US5446137A
Expired / Lapsed
US
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Oligonucleotides containing 4'-substituted nucleotides
Assignee: Siemens Healthcare Diagnostics GmbH Germany
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Filing: 1993-12-09
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Granted: 1995-08-29
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Expires: 2013-12-09
Abstract
Abstract This invention relates to oligonucleotides having at least one nucleotide that is substituted at the 4' position of the sugar moiety with a substituent other than hydrogen. These oligonucleotides are useful in hybridization assays and as therapeutic agents.
Inventors
- 👤 Hans Maag
- 👤 Samuel J. Rose
- 👤 Beat Schmidt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 02:33
CPC Classifications
C; C07; C07H; C07H21/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
136 words
An oligonucleotide which comprises at least one nucleotide having the structure: ##STR15## wherein: A is a purine or a pyrimidine; B and B' are selected from the group consisting of H, OH, F, OCH 3 and SCH 3 , provided that at least one is H; D' is selected from the group consisting of OH, O--P(O)(OH)--OX, O--P(S)(OH)--OX, O--P(S)(SH)--OX and O--P(O)(CH 3 )--OX, where X is selected from the group consisting of H, a nucleotide, and a protecting group; E' is RY, where Y is selected from the group consisting of H and a substituent that renders said nucleotide modifiable, separable or detectable and R is a linking group; and F is selected from the group consisting of OH and O--P(O)(OH)--OX, where X is selected from the group consisting of H, a nucleotide and a protecting group.
Claim 2
Dependent Claim
136 words
An oligonucleotide which comprises at least one nucleotide having the structure: ##STR15## wherein: A is a purine or a pyrimidine; B and B' are selected from the group consisting of H, OH, F, OCH 3 and SCH 3 , provided that at least one is H; D' is selected from the group consisting of OH, O--P(O)(OH)--OX, O--P(S)(OH)--OX, O--P(S)(SH)--OX and O--P(O)(CH 3 )--OX, where X is selected from the group consisting of H, a nucleotide, and a protecting group; E' is RY, where Y is selected from the group consisting of H and a substituent that renders said nucleotide modifiable, separable or detectable and R is a linking group; and F is selected from the group consisting of OH and O--P(O)(OH)--OX, where X is selected from the group consisting of H, a nucleotide and a protecting group.
Claim 3
Dependent Claim
22 words
The oligonucleotide of claim 1 wherein R is selected from the group consisting of alkylene, alkyl, alkenyl, alkadienyl, aralkyl, aminoalkyl and alkylether.
Claim 4
Dependent Claim
35 words
The oligonucleotide of claim 1 wherein said protecting group is selected from the group consisting of phthalyl, carbobenzyloxy, benzyl, benzoyl, trityl, monomethoxytrityl, dimethoxytrityl, acetyl, trifluoroacetyl, trimethylsilyl, t-butyl(dimethyl)silyl, t-butyl(diphenyl) silyl, carbonate, 2-trimethylsilylethyl, methoxymethyl, 2-methoxyethoxymethyl and dihydropyranyl.
Claim 5
Dependent Claim
9 words
The oligonucleotide of claim 1 wherein Y is biotin.
Claim 6
Dependent Claim
35 words
The oligonucleotide of claim 1 wherein Y is a reactive functional group that renders said oligonucleotide modifiable and is selected from the group consisting of NH 2 , SH, OH, COOH, NHC(O)CF 3 and CHO.
Claim 7
Dependent Claim
35 words
The oligonucleotide of claim 1 wherein Y is a substituent that renders said oligonucleotide modifiable and is selected from the group consisting of nucleic acid modifying catalysts, DNA intercalators, minor groove binders and cleavage agents.
Claim 8
Dependent Claim
23 words
The oligonucleotide of claim 6 wherein said nucleic acid modifying catalyst is selected from the group consisting of nucleases, methylases and metal chelates.
Claim 9
Dependent Claim
30 words
The oligonucleotide of claim 6 wherein said DNA intercalator is selected from the group consisting of ethidium, ethidium bromide, acridines, phenazine, phenazinium salts, pyrenes, diazapyrenes, psoralen, psoralen analogs and anthraquinones.
Claim 10
Dependent Claim
21 words
The oligonucleotide of claim 6 wherein said minor groove binder is selected from the group consisting of distamycin, netropsin and bis-benzimidazoles.
Claim 11
Dependent Claim
21 words
The oligonucleotide of claim 6 wherein said cleavage agent is selected from the group consisting of metal complexes and DNA intercalators.
Claim 12
Dependent Claim
21 words
The oligonucleotide of claim 1 wherein Y is selected from the group consisting of detectable labels and specific binding pair members.
Claim 13
Dependent Claim
23 words
The oligonucleotide of claim 11 wherein said detectable label is selected from the group consisting of enzymes, fluorescers, chemiluminescers, sensitizers, particles and catalysts.
Claim 14
Dependent Claim
22 words
The oligonucleotide of claim 1 wherein A is selected from the group consisting of adenine, guanine, xanthine, hypoxanthine, uracil, thymine and cytosine.
Claim 15
Dependent Claim
18 words
The oligonucleotide of claim 1 wherein A is selected from the group consisting of 5-(1-propynyl)pyrimidine, 5-halopyrimidines and 7-deaza-7-alkylpurines.
Claim 16
Independent Claim
46 words
A method of producing an oligonucleotide, which comprises the step of incorporating into said oligonucleotide at least one nucleotide having a substituent other than hydrogen at the 4' position of the sugar moiety, said substituent producing, or being capable of producing, the alteration of said oligonucleotide.
Claim 17
Independent Claim
46 words
A method of producing an oligonucleotide, which comprises the step of incorporating into said oligonucleotide at least one nucleotide having a substituent other than hydrogen at the 4' position of the sugar moiety, said substituent producing, or being capable of producing, the alteration of said oligonucleotide.
Claim 18
Dependent Claim
33 words
The method of claim 15 wherein said incorporating involves the step of synthesizing said oligonucleotide using a nucleotide precursor having a substituent other than hydrogen at the 4' position of the sugar moiety.
Claim 19
Dependent Claim
29 words
The method of claim 15 wherein said altering further comprises the step of hybridizing to said oligonucleotide a polynucleotide that lacks a nucleotide having a 4'-substituent other than hydrogen.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-08-28 | 1999-02-27 | 1999-08-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-08-28 | 2003-02-27 | 2003-08-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-08-28 | 2007-02-27 | 2007-08-29 | $7700.00 | Window Closed / Lapsed |