FLUORESCENCE QUANTUM YIELD DETERMINATION OF PYRIMIDINE(6-4) PYRIMIDONE PHOTOADDUCTS

被引:24
作者
BLAIS, J
DOUKI, T
VIGNY, P
CADET, J
机构
[1] UNIV PARIS 06,F-75231 PARIS 05,FRANCE
[2] CEA,DEPT RECH FONDAMENTALE MAT CONDENSEE,SESAM,LAN,F-38041 GRENOBLE,FRANCE
关键词
D O I
10.1111/j.1751-1097.1994.tb05055.x
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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'-melhylpyrimidin-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.
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收藏
页码:402 / 404
页数:3
相关论文
共 14 条
  • [1] [Anonymous], 1970, PHOTOPHYSICS AROMATI
  • [2] BRASH DE, 1988, PHOTOCHEM PHOTOBIOL, V48, P59
  • [3] Cadet J., 1990, BIOORGANIC PHOTOCHEM, P1
  • [4] CHATTOPADHYAYA JB, 1979, TETRAHEDRON LETT, P5059
  • [5] CHARACTERIZATION OF THE (6-4) PHOTOPRODUCT OF 2'-DEOXYCYTIDYLYL-(3'-GREATER-THAN-5')-THYMIDINE AND OF ITS DEWAR VALENCE ISOMER
    DOUKI, T
    VOITURIEZ, L
    CADET, J
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1991, 53 (03) : 293 - 297
  • [6] DOUKI T, 1991, Photochemistry and Photobiology, V53, p27S
  • [7] PYRIMIDINE ADDUCT FLUORESCENCE IN UV IRRADIATED NUCLEIC-ACIDS
    HAUSWIRTH, W
    WANG, SY
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1973, 51 (03) : 819 - 826
  • [8] EXCITED-STATE PROCESSES AND SOLUTION CONFORMATION OF DIPYRIMIDINE ADDUCTS
    HAUSWIRTH, W
    WANG, SY
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1977, 25 (02) : 161 - 166
  • [9] MITCHELL DL, 1988, PHOTOCHEM PHOTOBIOL, V48, P51
  • [10] THE BIOLOGY OF THE (6-4) PHOTOPRODUCT
    MITCHELL, DL
    NAIRN, RS
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1989, 49 (06) : 805 - 819