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Molecules 2017, 22(5), 812;

Evaluation of the Mycobactericidal Effect of Thio-functionalized Carbohydrate Derivatives

Institute of Medical Biology, Polish Academy of Sciences, Lodz 93-232, Poland
Department of Immunoparasitology, University of Lodz, Lodz 90-236, Poland
Department of Molecular Genetics, University of Lodz, Lodz 90-236, Poland
Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, Wilkes-Barre, PA 18766, USA
Authors to whom correspondence should be addressed.
Academic Editor: Daniela Barlocco
Received: 30 March 2017 / Revised: 5 May 2017 / Accepted: 11 May 2017 / Published: 16 May 2017
(This article belongs to the Special Issue Frontiers in Antimicrobial Drug Discovery and Design)
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Sugars with heteroatoms other than oxygen have attained considerable importance in glycobiology and in drug design since they are often more stable in blood plasma due to their resistance to enzymes, such as glycosidases, phosphorylases and glycosyltransferases. The replacement of oxygen atoms in sugars with sulfur forms thio-sugars, which are potentially useful for the treatment of diabetes and some bacterial and viral infections. Here, we evaluated the antibacterial activity of thio-functionalized carbohydrate derivatives. A set of 21 compounds was screened against acid-fast Mycobacterium tuberculosis (Mtb), gram-negative Escherichia coli and gram-positive Staphylococcus aureus. The tested carbohydrate derivatives were most effective against tubercle bacilli, with as many as five compounds (thioglycoside 6, thiosemicarbazone 16A, thiosemicarbazone 20, aminothiadiazole 23, and thiazoline 26) inhibiting its growth with MIC50 ≤ 50 µM/CFU. Only two compounds (aminothiadiazole 23 and thiazoline 26) were able to inhibit the growth of E. coli at concentrations below 1 mM, and one of them, aminothiadiazole 23, inhibited the growth of S. aureus at a concentration ≤1 mM. The five compounds affecting the growth of mycobacteria were either thiodisaccharides (6, 16A, and 20) or thioglycosides (23 and 26). All of these compounds (6, 16A, 20, 23, and 26) were able to inhibit the growth of Mtb deposited within human macrophages. However, three of the five selected compounds (6, 23, and 26) exhibited relatively high cytotoxicity in mouse fibroblasts at micromolar concentrations. The selected thio-sugars are very promising compounds, thus making them candidates for further modifications that would decrease their cytotoxicity against eukaryotic cells without affecting their antimycobacterial potential. View Full-Text
Keywords: thiosaccharides; Mycobacterium tuberculosis; bactericidal effect thiosaccharides; Mycobacterium tuberculosis; bactericidal effect

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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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Korycka-Machała, M.; Brzostek, A.; Dziadek, B.; Kawka, M.; Popławski, T.; Witczak, Z.J.; Dziadek, J. Evaluation of the Mycobactericidal Effect of Thio-functionalized Carbohydrate Derivatives. Molecules 2017, 22, 812.

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