Literature DB >> 27191599

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

Yibin Wang1, Shuo Liu2, Zechao Lin1, Yukai Fan1, Yinsheng Wang2, Xiaohua Peng1.   

Abstract

UV irradiation of several aryl boronates efficiently produced bifunctional benzyl cations that selectively form guanine-cytosine cross-links in DNA. Photoinduced homolysis of the C-Br bond took place with the aryl boronate bromides 3a and 4a, generating free radicals that were oxidized to benzyl cations via electron transfer. However, photoirradiation of the quaternary ammonium salts 3b and 4b led to heterolysis of C-N bond, directly producing benzyl cations. The electron-donating group in the aromatic ring greatly enhanced cross-linking efficiency.

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Year:  2016        PMID： 27191599      PMCID： PMC5609456          DOI： 10.1021/acs.orglett.6b00755

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  40 in total

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Review 3.  Psoralens as photoactive probes of nucleic acid structure and function: organic chemistry, photochemistry, and biochemistry.

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5.  Nucleoside-based diarylethene photoswitches and their facile incorporation into photoswitchable DNA.

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7.  Chemical structure and properties of interstrand cross-links formed by reaction of guanine residues with abasic sites in duplex DNA.

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8.  Nucleotide excision repair of a DNA interstrand cross-link produces single- and double-strand breaks.

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10.  Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.

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  2 in total

1.  Hydrogen peroxide activated quinone methide precursors with enhanced DNA cross-linking capability and cytotoxicity towards cancer cells.

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Journal:  Eur J Med Chem       Date:  2017-03-24       Impact factor: 6.514

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

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  2 in total

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