Synthesis, biophysical properties, and nuclease resistance properties of mired backbone oligodeoxynucleotides containing cationic internucleoside guanidinium linkages: Deoxynucleic guanidine/DNA chimeras

被引：60

作者：

Barawkar, DA ^{[1
]}

Bruice, TC ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem, Santa Barbara, CA 93106 USA

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 1998年 / 95卷 / 19期

关键词：

antisense; hybrid duplex; cationic oligonucleotide; DNR capping; exonuclease;

D O I：

10.1073/pnas.95.19.11047

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

The synthesis of mixed backbone oligodeoxynucleotides (18-mers) consisting of positively charged guanidinium linkages along with negatively charged phosphodiester linkages is carried out. The use of a base labile-protecting group for guanidinium linkage offers a synthetic strategy similar to standard oligonucleotide synthesis. The nuclease resistance of the oligodeoxyribonucleotides capped with guanidinium linkages at 5' and 3' ends are reported. The hybridization properties and sequence specificity of binding of these deoxynucleic guanidine/DNA chimeras with complementary DNA or RNA are described.

引用

页码：11047 / 11052

页数：6

共 28 条

[1] Synthesis of protected guanidinium linked dinucleoside incorporable into an oligonucleotide using solid phase DNA methodology [J].

Barawkar, DA ;

Linkletter, B ;

Bruice, TC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) :1517-1520

[2] Triplex formation at physiological pH by 5-Me-dC-N-4-(spermine) [X] oligodeoxynucleotides: Non protonation of N3 in X of X*G:C triad and effect of base mismatch ionic strength on triplex stabilities [J].

Barawkar, DA ;

Rajeev, KG ;

Kumar, VA ;

Ganesh, KN .

NUCLEIC ACIDS RESEARCH, 1996, 24 (07) :1229-1237

[3] Fidelity of binding of the guanidinium nucleic acid (DNG) d(Tg)(4)-T-azido with short strand DNA oligomers (A(5)G(3)A(5), GA(4)G(3)A(4)G, G(2)A(3)G(3)A(3)G(2), G(2)A(2)G(5)A(2)G(2)). A kinetic and thermodynamic study [J].

Blasko, A ;

Minyat, EE ;

Dempcy, RO ;

Bruice, TC .

BIOCHEMISTRY, 1997, 36 (25) :7821-7831

[4]

Connolly B. A., 1992, V211, P36

[5]

COOK PD, 1991, ANTI-CANCER DRUG DES, V6, P585

[6] Amide backbones with conformationally restricted furanose rings: Highly improved affinity of the modified oligonucleotides for their RNA complements [J].

DeMesmaeker, A ;

Lesueur, C ;

Bevierre, MO ;

Waldner, A ;

Fritsch, V ;

Wolf, RM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2790-2794

[7] ANTISENSE OLIGONUCLEOTIDES [J].

DEMESMAEKER, A ;

HANER, R ;

MARTIN, P ;

MOSER, HE .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) :366-374

[8] SYNTHESIS OF THE POLYCATION THYMIDYL DNG, ITS FIDELITY IN BINDING POLYANIONIC DNA/RNA, AND THE STABILITY AND NATURE OF THE HYBRID COMPLEXES [J].

DEMPCY, RO ;

BROWNE, KA ;

BRUICE, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :6140-6141

[9] Design and synthesis of ribonucleic guanidine: A polycationic analog of RNA [J].

Dempcy, RO ;

Luo, J ;

Bruice, TC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (09) :4326-4330

[10] OLIGONUCLEOTIDES WITH NOVEL, CATIONIC BACKBONE SUBSTITUENTS - AMINOETHYLPHOSPHONATES [J].

FATHI, R ;

HUANG, Q ;

COPPOLA, G ;

DELANEY, W ;

TEASDALE, R ;

KRIEG, AM ;

COOK, AF .

NUCLEIC ACIDS RESEARCH, 1994, 22 (24) :5416-5424

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