Literature DB >> 16045337

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

In Seok Hong1, Marc M Greenberg.   

Abstract

DNA is the target of many anti-cancer therapies. These agents damage the biopolymer by oxidation or by alkylation. Interstrand DNA cross-links are believed to be the source of cytotoxicity of anti-tumor agents, such as mitomycin C, which alkylate the biopolymer. In contrast, deoxyguanosine oxidation is the result of reaction between DNA and singlet oxygen, which is the damaging species produced in photodynamic therapy. We have shown that, upon oxidation by singlet oxygen, an analogue of thymidine (2) rearranges to a methide, which forms DNA-DNA interstrand cross-links. This novel process suggests that 2 may be a useful adjuvant in photodynamic therapy.

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Year:  2005        PMID: 16045337      PMCID: PMC1352307          DOI: 10.1021/ja053493m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

1.  Thermodynamic versus kinetic products of DNA alkylation as modeled by reaction of deoxyadenosine.

Authors:  W F Veldhuyzen; A J Shallop; R A Jones; S E Rokita
Journal:  J Am Chem Soc       Date:  2001-11-14       Impact factor: 15.419

Review 2.  DNA interstrand crosslinks: natural and drug-induced DNA adducts that induce unique cellular responses.

Authors:  Orlando D Schärer
Journal:  Chembiochem       Date:  2005-01       Impact factor: 3.164

3.  Characterization of 5-hydroxy-8-oxo-7,8-dihydroguanosine in the photosensitized oxidation of 8-oxo-7,8-dihydroguanosine and its rearrangement to spiroiminodihydantoin.

Authors:  Jeremy E B McCallum; Corrie Y Kuniyoshi; Christopher S Foote
Journal:  J Am Chem Soc       Date:  2004-12-29       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

Review 5.  Bleomycins: towards better therapeutics.

Authors:  Jingyang Chen; JoAnne Stubbe
Journal:  Nat Rev Cancer       Date:  2005-02       Impact factor: 60.716

6.  Gel electrophoretic detection of 7,8-dihydro-8-oxoguanine and 7, 8-dihydro-8-oxoadenine via oxidation by Ir (IV).

Authors:  J G Muller; V Duarte; R P Hickerson; C J Burrows
Journal:  Nucleic Acids Res       Date:  1998-05-01       Impact factor: 16.971

7.  Singlet oxygen induces oxidation of cellular DNA.

Authors:  J L Ravanat; P Di Mascio; G R Martinez; M H Medeiros; J Cadet
Journal:  J Biol Chem       Date:  2000-12-22       Impact factor: 5.157

8.  Formation of a methide derivative upon photolysis of thymidine bromohydrins.

Authors:  Thierry Douki; Guillaume Vadesne-Bauer; Jean Cadet
Journal:  J Org Chem       Date:  2003-01-24       Impact factor: 4.354

Review 9.  Photodynamic therapy for cancer.

Authors:  Dennis E J G J Dolmans; Dai Fukumura; Rakesh K Jain
Journal:  Nat Rev Cancer       Date:  2003-05       Impact factor: 60.716

10.  Formation of 13C-, 15N-, and 18O-labeled guanidinohydantoin from guanosine oxidation with singlet oxygen. Implications for structure and mechanism.

Authors:  Yu Ye; James G Muller; Wenchen Luo; Charles L Mayne; Anthony J Shallop; Roger A Jones; Cynthia J Burrows
Journal:  J Am Chem Soc       Date:  2003-11-19       Impact factor: 15.419

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  32 in total

1.  ROS-inducible DNA cross-linking agent as a new anticancer prodrug building block.

Authors:  Sheng Cao; Yibin Wang; Xiaohua Peng
Journal:  Chemistry       Date:  2012-02-29       Impact factor: 5.236

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

Review 3.  Biological properties of single chemical-DNA adducts: a twenty year perspective.

Authors:  James C Delaney; John M Essigmann
Journal:  Chem Res Toxicol       Date:  2007-12-12       Impact factor: 3.739

4.  Multinuclear NMR and kinetic analysis of DNA interstrand cross-link formation.

Authors:  Hui Ding; Ananya Majumdar; Joel R Tolman; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

5.  Replication termination mechanism as revealed by Tus-mediated polar arrest of a sliding helicase.

Authors:  Deepak Bastia; Shamsu Zzaman; Gregor Krings; Mukesh Saxena; Xiaohua Peng; Marc M Greenberg
Journal:  Proc Natl Acad Sci U S A       Date:  2008-08-15       Impact factor: 11.205

6.  Reactivity of Nucleic Acid Radicals.

Authors:  Marc M Greenberg
Journal:  Adv Phys Org Chem       Date:  2016       Impact factor: 2.833

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

Authors:  Yunyan Kuang; Huabing Sun; J Craig Blain; Xiaohua Peng
Journal:  Chemistry       Date:  2012-08-31       Impact factor: 5.236

8.  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

9.  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

10.  Chain and conformation stability of solid-state DNA: implications for room temperature storage.

Authors:  Jacques Bonnet; Marthe Colotte; Delphine Coudy; Vincent Couallier; Joseph Portier; Bénédicte Morin; Sophie Tuffet
Journal:  Nucleic Acids Res       Date:  2009-12-07       Impact factor: 16.971

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