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Open AccessArticle

Synthesis and Biological Evaluation of New Glycoconjugated LDH Inhibitors as Anticancer Agents

1
Dipartimento di Farmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy
2
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 3, 56124 Pisa, Italy
*
Authors to whom correspondence should be addressed.
Dedicated to the beloved memory of Prof. Cinzia Chiappe.
Molecules 2019, 24(19), 3520; https://doi.org/10.3390/molecules24193520
Received: 3 September 2019 / Revised: 26 September 2019 / Accepted: 27 September 2019 / Published: 28 September 2019
(This article belongs to the Section Bioorganic Chemistry)
Conjugation of known biologically active molecules to carbohydrate frameworks represents a valuable option for the preparation of hybrid, structurally-related families of compounds with the aim of modulating their biological response. Therefore, we present here a study on the preparation of d-galacto, d-manno, d-gluco, and d-lactose glycoconjugates of an established N-hydroxyindole-based (NHI) inhibitor of lactated dehydrogenase (LDH). Structural variations involved the sugar stereochemistry and size as well as the anchoring point of the NHI on the carbohydrate frame (either C-1 or C-6). In the case of the galactose anomeric glycoconjugate (C-1), intriguing solvent-dependent effects were observed in the glycosylation stereochemical outcome. The biological activity of the deprotected glycoconjugates in contrasting lactate formation and cancer cell proliferation are described. View Full-Text
Keywords: LDH inhibitors; glycoconjugates; anticancer agents LDH inhibitors; glycoconjugates; anticancer agents
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MDPI and ACS Style

D’Andrea, F.; Vagelli, G.; Granchi, C.; Guazzelli, L.; Tuccinardi, T.; Poli, G.; Iacopini, D.; Minutolo, F.; Di Bussolo, V. Synthesis and Biological Evaluation of New Glycoconjugated LDH Inhibitors as Anticancer Agents. Molecules 2019, 24, 3520.

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