WO1998004575A3 - Lipophilic oligonucleotide analogs - Google Patents

Lipophilic oligonucleotide analogs Download PDF

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Publication number
WO1998004575A3
WO1998004575A3 PCT/US1996/012530 US9612530W WO9804575A3 WO 1998004575 A3 WO1998004575 A3 WO 1998004575A3 US 9612530 W US9612530 W US 9612530W WO 9804575 A3 WO9804575 A3 WO 9804575A3
Authority
WO
WIPO (PCT)
Prior art keywords
lipophilic
oligonucleotide analogs
contain
oligonucleotides
substitutions
Prior art date
Application number
PCT/US1996/012530
Other languages
French (fr)
Other versions
WO1998004575A2 (en
Inventor
Norbert W Bischofberger
Kenneth W Kent
Richard W Wagner
Chris A Buhr
Kuei-Ying Lin
Original Assignee
Gilead Sciences Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Priority to EP96926831A priority Critical patent/EP0923596A2/en
Priority to CA002261704A priority patent/CA2261704A1/en
Priority to PCT/US1996/012530 priority patent/WO1998004575A2/en
Publication of WO1998004575A2 publication Critical patent/WO1998004575A2/en
Publication of WO1998004575A3 publication Critical patent/WO1998004575A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

Abstract

The invention discloses lipophilic oligonucleotide analogs that are capable of efficient passive diffusion across cell membranes. These oligonucleotides contain at least two nucleotide residues and have an octanol:water partition coefficient of about -0.3 to + 2.5 and a solubility in water of at least 0.001 νg/mL. Invention embodiments which include lipophilic oligonucleotide analogs having either at least 60 % of the internucleotide linkages are lipophilic, or at least 60 % of the bases contain lipophilic substitutions, or at least 60 % of the sugars contain lipophilic substitutions, or a combination of these sums to 60 %. These oligonucleotides may be conjugated to a label and used to visualize cells or subcellular compartments.
PCT/US1996/012530 1996-07-31 1996-07-31 Lipophilic oligonucleotide analogs WO1998004575A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP96926831A EP0923596A2 (en) 1996-07-31 1996-07-31 Lipophilic oligonucleotide analogs
CA002261704A CA2261704A1 (en) 1996-07-31 1996-07-31 Lipophilic oligonucleotide analogs
PCT/US1996/012530 WO1998004575A2 (en) 1996-07-31 1996-07-31 Lipophilic oligonucleotide analogs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA002261704A CA2261704A1 (en) 1996-07-31 1996-07-31 Lipophilic oligonucleotide analogs
PCT/US1996/012530 WO1998004575A2 (en) 1996-07-31 1996-07-31 Lipophilic oligonucleotide analogs

Publications (2)

Publication Number Publication Date
WO1998004575A2 WO1998004575A2 (en) 1998-02-05
WO1998004575A3 true WO1998004575A3 (en) 1998-03-19

Family

ID=25680807

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/012530 WO1998004575A2 (en) 1996-07-31 1996-07-31 Lipophilic oligonucleotide analogs

Country Status (3)

Country Link
EP (1) EP0923596A2 (en)
CA (1) CA2261704A1 (en)
WO (1) WO1998004575A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003256325A1 (en) 2002-06-26 2004-01-19 The Penn State Research Foundation Methods and materials for treating human papillomavirus infections
SG2014011381A (en) 2009-02-13 2014-06-27 Chem Inc X Methods of creating and screening dna-encoded libraries
EP3000898B1 (en) 2013-05-21 2020-11-18 Hitgen Inc. Drug target capturing method

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4904582A (en) * 1987-06-11 1990-02-27 Synthetic Genetics Novel amphiphilic nucleic acid conjugates
WO1990010448A2 (en) * 1989-03-07 1990-09-20 Genentech, Inc. Covalent conjugates of lipid and oligonucleotide
WO1993010820A1 (en) * 1991-11-26 1993-06-10 Gilead Sciences, Inc. Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines
EP0547008A1 (en) * 1991-11-26 1993-06-16 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. New antisense oligonucleotides
US5420330A (en) * 1990-09-07 1995-05-30 Pharmacia P-L Biochemicals Inc. Lipo-phosphoramidites
WO1996029337A1 (en) * 1995-03-23 1996-09-26 Hybridon, Inc. Thiono triester modified antisense oligodeoxynucleotide phosphorothioates
US5633360A (en) * 1992-04-14 1997-05-27 Gilead Sciences, Inc. Oligonucleotide analogs capable of passive cell membrane permeation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5484908A (en) 1991-11-26 1996-01-16 Gilead Sciences, Inc. Oligonucleotides containing 5-propynyl pyrimidines

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4904582A (en) * 1987-06-11 1990-02-27 Synthetic Genetics Novel amphiphilic nucleic acid conjugates
WO1990010448A2 (en) * 1989-03-07 1990-09-20 Genentech, Inc. Covalent conjugates of lipid and oligonucleotide
US5420330A (en) * 1990-09-07 1995-05-30 Pharmacia P-L Biochemicals Inc. Lipo-phosphoramidites
WO1993010820A1 (en) * 1991-11-26 1993-06-10 Gilead Sciences, Inc. Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines
EP0547008A1 (en) * 1991-11-26 1993-06-16 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. New antisense oligonucleotides
US5633360A (en) * 1992-04-14 1997-05-27 Gilead Sciences, Inc. Oligonucleotide analogs capable of passive cell membrane permeation
WO1996029337A1 (en) * 1995-03-23 1996-09-26 Hybridon, Inc. Thiono triester modified antisense oligodeoxynucleotide phosphorothioates

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
J.F.HUGHES ET AL.: "Lipid Membrane Permeability of 2'-Modified Derivatives of Phosphorothioate Oligonucleotides.", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 83, no. 4, April 1994 (1994-04-01), pages 597 - 600, XP002052615 *
J.M.DAGLE ET AL.: "Physical Properties of Oligonucleotides Containing Phosphoramidate-Modified Internucleoside Linkages.", NUCLEIC ACIDS RESEARCH., vol. 19, no. 8, 1991, OXFORD GB, pages 1805 - 1810, XP002052616 *
S.AKHTAR ET AL.: "Interactions of Antisense DNA Oligonucleotide Analogs with Phospholipid Membranes (Liposomes).", NUCLEIC ACIDS RESEARCH., vol. 19, no. 20, 1991, OXFORD GB, pages 5551 - 5559, XP002052617 *
Z.ZHANG ET AL.: "Thiono Triester Modified Antisense Oligonucleotides for Inhibition of Human Cytomegalovirus in vitro.", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 6, no. 16, August 1996 (1996-08-01), pages 1911 - 1916, XP000677176 *

Also Published As

Publication number Publication date
WO1998004575A2 (en) 1998-02-05
EP0923596A2 (en) 1999-06-23
CA2261704A1 (en) 1998-02-05

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