Cytotoxicity of Ru(II) piano-stool complexes with chloroquine and chelating ligands against breast and lung tumor cells: Interactions with DNA and BSA.
Identifieur interne : 000E91 ( Main/Exploration ); précédent : 000E90; suivant : 000E92Cytotoxicity of Ru(II) piano-stool complexes with chloroquine and chelating ligands against breast and lung tumor cells: Interactions with DNA and BSA.
Auteurs : Legna Colina-Vegas [Brésil] ; Wilmer Villarreal [Brésil] ; Maribel Navarro [Brésil] ; Clayton Rodrigues De Oliveira [Brésil] ; Angélica E. Graminha [Brésil] ; Pedro Ivo Da S. Maia [Brésil] ; Victor M. Deflon [Brésil] ; Antonio G. Ferreira [Brésil] ; Marcia Regina Cominetti ; Alzir A. Batista [Brésil]Source :
- Journal of inorganic biochemistry [ 1873-3344 ] ; 2015.
Descripteurs français
- KwdFr :
- ADN (), Animaux, Antinéoplasiques (), Antinéoplasiques (pharmacologie), Antinéoplasiques (synthèse chimique), Bovins, Chloroquine (), Chloroquine (pharmacologie), Chloroquine (synthèse chimique), Chélateurs (), Chélateurs (pharmacologie), Chélateurs (synthèse chimique), Complexes de coordination (), Complexes de coordination (pharmacologie), Complexes de coordination (synthèse chimique), Femelle, Humains, Intercalants (), Intercalants (pharmacologie), Intercalants (synthèse chimique), Lignée cellulaire tumorale, Ruthénium (), Sites de fixation, Souris, Spectroscopie par résonance magnétique du proton, Structure moléculaire, Sérumalbumine bovine (), Techniques électrochimiques, Thermodynamique, Tumeurs du poumon, Tumeurs du sein.
- MESH :
- pharmacologie : Antinéoplasiques, Chloroquine, Chélateurs, Complexes de coordination, Intercalants.
- synthèse chimique : Antinéoplasiques, Chloroquine, Chélateurs, Complexes de coordination, Intercalants.
- ADN, Animaux, Antinéoplasiques, Bovins, Chloroquine, Chélateurs, Complexes de coordination, Femelle, Humains, Intercalants, Lignée cellulaire tumorale, Ruthénium, Sites de fixation, Souris, Spectroscopie par résonance magnétique du proton, Structure moléculaire, Sérumalbumine bovine, Techniques électrochimiques, Thermodynamique, Tumeurs du poumon, Tumeurs du sein.
English descriptors
- KwdEn :
- Animals, Antineoplastic Agents (chemical synthesis), Antineoplastic Agents (chemistry), Antineoplastic Agents (pharmacology), Binding Sites, Breast Neoplasms, Cattle, Cell Line, Tumor, Chelating Agents (chemical synthesis), Chelating Agents (chemistry), Chelating Agents (pharmacology), Chloroquine (chemical synthesis), Chloroquine (chemistry), Chloroquine (pharmacology), Coordination Complexes (chemical synthesis), Coordination Complexes (chemistry), Coordination Complexes (pharmacology), DNA (chemistry), Electrochemical Techniques, Female, Humans, Intercalating Agents (chemical synthesis), Intercalating Agents (chemistry), Intercalating Agents (pharmacology), Lung Neoplasms, Mice, Molecular Structure, Proton Magnetic Resonance Spectroscopy, Ruthenium (chemistry), Serum Albumin, Bovine (chemistry), Thermodynamics.
- MESH :
- chemical , chemical synthesis : Antineoplastic Agents, Chelating Agents, Chloroquine, Coordination Complexes, Intercalating Agents.
- chemical , chemistry : Antineoplastic Agents, Chelating Agents, Chloroquine, Coordination Complexes, DNA, Intercalating Agents, Ruthenium, Serum Albumin, Bovine.
- chemical , pharmacology : Antineoplastic Agents, Chelating Agents, Chloroquine, Coordination Complexes, Intercalating Agents.
- Animals, Binding Sites, Breast Neoplasms, Cattle, Cell Line, Tumor, Electrochemical Techniques, Female, Humans, Lung Neoplasms, Mice, Molecular Structure, Proton Magnetic Resonance Spectroscopy, Thermodynamics.
