Novel non-toxic high efficient antibacterial azido chitosan derivatives with potential application in food coatings

Andreii S Kritchenkov; Anton R Egorov; Margarita N Kurasova; Olga V Volkova; Tatyana V Meledina; Nikita A Lipkan; Alexander G Tskhovrebov; Aleh V Kurliuk; Tatsiana V Shakola; Artem P Dysin; Mikhail Yu Egorov; Elizaveta A Savicheva; Wesley Moreira Dos Santos

doi:10.1016/j.foodchem.2019.125247

Novel non-toxic high efficient antibacterial azido chitosan derivatives with potential application in food coatings

Food Chem. 2019 Dec 15:301:125247. doi: 10.1016/j.foodchem.2019.125247. Epub 2019 Jul 24.

Affiliations

¹ Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow 117198, Russian Federation; Institute of Macromolecular Compounds of the Russian Academy of Sciences, Bolshoi pr. VO 31, St. Petersburg 199004, Russian Federation; Saint-Petersburg National Research University of Information Technologies, Mechanics, and Optics, Kronverkskii pr. 49, St. Petersburg 197101, Russian Federation. Electronic address: kritchenkov-as@rudn.ru.
² Institute of Macromolecular Compounds of the Russian Academy of Sciences, Bolshoi pr. VO 31, St. Petersburg 199004, Russian Federation; Saint-Petersburg National Research University of Information Technologies, Mechanics, and Optics, Kronverkskii pr. 49, St. Petersburg 197101, Russian Federation.
³ Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow 117198, Russian Federation.
⁴ Saint-Petersburg National Research University of Information Technologies, Mechanics, and Optics, Kronverkskii pr. 49, St. Petersburg 197101, Russian Federation.
⁵ N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Kosygina Street 4, Building 1, Moscow 119991, Russian Federation.
⁶ Vitebsk State Medical University, Frunze av. 27, Vitebsk 210009, Belarus.
⁷ Peter the Great Saint Petersburg Polytechnic University, 29 Polytechnicheskaya Street, St. Petersburg 195251, Russian Federation.
⁸ Max Planck Institute for Biophysical Chemistry, Am Fassberg 1, Göttingen 37077, Germany.

PMID: 31377626
DOI: 10.1016/j.foodchem.2019.125247

Abstract

In this work, we developed a simple method for the preparation of N-(3-azido-2-hydroxypropyl)chitosan. We compared the antibacterial activity of N-(3-azido-2-hydroxypropyl)chitosans and previously synthesized N-(2-azidoethyl)chitosans. N-(3-azido-2-hydroxypropyl)chitosans possess higher antibacterial effect which is comparable with that of ampicillin and gentamicin. The effect is due to azido pharmacophore -CH₂-CH(OH)-CH₂-N₃ (for N-(3-azido-2-hydroxypropyl)chitosan) or -CH₂-CH₂-N₃ (for N-(2-azidoethyl)chitosan) introduced in chitosan chain, since the corresponding organic azides NH₂-CH₂-CH₂-N₃ and NH₂-CH₂-CH₂-N₃ are characterized by high antibacterial activity. However, high antibacterial organic azides NH₂-CH₂-CH₂-N₃ and NH₂-CH₂-CH₂-N₃ are characterized by high toxicity. Their conjugation to the chitosan chain saves their antibacterial effect, but strongly diminishes their toxicity, and the toxicity of the resulting derivatives is comparable with that of the starting chitosan. These findings are of interest to food science, since novel effective food coatings can be developed on basis of prepared derivatives.

Keywords: Antibacterial activity; Chitosan; Food chemistry; Food coatings; Organic azides.

MeSH terms

Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / pharmacology*
Anti-Bacterial Agents / toxicity
Azides / chemistry*
Chitosan / chemistry*
Chitosan / pharmacology*
Chitosan / toxicity
Food Packaging*

Substances

Anti-Bacterial Agents
Azides
Chitosan