Reactivity of cosmetic UV filters towards skin proteins: model studies with Boc-lysine, Boc-Gly-Phe-Gly-Lys-OH, BSA and gelatin.
Identifieur interne : 000011 ( PubMed/Checkpoint ); précédent : 000010; suivant : 000012Reactivity of cosmetic UV filters towards skin proteins: model studies with Boc-lysine, Boc-Gly-Phe-Gly-Lys-OH, BSA and gelatin.
Auteurs : C. Stiefel [Allemagne] ; W. SchwackSource :
- International journal of cosmetic science [ 1468-2494 ] ; 2014.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Gelatin, Serum Albumin, Bovine, Sunscreening Agents.
- drug effects : Skin.
- Animals, Humans, Keratins, Ultraviolet Rays.
Abstract
Organic UV filters are used as active ingredients in most sunscreens and also in a variety of daily care products. Their good (photo) stability is of special interest to guarantee protective function and to prevent interactions with the human skin. Due to the mostly electrophilic character of the UV filters, reactions with nucleophilic protein moieties like lysine side chains are conceivable. Prior studies showed that the UV filters octocrylene (OCR), butyl methoxydibenzoylmethane (BM-DBM), ethylhexyl salicylate (EHS), ethylhexyl methoxycinnamate (EHMC), benzophenone-3 (BP-3), ethylhexyl triazone (EHT) and dibenzoylmethane (DBM) were able to covalently bind to an HPTLC amino phase and the amino acid models ethanolamine and butylamine after slightly heating and/or radiation.
DOI: 10.1111/ics.12157
PubMed: 25130261
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Reactivity of cosmetic UV filters towards skin proteins: model studies with Boc-lysine, Boc-Gly-Phe-Gly-Lys-OH, BSA and gelatin.</title><author><name sortKey="Stiefel, C" sort="Stiefel, C" uniqKey="Stiefel C" first="C" last="Stiefel">C. Stiefel</name><affiliation wicri:level="4"><nlm:affiliation>Institute of Food Chemistry, University of Hohenheim, Garbenstrasse 28, Stuttgart, 70599, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institute of Food Chemistry, University of Hohenheim, Garbenstrasse 28, Stuttgart, 70599</wicri:regionArea><placeName><region type="land" nuts="1">Bade-Wurtemberg</region><region type="district" nuts="2">District de Stuttgart</region><settlement type="city">Stuttgart</settlement></placeName><orgName type="university">Université de Hohenheim</orgName></affiliation></author><author><name sortKey="Schwack, W" sort="Schwack, W" uniqKey="Schwack W" first="W" last="Schwack">W. Schwack</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2014">2014</date><idno type="RBID">pubmed:25130261</idno><idno type="pmid">25130261</idno><idno type="doi">10.1111/ics.12157</idno><idno type="wicri:Area/PubMed/Corpus">000014</idno><idno type="wicri:Area/PubMed/Curation">000014</idno><idno type="wicri:Area/PubMed/Checkpoint">000014</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Reactivity of cosmetic UV filters towards skin proteins: model studies with Boc-lysine, Boc-Gly-Phe-Gly-Lys-OH, BSA and gelatin.</title><author><name sortKey="Stiefel, C" sort="Stiefel, C" uniqKey="Stiefel C" first="C" last="Stiefel">C. Stiefel</name><affiliation wicri:level="4"><nlm:affiliation>Institute of Food Chemistry, University of Hohenheim, Garbenstrasse 28, Stuttgart, 70599, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institute of Food Chemistry, University of Hohenheim, Garbenstrasse 28, Stuttgart, 70599</wicri:regionArea><placeName><region type="land" nuts="1">Bade-Wurtemberg</region><region type="district" nuts="2">District de Stuttgart</region><settlement type="city">Stuttgart</settlement></placeName><orgName type="university">Université de Hohenheim</orgName></affiliation></author><author><name sortKey="Schwack, W" sort="Schwack, W" uniqKey="Schwack W" first="W" last="Schwack">W. Schwack</name></author></analytic><series><title level="j">International journal of cosmetic science</title><idno type="eISSN">1468-2494</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Gelatin (chemistry)</term><term>Humans</term><term>Keratins</term><term>Serum Albumin, Bovine (chemistry)</term><term>Skin (drug effects)</term><term>Sunscreening Agents (chemistry)</term><term>Ultraviolet Rays</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Gelatin</term><term>Serum Albumin, Bovine</term><term>Sunscreening Agents</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Skin</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Humans</term><term>Keratins</term><term>Ultraviolet Rays</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Organic UV filters are used as active ingredients in most sunscreens and also in a variety of daily care products. Their good (photo) stability is of special interest to guarantee protective function and to prevent interactions with the human skin. Due to the mostly electrophilic character of the UV filters, reactions with nucleophilic protein moieties like lysine side chains are conceivable. Prior studies showed that the UV filters octocrylene (OCR), butyl methoxydibenzoylmethane (BM-DBM), ethylhexyl salicylate (EHS), ethylhexyl methoxycinnamate (EHMC), benzophenone-3 (BP-3), ethylhexyl triazone (EHT) and dibenzoylmethane (DBM) were able to covalently bind to an HPTLC amino phase and the amino acid models ethanolamine and butylamine after slightly heating and/or radiation.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">25130261</PMID><DateCreated><Year>2014</Year><Month>11</Month><Day>07</Day></DateCreated><DateCompleted><Year>2015</Year><Month>07</Month><Day>07</Day></DateCompleted><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1468-2494</ISSN><JournalIssue CitedMedium="Internet"><Volume>36</Volume><Issue>6</Issue><PubDate><Year>2014</Year><Month>Dec</Month></PubDate></JournalIssue><Title>International journal of cosmetic science</Title><ISOAbbreviation>Int J Cosmet Sci</ISOAbbreviation></Journal><ArticleTitle>Reactivity of cosmetic UV filters towards skin proteins: model studies with Boc-lysine, Boc-Gly-Phe-Gly-Lys-OH, BSA and gelatin.