Chiral Platinum(II) Complexes Featuring Phosphine and Chloroquine Ligands as Cytotoxic and Monofunctional DNA-Binding Agents.
Identifieur interne : 000E98 ( Main/Exploration ); précédent : 000E97; suivant : 000E99Chiral Platinum(II) Complexes Featuring Phosphine and Chloroquine Ligands as Cytotoxic and Monofunctional DNA-Binding Agents.
Auteurs : Wilmer Villarreal [Brésil] ; Legna Colina-Vegas [Brésil] ; Clayton Rodrigues De Oliveira [Brésil] ; Juan C. Tenorio [Brésil] ; Javier Ellena [Brésil] ; Fábio C. Gozzo [Brésil] ; Marcia Regina Cominetti [Brésil] ; Antonio G. Ferreira [Brésil] ; Marco Antonio Barbosa Ferreira [Brésil] ; Maribel Navarro [Brésil] ; Alzir A. Batista [Brésil]Source :
- Inorganic chemistry [ 1520-510X ] ; 2015.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Chloroquine, DNA, Phosphines, Platinum.
- Cell Line, Tumor, Circular Dichroism, Humans, Ligands, Magnetic Resonance Spectroscopy, Mass Spectrometry, Stereoisomerism.
Abstract
Chiral molecules in nature are involved in many biological events; their selectivity and specificity make them of great interest for understanding the behavior of bioactive molecules, by providing information about the chiral discrimination. Inspired by these conformational properties, we present the design and synthesis of novel chiral platinum(II) complexes featuring phosphine and chloroquine ligands with the general formula [PtCl(P)2(CQ)]PF6 (where (P)2 = triphenylphosphine (PPh3) (5), 1,3-bis(diphenylphosphine)propane (dppp) (6), 1,4-bis(diphenylphosphine)butane (dppb) (7), 1,1'-bis(diphenylphosphine)ferrocene (dppf) (8), and CQ = chloroquine] and their precursors of the type [PtCl2(P)2] are described. The complexes were characterized by elemental analysis, absorption spectroscopy in the infrared and ultraviolet-visible (UV-vis) regions, multinuclear ((1)H, (13)C, (31)P, (15)N, and (195)Pt) NMR spectroscopy, cyclic voltammetry, and mass spectrometry (in the case of chloroquine complexes). The interactions of the new platinum-chloroquine complexes with both albumin (BSA), using fluorescence spectroscopy, and DNA, by four widely reported methods were also evaluated. These experiments showed that these Pt-CQ complexes interact strongly with DNA and have high affinities for BSA, in contrast to CQ and CQDP (chloroquine diphosphate), which interact weakly with these biomolecules. Additional assays were performed in order to investigate the cytotoxicity of the platinum complexes against two healthy cell lines (mouse fibroblasts (L929) and the Chinese hamster lung (V79-4)) and four tumor cell lines (human breast (MDA-MB-231 and MCF-7), human lung (A549), and human prostate (DU-145)). The results suggest that the Pt-CQ complexes are generally more cytotoxic than the free CQ, showing that they are promising as anticancer drugs.
DOI: 10.1021/acs.inorgchem.5b01647
PubMed: 26606142
Affiliations:
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Tenorio</name><affiliation wicri:level="4"><nlm:affiliation>Instituto de Física de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos-SP, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Instituto de Física de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos-SP</wicri:regionArea><placeName><region type="state">État de São Paulo</region><settlement type="city">São Paulo</settlement></placeName><orgName type="university">Université de São Paulo</orgName></affiliation></author><author><name sortKey="Ellena, Javier" sort="Ellena, Javier" uniqKey="Ellena J" first="Javier" last="Ellena">Javier Ellena</name><affiliation wicri:level="4"><nlm:affiliation>Instituto de Física de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos-SP, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Instituto de Física de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos-SP</wicri:regionArea><placeName><region type="state">État de São Paulo</region><settlement type="city">São Paulo</settlement></placeName><orgName type="university">Université de São Paulo</orgName></affiliation></author><author><name sortKey="Gozzo, Fabio C" sort="Gozzo, Fabio C" uniqKey="Gozzo F" first="Fábio C" last="Gozzo">Fábio C. Gozzo</name><affiliation wicri:level="2"><nlm:affiliation>Instituto de Química, Universidade Estadual de