Title

Synthesis and Bioactivity Investigation of Quinone-based Dimeric Cationic Triazolium Amphiphiles Selective against Resistant Fungal and Bacterial Pathogens

Document Type

Article

Journal/Book Title

European Journal of Medicinal Chemistry

Publication Date

1-27-2017

Publisher

Elsevier

Volume

126

First Page

696

Last Page

704

DOI

10.1016/j.ejmech.2016.12.008

Abstract

A series of synthetic dimeric cationic anthraquinone analogs (CAAs) with potent antimicrobial activities against a broad range of fungi and bacteria were developed. These compounds were prepared in 2–3 steps with high overall yield and possess alkyl chain, azole, quinone, and quaternary ammonium complexes (QACs). In vitro biological evaluations reveal prominent inhibitory activities of lead compounds against several drug-susceptible and drug-resistant fungal and bacterial strains, including MRSA, VRE, Candida albicans and Aspergillus flavus. Mode of action investigation reveals that the synthesized dimeric CAA's can disrupt the membrane integrity of fungi. Computational studies reveal possible designs that can revive the activity of QACs against drug-resistant bacteria. Cytotoxicity assays in SKOV-3, a cancer cell line, show that the lead compounds are selectively toxic to fungi and bacteria over human cells.

Comments

PubMed PMID: 27951483

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