SYNTHESIS AND INCORPORATION OF METHYLENEOXY(METHYLIMINO) LINKED THYMIDINE DIMER INTO ANTISENSE OLIGONUCLEOSIDES

被引:20
作者
DEBART, F [1 ]
VASSEUR, JJ [1 ]
SANGHVI, YS [1 ]
COOK, PD [1 ]
机构
[1] ISIS PHARMACEUT,2280 FARADAY AVE,CARLSBAD,CA 92008
关键词
ANTISENSE; OLIGONUCLEOTIDES; NUCLEOSIDES; THYMIDINE DIMER; PHOSPHATE BACKBONE;
D O I
10.1016/S0960-894X(00)80412-6
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A convenient synthesis of a thymidine (T) nucleoside dimer (T-3'-CH2-0-NCH3-5'-T) 12 has been accomPlished via a nucleoside coupling reaction. An alternative synthesis of 3'-deoxy-3'-C-hydroxymethylthymidine is described. The new dimer and methodology is useful for the development of backbone-modified antisense oligonucleosides.
引用
收藏
页码:1479 / 1482
页数:4
相关论文
共 26 条
[1]   ALDOL REACTION OF NUCLEOSIDE 5'-CARBOXALDEHYDES WITH ACETONE - SYNTHESIS OF 5'-C-CHAIN EXTENDED THYMIDINE DERIVATIVES [J].
CAMARASA, MJ ;
DELASHERAS, FG ;
PEREZPEREZ, MJ .
NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (04) :533-546
[2]  
COOK PD, 1991, ANTI-CANCER DRUG DES, V6, P585
[3]  
CROOKE ST, 1992, ANNU REV PHARMACOL, V32, P329
[4]   IMPROVED FREE-ENERGY PARAMETERS FOR PREDICTIONS OF RNA DUPLEX STABILITY [J].
FREIER, SM ;
KIERZEK, R ;
JAEGER, JA ;
SUGIMOTO, N ;
CARUTHERS, MH ;
NEILSON, T ;
TURNER, DH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (24) :9373-9377
[5]   EFFECTS OF PHOSPHOROTHIOATE CAPPING ON ANTISENSE OLIGONUCLEOTIDE STABILITY, HYBRIDIZATION AND ANTIVIRAL EFFICACY VERSUS HERPES-SIMPLEX VIRUS-INFECTION [J].
HOKE, GD ;
DRAPER, K ;
FREIER, SM ;
GONZALEZ, C ;
DRIVER, VB ;
ZOUNES, MC ;
ECKER, DJ .
NUCLEIC ACIDS RESEARCH, 1991, 19 (20) :5743-5748
[6]   BUILDING-BLOCKS FOR OLIGONUCLEOTIDE ANALOGS WITH DIMETHYLENE SULFIDE, SULFOXIDE, AND SULFONE GROUPS REPLACING PHOSPHODIESTER LINKAGES [J].
HUANG, Z ;
SCHNEIDER, KC ;
BENNER, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3869-3882
[7]  
IVERSEN P, 1991, ANTI-CANCER DRUG DES, V6, P531
[8]   CELLULAR UPTAKE OF ANTISENSE OLIGODEOXYNUCLEOTIDES [J].
JAROSZEWSKI, JW ;
COHEN, JS .
ADVANCED DRUG DELIVERY REVIEWS, 1991, 6 (03) :235-250
[9]  
KOSTER H, 1982, TETRAHEDRON LETT, V26, P2641
[10]   DEOXYOLIGONUCLEOTIDES BEARING NEUTRAL ANALOGS OF PHOSPHODIESTER LINKAGES RECOGNIZE DUPLEX DNA VIA TRIPLE-HELIX FORMATION [J].
MATTEUCCI, M ;
LIN, KY ;
BUTCHER, S ;
MOULDS, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7767-7768