346706-14-7

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• 15529-90-5 (triethylphosphine)chlorogold(I) 
• 1074-36-8 4-mercaptobenzoic acid 

Relevant academic research and scientific papers

Bimetallic titanocene-gold phosphane complexes inhibit invasion, metastasis, and angiogenesis-associated signaling molecules in renal cancer

Following promising recent in vitro and in vivo studies of the anticancer efficacies of heterometallic titanocene–gold chemotherapeutic candidates against renal cancer, we report here on the synthesis, characterization, stability studies and biological evaluation of a new titanocene complex containing a gold-triethylphosphane fragment [(η-C5H5)2TiMe(μ-mba)Au(PEt3)] (4) Titanofin. The compound is more stable in physiological fluid than those previously reported, and it is highly cytotoxic against a line of human clear cell renal carcinoma. We describe here preliminary mechanistic data for this compound and previously reported [(η-C5H5)2TiMe(μ-mba)Au(PPh3)] (2) Titanocref which displayed remarkable activity in an in vivo mouse model. Mechanistic studies were carried out in the human clear cell renal carcinoma Caki-1 line for the bimetallic compounds [(η-C5H5)2TiMe(μ-mba)Au(PR3)] (PR3 = PPh3 2 Titanocref and PEt3 4 Titanofin), the two monometallic gold derivatives [Au(Hmba)(PR3)] (PR3 = PPh3 1 cref; PEt3 3 fin), titanocene dichloride and Auranofin as controls. These studies indicate that bimetallic compounds Titanocref (2) and Titanofin (4) are more cytotoxic than gold monometallic derivatives (1 and 3) and significantly more cytotoxic than titanocene dichloride while being quite selective. Titanocref (2) and Titanofin (4) inhibit migration, invasion, and angiogenic assembly along with molecular markers associated with these processes such as prometastatic IL(s), MMP(s), TNF-α and proangiogenic VEGF, FGF-basic. The bimetallic compounds also strongly inhibit the mitochondrial protein TrxR often overexpressed in cancer cells evading apoptosis and also inhibit FOXC2, PECAM-1, and HIF-1α whose overexpression is linked to resistance to genotoxic chemotherapy. In summary, bimetallic titanocene-gold phosphane complexes (Titanocref 2 and Titanofin 4) are very promising candidates for further preclinical evaluations for the treatment of renal cancer.

Structural diversity in gold(I) complexes of 4-sulfanylbenzoic acid

Treatment of the gold(I) halide species AuLCl (where L = PMe3, PEt3, PPh3, PPh2(C5H4N-2) or SPPh3) and (AuCl)2(P-P) (where P-P = 1,4-bis(diphenylphosphino)butane or 1,1′-bis(diphenylphosphino)ferrocene) with 4-sulfanylbenzoic acid (1 or 2 equivalents as required) in the presence of sodium methoxide provided the corresponding phosphine gold(I) thiolate complexes AuL(4-SC6H4CO2H) and [Au(4-SC6H4CO2H)]2(P-P), respectively. Addition of two equivalents of the acid (in the presence of NaOMe) to [N(PPh3)2][AuCl2] yielded the dithiolate species [(N(PPh)3)2][Au(4-SC6 H4CO2H)2]. A polyaurated product [(Ph3PAu)2(4-SC6H4 CO2H)]BF4 was obtained on treating the acid with the oxonium complex [(Ph3PAu)3O]BF4. The species AuL(4-SC6H4CO2H) (L = PEt3, PPh3 or PPh2C5H4N-2)) have been investigated crystallographically and reveal diverse structures incorporating aurophilic contacts, Au···S interactions and hydrogen bonding.