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Literature DB >> 9871613

DNA cleavage by 7-methylbenzopentathiepin: a simple analog of the antitumor antibiotic varacin.

Abstract

The compound 7-methylbenzopentathiepin, a simple analog of the benzopentathiepin antitumor antibiotic varacin, was shown to be a potent thiol-dependent DNA-cleaving agent. Biological experiments previously suggested that DNA cleavage might play a role in the cytotoxicity of varacin; however, this is the first direct evidence that benzopentathiepins can cause DNA strand breaks under physiologically relevant conditions.

Entities: Chemical Disease

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Year: 1998 PMID： 9871613 DOI： 10.1016/s0960-894x(98)00066-3

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

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Cited

14 in total

1. Generation of DNA-damaging reactive oxygen species via the autoxidation of hydrogen sulfide under physiologically relevant conditions: chemistry relevant to both the genotoxic and cell signaling properties of H(2)S.

Authors: Marjorie Hoffman; Anuruddha Rajapakse; Xiulong Shen; Kent S Gates
Journal: Chem Res Toxicol Date: 2012-06-04 Impact factor: 3.739

2. DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide.

Authors: Venkatraman Junnotula; Anuruddha Rajapakse; Leire Arbillaga; Adela López de Cerain; Beatriz Solano; Raquel Villar; Antonio Monge; Kent S Gates
Journal: Bioorg Med Chem Date: 2010-03-19 Impact factor: 3.641

3. Synthesis and characterization of a small analogue of the anticancer natural product leinamycin.

Authors: Kripa Keerthi; Anuruddha Rajapakse; Daekyu Sun; Kent S Gates
Journal: Bioorg Med Chem Date: 2012-10-27 Impact factor: 3.641

4. A new synthetic varacin analogue, 8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine hydrochloride (TC-2153), decreased hereditary catalepsy and increased the BDNF gene expression in the hippocampus in mice.

Authors: Alexander V Kulikov; Maria A Tikhonova; Elizabeth A Kulikova; Konstantin P Volcho; Tatyana M Khomenko; Nariman F Salakhutdinov; Nina K Popova
Journal: Psychopharmacology (Berl) Date: 2011-11-30 Impact factor: 4.530

DNA cleavage by 7-methylbenzopentathiepin: a simple analog of the antitumor antibiotic varacin.

1. Generation of DNA-damaging reactive oxygen species via the autoxidation of hydrogen sulfide under physiologically relevant conditions: chemistry relevant to both the genotoxic and cell signaling properties of H(2)S.

2. DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide.

3. Synthesis and characterization of a small analogue of the anticancer natural product leinamycin.

4. A new synthetic varacin analogue, 8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine hydrochloride (TC-2153), decreased hereditary catalepsy and increased the BDNF gene expression in the hippocampus in mice.

5. Thiol-activated DNA damage by α-bromo-2-cyclopentenone.

6. Entering the leinamycin rearrangement via 2-(trimethylsilyl)ethyl sulfoxides.

7. Characterization of DNA damage induced by a natural product antitumor antibiotic leinamycin in human cancer cells.

8. Characterization of a covalent polysulfane bridge in copper-zinc superoxide dismutase .

Review 9. Redox-directed cancer therapeutics: molecular mechanisms and opportunities.

10. Possible chemical mechanisms underlying the antitumor activity of S-deoxyleinamycin.