5‐Nitrofuryl‐Containing Thiosemicarbazone Gold(I) Compounds: Synthesis, Stability Studies, and Anticancer Activity
Abstract
This work describes the synthesis of four gold(I) [AuClL] compounds containing chloro and biologically active protonated thiosemicarbazones based on 5‐nitrofuryl (L=HSTC). The stability of the compounds in dichloromethane, DMSO, and DMSO/culture media solutions was investigated by spectroscopy, cyclic voltammetry, and conductimetry, indicating the formation 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 the compounds in dichlomethane/n‐hexane solution and characterized by X‐ray crystallography revealing a Au−Au bond, and deprotonated thiosemicarbazone (TSC). The cytotoxicity of the gold compounds and thiosemicarbazone ligands was evaluated against selected cancer cell lines and compared to that of Auranofin. Studies of the most stable, cytotoxic, and selective compound on a renal cancer cell line (Caki‐1) demonstrated its relevant antimigratory and anti‐angiogenic properties, and preferential accumulation in the cell nuclei. Its mode of action seems to involve interaction with DNA, and subsequent cell death via apoptosis.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- May 16, 2023
- Source ID
- 10.1002/cplu.202300115
Entities
People
- Claudio Olea Azar
- Dinorah Gambino
- Eric Gavrilov
- Esteban Rodríguez‐arce
- Ignacio Esteban León
- Lucía Otero
- María Contel
- Michelle C Neary
- Nazia Nayeem
- Ximena Alvite
Organizations
- Air Force Office of Scientific Research
- Brooklyn College
- CUNY Graduate School and University Center
- City University of New York
- Fulbright Austria
- Hunter College
- National Scientific and Technical Research Council
- University of the Republic