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A convenient synthesis of 5'-triantennary N-acetyl-galactosamine clusters based on nitromethanetrispropionic acid.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2016 May 01; Vol. 26 (9), pp. 2194-7. Date of Electronic Publication: 2016 Mar 17. - Publication Year :
- 2016
-
Abstract
- A convenient method for the synthesis of several triantennary GalNAc clusters based on a nitromethanetrispropionic acid core was developed. The synthetic approach involves pentafluorophenolic ester intermediates which can be used in a one-pot, seven reaction procedure to quickly prepare a variety of triantennary GalNAc conjugated ASOs. The GalNAc clusters were conjugated to the 5'-end of an antisense oligonucleotide and evaluated for activity in primary mouse hepatocytes where they showed ∼10-fold improvement in activity.<br /> (Copyright © 2016 Elsevier Ltd. All rights reserved.)
- Subjects :
- Acetylgalactosamine pharmacology
Animals
Hepatocytes drug effects
Hepatocytes metabolism
Indicators and Reagents
Mice
Nitro Compounds pharmacology
Oligonucleotides, Antisense pharmacology
Propionates pharmacology
Scavenger Receptors, Class B metabolism
Acetylgalactosamine analogs & derivatives
Acetylgalactosamine chemical synthesis
Nitro Compounds chemical synthesis
Oligonucleotides, Antisense chemical synthesis
Propionates chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 26
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 27025342
- Full Text :
- https://doi.org/10.1016/j.bmcl.2016.03.070