Dinuclear triphenylphosphinegold(I) sulfanylcarboxylates: Synthesis, structure and cytotoxic activity against cancer cell lines.
Compounds of the type [(AuPPh(3))(2)(xspa)]; H(2)xspa [x:p=3-phenyl-, f=3-(2-furyl)-, t=3-(2-thienyl)-, -o-py=3-(2-pyridyl)-, Clp=3-(2-chlorophenyl)-, -o-mp=3-(2-methoxyphenyl)-, -p-mp=3-(4-methoxyphenyl)-, -o-hp=3-(2-hydroxyphenyl)-, -p-hp=3-(4-hydroxyphenyl)-, -diBr-o-hp=3-(3,5-dibromo-2-hydroxyphenyl)-; spa=2-sulfanyl propenoato] were synthesized and characterized by IR and NMR ((1)H, (13)C and (31)P) spectroscopy and by FAB mass spectrometry. The structures of [(AuPPh(3))(2)(Clpspa)], [(AuPPh(3))(2)(o-hpspa)], [(AuPPh(3))(2)(p-hpspa)].MeOH and [(AuPPh(3))(2)(diBr-o-hpspa)].2Me(2)CO show the dinuclear nature of the complexes with the two gold atoms, one of which is also O-bonded to an O atom of the carboxylate group, bonded to the S atom. The in vitro antitumor activities against the HeLa-229, A2780 and A2780cis cell lines were determined and the compounds were found to be highly effective, in particular against the A2780cis cell line, with eight of the nine compounds having IC(50) values better than that of cisplatin. This behavior is indicative of a high ability to circumvent the cellular resistance to this drug.
Departamento de Química Inorgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Galicia, Spain.
Elena
E
Barreiro
José S
JS
Casas
María D
MD
Couce
Agustín
A
Sánchez
Angeles
A
Sánchez-González
José
J
Sordo
José M
JM
Varela
Ezequiel M Vázquez
EM
López
D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor / Q000187:drug effects*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D050607:Organogold Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D002264:Carboxylic Acids; D050607:Organogold Compounds