2-methyladenosine-substituted 2′,5′-oligoadenylates:: Conformations, 2-5A binding and catalytic activities with human ribonuclease L

被引：6

作者：

Kitade, Y ^{[1
]}

Wakana, M

Tsuboi, T

Yatome, C

Bayly, SF

Player, MR

Torrence, PF

机构：

[1] Gifu Univ, Fac Engn, Dept Biomol Sci, Lab Mol Biochem, Gifu 5011193, Japan

[2] NIDDKD, Sect Biomed Chem, Med Chem Lab, NIH, Bethesda, MD 20892 USA

[3] No Arizona Univ, Dept Chem, Flagstaff, AZ 86011 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 04期

关键词：

D O I：

10.1016/S0960-894X(99)00703-9

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

2-Methyladenosine-substituted analogues of 2-5A, p5'A2'p5'A2'p5'(me(2)A), p5'(me(2)A)2'p5'A2'p5'A, and p5'(me(2)A) 2'p5'(me(2)A)2'p5'(me(2)A), were prepared via a modification of a lead ion-catalyzed ligation reaction. These 5'-monophosphates were subsequently converted into the corresponding 5'-triphosphates. Both binding and activation of human recombinant RNase L by various 2-methyladenosine-substituted 2-5A analogues were examined. Among the 2-5A analogues, p5'A2'p5'A2'p5'(me(2)A) showed the strongest binding affinity and was as effective as 2-5A itself as an activator of RNase L. The CD spectra of both p5'(me(2)A)2'p5'A2'p5'A and p5'A2'p5'A2'p5'(me(2)A) were superimposable on that of p5'A2'p5'A2'p5'A. indicative of an anti orientation about the base-glycoside bonds as in naturally occurring 2-5A. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：329 / 331

页数：3

共 14 条

[1]

DONG BH, 1994, J BIOL CHEM, V269, P14153

[2] CONVENIENT METHOD FOR THE SYNTHESIS OF C-ALKYLATED PURINE NUCLEOSIDES - PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF HALOGENOPURINE NUCLEOSIDES WITH TRIALKYLALUMINUMS [J].

HIROTA, K ;

KITADE, Y ;

KANBE, Y ;

MAKI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5268-5270

[3] IMPROVED SYNTHESIS AND ANTITUMOR-ACTIVITY OF 2-BROMO-2'-DEOXYADENOSINE [J].

HUANG, MC ;

AVERY, TL ;

BLAKLEY, RL ;

SECRIST, JA ;

MONTGOMERY, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (06) :800-802

[4] PPPA2'P5'A2'P5'-A - INHIBITOR OF PROTEIN-SYNTHESIS SYNTHESIZED WITH AN ENZYME FRACTION FROM INTERFERON-TREATED CELLS [J].

KERR, IM ;

BROWN, RE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1978, 75 (01) :256-260

[5] 2-bromoadenosine-substituted 2′,5′-oligoadenylates modulate binding and activation abilities of human recombinant RNase 1 [J].

Kitade, Y ;

Wakana, M ;

Terai, S ;

Tsuboi, T ;

Nakanishi, M ;

Yatome, C ;

Dong, BH ;

Silverman, RH ;

Torrence, PF .

NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (12) :2323-2333

[6] 8-METHYLADENOSINE-SUBSTITUTED ANALOGS OF 2-5A - SYNTHESIS AND THEIR BIOLOGICAL-ACTIVITIES [J].

KITADE, Y ;

NAKATA, Y ;

HIROTA, K ;

MAKI, Y ;

PABUCCUOGLU, A ;

TORRENCE, PF .

NUCLEIC ACIDS RESEARCH, 1991, 19 (15) :4103-4108

[7] URIDINE ANALOGS OF 2',5'-OLIGOADENYLATES - ON THE BIOLOGICAL ROLE OF THE MIDDLE BASE OF 2-5A TRIMER [J].

KITADE, Y ;

ALSTER, DK ;

PABUCCUOGLU, A ;

TORRENCE, PF .

BIOORGANIC CHEMISTRY, 1991, 19 (03) :283-299

[8]

Knight M, 1981, Methods Enzymol, V79, P216

[9]

LESIAK K, 1987, J BIOL CHEM, V262, P1961

[10] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF OLIGO(8-BROMOADENYLATES) AS ANALOGS OF 5'-O-TRIPHOSPHOADENYLYL(2'-]5')ADENYLYL(2'-]5')ADENOSINE [J].

LESIAK, K ;

TORRENCE, PF .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) :1015-1022

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