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Literature DB >> 12553783

A potent, water-soluble and photoinducible DNA cross-linking agent.

Ping Wang¹, Renpeng Liu, Xiaojun Wu, Hongjuan Ma, Xiaoping Cao, Ping Zhou, Jiangye Zhang, Xiaocheng Weng, Xiao-Lian Zhang, Jun Qi, Xiang Zhou, Linhong Weng.

Abstract

Water-soluble DNA cross-linking phenol and biphenol derivatives 3 and 6 have been synthesized by a Mannich reaction. Both of them can cross-link DNA by photoactivation using visible light (wavelength > 400 nm). Compound 6 can cross-link DNA at pH 5.0 and 7.7, whereas no cross-link was observed at pH 10.0. Density functional theory (DFT) calculation indicated that 6 displays a twist structure. Therefore, it could bind to DNA naturally and has potent property to cross-link DNA after photoactivation.

Entities: Chemical

Mesh：

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Year: 2003 PMID： 12553783 DOI： 10.1021/ja029040o

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

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Cited

13 in total

A potent, water-soluble and photoinducible DNA cross-linking agent.

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

2. Selective and Reversible Photochemical Derivatization of Cysteine Residues in Peptides and Proteins.

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

4. Unraveling Reversible DNA Cross-Links with a Biological Machine.

5. Hydrogen peroxide inducible DNA cross-linking agents: targeted anticancer prodrugs.

6. Substituents on quinone methides strongly modulate formation and stability of their nucleophilic adducts.

7. Directing Quinone Methide-Dependent Alkylation and Cross-Linking of Nucleic Acids with Quaternary Amines.

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

9. A diazirine-based nucleoside analogue for efficient DNA interstrand photocross-linking.

10. Imines that react with phenols in water over a wide pH range.