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Expert Opin Drug Discov. 2012 Jul;7(7):549-60. doi: 10.1517/17460441.2012.688743. Epub 2012 May 19.

Rhodanine as a scaffold in drug discovery: a critical review of its biological activities and mechanisms of target modulation.

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1
University of Ljubljana, Faculty of Pharmacy, Ljubljana, Slovenia.

Abstract

INTRODUCTION:

Rhodanine-based compounds have been associated with numerous biological activities. After many years of research in drug discovery, they have gained a reputation as being pan assay interference compounds (PAINS) and frequent hitters in screening campaigns. Rhodanine-based compounds are also aggregators that can non-specifically interact with target proteins as well as Michael acceptors and interfere photometrically in biological assays due to their color.

AREAS COVERED:

The authors review the recently reported biological activities of rhodanine-based compounds. Furthermore, the article provides details of their synthesis and occurrence in compound libraries through high-throughput screening (HTS) and virtual high-throughput screening (VHTS). Additionally, the authors provide the reader with possible mechanisms of non-specific target modulation, analysis of the crystal structures of enzyme-rhodanine complexes and a comparison of rhodanine and thiazolidine-2,4-dione moieties.

EXPERT OPINION:

The biological activity of compounds possessing a rhodanine moiety should be considered very critically despite the convincing data obtained in biological assays. In addition to the lack of selectivity, unusual structure-activity relationship profiles and safety and specificity problems mean that rhodanines are generally not optimizable.

PMID:
22607309
DOI:
10.1517/17460441.2012.688743
[Indexed for MEDLINE]
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