Literature DB >> 26342869

Synthesis and evaluation of a bis-3-chloropiperidine derivative incorporating an anthraquinone pharmacophore.

Ivonne Zuravka1, Alice Sosic2, Barbara Gatto3, Richard Göttlich4.   

Abstract

With the aim to attain an alkylating agent with enhanced DNA-affinity, we have successfully synthesised lysine-linked bis-3-chloropiperidine 1 bearing an anthraquinone moiety known to bind double-stranded DNA. Consistent with our expectations, compound 1 appears to intercalate into the DNA double helix, which can be observed by conformational changes of plasmid DNA suggesting alkylation and intercalation-induced DNA unwinding. The results of this work can provide a meaningful starting point for investigating the molecular mechanism of action of this novel DNA alkylating conjugate 1 with improved affinity for DNA.
Copyright © 2015 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Alkylating agents; Anthraquinone; DNA cleavage; Intercalation; Nitrogen mustard

Mesh：

Substances：

Year:  2015        PMID： 26342869     DOI： 10.1016/j.bmcl.2015.08.042

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  7 in total

1.  Decoding mechanism of action and sensitivity to drug candidates from integrated transcriptome and chromatin state.

Authors:  Caterina Carraro; Lorenzo Bonaguro; Jonas Schulte-Schrepping; Arik Horne; Marie Oestreich; Stefanie Warnat-Herresthal; Tim Helbing; Michele De Franco; Kristian Haendler; Sach Mukherjee; Thomas Ulas; Valentina Gandin; Richard Goettlich; Anna C Aschenbrenner; Joachim L Schultze; Barbara Gatto
Journal:  Elife       Date:  2022-08-31       Impact factor: 8.713

Review 2.  Journey of anthraquinones as anticancer agents - a systematic review of recent literature.

Authors:  M Shaheer Malik; Reem I Alsantali; Rabab S Jassas; Abdulrahman A Alsimaree; Riyaz Syed; Meshari A Alsharif; Kulkarni Kalpana; Moataz Morad; Ismail I Althagafi; Saleh A Ahmed
Journal:  RSC Adv       Date:  2021-11-05       Impact factor: 4.036

3.  Direct and Topoisomerase II Mediated DNA Damage by Bis-3-chloropiperidines: The Importance of Being an Earnest G.

Authors:  Alice Sosic; Ivonne Zuravka; Nina-Katharina Schmitt; Angelica Miola; Richard Göttlich; Dan Fabris; Barbara Gatto
Journal:  ChemMedChem       Date:  2017-08-10       Impact factor: 3.466

4.  Behind the Mirror: Chirality Tunes the Reactivity and Cytotoxicity of Chloropiperidines as Potential Anticancer Agents.

Authors:  Caterina Carraro; Alexander Francke; Alice Sosic; Franziska Kohl; Tim Helbing; Michele De Franco; Daniele Fabris; Richard Göttlich; Barbara Gatto
Journal:  ACS Med Chem Lett       Date:  2019-02-13       Impact factor: 4.345

5.  Bis-3-Chloropiperidines Targeting TAR RNA as A Novel Strategy to Impair the HIV-1 Nucleocapsid Protein.

Authors:  Alice Sosic; Giulia Olivato; Caterina Carraro; Richard Göttlich; Dan Fabris; Barbara Gatto
Journal:  Molecules       Date:  2021-03-26       Impact factor: 4.411

6.  1-Hydroxyanthraquinones Containing Aryl Substituents as Potent and Selective Anticancer Agents.

Authors:  Nafisa S Sirazhetdinova; Victor A Savelyev; Tatyana S Frolova; Dmitry S Baev; Lyubov S Klimenko; Ivan V Chernikov; Olga S Oleshko; Teresa A Sarojan; Andrey G Pokrovskii; Elvira E Shults
Journal:  Molecules       Date:  2020-05-29       Impact factor: 4.411

7.  In Vitro Evaluation of Bis-3-Chloropiperidines as RNA Modulators Targeting TAR and TAR-Protein Interaction.

Authors:  Alice Sosic; Giulia Olivato; Caterina Carraro; Richard Göttlich; Dan Fabris; Barbara Gatto
Journal:  Int J Mol Sci       Date:  2022-01-06       Impact factor: 5.923
  7 in total

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