Literature DB >> 22936396

Hypoxia-selective DNA interstrand cross-link formation by two modified nucleosides.

Yunyan Kuang1, Huabing Sun, J Craig Blain, Xiaohua Peng.   

Abstract

The clean crossed code: Two nitroimidazole-modified thymidines 1 a and 1 b were synthesized and incorporated into DNA oligomers. The 350 nm photolysis of 1 a and 1 b generated a 5-(2'-deoxyuridinyl)methyl radical that induced DNA interstrand cross-links (ICL; see scheme). A higher ICL yield was observed under hypoxic conditions than under aerobic conditions.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22936396      PMCID: PMC3525362          DOI: 10.1002/chem.201201960

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  24 in total

Review 1.  Formation and repair of interstrand cross-links in DNA.

Authors:  David M Noll; Tracey McGregor Mason; Paul S Miller
Journal:  Chem Rev       Date:  2006-02       Impact factor: 60.622

2.  Radiosensitization by a modified nucleotide that produces DNA interstrand cross-links under hypoxic conditions.

Authors:  In Seok Hong; Hui Ding; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419

3.  DNA interstrand cross-link formation initiated by reaction between singlet oxygen and a modified nucleotide.

Authors:  In Seok Hong; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

4.  Efficient DNA interstrand cross-link formation from a nucleotide radical.

Authors:  In Seok Hong; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

5.  The reactivity of the 5-hydroxy-5,6-dihydrothymidin-6-yl radical in oligodeoxyribonucleotides.

Authors:  Qibin Zhang; Yinsheng Wang
Journal:  Chem Res Toxicol       Date:  2005-12       Impact factor: 3.739

6.  Mild generation of 5-(2'-deoxyuridinyl)methyl radical from a phenyl selenide precursor.

Authors:  In Seok Hong; Marc M Greenberg
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

7.  Oxygen independent DNA interstrand cross-link formation by a nucleotide radical.

Authors:  In Seok Hong; Hui Ding; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

8.  Interstrand cross-links: a new type of gamma-ray damage in bromodeoxyuridine-substituted DNA.

Authors:  Sylvain Cecchini; Sonia Girouard; Michael A Huels; Léon Sanche; Darel J Hunting
Journal:  Biochemistry       Date:  2005-02-15       Impact factor: 3.162

Review 9.  Radiation-activated prodrugs as hypoxia-selective cytotoxins: model studies with nitroarylmethyl quaternary salts.

Authors:  W R Wilson; M Tercel; R F Anderson; W A Denny
Journal:  Anticancer Drug Des       Date:  1998-09

10.  The histological structure of some human lung cancers and the possible implications for radiotherapy.

Authors:  R H THOMLINSON; L H GRAY
Journal:  Br J Cancer       Date:  1955-12       Impact factor: 7.640

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  6 in total

1.  Photoswitchable formation of a DNA interstrand cross-link by a coumarin-modified nucleotide.

Authors:  Mohammad Mojibul Haque; Huabing Sun; Shuo Liu; Yinsheng Wang; Xiaohua Peng
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

2.  Deconvoluting the reactivity of two intermediates formed from modified pyrimidines.

Authors:  Liwei Weng; Sonia M Horvat; Carl H Schiesser; Marc M Greenberg
Journal:  Org Lett       Date:  2013-07-03       Impact factor: 6.005

3.  Spatial and Temporal Resolution of the Oxygen-Independent Photoinduced DNA Interstrand Cross-Linking by a Nitroimidazole Derivative.

Authors:  Abdelazim M A Abdelgawwad; Antonio Monari; Iñaki Tuñón; Antonio Francés-Monerris
Journal:  J Chem Inf Model       Date:  2022-06-30       Impact factor: 6.162

4.  Photochemical Generation of Benzyl Cations That Selectively Cross-Link Guanine and Cytosine in DNA.

Authors:  Yibin Wang; Shuo Liu; Zechao Lin; Yukai Fan; Yinsheng Wang; Xiaohua Peng
Journal:  Org Lett       Date:  2016-05-18       Impact factor: 6.005

5.  Independent Generation and Reactivity of Thymidine Radical Cations.

Authors:  Huabing Sun; Marisa L Taverna Porro; Marc M Greenberg
Journal:  J Org Chem       Date:  2017-10-10       Impact factor: 4.354

6.  Conformational polymorphism or structural invariance in DNA photoinduced lesions: implications for repair rates.

Authors:  François Dehez; Hugo Gattuso; Emmanuelle Bignon; Christophe Morell; Elise Dumont; Antonio Monari
Journal:  Nucleic Acids Res       Date:  2017-04-20       Impact factor: 16.971

  6 in total

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