol</title></host><title>Synthesis and reactivity toward nucleophilic amino acids of 2,5‐[13C]‐dimethyl‐p‐benzoquinonediimine.</title></json:item><json:item><author><json:item><name>J Eilstein</name></json:item><json:item><name>E Gimenez‐Arnau</name></json:item><json:item><name>D Duche</name></json:item><json:item><name>F Rousset</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>20</volume><pages><last>1161.</last><first>1155</first></pages><author></author><title>Chem Res Toxicol</title></host><title>Mechanistic studies on the lysine‐induced N‐formylation of 2,5‐dimethyl‐p‐benzoquinonediimine.</title></json:item><json:item><author><json:item><name>J Eilstein</name></json:item><json:item><name>E Gimenez‐Arnau</name></json:item><json:item><name>D Duche</name></json:item><json:item><name>N Cavusoglu</name></json:item><json:item><name>G Hussler</name></json:item><json:item><name>F Rousset</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>16</volume><pages><last>5489.</last><first>5482</first></pages><author></author><title>Bioorg Med Chem</title></host><title>Sensitization to p‐amino aromatic compounds: study of the covalent binding of 2,5‐dimethyl‐p‐benzoquinonediimine to a model peptide by electrospray ionization tandem mass spectrometry.</title></json:item><json:item><author><json:item><name>C Jenkinson</name></json:item><json:item><name>R E Jenkins</name></json:item><json:item><name>J L Maggs</name></json:item><json:item><name>N R Kitteringham</name></json:item><json:item><name>M Aleksic</name></json:item><json:item><name>B K Park</name></json:item><json:item><name>D J. Naisbitt</name></json:item></author><host><volume>22</volume><pages><last>1180.</last><first>1172</first></pages><author></author><title>Chem Res Toxicol</title></host><title>A mechanistic investigation into the irreversible protein binding and antigenicity of p‐phenylenediamine.</title></json:item><json:item><author><json:item><name>A Natsch</name></json:item><json:item><name>H. Gfeller</name></json:item></author><host><volume>106</volume><pages><last>478.</last><first>464</first></pages><author></author><title>Toxicol Sci</title></host><title>LC‐MS‐based characterization of the peptide reactivity of chemicals to improve the in vitro prediction of the skin sensitization potential.</title></json:item><json:item><author><json:item><name>M Divkovic</name></json:item><json:item><name>C K Pease</name></json:item><json:item><name>G F Gerberick</name></json:item><json:item><name>D A. Basketter</name></json:item></author><host><volume>53</volume><pages><last>200.</last><first>189</first></pages><author></author><title>Contact Dermatitis</title></host><title>Hapten–protein binding: from theory to practical application in the in vitro prediction of skin sensitization.</title></json:item><json:item><author><json:item><name>F Gerberick</name></json:item><json:item><name>M Aleksic</name></json:item><json:item><name>D Basketter</name></json:item></author><host><volume>36</volume><pages><last>242.</last><first>215</first></pages><author></author><title>Altern Lab Anim</title></host><title>Chemical reactivity measurement and the predicitve identification of skin sensitisers. The report and recommendations of ECVAM Workshop 64.</title></json:item><json:item><host><pages><first>310</first></pages><author></author><title>Smith C K, Hotchkiss S A M. Allergic Contact Dermatitis: Chemical and Metabolic Mechanisms: London and New York, Taylor and Francis, 2001: 310pp.</title></host></json:item><json:item><author><json:item><name>E Meschkat</name></json:item><json:item><name>M D Barratt</name></json:item><json:item><name>J. Lepoittevin</name></json:item></author><host><volume>14</volume><pages><last>117.</last><first>110</first></pages><author></author><title>Chem Res Toxicol</title></host><title>Studies of the chemical selectivity of hapten, reactivity, and skin sensitization potency. 1. Synthesis and studies on the reactivity toward model nucleophiles of the (13)C‐labeled skin sensitizers hex‐1‐ene‐ and hexane‐1,3‐sultones.</title></json:item><json:item><author><json:item><name>R Alvarez‐Sanchez</name></json:item><json:item><name>D Basketter</name></json:item><json:item><name>C Pease</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>16</volume><pages><last>636.</last><first>627</first></pages><author></author><title>Chem Res Toxicol</title></host><title>Studies of chemical selectivity of hapten, reactivity, and skin sensitization potency. 