Improvement of meta-tetra(Hydroxyphenyl)chlorin-Like Photosensitizer Selectivity with Folate-Based Targeted Delivery. Synthesis and in Vivo Delivery Studies
Identifieur interne : 001110 ( Main/Exploration ); précédent : 001109; suivant : 001111Improvement of meta-tetra(Hydroxyphenyl)chlorin-Like Photosensitizer Selectivity with Folate-Based Targeted Delivery. Synthesis and in Vivo Delivery Studies
Auteurs : Julien Gravier [France] ; Raphaël Schneider [France] ; Céline Frochot [France] ; Thierry Bastogne [France] ; Frédéric Schmitt ; Jacques Didelon [Suisse] ; Francois Guillemin [France] ; Muriel Barberi-Heyob [France]Source :
- Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2008.
Descripteurs français
- Pascal (Inist)
- Dérivé de la porphyrine, Photosensibilisant, Sélectivité, Composé conjugué, Médicament ciblé, Synthèse chimique, In vivo, Activité biologique, Acide folique, Folate, Captation, Lignée KB, Cellule tumorale, Tumeur maligne, Souris, Voie intraveineuse, Accumulation biologique, Dérivé de la ptéridine, Homme, Animal, Côlon, Epiderme, Chlorine(20-[4-carboxyphényl-5,10,15-tris[3-hydroxyphényl]), Lignée HT29, Glutamique acide dérivé.
- Wicri :
- topic : Homme.
English descriptors
- KwdEn :
- Animal, Biological accumulation, Biological activity, Chemical synthesis, Colon, Conjugated compound, Epidermis, Folate, Folic acid, Human, In vivo, Intravenous administration, KB cell line, Malignant tumor, Mouse, Photosensitizer, Porphyrin derivatives, Pteridine derivatives, Selectivity, Targeted drug, Tumor cell, Uptake.
Abstract
The cell membrane folate receptor (FR) is a molecular target for tumor-selective drug delivery, including delivery of photosensitizers for anticancer photodynamic therapy (PDT). Tumor selectivity of metatetra(hydroxyphenyl)chlorin (m-THPC), a photosensitizer used in PDT clinical trials, demonstrates a low tumor-to-normal epithelial uptake ratio. We report on the synthesis and on the photophysical properties of a m-THPC-like photosensitizer 1 conjugated to folic acid (compound 8). A comparative study of the accumulation of photosensitizers 1 and 8 is described. Nude mice were xenografted with FR-α-positive KB or HT-29 cells lacking FR-α as a negative control. Using optical fiber fluorimetry, we demonstrated that conjugate 8 exhibited enhanced accumulation in KB tumors compared to 1 4 h after injection. No significant difference between KB and HT-29 tumors was observed in case of compound 1. Tumor-to-normal tissue ratio exhibited a very interesting selectivity for conjugate 8 (5:1) in KB tumors 4 h postinjection.
Affiliations:
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Synthesis and in Vivo Delivery Studies</title><author><name sortKey="Gravier, Julien" sort="Gravier, Julien" uniqKey="Gravier J" first="Julien" last="Gravier">Julien Gravier</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>SRSMC, Structure et Réactivité des Systèmes Moléculaires Complexes, Nancy University, BP 239</s1><s2>54506 Vandoeuvre-lès-Nancy</s2><s3>FRA</s3><sZ>1 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Vandoeuvre-lès-Nancy</settlement></placeName></affiliation></author><author><name sortKey="Schneider, Raphael" sort="Schneider, Raphael" uniqKey="Schneider R" first="Raphaël" last="Schneider">Raphaël Schneider</name><affiliation wicri:level="3"><inist:fA14 i1="02"><s1>DCPR, Département de Chimie Physique de Réactions, Nancy University, CNRS, 1 rue Grandville, BP 20451</s1><s2>54001 Nancy</s2><s3>FRA</s3><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Nancy</settlement></placeName></affiliation></author><author><name sortKey="Frochot, Celine" sort="Frochot, Celine" uniqKey="Frochot C" first="Céline" last="Frochot">Céline Frochot</name><affiliation wicri:level="3"><inist:fA14 i1="02"><s1>DCPR, Département de Chimie Physique de Réactions, Nancy University, CNRS, 1 rue Grandville, BP 20451</s1><s2>54001 Nancy</s2><s3>FRA</s3><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Nancy</settlement></placeName></affiliation></author><author><name sortKey="Bastogne, Thierry" sort="Bastogne, Thierry" uniqKey="Bastogne T" first="Thierry" last="Bastogne">Thierry Bastogne</name><affiliation wicri:level="3"><inist:fA14 i1="03"><s1>CRAN, Centre de Recherche en Automatique de Nancy, Nancy University, CNRS, CAV, Avenue de Bourgogne</s1><s2>54511 Vandoeuvre-lès-Nancy</s2><s3>FRA</s3><sZ>4 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Vandoeuvre-lès-Nancy</settlement></placeName></affiliation></author><author><name sortKey="Schmitt, Frederic" sort="Schmitt, Frederic" uniqKey="Schmitt F" first="Frédéric" last="Schmitt">Frédéric Schmitt</name></author><author><name sortKey="Didelon, Jacques" sort="Didelon, Jacques" uniqKey="Didelon J" first="Jacques" last="Didelon">Jacques Didelon</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>CAV, Centre Alexis Vautrin, Nancy University, University Institute of Pathology, CHUV, Bugnon 25</s1><s2>1011 Lausanne</s2><s3>CHE</s3><sZ>6 aut.