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 50 条

[41] PURINE 8-BROMINATION MODULATES THE RIBONUCLEASE-L BINDING AND ACTIVATION ABILITIES OF 2',5'-OLIGOADENYLATES - POSSIBLE INFLUENCE OF GLYCOSYL TORSION ANGLE
LESIAK, K
TORRENCE, PF
JOURNAL OF BIOLOGICAL CHEMISTRY, 1987, 262 (05) : 1961 - 1965
[42] REGULATION OF LEVEL OF 2',5'-OLIGOADENYLATES IN MOUSE L-CELLS
ZHELKOVSKII, AM
KOLBANOVSKAYA, EY
PIVAZYAN, AD
KARPEISKII, MY
MOLECULAR BIOLOGY, 1985, 19 (02) : 404 - 409
[43] Efficient functionalization of 2',5'-oligoadenylates with sulfur
Lesiak, Krystyna
Torrence, Paul F.
Bioconjugate Chemistry, 8 (02): : 199 - 203
[44] REPLACEMENT OF THE RIBOFURANOSE OXYGEN OF 2-5A DERIVATIVES BY METHYLENE - SYNTHESIS OF AN ARISTEROMYCIN ANALOG OF 2-5A CORE 5'-MONOPHOSPHATE (5'-O-PHOSPHORYLADENYLYL)(2'-]5')ADENYLYL(2'-]5')ADENOSINE
SAWAI, H
LESIAK, K
IMAI, J
TORRENCE, PF
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (09) : 1376 - 1380
[45] ANALYSIS OF 2',5'-OLIGOADENYLATES IN CELLS AND TISSUES
REID, TR
HERSH, CL
KERR, IM
STARK, GR
ANALYTICAL BIOCHEMISTRY, 1984, 136 (01) : 136 - 141
[46] SYNTHESIS OF ADENYLYL-(2'-]5')-ADENYLYL-(2'-]5')-ADENOSINE (2-5A CORE)
CHATTOPADHYAYA, JB
TETRAHEDRON LETTERS, 1980, 21 (42) : 4113 - 4116
[47] The 2′-5′-Oligoadenylate Synthetase 3 Enzyme Potently Synthesizes the 2′-5′-Oligoadenylates Required for RNase L Activation
Ibsen, Mikkel Soes
Gad, Hans Henrik
Thavachelvam, Karthiga
Boesen, Thomas
Despres, Philippe
Hartmann, Rune
JOURNAL OF VIROLOGY, 2014, 88 (24) : 14222 - 14231
[48] A scientific journey through the 2-5A/RNase L system
Silverman, Robert H.
CYTOKINE & GROWTH FACTOR REVIEWS, 2007, 18 (5-6) : 381 - 388
[49] BINDING AND ACTIVATION OF RNASE-L BY 2-5A ANALOGS WITH ALTERNATING CORDYCEPIN AND ADENOSINE RESIDUES
SOBOL, RW
KARIKO, K
LI, SW
CHARUBALA, R
PFLEIDERER, W
SUHADOLNIK, RJ
FEDERATION PROCEEDINGS, 1987, 46 (06) : 2083 - 2083
[50] Efficient functionalization of 2',5'-oligoadenylates with sulfur
Lesiak, K
Torrence, PF
BIOCONJUGATE CHEMISTRY, 1997, 8 (02) : 199 - 203

← 1 2 3 4 5 →