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Nucleic Acids Research, 1991, Vol. 19, No. 15 4103-4108
© 1991

CHEMISTRY

8-Methyladenosine-substituted analogues of 2-5A: synthesis and their biological activities

Yukio Kitade*, Yoshitaka Nakata, Kosaku Hirota, Yoshifumi Maki, Aysun Pabuccuoglu1,+ and Paul F. Torrence1

Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University 5-6-1 Mitahora-higashi, Gifu 502, Japan 1Section on Biomedical Chemistry, Laboratory of Medicinal Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health Building 8, room B2A02, Bethesda, MD 20892, USA

* To who m correspondence should be addressed

Received May 24, 1991. Revised July 9, 1991. Accepted July 9, 1991.

8-Methyladenosine-substituted analogues of 2-5A, p5'A2'p5'A2'p5'(me8A) p5'A2'p5'(me8A)2' p5'(me8A), p5'(me8A)2'p5'(me8A)2'p5'(me8A), and p5'(me8A) 2'p5'A2'p5'A, were prepared via a modification of a lead ion-catalyzed ligation reaction. These 2-5A monophosphates were converted into the corresponding 5'-triphosphates. Substitution of an 8-methyladenosine residue at the third position (2'-terminus) of the oligonucleotides increased the stability to snake venom phosphodlesterase digestion. Both binding and activation of mouse liver 2-5A dependent ribonuclease (RNase L) by the various 8-methyladenosine-substituted 2-5A analogues were examined. Among the 8-methyladenosine-substltuted trimer analogues, the analogues with 8-methyladenosine residing in the 2'-terminal position showed the strongest binding affinity and were several times more effective than 2-5A itself as an inhibitor of translation.

+Present address: Faculty of Pharmacy, Aegean University, Bornova-Izmir, Turkey


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