</sZ></inist:fA14><country>Suisse</country><placeName><settlement type="city">Lausanne</settlement><region nuts="3" type="region">Canton de Vaud</region></placeName></affiliation></author><author><name sortKey="Guillemin, Francois" sort="Guillemin, Francois" uniqKey="Guillemin F" first="Francois" last="Guillemin">Francois Guillemin</name><affiliation wicri:level="3"><inist:fA14 i1="03"><s1>CRAN, Centre de Recherche en Automatique de Nancy, Nancy University, CNRS, CAV, Avenue de Bourgogne</s1><s2>54511 Vandoeuvre-lès-Nancy</s2><s3>FRA</s3><sZ>4 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Vandoeuvre-lès-Nancy</settlement></placeName></affiliation></author><author><name sortKey="Barberi Heyob, Muriel" sort="Barberi Heyob, Muriel" uniqKey="Barberi Heyob M" first="Muriel" last="Barberi-Heyob">Muriel Barberi-Heyob</name><affiliation wicri:level="3"><inist:fA14 i1="03"><s1>CRAN, Centre de Recherche en Automatique de Nancy, Nancy University, CNRS, CAV, Avenue de Bourgogne</s1><s2>54511 Vandoeuvre-lès-Nancy</s2><s3>FRA</s3><sZ>4 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Vandoeuvre-lès-Nancy</settlement></placeName></affiliation></author></analytic><series><title level="j" type="main">Journal of medicinal chemistry : (Print)</title><title level="j" type="abbreviated">J. med. chem. : (Print)</title><idno type="ISSN">0022-2623</idno><imprint><date when="2008">2008</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Journal of medicinal chemistry : (Print)</title><title level="j" type="abbreviated">J. med. chem. : (Print)</title><idno type="ISSN">0022-2623</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animal</term><term>Biological accumulation</term><term>Biological activity</term><term>Chemical synthesis</term><term>Colon</term><term>Conjugated compound</term><term>Epidermis</term><term>Folate</term><term>Folic acid</term><term>Human</term><term>In vivo</term><term>Intravenous administration</term><term>KB cell line</term><term>Malignant tumor</term><term>Mouse</term><term>Photosensitizer</term><term>Porphyrin derivatives</term><term>Pteridine derivatives</term><term>Selectivity</term><term>Targeted drug</term><term>Tumor cell</term><term>Uptake</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Dérivé de la porphyrine</term><term>Photosensibilisant</term><term>Sélectivité</term><term>Composé conjugué</term><term>Médicament ciblé</term><term>Synthèse chimique</term><term>In vivo</term><term>Activité biologique</term><term>Acide folique</term><term>Folate</term><term>Captation</term><term>Lignée KB</term><term>Cellule tumorale</term><term>Tumeur maligne</term><term>Souris</term><term>Voie intraveineuse</term><term>Accumulation biologique</term><term>Dérivé de la ptéridine</term><term>Homme</term><term>Animal</term><term>Côlon</term><term>Epiderme</term><term>Chlorine(20-[4-carboxyphényl-5,10,15-tris[3-hydroxyphényl])</term><term>Lignée HT29</term><term>Glutamique acide dérivé</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Homme</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The cell membrane folate receptor (FR) is a molecular target for tumor-selective drug delivery, including delivery of photosensitizers for anticancer photodynamic therapy (PDT). Tumor selectivity of metatetra(hydroxyphenyl)chlorin (m-THPC), a photosensitizer used in PDT clinical trials, demonstrates a low tumor-to-normal epithelial uptake ratio. We report on the synthesis and on the photophysical properties of a m-THPC-like photosensitizer 1 conjugated to folic acid (compound 8). A comparative study of the accumulation of photosensitizers 1 and 8 is described. Nude mice were xenografted with FR-α-positive KB or HT-29 cells lacking FR-α as a negative control. Using optical fiber fluorimetry, we demonstrated that conjugate 8 exhibited enhanced accumulation in KB tumors compared to 1 4 h after injection. No significant difference between KB and HT-29 tumors was observed in case of compound 1. Tumor-to-normal tissue ratio exhibited a very interesting selectivity for conjugate 8 (5:1) in KB tumors 4 h postinjection.</div></front></TEI><affiliations><list><country><li>France</li><li>Suisse</li></country><region><li>Canton de Vaud</li><li>Grand Est</li><li>Lorraine (région)</li></region><settlement><li>Lausanne</li><li>Nancy</li><li>Vandoeuvre-lès-Nancy</li></settlement></list><tree><noCountry><name sortKey="Schmitt, Frederic" sort="Schmitt, Frederic" uniqKey="Schmitt F" first="Frédéric" last="Schmitt">Frédéric Schmitt</name></noCountry><country name="France"><region name="Grand Est"><name sortKey="Gravier, Julien" sort="Gravier, Julien" uniqKey="Gravier J" first="Julien" last="Gravier">Julien Gravier</name></region><name sortKey="Barberi Heyob, Muriel" sort="Barberi Heyob, Muriel" uniqKey="Barberi Heyob M" first="Muriel" last="Barberi-Heyob">Muriel Barberi-Heyob</name><name sortKey="Bastogne, Thierry" sort="Bastogne, Thierry" uniqKey="Bastogne T" first="Thierry" last="Bastogne">Thierry Bastogne</name><name sortKey="Frochot, Celine" sort="Frochot, Celine" uniqKey="Frochot C" first="Céline" last="Frochot">Céline Frochot</name><name sortKey="Guillemin, Francois" sort="Guillemin, Francois" uniqKey="Guillemin F" first="Francois" last="Guillemin">Francois Guillemin</name><name sortKey="Schneider, Raphael" sort="Schneider, Raphael" uniqKey="Schneider R" first="Raphaël" last="Schneider">Raphaël Schneider</name></country><country name="Suisse"><region name="Canton de Vaud"><name sortKey="Didelon, Jacques" sort="Didelon, Jacques" uniqKey="Didelon J" first="Jacques" last="Didelon">Jacques Didelon</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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