Synthesis, Characterization, and Antiproliferative Activity of Novel Chiral [QuinoxP*AuCl2]+ Complexes

Autor:	Samuel Ofori, Sean Parkin, Adedamola S. Arojojoye, Samuel G. Awuah, R. Tyler Mertens
Rok vydání:	2020
Předmět:	Stereochemistry cisplatin Pharmaceutical Science chemistry.chemical_element Antineoplastic Agents Crystallography X-Ray 010402 general chemistry 01 natural sciences Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Quinoxaline lcsh:Organic chemistry antiproliferative Cell Line Tumor Drug Discovery Humans Reactivity (chemistry) Physical and Theoretical Chemistry Cell Proliferation ligands 010405 organic chemistry Chemistry Ligand Organic Chemistry auranofin Stereoisomerism Glutathione gold QuinoxP 0104 chemical sciences Ruthenium anticancer activity Chemistry (miscellaneous) Molecular Medicine Enantiomer Platinum Stoichiometry
Zdroj:	Molecules Volume 25 Issue 23 Molecules, Vol 25, Iss 5735, p 5735 (2020)
ISSN:	1420-3049
DOI:	10.3390/molecules25235735
Popis:	Herein is reported the synthesis of two Au(III) complexes bearing the (R,R)-(&ndash )-2,3-Bis(tert-butylmethylphosphino)quinoxaline (R,R-QuinoxP*) or (S,S)-(+)-2,3-Bis(tert-butylmethylphosphino)quinoxaline (S,S-QuinoxP*) ligands. By reacting two stoichiometric equivalents of HAuCl4.3H2O to one equivalent of the corresponding QuinoxP* ligand, (R,R)-(&ndash )-2,3-Bis(tert-butylmethylphosphino)quinoxalinedichlorogold(III) tetrachloroaurates(III) (1) and (S,S)-(+)-2,3-Bis(tert-butylmethylphosphino)quinoxalinedichlorogold(III) tetrachloroaurates(III) (2) were formed, respectively, in moderate yields. The structure of (S,S)-(+)-2,3-Bis(tert-butylmethylphosphino)quinoxalinedichlorogold(III) tetrachloroaurates(III) (2) was further confirmed by X-ray crystallography. The antiproliferative activities of the two compounds were evaluated in a panel of cell lines and exhibited promising results comparable to auranofin and cisplatin with IC50 values between 1.08 and 4.83 µ M. It is noteworthy that in comparison to other platinum and ruthenium enantiomeric complexes, the two enantiomers (1 and 2) do not exhibit different cytotoxic effects. The compounds exhibited stability in biologically relevant media over 48 h as well as inert reactivity to excess glutathione at 37 ° C. These results demonstrate that the Au(III) atom, stabilized by the QuinoxP* ligand, can provide exciting compounds for novel anticancer drugs. These complexes provide a new scaffold to further develop a robust and diverse library of chiral phosphorus Au(III) complexes.
Databáze:	OpenAIRE
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