REMARKABLE ENHANCEMENT OF BINDING-AFFINITY OF HETEROCYCLE-MODIFIED DNA TO DNA AND RNA - SYNTHESIS, CHARACTERIZATION AND BIOPHYSICAL EVALUATION OF N-2-IMIDAZOLYLPROPYLGUANINE AND N-2-IMIDAZOLYLPROPYL-2-AMINOADENINE MODIFIED OLIGONUCLEOTIDES

被引:38
作者
RAMASAMY, KS
ZOUNES, M
GONZALEZ, C
FREIER, SM
LESNIK, EA
CUMMINS, LL
GRIFFEY, RH
MONIA, BP
COOK, PD
机构
[1] ISIS Pharmaceuticals, Carlsbad, CA 92008
关键词
D O I
10.1016/S0040-4039(00)76514-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oligonucleotides containing novel N-2-Imidazolylpropylguanine and N-2-Imidazolylpropyl-2-aminoadenine moieties were synthesized and studied for their hybridization and biophysical properties. Interestingly, these heterocycle modified oligonucleotides showed a remarkable enhancement of heteroduplex binding affinity when hybridized to complementary DNA.
引用
收藏
页码:215 / 218
页数:4
相关论文
共 21 条
[1]   SITE-SPECIFIC EXCISION FROM RNA BY RNASE-H AND MIXED-PHOSPHATE-BACKBONE OLIGODEOXYNUCLEOTIDES [J].
AGRAWAL, S ;
MAYRAND, SH ;
ZAMECNIK, PC ;
PEDERSON, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (04) :1401-1405
[2]  
BRESLAUER KJ, 1991, P NATL ACAD SCI USA, V8, P3746
[3]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF SELECTED 2,6-DISUBSTITUTED-(2-DEOXY-ALPHA-D-ERYTHRO-PENTOFURANOSYL) AND -BETA-D-ERYTHRO-PENTOFURANOSYL)PURINES [J].
CHRISTENSEN, LF ;
BROOM, AD .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (07) :735-+
[4]  
COOK PD, 1991, ANTI-CANCER DRUG DES, V6, P585
[5]  
COOK PD, 1993, MED CHEM STRATEGIES
[6]   PATHWAYS OF DEGRADATION AND MECHANISM OF ACTION OF ANTISENSE OLIGONUCLEOTIDES IN XENOPUS-LAEVIS EMBRYOS [J].
DAGLE, JM ;
WEEKS, DL ;
WALDER, JA .
ANTISENSE RESEARCH AND DEVELOPMENT, 1991, 1 (01) :11-20
[7]  
Freier SM, 1992, GENE REGULATION BIOL, P95
[8]   THE PARA-NITROPHENYLETHYL (NPE) GROUP - A VERSATILE NEW BLOCKING GROUP FOR PHOSPHATE AND AGLYCONE PROTECTION IN NUCLEOSIDES AND NUCLEOTIDES [J].
HIMMELSBACH, F ;
SCHULZ, BS ;
TRICHTINGER, T ;
CHARUBALA, R ;
PFLEIDERER, W .
TETRAHEDRON, 1984, 40 (01) :59-72
[9]   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
[10]   SYNTHESIS OF VARIOUS BRANCHED TRIRIBONUCLEOSIDE DIPHOSPHATES BY SITE-SPECIFIC MODIFICATION OF A DIPHENYLCARBAMOYL-PROTECTED GUANINE RESIDUE [J].
HUSS, S ;
GOSSELIN, G ;
IMBACH, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :499-506