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Literature DB >> 1630912

Synthesis and physical properties of anti-HIV antisense oligonucleotides bearing terminal lipophilic groups.

C MacKellar¹, D Graham, D W Will, S Burgess, T Brown.

Abstract

A number of phosphoramidite monomers have been prepared and used in the synthesis of antisense phosphorothioate oligonucleotides bearing 5'-polyalkyl and cholesterol moieties. Similar groups have also been attached to the 3'-end of oligonucleotides by means of functionalised CPG. Melting temperatures of duplexes formed between phosphorothioate oligonucleotides with lipophilic end-groups and complementary DNA strands were found to be identical to those formed by the equivalent unmodified phosphorothioates.

Entities: Chemical

Mesh：

Substances：

Year: 1992 PMID： 1630912 PMCID： PMC312497 DOI： 10.1093/nar/20.13.3411

Source DB: PubMed Journal: Nucleic Acids Res ISSN： 0305-1048 Impact factor: 16.971

15 in total

1. Acridine- and cholesterol-derivatized solid supports for improved synthesis of 3'-modified oligonucleotides.

Authors: M W Reed; A D Adams; J S Nelson; R B Meyer
Journal: Bioconjug Chem Date: 1991 Jul-Aug Impact factor: 4.774

2. Stepwise mechanism of HIV reverse transcriptase: primer function of phosphorothioate oligodeoxynucleotide.

Authors: C Majumdar; C A Stein; J S Cohen; S Broder; S H Wilson
Journal: Biochemistry Date: 1989-02-07 Impact factor: 3.162

3. Synthesis of alkylating oligonucleotide derivatives containing cholesterol or phenazinium residues at their 3'-terminus and their interaction with DNA within mammalian cells.

Authors: A S Boutorin; L V Gus'kova; E M Ivanova; N D Kobetz; V F Zarytova; A S Ryte; L V Yurchenko; V V Vlassov
Journal: FEBS Lett Date: 1989-08-28 Impact factor: 4.124

4. Inhibition of vesicular stomatitis virus protein synthesis and infection by sequence-specific oligodeoxyribonucleoside methylphosphonates.

Authors: C H Agris; K R Blake; P S Miller; M P Reddy; P O Ts'o
Journal: Biochemistry Date: 1986-10-07 Impact factor: 3.162

5. Regulation of viral expression of human immunodeficiency virus in vitro by an antisense phosphorothioate oligodeoxynucleotide against rev (art/trs) in chronically infected cells.

Authors: M Matsukura; G Zon; K Shinozuka; M Robert-Guroff; T Shimada; C A Stein; H Mitsuya; F Wong-Staal; J S Cohen; S Broder
Journal: Proc Natl Acad Sci U S A Date: 1989-06 Impact factor: 11.205

6. Chemical and enzymatic biotin-labeling of oligodeoxyribonucleotides.

Authors: T Kempe; W I Sundquist; F Chow; S L Hu
Journal: Nucleic Acids Res Date: 1985-01-11 Impact factor: 16.971

7. Synthesis, hybridization properties and antiviral activity of lipid-oligodeoxynucleotide conjugates.

Authors: R G Shea; J C Marsters; N Bischofberger
Journal: Nucleic Acids Res Date: 1990-07-11 Impact factor: 16.971

8. Oligonucleotide N-alkylphosphoramidates: synthesis and binding to polynucleotides.

Authors: A Jäger; M J Levy; S M Hecht
Journal: Biochemistry Date: 1988-09-20 Impact factor: 3.162

9. Oligodeoxynucleoside phosphoramidates and phosphorothioates as inhibitors of human immunodeficiency virus.

Authors: S Agrawal; J Goodchild; M P Civeira; A H Thornton; P S Sarin; P C Zamecnik
Journal: Proc Natl Acad Sci U S A Date: 1988-10 Impact factor: 11.205

10. Short modified antisense oligonucleotides directed against Ha-ras point mutation induce selective cleavage of the mRNA and inhibit T24 cells proliferation.

Authors: T Saison-Behmoaras; B Tocqué; I Rey; M Chassignol; N T Thuong; C Hélène
Journal: EMBO J Date: 1991-05 Impact factor: 11.598

16 in total

1. Site-specific introduction of functional groups into phosphodiester oligodeoxynucleotides and their thermal stability and nuclease-resistance properties.

Authors: Y Nomura; Y Ueno; A Matsuda
Journal: Nucleic Acids Res Date: 1997-07-15 Impact factor: 16.971

Review 2. Inhibition of gene expression with ribozymes.

Authors: P Marschall; J B Thomson; F Eckstein
Journal: Cell Mol Neurobiol Date: 1994-10 Impact factor: 5.046

3. Synthesis and hybridization properties of oligonucleotides containing 2'-O-modified ribonucleotides.

Authors: T H Keller; R Häner
Journal: Nucleic Acids Res Date: 1993-09-25 Impact factor: 16.971

4. Modulation of oligonucleotide duplex and triplex stability via hydrophobic interactions.

Authors: S M Gryaznov; D H Lloyd
Journal: Nucleic Acids Res Date: 1993-12-25 Impact factor: 16.971

5. Sterol-modified phospholipids: cholesterol and phospholipid chimeras with improved biomembrane properties.

Authors: Zhaohua Huang; Francis C Szoka
Journal: J Am Chem Soc Date: 2008-10-25 Impact factor: 15.419

Review 6. Nucleoside, nucleotide and oligonucleotide based amphiphiles: a successful marriage of nucleic acids with lipids.

Authors: Arnaud Gissot; Michel Camplo; Mark W Grinstaff; Philippe Barthélémy
Journal: Org Biomol Chem Date: 2008-03-05 Impact factor: 3.876

Review 7. Bioconjugation of oligonucleotides for treating liver fibrosis.

Authors: Zhaoyang Ye; Houssam S Hajj Houssein; Ram I Mahato
Journal: Oligonucleotides Date: 2007

Review 8. Targeting hepatitis B therapy to the liver. Clinical pharmacokinetic considerations.

Authors: P C Rensen; R L de Vrueh; T J van Berkel
Journal: Clin Pharmacokinet Date: 1996-08 Impact factor: 6.447

9. The production of PCR products with 5' single-stranded tails using primers that incorporate novel phosphoramidite intermediates.

Authors: C R Newton; D Holland; L E Heptinstall; I Hodgson; M D Edge; A F Markham; M J McLean
Journal: Nucleic Acids Res Date: 1993-03-11 Impact factor: 16.971

10. Inhibition of hormone-stimulated steroidogenesis in cultured Leydig tumor cells by a cholesterol-linked phosphorothioate oligodeoxynucleotide antisense to diazepam-binding inhibitor.

Authors: N Boujrad; J R Hudson; V Papadopoulos
Journal: Proc Natl Acad Sci U S A Date: 1993-06-15 Impact factor: 11.205