Synthesis, structure and cytotoxicity of triphenylphosphinegold(I) sulfanylpropenoates.
The reaction of triphenylphosphinegold(I) chloride in ethanol in a 1:1 molar ratio with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x: p=3-phenyl-, 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)-, f=3-(2-furyl)-, t=3-(2-thienyl)-, -o-py=3-(2-pyridyl)-; spa=2-sulfanylpropenoato] gave compounds of the type [Au(PPh(3))(Hxspa)], which were isolated and characterized as solids by elemental analysis, IR spectroscopy and FAB mass spectrometry and in solution by (1)H, (13)C and (31)P NMR spectroscopy. The structures of the complexes [Au(PPh(3))(HClpspa)], [Au(PPh(3))(H-o-mpspa)] and [Au(PPh(3))(H-p-mpspa)].2/3C(3)H(6)O were determined by X-ray diffractometry. Hydrogen bonding was found along with Au-S and Au-P bonds in all cases and weak pi-pi stacking was found in the H-p-mpspa derivative. The in vitro antitumour activities against the HeLa-229, A2780 and A2780cis cell lines were determined for all complexes.
Barreiro
Elena
E
Departamento de Química Inorgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Galicia, Spain.
Casas
José S
JS
Couce
María D
MD
Sánchez
Agustín
A
Sánchez-Gonzalez
Angeles
A
Sordo
José
J
Varela
José M
JM
Vázquez López
Ezequiel M
EM
D000179:Acrylates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D050607:Organogold Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010720:Phosphines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000179:Acrylates; D000970:Antineoplastic Agents; D050607:Organogold Compounds; D010720:Phosphines; C016798:triphenylphosphine gold chloride