Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers-Reference-Cited by-同舟云学术

Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers

Published:2023-12-19 Issue:1 Volume:6 Page:1-12
ISSN:2624-8549
Container-title:Chemistry
language:en
Short-container-title:Chemistry

Author:

Tsyganova Anna V.¹²,Petrov Artem O.¹,Shastin Alexey V.¹,Filatova Natalia V.¹,Mumyatova Victoria A.¹,Tarasov Alexander E.¹^ORCID,Lolaeva Alina V.¹,Malkov Georgiy V.¹^ORCID

Affiliation:

1. Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, the Russian Academy of Sciences, Chernogolovka 142432, Russia

2. Faculty of Fundamental Physical and Chemical Engineering, Lomonosov Moscow State University, Moscow 119991, Russia

Abstract

A new method for the synthesis of azido-propargyloxy derivatives of 1,3,5-triazine has been developed utilizing the nitrosation of hydrazyno-1,3,5-triazines. New hydrazines (2-hydrazino-4,6-bis(propargyloxy)-1,3,5-triazine and 2,4-dihydrazino-6-propargyloxy-1,3,5-triazine) were synthesized and characterized via FTIR, NMR spectroscopy and elemental analysis. The hyperbranched polymers with azide (diazide monomer) and propargyloxy terminal groups were obtained via the azide-alkyne polycycloaddition reaction of diazide and monoazide AB2-type monomers. The antibacterial activity against Escherichia coli bacteria of 2,4,6-trispropargyloxy-1,3,5-triazine, 2-azido-4,6-bispropargyloxy-1,3,5-triazine, and 2,4-diazido-6-propargyloxy-1,3,5-triazine and their hyperbranched polymers was studied. Only 2,4-diazido-6-propargyloxy-1,3,5-triazine has weak antibacterial activity in comparison with ampicillin. The cytotoxicity of these compounds against M-HeLa, FetMSC, and Vero cell lines was also studied. 2,4,6-trispropargyloxy-1,3,5-triazine does not show any cytotoxic effect (IC50 ≥ 280 µM). It was shown that the presence of an azide group in the compound directly affects the cytotoxic effect. Hyperbranched polymers have a less cytotoxic effect against M-HeLa (IC50 > 100) in comparison with monomers (IC50 = 90–99 µM). This makes it possible to use these polymers as the basis for biocompatible materials in biomedical applications.

Funder

Ministry of Education and Science of the Russian Federation

Publisher

MDPI AG

Subject

Organic Chemistry,Inorganic Chemistry,Electrochemistry,Chemistry (miscellaneous)

Link

https://www.mdpi.com/2624-8549/6/1/1/pdf

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