Ultrasound-assisted catalyst-free phenol-yne reaction for the synthesis of new water-soluble chitosan derivatives and their nanoparticles with enhanced antibacterial properties

This work describes ultrasound-assisted phenol-yne addition of p-hydroxybenzaldehyde and propargylic ester of betaine hydrochloride giving only 2-((3-(4-formylphenoxy)allyl)oxy)-N,N,N-trimethyl-2-oxoethan-1-aminium chloride as a product at 100 kHz 300 W in water. The ultrasonic assisted phenol-yne addition was enhanced to chitosan chemistry. Phenolic chitosan derivatives were obtained by treatment of chitosan with o-, m- or p-hydroxybenzaldehyde followed by reduction of the formed C[dbnd]N bound by NaBH4. The phenolic chitosan derivatives (phenolic component) were involved in ultrasound-mediated reaction with propargylic ester of betaine hydrochloride (yne component). The reaction led to betaine chitosan derivatives in different degree of substitution as o-, m- and p-isomers. The phenolic and betaine derivatives were tested as antibacterial agents against E. coli in comparison with reference antibiotic Tetracycline. Betaine derivatives showed high antibacterial activity. The most effective polymer was p-isomer of high substituted betaine derivative and its activity was more than 2 times higher than the activity of Tetracycline. The nanoparticles based on this polymer were obtained by ionic gelation method. They had 2Rh 126 nm, ξ-potential 20 mV and were more effective than the corresponding chitosan derivative. © 2019 Elsevier B.V.

Kritchenkov A.S. 1, 2 , Egorov A.R.2 , Volkova O.V.2 , Kritchenkov I.S.3, 4 , Kurliuk A.V.5 , Shakola T.V.5 , Khrustalev V.N. 1, 6
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 Saint Petersburg State University, Universitetskaya emb. 7/9, St. Petersburg, 199034, Russian Federation
  • 4 Institute of Technical Acoustics NAS of Belarus, Ludnikova Prosp. 13, Vitebsk, 210009, Belarus
  • 5 Vitebsk State Medical University, Frunze av. 27, Vitebsk, 210009, Belarus
  • 6 Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation
4 hydroxybenzaldehyde; betaine; betaine derivative; chitosan derivative; nanoparticle; phenol; polymer; tetracycline; water; antibacterial activity; Article; catalyst; chemical modification; chemical reaction; chemical structure; controlled study; drug activity; Escherichia coli; gelation; nonhuman; synthesis; ultrasound assisted catalyst free phenol yne reaction
Date of creation
Date of change
Short link

Other records