Solid support synthesis of ester linked hydrophobic conjugates of oligonucleotides

被引:22
作者
Guzaev, A [1 ]
Lönnberg, H [1 ]
机构
[1] Univ Turku, Dept Chem, FIN-20140 Turku, Finland
基金
芬兰科学院;
关键词
carboxylic acids and derivatives; nucleic acid analogues; phosphoramidites;
D O I
10.1016/S0040-4020(99)00501-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel non-nucleosidic phosphoramidite building block 2 was employed for multiple modification of oligonucleotides with hydrophobic octyl groups. Hydrophobic sites are attached via potentially biodegradable ester bonds that are demonstrated to withstand the conditions of DNA deprotection. The chimeric oligonucleotides are capable of forming triple helix complexes that are stabilized by forming a hydrophobic clamp consisting of terminal octyl groups. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9101 / 9116
页数:16
相关论文
共 46 条
[1]   PREPARATION OF OLIGONUCLEOTIDE-DEXAMETHASONE CONJUGATES [J].
ACEDO, M ;
TARRASON, G ;
PIULATS, J ;
MANN, M ;
WILM, M ;
ERITJA, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (15) :1577-1580
[2]  
*APPL BIOS DIV P E, USER B, V85, P94
[3]   LOOPED OLIGONUCLEOTIDES FORM STABLE HYBRID COMPLEXES WITH A SINGLE-STRANDED-DNA [J].
AZHAYEVA, E ;
AZHAYEV, A ;
GUZAEV, A ;
HOVINEN, J ;
LONNBERG, H .
NUCLEIC ACIDS RESEARCH, 1995, 23 (07) :1170-1176
[4]  
BILLHEIMER JT, 1990, ADV CHOLESTEROL RES, P7
[5]  
BOUTORIN A, 1990, FEBS LETT, V254, P129
[6]  
BUNDGAARD H, 1985, DESIGN PRODRUGS
[7]  
Cook P.D., 1993, ANTISENSE RES APPL, P149
[8]  
COOK PD, 1991, ANTI-CANCER DRUG DES, V6, P585
[9]  
Cook PD, 1998, HANDB EXP PHARM, V131, P51
[10]   DIALKYLFORMAMIDINES - DEPURINATION RESISTANT N-6-PROTECTING GROUP FOR DEOXYADENOSINE [J].
FROEHLER, BC ;
MATTEUCCI, MD .
NUCLEIC ACIDS RESEARCH, 1983, 11 (22) :8031-8036