Hybridization properties of base-modified oligonucleotides within the double and triple helix motif

被引:104
作者
Luyten, I [1 ]
Herdewijn, P [1 ]
机构
[1] Katholieke Univ Leuven, Rega Inst Med Res, Med Chem Lab, B-3000 Leuven, Belgium
关键词
modified nucleobase; oligomers; stability; hybridization properties; base pairing;
D O I
10.1016/S0223-5234(98)80016-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In this review we describe the influence of modified nucleobases in order to understand the changes they introduce in double and triple helix forming oligomers with the aim to study their potential therapeutic use in the antisense/antigene/ribozyme field. The hybridization properties of the studied modified oligomers depend on the structure of the modified nucleoside, the number of modifications, the selected sequence and the location of the modified nucleoside along the sequence. Unfortunately, most available information is based on melting point determination, eventually CD experiments and only in a few cases on X-ray and NMR studies which makes it difficult to put forward general rules for predicting modified nucleic acid structures. On the other hand, several of the described base modifications allow us to select new oligonucleotides with improved properties in the different application fields. (C) Elsevier, Paris.
引用
收藏
页码:515 / 576
页数:62
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共 466 条
  • [1] Insertion of 5-methyl-N-4-(1-pyrenylmethyl)cytidine into DNA. Duplex, three-way junction and triplex stabilities.
    AbdelRahman, AAH
    Ali, OM
    Pedersen, EB
    [J]. TETRAHEDRON, 1996, 52 (48) : 15311 - 15324
  • [2] SYNTHESIS AND BIOPHYSICAL AND BIOLOGICAL PROPERTIES OF OLIGONUCLEOTIDES CONTAINING 2-AZA-2'-DEOXYINOSINE
    ACEDO, M
    DECLERCQ, E
    ERITJA, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) : 6262 - 6269
  • [3] A CONVENIENT SYNTHESIS OF S-CYANOETHYL-PROTECTED 4-THIOURIDINE AND ITS INCORPORATION INTO OLIGORIBONUCLEOTIDES
    ADAMS, CJ
    MURRAY, JB
    ARNOLD, JRP
    STOCKLEY, PG
    [J]. TETRAHEDRON LETTERS, 1994, 35 (05) : 765 - 768
  • [4] INCORPORATION OF 6-THIOINOSINE INTO OLIGORIBONUCLEOTIDES
    ADAMS, CJ
    FARROW, MA
    MURRAY, JB
    KELLY, SM
    PRICE, NC
    STOCKLEY, PG
    [J]. TETRAHEDRON LETTERS, 1995, 36 (26) : 4637 - 4640
  • [5] FLUORESCENT OLIGONUCLEOTIDES AND DEOXYNUCLEOTIDE TRIPHOSPHATES - PREPARATION AND THEIR INTERACTION WITH THE LARGE (KLENOW) FRAGMENT OF ESCHERICHIA-COLI DNA-POLYMERASE-I
    ALLEN, DJ
    DARKE, PL
    BENKOVIC, SJ
    [J]. BIOCHEMISTRY, 1989, 28 (11) : 4601 - 4607
  • [6] A chemical method for site-specific modification of RNA: The convertible nucleoside approach
    Allerson, CR
    Chen, SL
    Verdine, GL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) : 7423 - 7433
  • [7] NUCLEOSIDES AND NUCLEOTIDES .22. SYNTHESIS OF A TRIDECANUCLEOSIDE DODECAPHOSPHATE CONTAINING THE UNNATURAL BASE 2(1H)-PYRIMIDINONE
    ALTERMATT, R
    TAMM, C
    [J]. HELVETICA CHIMICA ACTA, 1985, 68 (02) : 475 - 482
  • [8] THE STABILITY OF OLIGODEOXYRIBONUCLEOTIDE DUPLEXES CONTAINING DEGENERATE BASES
    ANAND, NN
    BROWN, DM
    SALISBURY, SA
    [J]. NUCLEIC ACIDS RESEARCH, 1987, 15 (20) : 8167 - 8176
  • [9] Synthesis of modified oligonucleotides and production of duplexes with covalently linked chains
    Antsypovich, SI
    Oretskaya, TS
    Volkov, EM
    Romanova, EA
    Tashlitsky, VN
    Blumenfeld, M
    Shabarova, ZA
    [J]. NUCLEOSIDES & NUCLEOTIDES, 1996, 15 (04): : 923 - 936
  • [10] OLIGONUCLEOTIDES TETHERED VIA NUCLEIC BASES - A POTENTIAL NEW SET OF COMPOUNDS FOR ALTERNATE STRAND TRIPLE-HELIX FORMATION
    ASSELINE, U
    THUONG, NT
    [J]. TETRAHEDRON LETTERS, 1993, 34 (26) : 4173 - 4176