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Synthesis, cytotoxicity and antioxidant activity of new conjugates of N-acetyl-d-glucosamine with α-aminophosphonates.
Khabibulina, Leysan R; Garifullin, Bulat F; Aznagulov, Ravil F; Andreeva, Olga V; Strobykina, Irina Yu; Belenok, Mayya G; Voloshina, Alexandra D; Abramova, Dinara F; Vyshtakalyuk, Alexandra B; Lyubina, Anna P; Amerhanova, Syumbelya K; Sharipova, Radmila R; Kataev, Vladimir E.
Afiliación
  • Khabibulina LR; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation; Kazan National Research Technological University, Karl Marx str., 68, Kazan, 420015, Russian Federation. Electronic address: khabibulina.
  • Garifullin BF; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation; Kazan National Research Technological University, Karl Marx str., 68, Kazan, 420015, Russian Federation.
  • Aznagulov RF; Kazan National Research Technological University, Karl Marx str., 68, Kazan, 420015, Russian Federation.
  • Andreeva OV; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Strobykina IY; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Belenok MG; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Voloshina AD; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Abramova DF; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation; Kazan National Research Technological University, Karl Marx str., 68, Kazan, 420015, Russian Federation.
  • Vyshtakalyuk AB; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Lyubina AP; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Amerhanova SK; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Sharipova RR; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
  • Kataev VE; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzov str., 8, Kazan, 420088, Russian Federation.
Carbohydr Res ; 541: 109146, 2024 Jul.
Article en En | MEDLINE | ID: mdl-38788561
ABSTRACT
A series of the first conjugates of N-acetyl-d-glucosamine with α-aminophosphonates was synthesized using the Kabachnik-Fields reaction, the Pudovik reaction, a copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC) and evaluated for the in vitro cytotoxicity against human cancer cell lines M - HeLa, HuTu-80, A549, PANC-1, MCF-7, T98G and normal lung fibroblast cells WI-38. The tested conjugates, with exception of compound 21b, considered as a lead compound, were either inactive against the used cancer cells or showed moderate cytotoxicity in the range of IC50 values 33-80 µM. The lead compound 21b, being non cytotoxic against normal human cells WI-38 (IC50 = 90 µM), demonstrated good activity (IC50 = 17 µM) against breast adenocarcinoma cells (MCF-7) which to be 1.5 times higher than the activity of the used reference anticancer drug tamoxifen (IC50 = 25.0 µM). A flexible receptor molecular docking simulation showed that the cytotoxicity of the synthesized conjugates of N-acetyl-d-glucosamine with α-aminophosphonates against breast adenocarcinoma MCF-7 cell line is due to their ability to inhibit EGFR kinase domain. In addition, it was found that conjugates 22a and 22b demonstrated antioxidant activity that was not typical for α-aminophosphonates.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Acetilglucosamina / Organofosfonatos / Simulación del Acoplamiento Molecular / Antineoplásicos / Antioxidantes Límite: Humans Idioma: En Revista: Carbohydr Res Año: 2024 Tipo del documento: Article Pais de publicación: Países Bajos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Acetilglucosamina / Organofosfonatos / Simulación del Acoplamiento Molecular / Antineoplásicos / Antioxidantes Límite: Humans Idioma: En Revista: Carbohydr Res Año: 2024 Tipo del documento: Article Pais de publicación: Países Bajos