Issue 38, 2013
From the journal:

Organic & Biomolecular Chemistry

Assessing the differential action on cancer cells of LDH-A inhibitors based on the N-hydroxyindole-2-carboxylate (NHI) and malonic (Mal) scaffolds†

Carlotta Granchi,a   Emilia C. Calvaresi,b   Tiziano Tuccinardi,a   Ilaria Paterni,a   Marco Macchia,a   Adriano Martinelli,a   Paul J. Hergenrother*bc  and  Filippo Minutolo*a  

* Corresponding authors

a Dipartimento di Farmacia, Università di Pisa, Via Bonanno 6, I-56126 Pisa, Italy
E-mail: filippo.minutolo@farm.unipi.it

b Department of Biochemistry, University of Illinois, Urbana, Illinois 61801, USA

c Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA
E-mail: hergenro@uiuc.edu

Abstract

A head-to-head study of representative examples of N-hydroxyindole-2-carboxylates (NHI) and malonic derivatives (Mal) as LDH-A inhibitors was conducted, comparing the enzyme inhibition potency, cellular uptake, reduction of lactate production in cancer cells and anti-proliferative activity. Among the compounds tested, methyl 1-hydroxy-6-phenyl-4-(trifluoromethyl)-1H-indole-2-carboxylate (2, NHI-2), a methyl ester belonging to the NHI class, displayed optimal properties in the cell-based assays, proving to be an efficient anti-glycolytic agent against cancer cells.

Graphical abstract: Assessing the differential action on cancer cells of LDH-A inhibitors based on the N-hydroxyindole-2-carboxylate (NHI) and malonic (Mal) scaffolds

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Article information

DOI
https://doi.org/10.1039/C3OB40870A
Article type
Paper
Submitted
26 Apr 2013
Accepted
31 Jul 2013
First published
01 Aug 2013

Org. Biomol. Chem., 2013,11, 6588-6596

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Assessing the differential action on cancer cells of LDH-A inhibitors based on the N-hydroxyindole-2-carboxylate (NHI) and malonic (Mal) scaffolds

C. Granchi, E. C. Calvaresi, T. Tuccinardi, I. Paterni, M. Macchia, A. Martinelli, P. J. Hergenrother and F. Minutolo, Org. Biomol. Chem., 2013, 11, 6588 DOI: 10.1039/C3OB40870A

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