Cytotoxicity of Triorganophosphinegold(I) n‐Mercaptobenzoates, n = 2, 3 and 4

Abstract

The results of cytotoxicity trials against a panel of seven human cell lines for a series of triorganophosphinegold(I) 3- and 4-mercaptobenzoates are reported. While the new compounds show moderate to high toxicity, their potencies are inferior to those reported previously for their isomeric 2- mercaptobenzoate derivatives. The results therefore suggest a structure-activity relationship in that the 2-isomeric species are more active, particularly against the non-small cell lung cancer and renal cancer cell lines, results that may indicate some selectivity in their cytotoxic profile.

Heterometallic titanium–gold complexes inhibit renal cancer cells in vitro and in vivo

“…Although the synthesis of gold compound 4 had been previously reported, 36 , 37 compound 4 as well as new compound 6 were synthesized in a more efficient manner 31 following the strategy established by Sordo and co-workers 38 for the synthesis of gold thiocarboxylate derivatives via selective deprotonation of the thiol over the carboxylic acid (see Experimental section). Compound 6 was isolated as a pale orange solid in high yield.…”

Room‐Temperature Columnar Mesophases in Triazine–Gold Thiolate Metal–Organic Supramolecular Aggregates

“…The gold complexes [AuCl(PCy 3 )],31 [(μ‐ S ‐binap)‐(AuCl) 2 ],32 [(μ‐ R ‐binap)‐(AuCl) 2 ],33 [{(C 10 H 21 O) 3 C 6 H 2 NH} 3 C 3 N 3 ],3b, 22 [Au(PR 3 )(2‐SC 6 H 4 COOH)] (R=Cy, Ph),23 and [Au(PPh 3 )(4‐SC 6 H 4 COOH)] (R=Cy, Ph),34, 24 had been reported previously and were prepared from a solution of the corresponding chloro complex in dichloromethane, by reaction with the corresponding 2‐ or 4‐sulfanylbenzoic acid (2‐ or 4‐thiosalicylic acid) in methanol with one equivalent of sodium methoxide.…”

Gold compounds in medicine: Potential anti-tumour agents

“…As part of an on-going attempt to alter the solubility characteristics of phosphinegold(I) thiolates, an isomeric series of n-mercaptobenzoates for n = 2-, 3-and 4-, were studied (36,37). For compounds of the general formula R3PAu(SC6H4-CO2H-n), those with n = 2 were more cytotoxic than the n = 3 and n = 4 analogues.…”

“…For compounds of the general formula R3PAu(SC6H4-CO2H-n), those with n = 2 were more cytotoxic than the n = 3 and n = 4 analogues. More exciting was the observation that for the n = 2 series, several of the compounds displayed selective activity against the A498 (renal cancer) and H226 (non-small cell lung cancer) cell lines, exhibited cytotoxicities far better than cisplatin and were more potent or had comparable potency to established anti-cancer compounds such as doxorubicin and methotrexate (36,37). On-going studies are focusing on determining the maximum tolerated doses and anti-tumour activities of these compounds; these results will be published in due course but are most encouraging.…”