EP 0790965 A1 19970827 - SYNTHESIS OF ?35 S-LABELED OLIGONUCLEOTIDES WITH 3H-1,2-BENZODITHIOL-3-1,1-DIOXIDE
Title (en)
SYNTHESIS OF ?35 S-LABELED OLIGONUCLEOTIDES WITH 3H-1,2-BENZODITHIOL-3-1,1-DIOXIDE
Title (de)
HERSTELLUNG VON 35S-MARKIERTEN OLIGONUKLEOTIDEN MITTELS 3H-1,2-BENZODITHIO-3-ONE-1,1-DIOXID
Title (fr)
SYNTHESE D'OLIGONUCLEOTIDES MARQUES AU ?35 S A L'AIDE DE 3H-1,2-BENZODITHIOL-3-ONE-1,1-DIOXYDE
Publication
Application
Priority
- US 9514259 W 19951106
- US 33510094 A 19941107
- US 49325795 A 19950621
- US 49333995 A 19950621
Abstract (en)
[origin: WO9614277A1] This invention provides a novel compound for <35>S-labelling oligonucleotides. The compound is <35>S-3H-1,2-benzodithiol-3-one-1,1 dioxide (1). In Structure (I), the asterisk indicates the position of the <35>S. Also provided is a method of synthesizing this compound, comprising first contacting <35>S-thiobenzoic acid (4) with thiosalicylic acid (5) in acid medium to yield the condensation product, <35>S-3H-1,2-benzodithiol-3-one (2). <35>S-3H-1,2-benzodithiol-3-one (2) is then oxidized with a suitable oxidating agent such as trifluoroacetic acid and hydrogen peroxide to yield the desired product, <35>S-3H-1,2-benzodithiol-3-one-1,1 dioxide (1). Any oligonucleotide susceptible to be oxidatively sulfurized by 3H-1,2-benzodithiol-3-one-1,1 dioxide can be labeled by <35>S-3H-1,2-benzodithiol-3-one-1,1 dioxide (1). Accordingly, this invention also provides novel methods for <35>S-labelling oligonucleotides. The compound and methods are useful for tracing biodistribution and degradation of antisense oligonucleotides in pharmacokinietic studies.
IPC 1-7
IPC 8 full level
C12N 15/09 (2006.01); C07B 59/00 (2006.01); C07D 339/04 (2006.01); C07H 21/00 (2006.01)
CPC (source: EP)
C07B 59/002 (2013.01); C07H 21/00 (2013.01)
Citation (search report)
See references of WO 9614277A1
Designated contracting state (EPC)
AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE
DOCDB simple family (publication)
WO 9614277 A1 19960517; AU 4101396 A 19960531; CN 1165508 A 19971119; EP 0790965 A1 19970827; JP H10509447 A 19980914
DOCDB simple family (application)
US 9514259 W 19951106; AU 4101396 A 19951106; CN 95196093 A 19951106; EP 95939047 A 19951106; JP 51542896 A 19951106