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Article

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

1
Department of Chemistry, University of Kentucky, Lexington, KY 40506, USA
2
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Kogularamanan Suntharalingam
Molecules 2020, 25(23), 5735; https://doi.org/10.3390/molecules25235735
Received: 19 November 2020 / Revised: 27 November 2020 / Accepted: 1 December 2020 / Published: 4 December 2020
(This article belongs to the Special Issue Metal Anticancer Complexes)
Herein is reported the synthesis of two Au(III) complexes bearing the (R,R)-(–)-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)-(–)-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 µM. 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. View Full-Text
Keywords: gold; cisplatin; auranofin; antiproliferative; anticancer activity; ligands; QuinoxP* gold; cisplatin; auranofin; antiproliferative; anticancer activity; ligands; QuinoxP*
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MDPI and ACS Style

Arojojoye, A.S.; Mertens, R.T.; Ofori, S.; Parkin, S.R.; Awuah, S.G. Synthesis, Characterization, and Antiproliferative Activity of Novel Chiral [QuinoxP*AuCl2]+ Complexes. Molecules 2020, 25, 5735. https://doi.org/10.3390/molecules25235735

AMA Style

Arojojoye AS, Mertens RT, Ofori S, Parkin SR, Awuah SG. Synthesis, Characterization, and Antiproliferative Activity of Novel Chiral [QuinoxP*AuCl2]+ Complexes. Molecules. 2020; 25(23):5735. https://doi.org/10.3390/molecules25235735

Chicago/Turabian Style

Arojojoye, Adedamola S., R. T. Mertens, Samuel Ofori, Sean R. Parkin, and Samuel G. Awuah 2020. "Synthesis, Characterization, and Antiproliferative Activity of Novel Chiral [QuinoxP*AuCl2]+ Complexes" Molecules 25, no. 23: 5735. https://doi.org/10.3390/molecules25235735

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