Novel heterocyclic chitosan derivatives and their derived nanoparticles: Catalytic and antibacterial properties

The metal-assisted nitrone-nitrile cycloaddition reaction is apply to empower chitosan chemistry. The ultrasonic irradiation has proven to efficiently accelerate the cycloaddition affording new heterocyclic (1,2,4-oxadiazoline) chitosan derivatives and avoiding ultrasonic degradation of the chitosan macromolecules. By varying the nitrone nature, both water- and toluene-soluble chitosan derivatives were successfully synthesized. Relying on the ionic gelation approach nanoparticles of heterocyclic chitosan derivatives were prepared. Water-soluble chitosan derivative demonstrated a high antibacterial activity coupled with low toxicity. The toxicity of the synthesized heterocyclic chitosan derivatives and their based nanoparticles are comparable with those of the starting chitosan, while their antibacterial activity is superior. Toluene-soluble derivatives are shown to be efficient homogeneous catalysts towards monoglyceride synthesis via the epoxide ring opening. They efficiently catalyze selective conversion of fatty acids and glycidol into corresponding monoglycerides allowing one to simplify significantly the procedure for separating the reaction product from the catalyst for its recovery and reusage. © 2020 Elsevier B.V.

Kritchenkov A.S. 1, 2, 3 , Egorov A.R. 1 , Artemjev A.A. 1, 4 , Kritchenkov I.S.5 , Volkova O.V.2 , Kiprushkina E.I.2 , Zabodalova L.A.2 , Suchkova E.P.2 , Yagafarov N.Z. 1, 6 , Tskhovrebov A.G.7 , Kurliuk A.V.8 , Shakola T.V.8 , Khrustalev V.N. 1, 9
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 A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova St. 28, Moscow, 119991, Russian Federation
  • 5 Saint Petersburg State University, Universitetskaya emb. 7/9, St. Petersburg, 199034, Russian Federation
  • 6 Pirogov Russian National Research Medical University, 1 Ostrovityanov Street, Moscow, 117997, Russian Federation
  • 7 N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Kosygina Street 4, Building 1, Moscow, 119991, Russian Federation
  • 8 Vitebsk State Medical University, Frunze av. 27, Vitebsk, 210009, Belarus
  • 9 Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation
Ключевые слова
Antibacterial activity; Catalytic activity; Chitosan; Cycloaddition; Heterocycles; Polysaccharides
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