Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes

A series of trans-6-phenylethenyl substituted pyridoxine derivatives, novel bioisosteric analogs of drugs based on trans-stilbene scaffold, were synthesized using the Wittig reaction of a bis-triphenylphosphonium pyridoxine derivative with various aromatic aldehydes. Two compounds demonstrated high...

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Main Authors: Mikhail V. Pugachev, Thang T. N. Nguyen, Timur M. Bulatov, Roman S. Pavelyev, Alfia G. Iksanova, Oksana V. Bondar, Konstantin V. Balakin, Yurii G. Shtyrlin
Format: Article
Language:English
Published: Wiley 2017-01-01
Series:Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2017/8281518
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author Mikhail V. Pugachev
Thang T. N. Nguyen
Timur M. Bulatov
Roman S. Pavelyev
Alfia G. Iksanova
Oksana V. Bondar
Konstantin V. Balakin
Yurii G. Shtyrlin
author_facet Mikhail V. Pugachev
Thang T. N. Nguyen
Timur M. Bulatov
Roman S. Pavelyev
Alfia G. Iksanova
Oksana V. Bondar
Konstantin V. Balakin
Yurii G. Shtyrlin
author_sort Mikhail V. Pugachev
collection DOAJ
description A series of trans-6-phenylethenyl substituted pyridoxine derivatives, novel bioisosteric analogs of drugs based on trans-stilbene scaffold, were synthesized using the Wittig reaction of a bis-triphenylphosphonium pyridoxine derivative with various aromatic aldehydes. Two compounds demonstrated high activity against the estrogen-dependent MCF-7 (breast cancer) cell line with IC50 in the range of 1.9–7.9 µM and very good selectivity for other studied normal and tumor cells, including the estrogen receptor negative MDA-MB-231 breast cancer cells. The active compounds possessed an intense blue fluorescence, and this feature allowed us to effectively visualize them in cytoplasm and in nucleus. The obtained results make the described chemotype a promising starting point for the development of new anticancer agents for the therapy of estrogen-dependent malignancies.
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institution Kabale University
issn 2090-9063
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language English
publishDate 2017-01-01
publisher Wiley
record_format Article
series Journal of Chemistry
spelling doaj-art-e9468e5668a14e069cfc2b7b173027442025-02-03T06:00:24ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/82815188281518Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-StilbenesMikhail V. Pugachev0Thang T. N. Nguyen1Timur M. Bulatov2Roman S. Pavelyev3Alfia G. Iksanova4Oksana V. Bondar5Konstantin V. Balakin6Yurii G. Shtyrlin7Kazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaA series of trans-6-phenylethenyl substituted pyridoxine derivatives, novel bioisosteric analogs of drugs based on trans-stilbene scaffold, were synthesized using the Wittig reaction of a bis-triphenylphosphonium pyridoxine derivative with various aromatic aldehydes. Two compounds demonstrated high activity against the estrogen-dependent MCF-7 (breast cancer) cell line with IC50 in the range of 1.9–7.9 µM and very good selectivity for other studied normal and tumor cells, including the estrogen receptor negative MDA-MB-231 breast cancer cells. The active compounds possessed an intense blue fluorescence, and this feature allowed us to effectively visualize them in cytoplasm and in nucleus. The obtained results make the described chemotype a promising starting point for the development of new anticancer agents for the therapy of estrogen-dependent malignancies.http://dx.doi.org/10.1155/2017/8281518
spellingShingle Mikhail V. Pugachev
Thang T. N. Nguyen
Timur M. Bulatov
Roman S. Pavelyev
Alfia G. Iksanova
Oksana V. Bondar
Konstantin V. Balakin
Yurii G. Shtyrlin
Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes
Journal of Chemistry
title Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes
title_full Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes
title_fullStr Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes
title_full_unstemmed Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes
title_short Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes
title_sort synthesis and antitumor activity of novel pyridoxine based bioisosteric analogs of trans stilbenes
url http://dx.doi.org/10.1155/2017/8281518
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