Synthesis of Norabietyl and Nordehydroabietyl Imidazolidine-2,4,5-Triones and Their Activity against Tyrosyl-DNA Phosphodiesterase 1-Reference-Cited by-同舟云学术

Synthesis of Norabietyl and Nordehydroabietyl Imidazolidine-2,4,5-Triones and Their Activity against Tyrosyl-DNA Phosphodiesterase 1

Published:2023-11-09 Issue:4 Volume:2023 Page:M1743
ISSN:1422-8599
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language:en
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Author:

Kovaleva Kseniya S.¹^ORCID,Yarovaya Olga I.¹^ORCID,Chernyshova Irina A.²,Zakharenko Alexandra L.²,Cheresiz Sergey V.³^ORCID,Azimirad Amirhossein³,Pokrovsky Andrey G.³,Lavrik Olga I.²^ORCID,Salakhutdinov Nariman F.¹

Affiliation:

1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentiev Ave. 9, Novosibirsk 630090, Russia

2. Novosibirsk Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrentiev Ave. 8, Novosibirsk 630090, Russia

3. V. Zelman Institute for the Medicine and Psychology, Novosibirsk State University, Pirogova St. 1, Novosibirsk 630090, Russia

Abstract

New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parabanic acid fragment made it possible to increase the solubility of compounds and conduct biological studies. The compounds inhibit the DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 in submicromolar concentrations. Cytotoxic concentrations were also studied on the glioblastoma cell line SNB19.

Funder

Russian Science Foundation

Government of the Novosibirsk Region

Publisher

MDPI AG

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

https://www.mdpi.com/1422-8599/2023/4/M1743/pdf

Reference28 articles.

1. Multiple Topoisomerase I (TopoI), Topoisomerase II (TopoII) and Tyrosyl-DNA Phosphodiesterase (TDP) inhibitors in the development of anticancer drugs;Baglini;Eur. J. Pharm. Sci.,2021

2. A eukaryotic enzyme that can disjoin dead-end covalent complexes between DNA and type I topoisomerases;Yang;Proc. Natl. Acad. Sci. USA,1996

3. A comprehensive review of topoisomerase inhibitors as anticancer agents in the past decade;Liang;Eur. J. Med. Chem.,2019

4. Tyrosyl-DNA-phosphodiesterases (TDP1 and TDP2);Pommier;DNA Repair,2014

5. TDP1 repairs nuclear and mitochondrial DNA damage induced by chain-terminating anticancer and antiviral nucleoside analogs;Huang;Nucleic Acids Res.,2013

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