Oligoribonucleoside and oligodeoxyribonucleoside boranophosphates

US5455233A · kind A · utility

Assignees

• University of North Carolina · US
• Duke University · US
• Boron Biologicals, Inc. · US

Inventors

• Bernard F. Spielvogel · Cary, US
• Anup Sood · Flemington, US
• Iris H. Hall · Chapel Hill, US
• Barbara Ramsay Shaw · Durham, US

Key dates

• Filing date: Sep 30, 1992
• Grant date: Oct 3, 1995
• Expiry date: Sep 30, 2012

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Disclosed are oligonucleoside boranophosphates, or salts thereof, comprising a chain of natural or modified ribonucleotides or deoxyribonucleotides, containing at least one boronated internucleotide phospodiester linkage of the formula: ##STR1## W is selected from the group consisting of .dbd.O, .dbd.S, --OPr, and --SPr where Pr is a base-labile protecting group. X is selected from the group consisting of --BH.sub.3, --BH.sub.2 R.sub.1, --BHR.sub.1 R.sub.2 and --BR.sub.1 R.sub.2 R.sub.3. R.sub.1 is selected from the group consisting of --R.sub.4, --COOH, --COOR.sub.4, --CONHR.sub.4, --CON(R.sub.4).sub.2, --CN.sup.+ R.sub.4 Z.sup.-, wherein Z.sup.- is an anion, --CN, carboxycholesteryl and carboxybenzyl, wherein R.sub.4 is C1 to C18 alkyl. R.sub.2 is selected from the group consisting of --R.sub.5, --COOH, --COOR.sub.5, --CONHR.sub.5, --CON(R.sub.5).sub.2, --CN.sup.+ R.sub.5 Z.sup.-, wherein Z.sup.- is an anion, --CN, carboxy- cholesteryl and carboxybenzyl, wherein R.sub.5 is C1 to C18 alkyl. R.sub.3 is selected from the group consisting of C1 to C3 alkyl. Most preferably, X is --BH.sub.3 and W is =0. Compounds of Formula (III) are useful as antisense agents and probes in molecular …