Antisense pro-drugs: 5'-ester oligodeoxynucleotides
Open Access
- 1 January 1994
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 22 (24), 5492-5496
- https://doi.org/10.1093/nar/22.24.5492
Abstract
Oligonucleotides bearing a terminal llpophlllc group attached through a biodegradable ester bond should be useful as antisense pro-drugs with improved cellular uptake. The synthesis of 5-ester oligonucleotides is, however, problematic due to lability of the ester bond during aqueous ammonia treatment that Is commonly used for the deprotectlon of synthetic oligonucleotides. The synthesis of 5'-palmltoyl oligodeoxynucleotides was accomplished In good yield by the use of a combination of base-labile tert-butylphenoxyacetyl amino protecting groups (t-BPA), the oxalyl-CPG anchor group, and ethanolamine (EA) as a deprotectlng reagent.Keywords
This publication has 20 references indexed in Scilit:
- On the rapid deprotection of synthetic oligonucleotides and analogsNucleic Acids Research, 1994
- [Use of hydrazine for rapid deblocking of synthetic oligonucleotides].1993
- Phosphorothioate-phosphodiester oligonucleotide co-polymers: assessment for antisense application.1993
- Labile exocyclic amine protection of nucleosides in DNA, RNA and oligonucleotide analog synthesis facililating N-deacylation, minimizing depurination and chain degradationBiochimie, 1993
- In vivo treatment of human leukemia in a scid mouse model with c-myb antisense oligodeoxynucleotides.Proceedings of the National Academy of Sciences, 1992
- GEM* 91—An Antisense Oligonucleotide Phosphorothioate as a Therapeutic Agent for AIDSAntisense Research and Development, 1992
- Synthesis, hybridization properties and antiviral activity of lipid-oligodeoxynucleotide conjugatesNucleic Acids Research, 1990
- Cholesteryl-conjugated oligonucleotides: synthesis, properties, and activity as inhibitors of replication of human immunodeficiency virus in cell culture.Proceedings of the National Academy of Sciences, 1989
- Synthesis of alkylating oligonucleotide derivatives containing cholesterol or phenazinium residues at their 3′‐terminus and their interaction with DNA within mammalian cellsFEBS Letters, 1989
- The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groupsNucleic Acids Research, 1987