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Volumn 6, Issue 3, 2000, Pages 475-484

Reaction of HO• with guanine derivatives in aqueous solution: Formation of two different redox-active OH-adduct radicals and their unimolecular transformation reactions. Properties of G(-H)•

Author keywords

DNA oxidation; Electron transfer; Kinetics; Radicals

Indexed keywords

DEOXYGUANOSINE; DNA; DRUG DERIVATIVE; GUANINE; HYDROXYL RADICAL;

EID: 0034602912     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (189)

References (63)
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    • In addition, other derivatives such as 5,6-dihydroxycytosine or thymine (and thymidine) glycol have been used to assess oxidative damage inflicted upon DNA in vivo (see ref. [6]).
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    • For a review, see ref. [13].
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    • This is consistent with results reported previously (see ref. [21])
    • This is consistent with results reported previously (see ref. [21]).
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    • a for this compound (see ref. [32]).
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    • It is interesting that 8-hydroxy-derivatives of dGuo were also not formed on photochemical production (by sensitization by riboflavin) of the radical cation of dGuo in dilute aqueous solution of dGuo, in contrast to when the dGuo radical cation was generated in ds DNA, in which 8-HOdGuo was produced in high yield (see H. Kasai, Z. Yamaizumi, M.Berger, J. Cadet, J. Am. Chem. Soc. 1992, 114, 9692). This can be explained by assuming a much longer lifetime of the radical cation in DNA (K. Hildenbrand, D. Schulte-Frohlinde, Free Radical Res. Commun. 1990, 11, 195, have measured the lifetime of the deprotonated dGuo radical cation in ds DNA in aqueous solution to be 5 s, while in ss DNA its lifetime was too short to be measured) compared with the monomeric dGuo, such that only in ds DNA the very slow hydration reaction has a chance to proceed (an alternative is that the hydration reaction is much faster in ds DNA than in the case of the "monomeric" radical cation). For further discussion, see A. Spassky, D. Angelov, Biochemistry 1997, 36, 6571 and D. Angelov, A. Spassky, M. Berger, J. Cadet, J. Am. Chem. Soc. 1997, 119, 11373.
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    • It is interesting that 8-hydroxy-derivatives of dGuo were also not formed on photochemical production (by sensitization by riboflavin) of the radical cation of dGuo in dilute aqueous solution of dGuo, in contrast to when the dGuo radical cation was generated in ds DNA, in which 8-HOdGuo was produced in high yield (see H. Kasai, Z. Yamaizumi, M.Berger, J. Cadet, J. Am. Chem. Soc. 1992, 114, 9692). This can be explained by assuming a much longer lifetime of the radical cation in DNA (K. Hildenbrand, D. Schulte-Frohlinde, Free Radical Res. Commun. 1990, 11, 195, have measured the lifetime of the deprotonated dGuo radical cation in ds DNA in aqueous solution to be 5 s, while in ss DNA its lifetime was too short to be measured) compared with the monomeric dGuo, such that only in ds DNA the very slow hydration reaction has a chance to proceed (an alternative is that the hydration reaction is much faster in ds DNA than in the case of the "monomeric" radical cation). For further discussion, see A. Spassky, D. Angelov, Biochemistry 1997, 36, 6571 and D. Angelov, A. Spassky, M. Berger, J. Cadet, J. Am. Chem. Soc. 1997, 119, 11373.
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    • It is interesting that 8-hydroxy-derivatives of dGuo were also not formed on photochemical production (by sensitization by riboflavin) of the radical cation of dGuo in dilute aqueous solution of dGuo, in contrast to when the dGuo radical cation was generated in ds DNA, in which 8-HOdGuo was produced in high yield (see H. Kasai, Z. Yamaizumi, M.Berger, J. Cadet, J. Am. Chem. Soc. 1992, 114, 9692). This can be explained by assuming a much longer lifetime of the radical cation in DNA (K. Hildenbrand, D. Schulte-Frohlinde, Free Radical Res. Commun. 1990, 11, 195, have measured the lifetime of the deprotonated dGuo radical cation in ds DNA in aqueous solution to be 5 s, while in ss DNA its lifetime was too short to be measured) compared with the monomeric dGuo, such that only in ds DNA the very slow hydration reaction has a chance to proceed (an alternative is that the hydration reaction is much faster in ds DNA than in the case of the "monomeric" radical cation). For further discussion, see A. Spassky, D. Angelov, Biochemistry 1997, 36, 6571 and D. Angelov, A. Spassky, M. Berger, J. Cadet, J. Am. Chem. Soc. 1997, 119, 11373.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11373
    • Angelov, D.1    Spassky, A.2    Berger, M.3    Cadet, J.4
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    • Addition of water at a position other than C8 is conceivable.
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    • • my be due to an impurity in the ribose used.
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    • note
    • The remaining 13-18% are due to radicals formed by H-abstraction from the deoxyribose moiety.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.