Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

Barbara Dmochowska; Karol Sikora; Anna Woziwodzka; Jacek Piosik; Beata Podgórska

doi:10.3762/bjoc.12.138

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

Beilstein J Org Chem. 2016 Jul 12:12:1434-9. doi: 10.3762/bjoc.12.138. eCollection 2016.

Authors

Barbara Dmochowska¹, Karol Sikora², Anna Woziwodzka³, Jacek Piosik³, Beata Podgórska⁴

Affiliations

¹ Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland.
² Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland; Faculty of Pharmacy, Medical University of Gdańsk, Gen. Hallera 107, 80-416 Gdańsk, Poland.
³ Laboratory of Biophysics, Intercollegiate Faculty of Biotechnology, University of Gdańsk and Medical University of Gdańsk, Antoniego Abrahama 58, 80-307 Gdańsk, Poland.
⁴ Department of Molecular Evolution, University of Gdańsk, Wita Stwosza 59, 80-308 Gdańsk, Poland.

Abstract

This paper presents a study on a series of quaternary ammonium salt (QAS) derivatives of glucopyranosides with an elongated hydrophobic hydrocarbon chain. The new N-[6-(β-D-glucopyranosyloxy)hexyl]ammonium bromides and their O-acetyl derivatives were analyzed via (1)H and (13)C NMR spectroscopy. The mutagenic activity of the newly synthesized QAS was investigated using two different techniques: The Vibrio harveyi luminescence assay and the Ames test. The obtained results support previous findings contesting QAS safety and indicate that QAS, specifically pyridinium derivatives, might be mutagenic.

Keywords: 6-bromohexyl D-glucopyranoside; microbiological mutagenicity test; quaternary ammonium salt.