Kun-hui Liu, Li-dan Wu, Xiao-ran Zou, Wen Yang, Qian Du, Hong-mei Su. Photochemical Hydrogen Abstraction and Electron Transfer Reactions of Tetrachlorobenzoquinone with Pyrimidine Nucleobases[J]. Chinese Journal of Chemical Physics , 2011, 24(5): 580-585. doi: 10.1088/1674-0068/24/05/580-585
Citation: Kun-hui Liu, Li-dan Wu, Xiao-ran Zou, Wen Yang, Qian Du, Hong-mei Su. Photochemical Hydrogen Abstraction and Electron Transfer Reactions of Tetrachlorobenzoquinone with Pyrimidine Nucleobases[J]. Chinese Journal of Chemical Physics , 2011, 24(5): 580-585. doi: 10.1088/1674-0068/24/05/580-585

Photochemical Hydrogen Abstraction and Electron Transfer Reactions of Tetrachlorobenzoquinone with Pyrimidine Nucleobases

doi: 10.1088/1674-0068/24/05/580-585
Funds:  This work was supported by the National Natural Sci-ence Foundation of China (No.20903104, No.21073201, and No.20733005) and the Chinese Academy of Sci-ences.
  • Received Date: 2011-08-22
  • Pentachlorophenol, a widespread environmental pollutant that is possibly carcinogenic to humans, is metabolically oxidized to tetrachloroquinone (TCBQ) which can result in DNA damage. We have investigated the photochemical reaction dynamics of TCBQ with two pyrimidine type nucleobases (thymine and uracil) upon UVA (355 nm) excitation using the technique of nanosecond time-resolved laser flash photolysis. It has been found that 355 nm excitation populates TCBQ molecules to their triplet state 3TCBQ*, which are highly reactive towards thymine or uracil and undergo two parallel reactions, the hydrogen abstraction and electron transfer, leading to the observed photoproducts of TCBQH· and TCBQ·- in transient absorption spectra. The concomitantly produced nucleobase radicals and radical cations are expected to induce a series of oxidative or strand cleavage damage to DNA afterwards. By characterizing the photochemical hydrogen abstraction and electron transfer reactions, our results provide potentially important molecular reaction mechanisms for understanding the carcinogenic effects of pentachlorophenol and its metabolites TCBQ.
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Photochemical Hydrogen Abstraction and Electron Transfer Reactions of Tetrachlorobenzoquinone with Pyrimidine Nucleobases

doi: 10.1088/1674-0068/24/05/580-585
Funds:  This work was supported by the National Natural Sci-ence Foundation of China (No.20903104, No.21073201, and No.20733005) and the Chinese Academy of Sci-ences.

Abstract: Pentachlorophenol, a widespread environmental pollutant that is possibly carcinogenic to humans, is metabolically oxidized to tetrachloroquinone (TCBQ) which can result in DNA damage. We have investigated the photochemical reaction dynamics of TCBQ with two pyrimidine type nucleobases (thymine and uracil) upon UVA (355 nm) excitation using the technique of nanosecond time-resolved laser flash photolysis. It has been found that 355 nm excitation populates TCBQ molecules to their triplet state 3TCBQ*, which are highly reactive towards thymine or uracil and undergo two parallel reactions, the hydrogen abstraction and electron transfer, leading to the observed photoproducts of TCBQH· and TCBQ·- in transient absorption spectra. The concomitantly produced nucleobase radicals and radical cations are expected to induce a series of oxidative or strand cleavage damage to DNA afterwards. By characterizing the photochemical hydrogen abstraction and electron transfer reactions, our results provide potentially important molecular reaction mechanisms for understanding the carcinogenic effects of pentachlorophenol and its metabolites TCBQ.

Kun-hui Liu, Li-dan Wu, Xiao-ran Zou, Wen Yang, Qian Du, Hong-mei Su. Photochemical Hydrogen Abstraction and Electron Transfer Reactions of Tetrachlorobenzoquinone with Pyrimidine Nucleobases[J]. Chinese Journal of Chemical Physics , 2011, 24(5): 580-585. doi: 10.1088/1674-0068/24/05/580-585
Citation: Kun-hui Liu, Li-dan Wu, Xiao-ran Zou, Wen Yang, Qian Du, Hong-mei Su. Photochemical Hydrogen Abstraction and Electron Transfer Reactions of Tetrachlorobenzoquinone with Pyrimidine Nucleobases[J]. Chinese Journal of Chemical Physics , 2011, 24(5): 580-585. doi: 10.1088/1674-0068/24/05/580-585

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