3. Synthesis and studies on the reactivity toward model nucleophiles of the 13C‐labeled skin sensitizers, 5‐chloro‐2‐methylisothiazol‐3‐one (MCI) and 2‐methylisothiazol‐3‐one (MI).</title></json:item><json:item><author><json:item><name>R Alvarez‐Sanchez</name></json:item><json:item><name>M Divkovic</name></json:item><json:item><name>D Basketter</name></json:item><json:item><name>C Pease</name></json:item><json:item><name>M Panico</name></json:item><json:item><name>A Dell</name></json:item><json:item><name>H Morris</name></json:item><json:item><name>J P. Lepoittevin</name></json:item></author><host><volume>17</volume><pages><last>1288.</last><first>1280</first></pages><author></author><title>Chem Res Toxicol</title></host><title>Effect of glutathione on the covalent binding of the 13C‐labeled skin sensitizer 5‐chloro‐2‐methylisothiazol‐3‐one to human serum albumin: identification of adducts by nuclear magnetic resonance, matrix‐assisted laser desorption/ionization mass spectrometry, and nanoelectrospray tandem mass spectrometry.</title></json:item><json:item><author><json:item><name>P Aeby</name></json:item><json:item><name>T Sieber</name></json:item><json:item><name>H Beck</name></json:item><json:item><name>G F Gerberick</name></json:item><json:item><name>C. Goebel</name></json:item></author><host><volume>129</volume><pages><last>109.</last><first>99</first></pages><author></author><title>J Invest Dermatol</title></host><title>Skin sensitization to p‐phenylenediamine: the diverging roles of oxidation and N‐acetylation for dendritic cell activation and the immune response.</title></json:item><json:item><author><json:item><name>B Blomeke</name></json:item><json:item><name>T Pietzsch</name></json:item><json:item><name>H F. Merk</name></json:item></author><host><volume>58</volume><pages><last>358.</last><first>355</first></pages><author></author><title>Contact Dermatitis</title></host><title>Elicitation response characteristics to mono‐ and to N,N′‐diacetyl‐para‐phenylenediamine.</title></json:item><json:item><author><json:item><name>N J Butcher</name></json:item><json:item><name>K F Ilett</name></json:item><json:item><name>R F. Minchin</name></json:item></author><host><volume>57</volume><pages><last>473.</last><first>468</first></pages><author></author><title>Mol Pharmacol</title></host><title>Substrate‐dependent regulation of human arylamine N‐acetyltransferase‐1 in cultured cells.</title></json:item><json:item><author><json:item><name>J M White</name></json:item><json:item><name>P Kullavanijaya</name></json:item><json:item><name>I Duangdeeden</name></json:item><json:item><name>R Zazzeroni</name></json:item><json:item><name>N J Gilmour</name></json:item><json:item><name>D A Basketter</name></json:item><json:item><name>J P. McFadden</name></json:item></author><host><volume>36</volume><pages><last>1293.</last><first>1289</first></pages><author></author><title>Clin Exp Allergy</title></host><title>p‐Phenylenediamine allergy: the role of Bandrowski's base.</title></json:item><json:item><author><json:item><name>J Hennen</name></json:item><json:item><name>P Aeby</name></json:item><json:item><name>C Goebel</name></json:item><json:item><name>T Schettgen</name></json:item><json:item><name>A Oberli</name></json:item><json:item><name>M Kalmes</name></json:item><json:item><name>B. Blomeke</name></json:item></author><host><volume>123</volume><pages><last>510.</last><first>501</first></pages><author></author><title>Toxicol Sci</title></host><title>Cross talk between keratinocytes and dendritic cells: impact on the prediction of sensitization.</title></json:item><json:item><author><json:item><name>M Krasteva</name></json:item><json:item><name>J F Nicolas</name></json:item><json:item><name>G Chabeau</name></json:item><json:item><name>J L Garrigue</name></json:item><json:item><name>H Bour</name></json:item><json:item><name>J Thivolet</name></json:item><json:item><name>D. Schmitt</name></json:item></author><host><volume>102</volume><pages><last>204.</last><first>200</first></pages><author></author><title>Int Arch Allergy Immunol</title></host><title>Dissociation of allergenic and immunogenic functions in contact sensitivity to para‐phenylenediamine.