Ferrocene Functionalized Endocrine Modulators as Anticancer Agents
Identifieur interne : 000263 ( France/Analysis ); précédent : 000262; suivant : 000264Ferrocene Functionalized Endocrine Modulators as Anticancer Agents
Auteurs : Elizabeth A. Hillard [France] ; Anne Vessières [France] ; Gerard Jaouen [France]Source :
- Topics in Organometallic Chemistry [ 1436-6002 ]
Abstract
Abstract: We present here some of our studies on the synthesis and behaviour of ferrocenyl selective endocrine receptor modulators against cancer cells, particularly breast and prostate cancers. The proliferative/anti-proliferative effects of compounds based on steroidal and non-steroidal endocrine modulators have been extensively explored in vitro. Structure–activity relationship studies of such molecules, particularly the hydroxyferrocifens and ferrocene phenols, have shown the effect of (1) the presence and the length of the N,N-dimethylamino side chain, (2) the presence and position of the phenol group, (3) the role of the ferrocenyl moiety, (4) that of conjugation, (5) phenyl functionalisation and (6) the placement of the phenyl group. Compounds possessing a ferrocene moiety linked to a p-phenol by a conjugated π-system are among the most potent of the series, with IC50 values ranging from 0.090 to 0.6µM on hormone independent breast cancer cells. Based on the SAR data and electrochemical studies, we have proposed an original mechanism to explain the unusual behaviour of these bioorganometallic species and coin the term “kronatropic” to qualify this effect, involving ROS production and bio-oxidation. In addition, the importance of formulation is underlined. We also discuss the behaviour of ferrocenyl androgens and anti-androgens for possible use against prostate cancers. In sum, ferrocene has proven to be a fascinating substituent due to its vast potential for oncology.
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DOI: 10.1007/978-3-642-13185-1_4
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Hillard</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>UMR 7223, Laboratoire Charles Friedel, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75231, Paris</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></affiliation></author><author><name sortKey="Vessieres, Anne" sort="Vessieres, Anne" uniqKey="Vessieres A" first="Anne" last="Vessières">Anne Vessières</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>UMR 7223, Laboratoire Charles Friedel, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75231, Paris</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></affiliation></author><author><name sortKey="Jaouen, Gerard" sort="Jaouen, Gerard" uniqKey="Jaouen G" first="Gerard" last="Jaouen">Gerard Jaouen</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>UMR 7223, Laboratoire Charles Friedel, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75231, Paris</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">France</country></affiliation></author></analytic><monogr></monogr><series><title level="s" type="main" xml:lang="en">Topics in Organometallic Chemistry</title><title level="s" type="abbrev">Topics Organomet.Chemistry</title><idno type="ISSN">1436-6002</idno><idno type="eISSN">1616-8534</idno><idno type="ISSN">1436-6002</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1436-6002</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: We present here some of our studies on the synthesis and behaviour of ferrocenyl selective endocrine receptor modulators against cancer cells, particularly breast and prostate cancers. The proliferative/anti-proliferative effects of compounds based on steroidal and non-steroidal endocrine modulators have been extensively explored in vitro. Structure–activity relationship studies of such molecules, particularly the hydroxyferrocifens and ferrocene phenols, have shown the effect of (1) the presence and the length of the N,N-dimethylamino side chain, (2) the presence and position of the phenol group, (3) the role of the ferrocenyl moiety, (4) that of conjugation, (5) phenyl functionalisation and (6) the placement of the phenyl group. Compounds possessing a ferrocene moiety linked to a p-phenol by a conjugated π-system are among the most potent of the series, with IC50 values ranging from 0.090 to 0.6µM on hormone independent breast cancer cells. Based on the SAR data and electrochemical studies, we have proposed an original mechanism to explain the unusual behaviour of these bioorganometallic species and coin the term “kronatropic” to qualify this effect, involving ROS production and bio-oxidation. In addition, the importance of formulation is underlined. We also discuss the behaviour of ferrocenyl androgens and anti-androgens for possible use against prostate cancers. In sum, ferrocene has proven to be a fascinating substituent due to its vast potential for oncology.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Île-de-France</li></region><settlement><li>Paris</li></settlement></list><tree><country name="France"><region name="Île-de-France"><name sortKey="Hillard, Elizabeth A" sort="Hillard, Elizabeth A" uniqKey="Hillard E" first="Elizabeth A." last="Hillard">Elizabeth A. Hillard</name></region><name sortKey="Jaouen, Gerard" sort="Jaouen, Gerard" uniqKey="Jaouen G" first="Gerard" last="Jaouen">Gerard Jaouen</name><name sortKey="Jaouen, Gerard" sort="Jaouen, Gerard" uniqKey="Jaouen G" first="Gerard" last="Jaouen">Gerard Jaouen</name><name sortKey="Vessieres, Anne" sort="Vessieres, Anne" uniqKey="Vessieres A" first="Anne" last="Vessières">Anne Vessières</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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