Design, synthesis and biological evaluation of novel N-phosphorylated and O-phosphorylated tacrine derivatives as potential drugs against Alzheimer’s disease - Publikacja - MOST Wiedzy

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Design, synthesis and biological evaluation of novel N-phosphorylated and O-phosphorylated tacrine derivatives as potential drugs against Alzheimer’s disease

Abstrakt

In this work, we designed, synthesised and biologically investigated a novel series of 14N- and O-phosphorylated tacrine derivatives as potential anti-Alzheimer’s disease agents. In the reaction of 9-chlorotacrine and corresponding diamines/aminoalkylalcohol we obtained diamino and aminoalkylhydroxy tacrine derivatives. Next, the compounds were acid to give final products 6–13 and 16–21 that were characterised by 1H, 13 C, 31P NMR and MS. The results of the docking studies revealed that the designed phosphorus hybrids, in theory can bind to AChE and BChE. All compounds exhibited significantly lower AutoDock Vina scores compared to tacrine. The inhibitory potency evaluation was performed using the Ellman’s method. The most inhibitory activity against AChE exhibited compound 8 with an IC50 value of 6.11nM and against BChE 13 with an IC50 value of 1.97 nM and they were 6- and 12-fold potent than tacrine. Compound 19 showed the lack of hepatocytotoxicity in MTT assay.

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Accepted albo Published Version
DOI:
Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1080/14756366.2022.2045591
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Creative Commons: CC-BY otwiera się w nowej karcie

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Kategoria:
Publikacja w czasopiśmie
Typ:
artykuły w czasopismach
Opublikowano w:
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY nr 37, strony 1012 - 1022,
ISSN: 1475-6366
Język:
angielski
Rok wydania:
2022
Opis bibliograficzny:
Przybyłowska M., Dzierzbicka K., Szymon K., Demkowicz S., Daśko M., Inkielewicz-Stępniak I.: Design, synthesis and biological evaluation of novel N-phosphorylated and O-phosphorylated tacrine derivatives as potential drugs against Alzheimer’s disease// JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY -Vol. 37,iss. 1 (2022), s.1012-1022
DOI:
Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1080/14756366.2022.2045591
Źródła finansowania:
  • Publikacja bezkosztowa
Weryfikacja:
Politechnika Gdańska

wyświetlono 183 razy

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