</title></json:item><json:item><host><author></author><title>Opinion on exposure to reactants and reaction products of oxidative hair dye formulations</title></host></json:item><json:item><author><json:item><name>M Aleksic</name></json:item><json:item><name>E Thain</name></json:item><json:item><name>D Roger</name></json:item><json:item><name>O Saib</name></json:item><json:item><name>M Davies</name></json:item><json:item><name>J Li</name></json:item><json:item><name>A Aptula</name></json:item><json:item><name>R. Zazzeroni</name></json:item></author><host><volume>108</volume><pages><last>411.</last><first>401</first></pages><author></author><title>Toxicol Sci</title></host><title>Reactivity profiling: covalent modification of single nucleophile peptides for skin sensitization risk assessment. Supplementary data. Supplementary Table S1.</title></json:item><json:item><author><json:item><name>A O Aptula</name></json:item><json:item><name>S J Enoch</name></json:item><json:item><name>D W. Roberts</name></json:item></author><host><volume>22</volume><pages><last>1547.</last><first>1541</first></pages><author></author><title>Chem Res Toxicol</title></host><title>Chemical mechanisms for skin sensitization by aromatic compounds with hydroxy and amino groups.</title></json:item><json:item><author><json:item><name>A Natsch</name></json:item><json:item><name>R Emter</name></json:item><json:item><name>G. Ellis</name></json:item></author><host><volume>107</volume><pages><last>121.</last><first>106</first></pages><author></author><title>Toxicol Sci</title></host><title>Filling the concept with data: integrating data from different in vitro and in silico assays on skin sensitizers to explore the battery approach for animal‐free skin sensitization testing.</title></json:item><json:item><author><json:item><name>J A Troutman</name></json:item><json:item><name>L M Foertsch</name></json:item><json:item><name>P S Kern</name></json:item></author><host><volume>122</volume><pages><last>436.</last><first>422</first></pages><author></author><title>Toxicol Sci</title></host><title>The incorporation of lysine into the peroxidase peptide reactivity assay for skin sensitization assessments.</title></json:item><json:item><author><json:item><name>C Jenkinson</name></json:item><json:item><name>R E Jenkins</name></json:item><json:item><name>M Aleksic</name></json:item><json:item><name>M Pirmohamed</name></json:item><json:item><name>D J Naisbitt</name></json:item><json:item><name>B K. Park</name></json:item></author><host><volume>130</volume><pages><last>742.</last><first>732</first></pages><author></author><title>J Invest Dermatol</title></host><title>Characterization of p‐phenylenediamine–albumin binding sites and T‐cell responses to hapten‐modified protein.</title></json:item><json:item><author><json:item><name>M Krasteva</name></json:item><json:item><name>B Bons</name></json:item><json:item><name>C Ryan</name></json:item><json:item><name>G F. Gerberick</name></json:item></author><host><volume>20</volume><pages><last>141.</last><first>123</first></pages><author></author><title>Dermatitis</title></host><title>Consumer allergy to oxidative hair coloring products: epidemiologic data in the literature.</title></json:item></refBibs><genre><json:string>review-article</json:string></genre><host><volume>68</volume><publisherId><json:string>COD</json:string></publisherId><pages><total>15</total><last>207</last><first>193</first></pages><issn><json:string>0105-1873</json:string></issn><issue>4</issue><genre><json:string>journal</json:string></genre><language><json:string>unknown</json:string></language><eissn><json:string>1600-0536</json:string></eissn><title>Contact Dermatitis</title><doi><json:string>10.1111/(ISSN)1600-0536</json:string></doi></host><categories><wos><json:string>science</json:string><json:string>dermatology</json:string><json:string>allergy</json:string></wos><scienceMetrix><json:string>health sciences</json:string><json:string>clinical medicine</json:string><json:string>dermatology & venereal diseases</json:string></scienceMetrix></categories><publicationDate>2013</publicationDate><copyrightDate>2013</copyrightDate><doi><json:string>10.1111/cod.12032</json:string></doi><id>E2D920629D7C2FBC62B8FB70853EA82879CAC6D0</id><score>0.5120842</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/E2D920629D7C2FBC62B8FB70853EA82879CAC6D0/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/E2D920629D7C2FBC62B8FB70853EA82879CAC6D0/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/E2D920629D7C2FBC62B8FB70853EA82879CAC6D0/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main" xml:lang="en">Penetration and haptenation of p‐phenylenediamine</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>Blackwell Publishing Ltd</publisher><pubPlace>Oxford, UK</pubPlace><availability><p>© 2013 John Wiley & Sons A/S</p></availability><date>2013</date></publicationStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a" type="main" xml:lang="en">Penetration and haptenation of p‐phenylenediamine</title><author xml:id="author-1"><persName><forename type="first">Laura M.