5‐Nitrofuryl‐Containing Thiosemicarbazone Gold(I) Compounds: Synthesis, Stability Studies, and Anticancer Activity

RODRÍGUEZ?ARCE, ESTEBAN; GAVRILOV, ERIC; ALVITE, XIMENA; NAYEEM, NAZIA; LEÓN, IGNACIO E.; NEARY, MICHELLE C.; OTERO, LUCÍA; GAMBINO, DINORAH; OLEA AZAR, CLAUDIO; CONTEL, MARÍA

ChemPlusChem

Wiley

Año: 2023

2192-6506

This work describes the synthesis of four gold(I) [AuClL]compounds containing chloro and biologically active protonatedthiosemicarbazones based on 5-nitrofuryl (L=HSTC). Thestability of the compounds in dichloromethane, DMSO, andDMSO/culture media solutions was investigated by spectroscopy,cyclic voltammetry, and conductimetry, indicating theformation overtime of cationic monometallic [Au(HTSC)(DMSO)]�or [Au(HTSC)2], and/or dimeric species. Neutral[{Au(TSC)}2�] species were obtained from one of thecompounds in dichlomethane/n-hexane solution and character-ized by X-ray crystallography revealing a Au Au bond, anddeprotonated thiosemicarbazone (TSC). The cytotoxicity of thegold compounds and thiosemicarbazone ligands was evaluatedagainst selected cancer cell lines and compared to that ofAuranofin. Studies of the most stable, cytotoxic, and selectivecompound on a renal cancer cell line (Caki-1) demonstrated itsrelevant antimigratory and anti-angiogenic properties, andpreferential accumulation in the cell nuclei. Its mode of actionseems to involve interaction with DNA, and subsequent celldeath via apoptosis.