Abstract
The synthesis and spectroscopic characterization of nine π-arene piano-stool ruthenium (II) complexes with aromatic dinitrogen chelating ligands or containing chloroquine (CQ), are described in this study: [Ru(η(6)-C10H14)(phen)Cl]PF6 (1), [Ru(η(6)-C10H14)(dphphen)Cl]PF6 (2), [Ru(η(6)-C10H14)(bipy)Cl]PF6 (3), [Ru(η(6)-C10H14)(dmebipy)Cl]PF6 (4) and [Ru(η(6)-C10H14)(bdutbipy)Cl]PF6 (5), [Ru(η(6)-C10H14)(phen)CQ](PF6)2 (6), [Ru(η(6)-C10H14)(dphphen)CQ](PF6)2 (7), [Ru(η(6)-C10H14)(bipy)CQ](PF6)2 (8), [Ru(η(6)-C10H14)(dmebipy)CQ](PF6)2 (9): [1,10-phenanthroline (phen), 4,7-diphenyl-1,10-phenanthroline (dphphen), 2,2'-bipyridine (bipy), 5,5'-dimethyl-2,2'-bipyridine (dmebipy), and 4,4'-di-t-butyl-2,2'-bipyridine (dbutbipy)]. The solid state structures of five ruthenium complexes (1-5) were determined by X-ray crystallography. Electrochemical experiments were performed by cyclic voltammetry to estimate the redox potential of the Ru(II)/Ru(III) couple in each case. Their interactions with DNA and BSA, and activity against four cell lines (L929, A549, MDA-MB-231 and MCF-7) were evaluated. Compounds 2, 6 through 9, interact with DNA which was comparable to the one observed for free chloroquine. The results of fluorescence titration revealed that these complexes strongly quenched the intrinsic fluorescence of BSA following a static quenching procedure. Binding constants (Kb) and the number of binding sites (n~1) were calculated using modified Stern-Volmer equations. The thermodynamic parameters ΔG at different temperatures were calculated and subsequently the values of ΔH and ΔS were also calculated, which revealed that hydrophobic and electrostatic interactions play a major role in the BSA-complex association. The MTT assay results indicated that complexes 2, 5 and 7 showed cytostatic effects at appreciably lower concentrations than those needed for cisplatin, chloroquine and doxorubicin.
DOI: 10.1016/j.jinorgbio.2015.07.016
PubMed: 26277415
Affiliations:
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Electronic address: esleg_24@hotmail.com.</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="Villarreal, Wilmer" sort="Villarreal, Wilmer" uniqKey="Villarreal W" first="Wilmer" last="Villarreal">Wilmer Villarreal</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 Duque de Caxias, RJ, Brazil.</nlm:affiliation><country xml:lang="fr">Brésil</country><wicri:regionArea>Instituto Nacional de Metrologia, Qualidade e Tecnologia, INMETRO, CEP 25250-020 Duque de Caxias, RJ</wicri:regionArea><placeName><region type="state">État de Rio de Janeiro</region></placeName></affiliation></author><author><name sortKey="De Oliveira, Clayton Rodrigues" sort="De Oliveira, Clayton Rodrigues" uniqKey="De Oliveira C" first="Clayton Rodrigues" last="De Oliveira">Clayton Rodrigues De Oliveira</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="Graminha, Angelica E" sort="Graminha, Angelica E" uniqKey="Graminha A" first="Angélica E" last="Graminha">Angélica E. Graminha</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="Maia, Pedro Ivo Da S" sort="Maia, Pedro Ivo Da S" uniqKey="Maia P" first="Pedro Ivo Da S" last="Maia">Pedro Ivo Da S. Maia</name><affiliation wicri:level="4"><nlm:affiliation>Instituto de Química 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 Química 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="Deflon, Victor M" sort="Deflon, Victor M" uniqKey="Deflon V" first="Victor M" last="Deflon">Victor M. Deflon</name><affiliation wicri:level="4"><nlm:affiliation>Instituto de Química 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 Química 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="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="Cominetti, Marcia Regina" sort="Cominetti, Marcia Regina" uniqKey="Cominetti M" first="Marcia Regina" last="Cominetti">Marcia Regina Cominetti</name><affiliation><nlm:affiliation>Departamento de Gerontologia, Universidade Federal de São Carlos - UFSCar, CEP 13565-905 São Carlos, SP Brazil.