</forename><surname>Pot</surname></persName><affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</affiliation></author><author xml:id="author-2"><persName><forename type="first">Simone M.</forename><surname>Scheitza</surname></persName><affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</affiliation></author><author xml:id="author-3"><persName><forename type="first">Pieter‐Jan</forename><surname>Coenraads</surname></persName><affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</affiliation></author><author xml:id="author-4"><persName><forename type="first">Brunhilde</forename><surname>Blömeke</surname></persName><email>bloemeke@uni‐trier.de</email><affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</affiliation></author></analytic><monogr><title level="j">Contact Dermatitis</title><idno type="pISSN">0105-1873</idno><idno type="eISSN">1600-0536</idno><idno type="DOI">10.1111/(ISSN)1600-0536</idno><imprint><publisher>Blackwell Publishing Ltd</publisher><pubPlace>Oxford, UK</pubPlace><date type="published" when="2013-04"></date><biblScope unit="volume">68</biblScope><biblScope unit="issue">4</biblScope><biblScope unit="page" from="193">193</biblScope><biblScope unit="page" to="207">207</biblScope></imprint></monogr><idno type="istex">E2D920629D7C2FBC62B8FB70853EA82879CAC6D0</idno><idno type="DOI">10.1111/cod.12032</idno><idno type="ArticleID">COD12032</idno></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>2013</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>Although p‐phenylenediamine (PPD) has been recognized as an extreme sensitizer for many years, the exact mechanism of sensitization has not been elucidated yet. Penetration and the ability to bind to proteins are the first two hurdles that an allergen has to overcome to be able to sensitize. This review is an overview of studies regarding PPD penetration through skin (analogues) and studies on the amino acids that are targeted by PPD. To complete this review, the auto‐oxidation and N‐acetylation steps involved in PPD metabolism are described. In summary, under normal hair dyeing exposure conditions, <1% of the applied PPD dose penetrates the skin. The majority (>80%) of PPD that penetrates will be converted into the detoxification products monoacetyl‐PPD and diacetyl‐PPD by the N‐acetyltransferase enzymes. The small amount of PPD that does not become N‐acetylated is susceptible to auto‐oxidation reactions, yielding protein‐reactive PPD derivatives. These derivatives may bind to specific amino acids, and some of the formed adducts might be the complexes responsible for sensitization. However, true in vivo evidence is lacking, and further research to unravel the definite mechanism of sensitization is needed.</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>keywords</head><item><term>haptenation</term></item><item><term>penetration</term></item><item><term>p‐phenylenediamine</term></item><item><term>protein binding</term></item><item><term>sensitization</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2013-04">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/E2D920629D7C2FBC62B8FB70853EA82879CAC6D0/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>Blackwell Publishing Ltd</publisherName><publisherLoc>Oxford, UK</publisherLoc></publisherInfo><doi origin="wiley" registered="yes">10.1111/(ISSN)1600-0536</doi><issn type="print">0105-1873</issn><issn type="electronic">1600-0536</issn><idGroup><id type="product" value="COD"></id><id type="publisherDivision" value="ST"></id></idGroup><titleGroup><title type="main" sort="CONTACT DERMATITIS">Contact Dermatitis</title></titleGroup></publicationMeta><publicationMeta level="part" position="04104"><doi origin="wiley">10.1111/cod.2013.68.issue-4</doi><numberingGroup><numbering type="journalVolume" number="68">68</numbering><numbering type="journalIssue" number="4">4</numbering></numberingGroup><coverDate startDate="2013-04">April 2013</coverDate></publicationMeta><publicationMeta