Cargando…

Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

The compounds produced by a living organism are most commonly as medicinal agents and starting materials for the preparation of new semi-synthetic derivatives. One of the largest groups of natural compounds consists of products containing a 1,4-benzoquinone subunit. This fragment occurs in three ene...

Descripción completa

Detalles Bibliográficos
Autores principales: Kadela-Tomanek, Monika, Bębenek, Ewa, Chrobak, Elwira, Latocha, Małgorzata, Boryczka, Stanisław
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155387/
https://www.ncbi.nlm.nih.gov/pubmed/28287461
http://dx.doi.org/10.3390/molecules22030447
_version_ 1783357891345907712
author Kadela-Tomanek, Monika
Bębenek, Ewa
Chrobak, Elwira
Latocha, Małgorzata
Boryczka, Stanisław
author_facet Kadela-Tomanek, Monika
Bębenek, Ewa
Chrobak, Elwira
Latocha, Małgorzata
Boryczka, Stanisław
author_sort Kadela-Tomanek, Monika
collection PubMed
description The compounds produced by a living organism are most commonly as medicinal agents and starting materials for the preparation of new semi-synthetic derivatives. One of the largest groups of natural compounds consists of products containing a 1,4-benzoquinone subunit. This fragment occurs in three enediyne antibiotics, dynemicin A, deoxydynemicin A, and uncilamicin, which exhibit high biological activity. A series of alkoxy derivatives containing 1,4-naphthoquinone, 5,8-quinolinedione, and 2-methyl-5,8-quinolinedione moieties was synthesized. Moreover, the 1,4-benzoquinone subunit was contacted with an enediyne fragment. All obtained compounds were characterized by spectroscopy and spectrometry methods. The resulting alkane, alkene, alkyne and enediyne derivatives were tested as antitumor agents. They showed high cytotoxic activity depending on the type of 1,4-benzoquinone subunit and the employed tumor cell lines. The synthesized derivatives fulfill the Lipinski Rule of Five and have low permeability through the blood–brain barrier.
format Online
Article
Text
id pubmed-6155387
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61553872018-11-13 Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity Kadela-Tomanek, Monika Bębenek, Ewa Chrobak, Elwira Latocha, Małgorzata Boryczka, Stanisław Molecules Article The compounds produced by a living organism are most commonly as medicinal agents and starting materials for the preparation of new semi-synthetic derivatives. One of the largest groups of natural compounds consists of products containing a 1,4-benzoquinone subunit. This fragment occurs in three enediyne antibiotics, dynemicin A, deoxydynemicin A, and uncilamicin, which exhibit high biological activity. A series of alkoxy derivatives containing 1,4-naphthoquinone, 5,8-quinolinedione, and 2-methyl-5,8-quinolinedione moieties was synthesized. Moreover, the 1,4-benzoquinone subunit was contacted with an enediyne fragment. All obtained compounds were characterized by spectroscopy and spectrometry methods. The resulting alkane, alkene, alkyne and enediyne derivatives were tested as antitumor agents. They showed high cytotoxic activity depending on the type of 1,4-benzoquinone subunit and the employed tumor cell lines. The synthesized derivatives fulfill the Lipinski Rule of Five and have low permeability through the blood–brain barrier. MDPI 2017-03-11 /pmc/articles/PMC6155387/ /pubmed/28287461 http://dx.doi.org/10.3390/molecules22030447 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kadela-Tomanek, Monika
Bębenek, Ewa
Chrobak, Elwira
Latocha, Małgorzata
Boryczka, Stanisław
Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
title Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
title_full Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
title_fullStr Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
title_full_unstemmed Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
title_short Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
title_sort alkoxy and enediyne derivatives containing 1,4-benzoquinone subunits—synthesis and antitumor activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155387/
https://www.ncbi.nlm.nih.gov/pubmed/28287461
http://dx.doi.org/10.3390/molecules22030447
work_keys_str_mv AT kadelatomanekmonika alkoxyandenediynederivativescontaining14benzoquinonesubunitssynthesisandantitumoractivity
AT bebenekewa alkoxyandenediynederivativescontaining14benzoquinonesubunitssynthesisandantitumoractivity
AT chrobakelwira alkoxyandenediynederivativescontaining14benzoquinonesubunitssynthesisandantitumoractivity
AT latochamałgorzata alkoxyandenediynederivativescontaining14benzoquinonesubunitssynthesisandantitumoractivity
AT boryczkastanisław alkoxyandenediynederivativescontaining14benzoquinonesubunitssynthesisandantitumoractivity