</nlm:affiliation><wicri:noCountry code="subField">SP Brazil</wicri:noCountry></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. Electronic address: daab@ufscar.br.</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">Journal of inorganic biochemistry</title><idno type="eISSN">1873-3344</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Antineoplastic Agents (chemical synthesis)</term><term>Antineoplastic Agents (chemistry)</term><term>Antineoplastic Agents (pharmacology)</term><term>Binding Sites</term><term>Breast Neoplasms</term><term>Cattle</term><term>Cell Line, Tumor</term><term>Chelating Agents (chemical synthesis)</term><term>Chelating Agents (chemistry)</term><term>Chelating Agents (pharmacology)</term><term>Chloroquine (chemical synthesis)</term><term>Chloroquine (chemistry)</term><term>Chloroquine (pharmacology)</term><term>Coordination Complexes (chemical synthesis)</term><term>Coordination Complexes (chemistry)</term><term>Coordination Complexes (pharmacology)</term><term>DNA (chemistry)</term><term>Electrochemical Techniques</term><term>Female</term><term>Humans</term><term>Intercalating Agents (chemical synthesis)</term><term>Intercalating Agents (chemistry)</term><term>Intercalating Agents (pharmacology)</term><term>Lung Neoplasms</term><term>Mice</term><term>Molecular Structure</term><term>Proton Magnetic Resonance Spectroscopy</term><term>Ruthenium (chemistry)</term><term>Serum Albumin, Bovine (chemistry)</term><term>Thermodynamics</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>Animaux</term><term>Antinéoplasiques ()</term><term>Antinéoplasiques (pharmacologie)</term><term>Antinéoplasiques (synthèse chimique)</term><term>Bovins</term><term>Chloroquine ()</term><term>Chloroquine (pharmacologie)</term><term>Chloroquine (synthèse chimique)</term><term>Chélateurs ()</term><term>Chélateurs (pharmacologie)</term><term>Chélateurs (synthèse chimique)</term><term>Complexes de coordination ()</term><term>Complexes de coordination (pharmacologie)</term><term>Complexes de coordination (synthèse chimique)</term><term>Femelle</term><term>Humains</term><term>Intercalants ()</term><term>Intercalants (pharmacologie)</term><term>Intercalants (synthèse chimique)</term><term>Lignée cellulaire tumorale</term><term>Ruthénium ()</term><term>Sites de fixation</term><term>Souris</term><term>Spectroscopie par résonance magnétique du proton</term><term>Structure moléculaire</term><term>Sérumalbumine bovine ()</term><term>Techniques électrochimiques</term><term>Thermodynamique</term><term>Tumeurs du poumon</term><term>Tumeurs du sein</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antineoplastic Agents</term><term>Chelating Agents</term><term>Chloroquine</term><term>Coordination Complexes</term><term>Intercalating Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antineoplastic Agents</term><term>Chelating Agents</term><term>Chloroquine</term><term>Coordination Complexes</term><term>DNA</term><term>Intercalating Agents</term><term>Ruthenium</term><term>Serum Albumin, Bovine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antineoplastic Agents</term><term>Chelating Agents</term><term>Chloroquine</term><term>Coordination Complexes</term><term>Intercalating Agents</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antinéoplasiques</term><term>Chloroquine</term><term>Chélateurs</term><term>Complexes de coordination</term><term>Intercalants</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antinéoplasiques</term><term>Chloroquine</term><term>Chélateurs</term><term>Complexes de coordination</term><term>Intercalants</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Binding Sites</term><term>Breast Neoplasms</term><term>Cattle</term><term>Cell Line, Tumor</term><term>Electrochemical Techniques</term><term>Female</term><term>Humans</term><term>Lung Neoplasms</term><term>Mice</term><term>Molecular Structure</term><term>Proton Magnetic Resonance Spectroscopy</term><term>Thermodynamics</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>Animaux</term><term>Antinéoplasiques</term><term>Bovins</term><term>Chloroquine</term><term>Chélateurs</term><term>Complexes