Campinas-UNICAMP, CEP 13083-970, Campinas-SP, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Instituto de Química, Universidade Estadual de Campinas-UNICAMP, CEP 13083-970, Campinas-SP</wicri:regionArea><placeName><region type="state">État de São Paulo</region></placeName></affiliation></author><author><name sortKey="Cominetti, Marcia Regina" sort="Cominetti, Marcia Regina" uniqKey="Cominetti M" first="Marcia Regina" last="Cominetti">Marcia Regina Cominetti</name><affiliation wicri:level="2"><nlm:affiliation>Departamento de Gerontologia, Universidade Federal de São Carlos-UFSCar, CEP , 13565-905, São Carlos-SP, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Departamento de Gerontologia, Universidade Federal de São Carlos-UFSCar, CEP , 13565-905, São Carlos-SP</wicri:regionArea><placeName><region type="state">État de São Paulo</region></placeName></affiliation></author><author><name sortKey="Ferreira, Antonio G" sort="Ferreira, Antonio G" uniqKey="Ferreira A" first="Antonio G" last="Ferreira">Antonio G. Ferreira</name><affiliation wicri:level="2"><nlm:affiliation>Departamento de Química, Universidade Federal de São Carlos-UFSCar, CEP 13565-905, São Carlos-SP, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Departamento de Química, Universidade Federal de São Carlos-UFSCar, CEP 13565-905, São Carlos-SP</wicri:regionArea><placeName><region type="state">État de São Paulo</region></placeName></affiliation></author><author><name sortKey="Ferreira, Marco Antonio Barbosa" sort="Ferreira, Marco Antonio Barbosa" uniqKey="Ferreira M" first="Marco Antonio Barbosa" last="Ferreira">Marco Antonio Barbosa Ferreira</name><affiliation wicri:level="2"><nlm:affiliation>Departamento de Química, Universidade Federal de São Carlos-UFSCar, CEP 13565-905, São Carlos-SP, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Departamento de Química, Universidade Federal de São Carlos-UFSCar, CEP 13565-905, São Carlos-SP</wicri:regionArea><placeName><region type="state">État de São Paulo</region></placeName></affiliation></author><author><name sortKey="Navarro, Maribel" sort="Navarro, Maribel" uniqKey="Navarro M" first="Maribel" last="Navarro">Maribel Navarro</name><affiliation wicri:level="2"><nlm:affiliation>Instituto Nacional de Metrologia, Qualidade e Tecnologia, INMETRO, CEP , 25250-020 Rio de Janeiro-RJ, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Instituto Nacional de Metrologia, Qualidade e Tecnologia, INMETRO, CEP , 25250-020 Rio de Janeiro-RJ</wicri:regionArea><placeName><region type="state">État de Rio de Janeiro</region></placeName></affiliation></author><author><name sortKey="Batista, Alzir A" sort="Batista, Alzir A" uniqKey="Batista A" first="Alzir A" last="Batista">Alzir A. Batista</name><affiliation wicri:level="2"><nlm:affiliation>Departamento de Química, Universidade Federal de São Carlos-UFSCar, CEP 13565-905, São Carlos-SP, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Departamento de Química, Universidade Federal de São Carlos-UFSCar, CEP 13565-905, São Carlos-SP</wicri:regionArea><placeName><region type="state">État de São Paulo</region></placeName></affiliation></author></analytic><series><title level="j">Inorganic chemistry</title><idno type="eISSN">1520-510X</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cell Line, Tumor</term><term>Chloroquine (chemistry)</term><term>Circular Dichroism</term><term>DNA (chemistry)</term><term>Humans</term><term>Ligands</term><term>Magnetic Resonance Spectroscopy</term><term>Mass Spectrometry</term><term>Phosphines (chemistry)</term><term>Platinum (chemistry)</term><term>Stereoisomerism</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>Chloroquine ()</term><term>Dichroïsme circulaire</term><term>Humains</term><term>Ligands</term><term>Lignée cellulaire tumorale</term><term>Phosphines ()</term><term>Platine ()</term><term>Spectrométrie de masse</term><term>Spectroscopie par résonance magnétique</term><term>Stéréoisomérie</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Chloroquine</term><term>DNA</term><term>Phosphines</term><term>Platinum</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line, Tumor</term><term>Circular Dichroism</term><term>Humans</term><term>Ligands</term><term>Magnetic Resonance Spectroscopy</term><term>Mass