Chemical Behavior and in Vitro Activity of Mixed Phosphine Gold(I) Compounds on Melanoma Cell Lines. (Articolo in rivista)

Type
Label
  • Chemical Behavior and in Vitro Activity of Mixed Phosphine Gold(I) Compounds on Melanoma Cell Lines. (Articolo in rivista) (literal)
Anno
  • 2008-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jm700978a (literal)
Alternative label
  • Caruso Francesco; Pettinari Claudio; Paduano Francesco; Villa Raffaella; Marchetti Fabio; Monti Elena; Rossi Miriam. (2008)
    Chemical Behavior and in Vitro Activity of Mixed Phosphine Gold(I) Compounds on Melanoma Cell Lines.
    in Journal of medicinal chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Caruso Francesco; Pettinari Claudio; Paduano Francesco; Villa Raffaella; Marchetti Fabio; Monti Elena; Rossi Miriam. (literal)
Pagina inizio
  • 1584 (literal)
Pagina fine
  • 1591 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 51 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 6 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche (CNR), c/o UniVersity of Rome Istituto Chimico, Piazzale Aldo Moro 5, 00185, Rome, Italy, Dipartimento di Scienze Chimiche, UniVersità di Camerino, Via S. Agostino 1, 62032 Camerino, MC, Italy, Department of Chemistry, Vassar College, Poughkeepsie, New York 12604-0484, U.O. 10, Dipartimento Sperimentale, Fondazione IRCCS \"Istituto Nazionale dei Tumori\", Via Venezian 1, 20133 Milan, Italy, and Dipartimento di Biologia Strutturale e Funzionale, UniVersità dell'Insubria (literal)
Titolo
  • Chemical Behavior and in Vitro Activity of Mixed Phosphine Gold(I) Compounds on Melanoma Cell Lines. (literal)
Abstract
  • 31P nuclear magnetic resonance and electrospray ionization-mass spectrometry studies on the melanoma cytotoxic chlorotriphenylphosphine-1,3-bis(diphenylphosphino)propanegold(I), [Au(DPPP)(PPh3)Cl], show partial decomposition that includes the novel dinuclear cation [Au2(DPPP)2Cl]+; its structure was calculated by using the density functional theory (DFT). Unexpectedly, by using the diphosphine ligand 1,2- bis(diphenylphosphino)ethane (DIPHOS), [{AuCl(PPh3)}2(?2-DIPHOS)] was obtained. Its X-ray crystal structure shows a unique triangular coordination sphere in contrast to the T-shaped geometry of related Au(I)-DIPHOS compounds. Its cytotoxic activity in JR8, SK-Mel-5, and 2/60 melanoma cell lines is dose-dependent and lower than that of [Au(DPPP)(PPh3)Cl] because of its nonchelating nature. An in vitro study of the effect of both Au compounds on the B16V melanoma cell line gives credence to this structure-activity relationship. IC50 indicates that both Au species are 10 times more active in B16V than in JR8, SK-Mel-5, and 2/60. Oxidation of [Au(DPPP)(PPh3)Cl] toward Au(III) compounds and phosphine-oxides is observed upon reaction with hypochlorite in water/dimethyl sulfoxide solution, mimicking endogenous hypochlorite. A related reaction involving the formation of [AuCl4]- is thermodynamically feasible according to DFT calculations (literal)
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