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Open AccessArticle

Synthesis and Antiproliferative Activity of Novel A-Ring Cleaved Glycyrrhetinic Acid Derivatives

1
Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Coimbra, 3000-548 Coimbra, Portugal
2
Centre for Neuroscience and Cell Biology, 3000-504 Coimbra, Portugal
3
Department of Biochemistry and Molecular Biomedicine, Faculty of Biology, University of Barcelona, Diagonal 643, 08028 Barcelona, Spain
4
Centro de Investigación Biomédica en Red de Enfermedades Hepáticas y Digestivas (CIBEREHD), Instituto de Salud Carlos III (ISCIII), 28029 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Academic Editor: Carlo Siciliano
Molecules 2019, 24(16), 2938; https://doi.org/10.3390/molecules24162938
Received: 27 July 2019 / Revised: 9 August 2019 / Accepted: 12 August 2019 / Published: 14 August 2019
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of new glycyrrhetinic acid derivatives was synthesized via the opening of its ring A along with the coupling of an amino acid. The antiproliferative activity of the derivatives was evaluated against a panel of nine human cancer cell lines. Compound 17 was the most active compound, with an IC50 of 6.1 µM on Jurkat cells, which is 17-fold more potent than that of glycyrrhetinic acid, and was up to 10 times more selective toward that cancer cell line. Further biological investigation in Jurkat cells showed that the antiproliferative activity of compound 17 was due to cell cycle arrest at the S phase and induction of apoptosis. View Full-Text
Keywords: pentacyclic triterpenoids; glycyrrhetinic acid; A-ring cleaved derivatives; antiproliferative activity; cell cycle arrest; apoptosis pentacyclic triterpenoids; glycyrrhetinic acid; A-ring cleaved derivatives; antiproliferative activity; cell cycle arrest; apoptosis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Alho, D.P.; Salvador, J.A.; Cascante, M.; Marin, S. Synthesis and Antiproliferative Activity of Novel A-Ring Cleaved Glycyrrhetinic Acid Derivatives. Molecules 2019, 24, 2938.

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