Design of artificial nucleobases for the recognition of the AT inversion by triple-helix forming oligonucleotides: A structure stability relationship study and neighbour bases effect

被引:45
作者
Guianvarc'h, D
Fourrey, JL
Maurisse, R
Sun, HS
Benhida, R
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[2] Univ Nice, UMR 6001 CNRS, Chim Bioorgan Lab, F-06108 Nice 2, France
[3] Museum Natl Hist Nat, UMR 8646 CNRS, UR 565 INSERM, Biophys Lab, F-75231 Paris 05, France
关键词
D O I
10.1016/S0968-0896(03)00229-3
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
We report herein on the synthesis, the incorporation into triplex forming oligonucleotides (TFO) and the recognition properties of a series of synthetic nucleosides designed for the specific recognition of an inverted A.T base pair in a pyrimidine triple helix motif. These analogues were designed on the basis of the results obtained with our previously reported compounds S and B-t, in order to define a structure-stability relationship. We report also on the chemical nature effect of the bases flanking S in the case of S-containing TFOs, in order to get further informations about the recognition process within the A.TxS triplet. This study establishes guidelines for the conception of more potent analogues for the recognition of both A.T and G.C inverted base pairs. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2751 / 2759
页数:9
相关论文
共 31 条
  • [1] BASHA A, 1977, TETRAHEDRON LETT, P4171
  • [2] Synthesis of 6-allyl and 6-heteroarylindoles by palladium catalyzed Stille cross-coupling reaction
    Benhida, R
    Lecubin, F
    Fourrey, JL
    Castellanos, LR
    Quintero, L
    [J]. TETRAHEDRON LETTERS, 1999, 40 (31) : 5701 - 5703
  • [3] ENERGETICS OF FORMATION OF 16 TRIPLE-HELICAL COMPLEXES WHICH VARY AT A SINGLE POSITION WITHIN A PYRIMIDINE MOTIF
    BEST, GC
    DERVAN, PB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (04) : 1187 - 1193
  • [4] Towards a general triple helix mediated DNA recognition scheme
    Doronina, SO
    Behr, JP
    [J]. CHEMICAL SOCIETY REVIEWS, 1997, 26 (01) : 63 - 71
  • [5] AZOLE SUBSTITUTED OLIGONUCLEOTIDES PROMOTE ANTIPARALLEL TRIPLEX FORMATION AT NON-HOMOPURINE DUPLEX TARGETS
    DURLAND, RH
    RAO, TS
    BODEPUDI, V
    SETH, DM
    JAYARAMAN, K
    REVANKAR, GR
    [J]. NUCLEIC ACIDS RESEARCH, 1995, 23 (04) : 647 - 653
  • [6] TRIPLEX DNA STRUCTURES
    FRANKKAMENETSKII, MD
    MIRKIN, SM
    [J]. ANNUAL REVIEW OF BIOCHEMISTRY, 1995, 64 : 65 - 95
  • [7] Progress in developments of triplex-based strategies
    Giovannangeli, C
    Helene, C
    [J]. ANTISENSE & NUCLEIC ACID DRUG DEVELOPMENT, 1997, 7 (04): : 413 - 421
  • [8] Towards mixed sequence recognition by triple helix formation
    Gowers, DM
    Fox, KR
    [J]. NUCLEIC ACIDS RESEARCH, 1999, 27 (07) : 1569 - 1577
  • [9] ENERGETICS OF FORMATION OF 16 TRIPLE-HELICAL COMPLEXES WHICH VARY AT A SINGLE POSITION WITHIN A PURINE MOTIF
    GREENBERG, WA
    DERVAN, PB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (18) : 5016 - 5022
  • [10] RECOGNITION OF ALL 4 BASE-PAIRS OF DOUBLE-HELICAL DNA BY TRIPLE-HELIX FORMATION - DESIGN OF NONNATURAL DEOXYRIBONUCLEOSIDES FOR PYRIMIDINE.PURINE BASE PAIR BINDING
    GRIFFIN, LC
    KIESSLING, LL
    BEAL, PA
    GILLESPIE, P
    DERVAN, PB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 7976 - 7982