A novel DNA hairpin substrate for bleomycin

被引:16
作者
Akiyama, Yoshitsugu [1 ]
Ma, Qian [1 ]
Edgar, Erin [2 ]
Laikhter, Andrei [2 ]
Hecht, Sidney M. [1 ]
机构
[1] Univ Virginia, Dept Biol & Chem, Charlottesville, VA 22904 USA
[2] Integrated DNA Technologies, Coralville, IA 52241 USA
关键词
D O I
10.1021/ol800445x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 16-nucleotide DNA hairpin containing 4-aminobenzo[g]quinazoline-2-one 2'-deoxyribose at position 15 has been prepared and found to lack significant fluorescence, When treated with Fe(II).BLM, the hairpin was found to undergo oxidative transformation selectively at position 15. The predominant fluorescent product was characterized and quantified. The pro-fluorescent DNA hairpin was used as a substrate for 15 bleomycin congeners, and the results were compared with those obtained following cleavage of a radiolabeled DNA duplex and PAGE analysis.
引用
收藏
页码:2127 / 2130
页数:4
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共 66 条
  • [1] RNA cleavage and inhibition of protein synthesis by bleomycin
    Abraham, AT
    Lin, JJ
    Newton, DL
    Rybak, S
    Hecht, SM
    [J]. CHEMISTRY & BIOLOGY, 2003, 10 (01): : 45 - 52
  • [2] TOTAL SYNTHESIS OF (-)-PYRIMIDOBLAMIC ACID AND DEGLYCOBLEOMYCIN A2
    BOGER, DL
    MENEZES, RF
    HONDA, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (02): : 273 - 275
  • [3] Definition of the effect and role of the bleomycin A2 valerate substituents:: Preorganization of a rigid, compact conformation implicated in sequence-selective DNA cleavage
    Boger, DL
    Ramsey, TM
    Cai, H
    Hoehn, ST
    Stubbe, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) : 9149 - 9158
  • [4] A systematic evaluation of the bleomycin A2 L-threonine side chain:: Its role in preorganization of a compact conformation implicated in sequence-selective DNA cleavage
    Boger, DL
    Ramsey, TM
    Cai, H
    Hoehn, ST
    Stubbe, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) : 9139 - 9148
  • [5] SYNTHESIS AND EVALUATION OF THE FULLY FUNCTIONALIZED BLEOMYCIN A(2) METAL-BINDING DOMAIN-CONTAINING THE 2-O-(3-O-CARBAMOYL-ALPHA-D-MANNOPYRANOSYL)-ALPHA-L-GULOPYRANOSYL DISACCHARIDE
    BOGER, DL
    TERAMOTO, S
    HONDA, T
    ZHOU, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) : 7338 - 7343
  • [6] KEY SYNTHETIC ANALOGS OF BLEOMYCIN A(2) THAT DIRECTLY ADDRESS THE EFFECT AND ROLE OF THE DISACCHARIDE - DEMANNOSYLBLEOMYCIN A(2) AND ALPHA-D-MANNOPYRANOSYLDEGLYCOBLEOMYCIN A(2)
    BOGER, DL
    TERAMOTO, S
    ZHOU, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) : 7344 - 7356
  • [7] Assessment of the role of the bleomycin A2 pyrimidoblamic acid C4 amino group
    Boger, DL
    Ramsey, TM
    Cai, H
    Hoehn, ST
    Kozarich, JW
    Stubbe, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) : 53 - 65
  • [8] Deglycosylated bleomycin induces apoptosis in lymphorna cell via c-jun NH2-terminal kinase but not reactive oxygen species
    Brahim, Souhir
    Prevotat, Laurent
    Yatouji, Sonia
    Merino, Delphine
    Cortier, Marion
    Rebe, Cedric
    Micheau, Olivier
    Kenani, Abderraouf
    Bettaieb, Ali
    [J]. BIOCHEMICAL PHARMACOLOGY, 2007, 74 (10) : 1445 - 1455
  • [9] SITE-SPECIFIC CLEAVAGE OF RNA BY FE(II).BLEOMYCIN
    CARTER, BJ
    DEVROOM, E
    LONG, EC
    VANDERMAREL, GA
    VANBOOM, JH
    HECHT, SM
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (23) : 9373 - 9377
  • [10] Bleomycins: Towards better therapeutics
    Chen, JY
    Stubbe, J
    [J]. NATURE REVIEWS CANCER, 2005, 5 (02) : 102 - 112