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嘧啶(6-4)嘧啶酮光加合物的荧光量子产率测定

Fluorescence quantum yield determination of pyrimidine (6-4) pyrimidone photoadducts.

作者信息

Blais J, Douki T, Vigny P, Cadet J

机构信息

L.P.C.B. (C.N.R.S. URA 198), Institut Curie et Université Pierre et Marie Curie, Paris, France.

出版信息

Photochem Photobiol. 1994 Apr;59(4):402-4. doi: 10.1111/j.1751-1097.1994.tb05055.x.

DOI:10.1111/j.1751-1097.1994.tb05055.x
PMID:8022882
Abstract

An extensive study of the fluorescence characteristics of pyrimidine (6-4) pyrimidone photoadducts, a major class of far-UV-induced DNA lesions, was carried out on dinucleoside monophosphate (6-4) photoadducts, including thymidylyl-(3'-->5')-thymidine (TpT), 2'-deoxycytidylyl-(3'-5')-thymidine, thymidylyl-(3'-->5')-2'-deoxycytidine, 2'-deoxyuridylyl-(3'-->5')-thymidine, 5-methyl-2'-deoxycytidylyl-(3'-5')- thymidine (6-4) photoadducts and the corresponding base (6-4) photoadducts, 6-4'-(5'-methylpyrimidin-2'-one) thymine (TT), 5-hydroxy-6-4'-(5'-methylpyrimidin-2'-one)-5,6-dihydrothymine (CT), 5-amino-6-4'-(pyrimidin-2'-one)-5,6-dihydrothymine (UC) obtained by mild acidic hydrolysis of the former derivatives. The fluorescence quantum yield (phi F) of these compounds was found to depend on one hand, on the nature of the two bases involved and the base substituent and, on the other hand, on the presence of the phosphate group. The hydrolysis of the phosphodiester bond was shown to enhance phi F, the larger effect being observed in the case of the thymine-thymine photoadducts with a seven-fold increase of the phi F value in the case of TT as compared to TpT (0.21 and 0.03, respectively). These results are discussed in terms of structural considerations.

摘要

对嘧啶(6-4)嘧啶酮光加合物(一类主要的远紫外线诱导的DNA损伤)的荧光特性进行了广泛研究,该研究针对二核苷单磷酸(6-4)光加合物展开,包括胸苷酰-(3'→5')-胸苷(TpT)、2'-脱氧胞苷酰-(3'-5')-胸苷、胸苷酰-(3'→5')-2'-脱氧胞苷、2'-脱氧尿苷酰-(3'→5')-胸苷、5-甲基-2'-脱氧胞苷酰-(3'-5')-胸苷(6-4)光加合物以及相应的碱基(6-4)光加合物,即6-4'-(5'-甲基嘧啶-2'-酮)胸腺嘧啶(TT)、5-羟基-6-4'-(5'-甲基嘧啶-2'-酮)-5,6-二氢胸腺嘧啶(CT)、5-氨基-6-4'-(嘧啶-2'-酮)-5,6-二氢胸腺嘧啶(UC),这些碱基(6-4)光加合物是通过对前体衍生物进行温和酸性水解得到的。发现这些化合物的荧光量子产率(φF)一方面取决于所涉及的两个碱基的性质和碱基取代基,另一方面取决于磷酸基团的存在。结果表明,磷酸二酯键的水解会提高φF,在胸腺嘧啶-胸腺嘧啶光加合物的情况下观察到的影响更大,与TpT相比,TT的φF值增加了七倍(分别为0.21和0.03)。从结构方面对这些结果进行了讨论。

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