Ultrasound-assisted catalyst-free thiol-yne click reaction in chitosan chemistry: Antibacterial and transfection activity of novel cationic chitosan derivatives and their based nanoparticles

In this work, we demonstrate that the thiol-yne click reaction could be efficiently mediated by ultrasonic irradiation and implement the ultrasound-assisted thiol-yne click reaction to chitosan chemistry as a polymer-analogous transformation. We optimize power and frequency of ultrasound to preserve selectivity of the click reaction and avoid ultrasonic degradation of the chitosan polymer chain. Thus, we obtain a new water-soluble betaine. Using ionic gelation of the obtained betaine derivatives of chitosan, we prepare nanoparticles with a unimodal size distribution. Furthermore, we present results of antibacterial and transfection activity tests for the chitosan derivatives and their based nanoparticles. The derivative with a medium molecular weight and a high degree of substitution demonstrated the best antibacterial effect. It derived nanoparticles with a size of ca. 100 nm and ζ-potential of ca. +69 mV revealed even higher antibacterial activity, slightly superior to commercial antibiotics ampicillin and gentamicin. On the contrary, the obtained polymers possess a much more pronounced transfection activity as compared with their based nanoparticles and species with a low degree of substitution acts as the most efficient transfecting agent. Moreover, the obtained betaine chitosan derivatives as well as their derived nanoparticles are non-toxic. © 2019

Kritchenkov A.S. 1, 2, 3 , Egorov A.R. 1 , Artemjev A.A. 1 , Kritchenkov I.S.4 , Volkova O.V.2 , Kurliuk A.V.5 , Shakola T.V.5 , Rubanik V.V.3 , Tskhovrebov A.G. 6 , Yagafarov N.Z. 1, 7 , Khrustalev V.N. 1, 8
Elsevier B.V.
  • 1 Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya St. 6, Moscow, 117198, Russian Federation
  • 2 Saint Petersburg National Research University of Information Technologies, Mechanics, and Optics, Kronverkskii pr. 49, St. Petersburg, 197101, Russian Federation
  • 3 Institute of Technical Acoustics NAS of Belarus, Ludnikova Prosp. 13, Vitebsk, 210009, Belarus
  • 4 Saint Petersburg State University, Universitetskaya emb. 7/9, St. Petersburg, 199034, Russian Federation
  • 5 Vitebsk State Medical University, Frunze av. 27, Vitebsk, 210009, Belarus
  • 6 N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Kosygina Street 4, Building 1, Moscow, 119991, Russian Federation
  • 7 Pirogov Russian National Research Medical University, 1 Ostrovityanov Street, Moscow, 117997, Russian Federation
  • 8 Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation
Ключевые слова
Antibacterial activity; Chitosan; Click reaction; Thiol-yne; Transfection activity
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