Toward “E-Ring-Free” Lamellarin Analogues : Synthesis and Preliminary Biological Evaluation

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Daniil A. Rusanov
  • Samah Mutasim Alfadul
  • Ekaterina Yu. Portnyagina
  • Eugenia A. Silyanova
  • Nikita A. Kuznetsov
  • Kirill E. Podpovetny
  • Alexander V. Samet
  • Victor V. Semenov

Related Research Unit(s)

Detail(s)

Original languageEnglish
Article numbere202300161
Journal / PublicationChemBioChem
Volume24
Issue number11
Online published12 Apr 2023
Publication statusPublished - 1 Jun 2023

Abstract

Since the discovery of anticancer properties of a naturally occurring hexacyclic marine alkaloid Lamellarin D, the attempts have been made to prepare its synthetic analogues and elucidate the effects of each structural component on their activity profile. While F-ring-free, A-ring-free and B-ring-open lamellarins are known, E-ring-free analogues have never been investigated. In this work, we developed a facile and straightforward synthetic method toward E-ring-free lamellarin analogues based on the [3+2]-cycloaddition. For the first time, we prepared several pentacyclic lamellarin analogues without E-ring in their structure and assessed their cytotoxicity in a panel of cancer cell lines in comparison with several hexacyclic lamellarins. E-ring-free lamellarins were devoid of cytotoxicity due to their poor solubility in cellular environment. © 2023 Wiley-VCH GmbH.

Research Area(s)

  • anticancer activity, lamellarin analogues, marine drugs, pyridinium ylides, [3+2]-cycloaddition

Citation Format(s)

Toward “E-Ring-Free” Lamellarin Analogues: Synthesis and Preliminary Biological Evaluation. / Rusanov, Daniil A.; Mutasim Alfadul, Samah; Portnyagina, Ekaterina Yu. et al.
In: ChemBioChem, Vol. 24, No. 11, e202300161, 01.06.2023.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review