Document Detail

Synthesis and biological activity of uronic acid analogues of 2-5A[5'-O-triphosphoryladenylyl(2----5')adenylyl-(2'----5')adenosine].
MedLine Citation:
PMID:  1525304     Owner:  NLM     Status:  MEDLINE    
The oligonucleotide ppp5'A2'p5'A2'p5'A, known as 2-5A, is a potent translational inhibitor involved in some aspects of interferon action. To explore the specific function of the charged 5'-triphosphate moiety, we prepared a series of congeners in which the 5' region was hypermodified. Thus, uronic acid derivatives were substituted for the 5' terminal adenosine residue of 2-5A. Compounds 9, 10, 11 and 12 carried adenosine 5'-uronic acid, ethyl adenosine 5'-uronate, adenosine 5'-uronamide, and adenosine 5'-(N-ethyl)uronamide, respectively, in place of the 5' terminal adenosine triphosphate moiety of 2-5A. While all the analogues showed some weak interaction with the 2-5A-dependent endonuclease (RNase L), compound 9 showed the strongest binding ability, and while unable to activate the mouse RNase L, could activate human RNase at a concentration 100-fold greater than that required for the parent 2-5A. This result suggests that the function of the 5'(poly)phosphate moiety of 2-5A may be fulfilled by some other anionic moiety.
J E Kinjo; A Pabuccuoglu; D K Alster; K Lesiak; P F Torrence
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Drug design and discovery     Volume:  8     ISSN:  1055-9612     ISO Abbreviation:  Drug Des Discov     Publication Date:  1992 Feb 
Date Detail:
Created Date:  1992-10-19     Completed Date:  1992-10-19     Revised Date:  2011-06-17    
Medline Journal Info:
Nlm Unique ID:  9200627     Medline TA:  Drug Des Discov     Country:  SWITZERLAND    
Other Details:
Languages:  eng     Pagination:  241-54     Citation Subset:  IM    
Section of Biomedical Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892.
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MeSH Terms
Adenine Nucleotides / chemical synthesis*,  pharmacology
Cell Line
Endoribonucleases / metabolism
Liver / drug effects,  enzymology
Lymphoid Tissue / cytology,  drug effects,  enzymology
Oligonucleotides / chemical synthesis*,  pharmacology
Oligoribonucleotides / chemical synthesis*,  pharmacology
Protein Synthesis Inhibitors / chemical synthesis*,  pharmacology
Uronic Acids / chemical synthesis*,  pharmacology
Reg. No./Substance:
0/Adenine Nucleotides; 0/Oligonucleotides; 0/Oligoribonucleotides; 0/Protein Synthesis Inhibitors; 0/Uronic Acids; 61172-40-5/2',5'-oligoadenylate; EC 3.1.-/Endoribonucleases; EC 3.1.26.-/2-5A-dependent ribonuclease

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