level="unit" type="reviewArticle" position="1" status="forIssue"><doi origin="wiley">10.1111/cod.12032</doi><idGroup><id type="unit" value="COD12032"></id></idGroup><countGroup><count type="pageTotal" number="15"></count></countGroup><titleGroup><title type="tocHeading1">Review Article</title></titleGroup><copyright>© 2013 John Wiley & Sons A/S</copyright><eventGroup><event type="xmlConverted" agent="Converter:BPG_TO_WML3G version:3.2.0 mode:FullText" date="2013-03-20"></event><event type="firstOnline" date="2013-03-20"></event><event type="publishedOnlineFinalForm" date="2013-03-20"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-16"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.6.4 mode:FullText" date="2015-10-02"></event></eventGroup><numberingGroup><numbering type="pageFirst" number="193">193</numbering><numbering type="pageLast" number="207">207</numbering></numberingGroup><correspondenceTo>Professor Dr Brunhilde Blömeke, Department of Environmental Toxicology, University Trier, Universitätsring 15, Bldg N, 54286 Trier, Germany. Tel: +49(0) 651 201 3781; Fax: +49(0) 651 201 3780. E‐mail: <email normalForm="bloemeke@uni-trier.de">bloemeke@uni‐trier.de</email></correspondenceTo><linkGroup><link type="toTypesetVersion" href="file:COD.COD12032.pdf"></link></linkGroup></publicationMeta><contentMeta><unparsedEditorialHistory>Accepted for publication 30 October 2012</unparsedEditorialHistory><countGroup><count type="figureTotal" number="1"></count><count type="tableTotal" number="2"></count><count type="formulaTotal" number="0"></count><count type="referenceTotal" number="95"></count></countGroup><titleGroup><title type="main">Penetration and haptenation of <i>p</i>‐phenylenediamine</title><title type="shortAuthors">POT ET AL.</title></titleGroup><creators><creator creatorRole="author" xml:id="cr1" affiliationRef="#a1"><personName><givenNames>Laura M.</givenNames><familyName>Pot</familyName></personName></creator><creator creatorRole="author" xml:id="cr2" affiliationRef="#a2"><personName><givenNames>Simone M.</givenNames><familyName>Scheitza</familyName></personName></creator><creator creatorRole="author" xml:id="cr3" affiliationRef="#a1"><personName><givenNames>Pieter‐Jan</givenNames><familyName>Coenraads</familyName></personName></creator><creator creatorRole="author" xml:id="cr4" affiliationRef="#a2" corresponding="yes"><personName><givenNames>Brunhilde</givenNames><familyName>Blömeke</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="a1" countryCode="NL"><unparsedAffiliation><i>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</i></unparsedAffiliation></affiliation><affiliation xml:id="a2" countryCode="DE"><unparsedAffiliation><i>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</i></unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en"><keyword xml:id="k1">haptenation</keyword><keyword xml:id="k2">penetration</keyword><keyword xml:id="k3"><i>p</i>‐phenylenediamine</keyword><keyword xml:id="k4">protein binding</keyword><keyword xml:id="k5">sensitization</keyword></keywordGroup><abstractGroup><abstract type="main" xml:lang="en"><p>Although <i>p</i>‐phenylenediamine (PPD) has been recognized as an extreme sensitizer for many years, the exact mechanism of sensitization has not been elucidated yet. Penetration and the ability to bind to proteins are the first two hurdles that an allergen has to overcome to be able to sensitize. This review is an overview of studies regarding PPD penetration through skin (analogues) and studies on the amino acids that are targeted by PPD. To complete this review, the auto‐oxidation and <i>N</i>‐acetylation steps involved in PPD metabolism are described. In summary, under normal hair dyeing exposure conditions, <1% of the applied PPD dose penetrates the skin. The majority (>80%) of PPD that penetrates will be converted into the detoxification products monoacetyl‐PPD and diacetyl‐PPD by the <i>N</i>‐acetyltransferase enzymes. The small amount of PPD that does not become <i>N</i>‐acetylated is susceptible to auto‐oxidation reactions, yielding protein‐reactive PPD derivatives. These derivatives may bind to specific amino acids, and some of the formed adducts might be the complexes responsible for sensitization. However, true <i>in vivo</i> evidence is lacking, and further research to unravel the definite mechanism of sensitization is needed.