Spectrometry</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>Chloroquine</term><term>Dichroïsme circulaire</term><term>Humains</term><term>Ligands</term><term>Lignée cellulaire tumorale</term><term>Phosphines</term><term>Platine</term><term>Spectrométrie de masse</term><term>Spectroscopie par résonance magnétique</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Chiral molecules in nature are involved in many biological events; their selectivity and specificity make them of great interest for understanding the behavior of bioactive molecules, by providing information about the chiral discrimination. Inspired by these conformational properties, we present the design and synthesis of novel chiral platinum(II) complexes featuring phosphine and chloroquine ligands with the general formula [PtCl(P)2(CQ)]PF6 (where (P)2 = triphenylphosphine (PPh3) (5), 1,3-bis(diphenylphosphine)propane (dppp) (6), 1,4-bis(diphenylphosphine)butane (dppb) (7), 1,1'-bis(diphenylphosphine)ferrocene (dppf) (8), and CQ = chloroquine] and their precursors of the type [PtCl2(P)2] are described. The complexes were characterized by elemental analysis, absorption spectroscopy in the infrared and ultraviolet-visible (UV-vis) regions, multinuclear ((1)H, (13)C, (31)P, (15)N, and (195)Pt) NMR spectroscopy, cyclic voltammetry, and mass spectrometry (in the case of chloroquine complexes). The interactions of the new platinum-chloroquine complexes with both albumin (BSA), using fluorescence spectroscopy, and DNA, by four widely reported methods were also evaluated. These experiments showed that these Pt-CQ complexes interact strongly with DNA and have high affinities for BSA, in contrast to CQ and CQDP (chloroquine diphosphate), which interact weakly with these biomolecules. Additional assays were performed in order to investigate the cytotoxicity of the platinum complexes against two healthy cell lines (mouse fibroblasts (L929) and the Chinese hamster lung (V79-4)) and four tumor cell lines (human breast (MDA-MB-231 and MCF-7), human lung (A549), and human prostate (DU-145)). The results suggest that the Pt-CQ complexes are generally more cytotoxic than the free CQ, showing that they are promising as anticancer drugs. </div></front></TEI><affiliations><list><country><li>Brésil</li></country><region><li>État de Rio de Janeiro</li><li>État de São Paulo</li></region><settlement><li>São Paulo</li></settlement><orgName><li>Université de São Paulo</li></orgName></list><tree><country name="Brésil"><region name="État de São Paulo"><name sortKey="Villarreal, Wilmer" sort="Villarreal, Wilmer" uniqKey="Villarreal W" first="Wilmer" last="Villarreal">Wilmer Villarreal</name></region><name sortKey="Batista, Alzir A" sort="Batista, Alzir A" uniqKey="Batista A" first="Alzir A" last="Batista">Alzir A. Batista</name><name sortKey="Colina Vegas, Legna" sort="Colina Vegas, Legna" uniqKey="Colina Vegas L" first="Legna" last="Colina-Vegas">Legna Colina-Vegas</name><name sortKey="Cominetti, Marcia Regina" sort="Cominetti, Marcia Regina" uniqKey="Cominetti M" first="Marcia Regina" last="Cominetti">Marcia Regina Cominetti</name><name sortKey="Ellena, Javier" sort="Ellena, Javier" uniqKey="Ellena J" first="Javier" last="Ellena">Javier Ellena</name><name sortKey="Ferreira, Antonio G" sort="Ferreira, Antonio G" uniqKey="Ferreira A" first="Antonio G" last="Ferreira">Antonio G. Ferreira</name><name sortKey="Ferreira, Marco Antonio Barbosa" sort="Ferreira, Marco Antonio Barbosa" uniqKey="Ferreira M" first="Marco Antonio Barbosa" last="Ferreira">Marco Antonio Barbosa Ferreira</name><name sortKey="Gozzo, Fabio C" sort="Gozzo, Fabio C" uniqKey="Gozzo F" first="Fábio C" last="Gozzo">Fábio C. Gozzo</name><name sortKey="Navarro, Maribel" sort="Navarro, Maribel" uniqKey="Navarro M" first="Maribel" last="Navarro">Maribel Navarro</name><name sortKey="Rodrigues De Oliveira, Clayton" sort="Rodrigues De Oliveira, Clayton" uniqKey="Rodrigues De Oliveira C" first="Clayton" last="Rodrigues De Oliveira">Clayton Rodrigues De Oliveira</name><name sortKey="Tenorio, Juan C" sort="Tenorio, Juan C" uniqKey="Tenorio J" first="Juan C" last="Tenorio">Juan C. Tenorio</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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