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Nucleic Acids Research, Vol 26, Issue 14 3350-3357, Copyright © 1998 by Oxford University Press

ARTICLES

Biophysical and antisense properties of oligodeoxynucleotides containing 7-propynyl-, 7-iodo- and 7-cyano-7-deaza-2-amino-2'- deoxyadenosines

G Balow, V Mohan, EA Lesnik, JF Johnston, BP Monia and OL Acevedo
Department of Medicinal Chemistry and Antisense Biology, Isis Pharmaceuticals Inc., Carlsbad, CA 92008, USA.

The synthesis of 7-propynyl-, 7-iodo- and 7-cyano-7-deaza-2-amino-2'- deoxyadenosines is described. The nucleosides were synthesized, functionalized into the phosphoramidites and incorporated into oligodeoxynucleotides. Spectroscopic melting experiments against complementary RNA showed increases of 3-4 degreesC per modification for single substitutions and smaller increases per incorporation for multiple substitutions relative to unmodified control sequences. The 7- propyne and 7-iodo nucleosides were incorporated into antisense sequences targeting the 3'-UTR of murine C- raf mRNA. Both nucleosides demonstrated substitution-dependent potency. The sequences with three and four substitutions of the 7-propyne-7-deaza-2-amino-2'- deoxyadenosine exhibited a 2-3-fold increase in potency over unmodifed controls.
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