</ArticleTitle><Pagination><MedlinePgn>561-70</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1111/ics.12157</ELocationID><Abstract><AbstractText Label="OBJECTIVE" NlmCategory="OBJECTIVE">Organic UV filters are used as active ingredients in most sunscreens and also in a variety of daily care products. Their good (photo) stability is of special interest to guarantee protective function and to prevent interactions with the human skin. Due to the mostly electrophilic character of the UV filters, reactions with nucleophilic protein moieties like lysine side chains are conceivable. Prior studies showed that the UV filters octocrylene (OCR), butyl methoxydibenzoylmethane (BM-DBM), ethylhexyl salicylate (EHS), ethylhexyl methoxycinnamate (EHMC), benzophenone-3 (BP-3), ethylhexyl triazone (EHT) and dibenzoylmethane (DBM) were able to covalently bind to an HPTLC amino phase and the amino acid models ethanolamine and butylamine after slightly heating and/or radiation.</AbstractText><AbstractText Label="METHODS" NlmCategory="METHODS">Boc-protected lysine, the tetrapeptide Boc-Gly-Phe-Gly-Lys-OH, bovine serum albumin (BSA) and porcine gelatin were used as more complex models to determine the reactivity of the mentioned UV filters towards skin proteins under thermal or UV irradiation conditions.</AbstractText><AbstractText Label="RESULTS" NlmCategory="RESULTS">After gentle heating at 37°C, benzophenone imines were identified as reaction products of BP-3 and OCR with Boc-lysine and the tetrapeptide, whereas DBM and BM-DBM yielded enamines. For EHMC, a Michael-type reaction occurred, which resulted in addition of Boc-lysine or the tetrapeptide to the conjugated double bond. Ester aminolysis of EHS and EHT mainly afforded the corresponding amides. Reactions of the UV filters with BSA changed the UV spectrum of BSA, generally associated with an increase of the absorption strength in the UVA or UVB range. For all protein models, the UV filters showed an increasing reactivity in the order EHT < EHMC < EHS < BP-3 < OCR < DBM < BM-DBM.</AbstractText><AbstractText Label="CONCLUSION" NlmCategory="CONCLUSIONS">Especially the UV absorbers BM-DBM, OCR and BP-3, which are seen as common allergens or photoallergens, showed a high reactivity towards the different skin protein models. As the formation of protein adducts is recognized as important key element in the induction of skin sensitization, the results of this study can contribute to a better understanding of the underlying chemical mechanisms of such reactions.</AbstractText><CopyrightInformation>© 2014 Society of Cosmetic Scientists and the Société Française de Cosmétologie.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Stiefel</LastName><ForeName>C</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Institute of Food Chemistry, University of Hohenheim, Garbenstrasse 28, Stuttgart, 70599, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Schwack</LastName><ForeName>W</ForeName><Initials>W</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>09</Month><Day>11</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Int J Cosmet Sci</MedlineTA><NlmUniqueID>8007161</NlmUniqueID><ISSNLinking>0142-5463</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012710">Serum Albumin, Bovine</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013473">Sunscreening Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>68238-35-7</RegistryNumber><NameOfSubstance UI="D007633">Keratins</NameOfSubstance></Chemical><Chemical><RegistryNumber>9000-70-8</RegistryNumber><NameOfSubstance UI="D005780">Gelatin</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N" UI="D000818">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D005780">Gelatin</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D006801">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D007633">Keratins</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D012710">Serum Albumin, Bovine</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D012867">Skin</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000187">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D013473">Sunscreening Agents</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D014466">Ultraviolet Rays</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">UV absorbers</Keyword><Keyword MajorTopicYN="N">chemical analysis</Keyword><Keyword MajorTopicYN="N">safety testing</Keyword><Keyword MajorTopicYN="N">skin sensitization</Keyword><Keyword MajorTopicYN="N">spectroscopy</Keyword><Keyword MajorTopicYN="N">sun protection</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year><Month>6</Month><Day>2</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2014</Year><Month>7</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="aheadofprint"><Year>2014</Year><Month>9</Month><Day>11</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>8</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>8</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>7</Month><Day>8</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25130261</ArticleId><ArticleId IdType="doi">10.1111/ics.12157</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Allemagne</li></country><region><li>Bade-Wurtemberg</li><li>District de Stuttgart</li></region><settlement><li>Stuttgart</li></settlement><orgName><li>Université de Hohenheim</li></orgName></list><tree><noCountry><name sortKey="Schwack, W" sort="Schwack, W" uniqKey="Schwack W" first="W" last="Schwack">W. Schwack</name></noCountry><country name="Allemagne"><region name="Bade-Wurtemberg"><name sortKey="Stiefel, C" sort="Stiefel, C" uniqKey="Stiefel C" first="C" last="Stiefel">C. Stiefel</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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