de coordination</term><term>Femelle</term><term>Humains</term><term>Intercalants</term><term>Lignée cellulaire tumorale</term><term>Ruthénium</term><term>Sites de fixation</term><term>Souris</term><term>Spectroscopie par résonance magnétique du proton</term><term>Structure moléculaire</term><term>Sérumalbumine bovine</term><term>Techniques électrochimiques</term><term>Thermodynamique</term><term>Tumeurs du poumon</term><term>Tumeurs du sein</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The synthesis and spectroscopic characterization of nine π-arene piano-stool ruthenium (II) complexes with aromatic dinitrogen chelating ligands or containing chloroquine (CQ), are described in this study: [Ru(η(6)-C10H14)(phen)Cl]PF6 (1), [Ru(η(6)-C10H14)(dphphen)Cl]PF6 (2), [Ru(η(6)-C10H14)(bipy)Cl]PF6 (3), [Ru(η(6)-C10H14)(dmebipy)Cl]PF6 (4) and [Ru(η(6)-C10H14)(bdutbipy)Cl]PF6 (5), [Ru(η(6)-C10H14)(phen)CQ](PF6)2 (6), [Ru(η(6)-C10H14)(dphphen)CQ](PF6)2 (7), [Ru(η(6)-C10H14)(bipy)CQ](PF6)2 (8), [Ru(η(6)-C10H14)(dmebipy)CQ](PF6)2 (9): [1,10-phenanthroline (phen), 4,7-diphenyl-1,10-phenanthroline (dphphen), 2,2'-bipyridine (bipy), 5,5'-dimethyl-2,2'-bipyridine (dmebipy), and 4,4'-di-t-butyl-2,2'-bipyridine (dbutbipy)]. The solid state structures of five ruthenium complexes (1-5) were determined by X-ray crystallography. Electrochemical experiments were performed by cyclic voltammetry to estimate the redox potential of the Ru(II)/Ru(III) couple in each case. Their interactions with DNA and BSA, and activity against four cell lines (L929, A549, MDA-MB-231 and MCF-7) were evaluated. Compounds 2, 6 through 9, interact with DNA which was comparable to the one observed for free chloroquine. The results of fluorescence titration revealed that these complexes strongly quenched the intrinsic fluorescence of BSA following a static quenching procedure. Binding constants (Kb) and the number of binding sites (n~1) were calculated using modified Stern-Volmer equations. The thermodynamic parameters ΔG at different temperatures were calculated and subsequently the values of ΔH and ΔS were also calculated, which revealed that hydrophobic and electrostatic interactions play a major role in the BSA-complex association. The MTT assay results indicated that complexes 2, 5 and 7 showed cytostatic effects at appreciably lower concentrations than those needed for cisplatin, chloroquine and doxorubicin. </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><noCountry><name sortKey="Cominetti, Marcia Regina" sort="Cominetti, Marcia Regina" uniqKey="Cominetti M" first="Marcia Regina" last="Cominetti">Marcia Regina Cominetti</name></noCountry><country name="Brésil"><region name="État de São Paulo"><name sortKey="Colina Vegas, Legna" sort="Colina Vegas, Legna" uniqKey="Colina Vegas L" first="Legna" last="Colina-Vegas">Legna Colina-Vegas</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="De Oliveira, Clayton Rodrigues" sort="De Oliveira, Clayton Rodrigues" uniqKey="De Oliveira C" first="Clayton Rodrigues" last="De Oliveira">Clayton Rodrigues De Oliveira</name><name sortKey="Deflon, Victor M" sort="Deflon, Victor M" uniqKey="Deflon V" first="Victor M" last="Deflon">Victor M. Deflon</name><name sortKey="Ferreira, Antonio G" sort="Ferreira, Antonio G" uniqKey="Ferreira A" first="Antonio G" last="Ferreira">Antonio G. Ferreira</name><name sortKey="Graminha, Angelica E" sort="Graminha, Angelica E" uniqKey="Graminha A" first="Angélica E" last="Graminha">Angélica E. Graminha</name><name sortKey="Maia, Pedro Ivo Da S" sort="Maia, Pedro Ivo Da S" uniqKey="Maia P" first="Pedro Ivo Da S" last="Maia">Pedro Ivo Da S. Maia</name><name sortKey="Navarro, Maribel" sort="Navarro, Maribel" uniqKey="Navarro M" first="Maribel" last="Navarro">Maribel Navarro</name><name sortKey="Villarreal, Wilmer" sort="Villarreal, Wilmer" uniqKey="Villarreal W" first="Wilmer" last="Villarreal">Wilmer Villarreal</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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