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
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
收藏
页码:329 / 331
页数:3
相关论文
共 50 条
  • [1] Ribonuclease L, a 2-5A-Dependent enzyme: Purification to homogeneity and assays for 2-5A binding and catalytic activity
    Player, MR
    Wondrak, EM
    Bayly, SF
    Torrence, PF
    METHODS-A COMPANION TO METHODS IN ENZYMOLOGY, 1998, 15 (03): : 243 - 253
  • [2] PRACTICAL SYNTHESIS OF 2'-5'-LINKED OLIGOADENYLATES (2-5A OLIGOMERS)
    NOYORI, R
    UCHIYAMA, M
    NOBORI, T
    HIROSE, M
    HAYAKAWA, Y
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) : 205 - 225
  • [3] Structural basis for recognition of 2′,5′-linked oligoadenylates by human ribonuclease L
    Tanaka, N
    Nakanishi, M
    Kusakabe, Y
    Goto, Y
    Kitade, Y
    Nakamura, KT
    EMBO JOURNAL, 2004, 23 (20): : 3929 - 3938
  • [4] 8-METHYLADENOSINE-SUBSTITUTED ANALOGS OF 2-5A - SYNTHESIS AND THEIR BIOLOGICAL-ACTIVITIES
    KITADE, Y
    NAKATA, Y
    HIROTA, K
    MAKI, Y
    PABUCCUOGLU, A
    TORRENCE, PF
    NUCLEIC ACIDS RESEARCH, 1991, 19 (15) : 4103 - 4108
  • [5] Synthesis and Enzymatic Deprotection of Fully Protected 2′-5′ Oligoadenylates (2-5A): Towards a Prodrug Strategy for Short 2-5A
    Kiuru, Emilia
    Ora, Mikko
    Beigelman, Leonid
    Blatt, Lawrence
    Loennberg, Harri
    CHEMISTRY & BIODIVERSITY, 2012, 9 (04) : 669 - 688
  • [6] Recognition of 2′,5′-linked oligoadenylates by human ribonuclease L: molecular dynamics study
    Malac, Kamil
    Barvik, Ivan
    JOURNAL OF MOLECULAR MODELING, 2014, 20 (04)
  • [7] 5′-O-Dephosphorylated 2′,5′-oligoadenylate (2-5A) with 8-methyladenosine at the 2′-terminus activates human RNase L
    Nagaoka, Kumi
    Kitamura, Yoshiaki
    Ueno, Yoshihito
    Kitade, Yukio
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (03) : 1186 - 1188
  • [8] Recognition of 2′,5′-linked oligoadenylates by human ribonuclease L: molecular dynamics study
    Kamil Maláč
    Ivan Barvík
    Journal of Molecular Modeling, 2014, 20
  • [9] 8-METHYLADENOSINE-SUBSTITUTED ANALOGS OF 2-5A - SYNTHESIS AND PROPERTIES
    KITADE, Y
    NAKATA, Y
    HIROTA, K
    MAKI, Y
    PABUCCOGLU, A
    TORRENCE, PF
    SIXTEENTH SYMPOSIUM ON NUCLEIC ACIDS CHEMISTRY, 1989, 21 : 93 - 94
  • [10] URIDINE ANALOGS OF 2',5'-OLIGOADENYLATES - ON THE BIOLOGICAL ROLE OF THE MIDDLE BASE OF 2-5A TRIMER
    KITADE, Y
    ALSTER, DK
    PABUCCUOGLU, A
    TORRENCE, PF
    BIOORGANIC CHEMISTRY, 1991, 19 (03) : 283 - 299