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Penetration and haptenation of p‐phenylenediamine</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Penetration and haptenation of p‐phenylenediamine</title></titleInfo><name type="personal"><namePart type="given">Laura M.</namePart><namePart type="family">Pot</namePart><affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Simone M.</namePart><namePart type="family">Scheitza</namePart><affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Pieter‐Jan</namePart><namePart type="family">Coenraads</namePart><affiliation>Department of Dermatology, University Medical Centre Groningen, University of Groningen, 9700 RB Groningen, The Netherlands</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Brunhilde</namePart><namePart type="family">Blömeke</namePart><affiliation>Department of Environmental Toxicology, University Trier, Universitätsring 15, 54286 Trier, Germany</affiliation><affiliation>E-mail: bloemeke@uni‐trier.de</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="review-article" displayLabel="reviewArticle"></genre><originInfo><publisher>Blackwell Publishing Ltd</publisher><place><placeTerm type="text">Oxford, UK</placeTerm></place><dateIssued encoding="w3cdtf">2013-04</dateIssued><edition>Accepted for publication 30 October 2012</edition><copyrightDate encoding="w3cdtf">2013</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType><extent unit="figures">1</extent><extent unit="tables">2</extent><extent unit="references">95</extent></physicalDescription><abstract lang="en">Although p‐phenylenediamine (PPD) has been recognized as an extreme sensitizer for many years, the exact mechanism of sensitization has not been elucidated yet. Penetration and the ability to bind to proteins are the first two hurdles that an allergen has to overcome to be able to sensitize. This review is an overview of studies regarding PPD penetration through skin (analogues) and studies on the amino acids that are targeted by PPD. To complete this review, the auto‐oxidation and N‐acetylation steps involved in PPD metabolism are described. In summary, under normal hair dyeing exposure conditions, <1% of the applied PPD dose penetrates the skin. The majority (>80%) of PPD that penetrates will be converted into the detoxification products monoacetyl‐PPD and diacetyl‐PPD by the N‐acetyltransferase enzymes. The small amount of PPD that does not become N‐acetylated is susceptible to auto‐oxidation reactions, yielding protein‐reactive PPD derivatives. These derivatives may bind to specific amino acids, and some of the formed adducts might be the complexes responsible for sensitization. However, true in vivo evidence is lacking, and further research to unravel the definite mechanism of sensitization is needed.</abstract><subject lang="en"><genre>keywords</genre><topic>haptenation</topic><topic>penetration</topic><topic>p‐phenylenediamine</topic><topic>protein binding</topic><topic>sensitization</topic></subject><relatedItem type="host"><titleInfo><title>Contact Dermatitis</title></titleInfo><genre type="journal">journal</genre><identifier type="ISSN">0105-1873</identifier><identifier type="eISSN">1600-0536</identifier><identifier type="DOI">10.1111/(ISSN)1600-0536</identifier><identifier type="PublisherID">COD</identifier><part><date>2013</date><detail type="volume"><caption>vol.</caption><number>68</number></detail><detail type="issue"><caption>no.</caption><number>4</number></detail><extent unit="pages"><start>193</start><end>207</end><total>15</total></extent></part></relatedItem><identifier type="istex">E2D920629D7C2FBC62B8FB70853EA82879CAC6D0</identifier><identifier type="DOI">10.1111/cod.12032</identifier><identifier type="ArticleID">COD12032</identifier><accessCondition type="use and reproduction" contentType="copyright">© 2013 John Wiley & Sons A/S</accessCondition><recordInfo><recordContentSource>WILEY</recordContentSource><recordOrigin>Blackwell Publishing Ltd</recordOrigin></recordInfo></mods></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Rhénanie/explor/UnivTrevesV1/Data/Istex/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 001699 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Istex/Corpus/biblio.hfd -nk 001699 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Rhénanie
|area= UnivTrevesV1
|flux= Istex
|étape= Corpus
|type= RBID
|clé= ISTEX:E2D920629D7C2FBC62B8FB70853EA82879CAC6D0
|texte= Penetration and haptenation of p‐phenylenediamine
}}
| This area was generated with Dilib version V0.6.31. |  |