US5177196A
Expired / Lapsed
US
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Oligo (α-arabinofuranosyl nucleotides) and α-arabinofuranosyl precursors thereof
Assignee: Epoch Biosciences Inc
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Filing: 1990-08-16
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Granted: 1993-01-05
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Expires: 2010-08-16
Abstract
Abstract Novel oligonucleotides formed from α-D-arabinofuranosyl nucleoside monomers, including oligonucleotides in which one or more of the monomer units is functionalized, are disclosed herein, as well as functionalized monomeric α-D-arabinofuranosyl nucleosides and nucleotides. A generic formula for the oligomers is: ##STR1## in which B is a nucleotide base which will vary from one monomeric unit to the next in a preselected oligonucleotide sequence; R is phosphate, phsophorothioate, phosphoramidate, or alkanephosphonate; t is 1 for functionalized monomeric units and zero for the others; W is a chemical linker arm; A is a functional group; and n is the number of monomeric units in the oligomer. The oligomers are useful for diagnostic and chemotherapeutic uses. A novel reaction is also disclosed, in which an α-D-arabinofuranosyl nucleoside with exposed hydroxyls at the 2'- and 3'-positions is selectively protected at the 2'-position in a single reaction.
Inventors
- 👤 Rich B. Meyer, Jr.
- 👤 A. David Adams
- 👤 Charles R. Petrie
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 18:40
CPC Classifications
C; C07; C07H; C07H21/00; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C07H23/00
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
264 words
An oligonucleotide comprising a chain of nucleotide units, each said nucleotide unit having the formula ##STR8## in which: R is a member selected from the group consisting of phosphate, phosphorothioate, phosphoramidate, and alkanephosphonate, and either is the same in all said nucleotide units or varies among said nucleotide units; B is a nucleotide base, or a nucleotide base bearing a radioactive atom; W is an alkylene group having 1 to 12 carbon atoms; an alkenylene group of 2 to 12 carbon atoms and 1 or 2 olefinic bonds; an alkynylene group of 2 to 12 carbon atoms and 1 or 2 acetylenic bonds; --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy-substituted alkylene group having 1 to 12 carbon atoms, --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy-substituted alkenylene group of 2 to 12 carbon atoms and 1 or 2 olefinic bonds, or --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy-substituted alkynylene group of 2 to 12 carbon atoms and 1 or 2 acetylenic bonds, said W forming a linking group between a and B wherein the --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy groups are remote from B; A is an intercalator, a crosslinking agent, an antibody having a binding site specific for double-stranded DNA, a reporter group, or a biotin residue and A either is the same in all said nucleotide units where t is 1, or varies among said nucleotide units; and t is zero or 1, and either is the same in all said nucleotide units or varies among said nucleotide units.
Claim 2
Dependent Claim
264 words
An oligonucleotide comprising a chain of nucleotide units, each said nucleotide unit having the formula ##STR8## in which: R is a member selected from the group consisting of phosphate, phosphorothioate, phosphoramidate, and alkanephosphonate, and either is the same in all said nucleotide units or varies among said nucleotide units; B is a nucleotide base, or a nucleotide base bearing a radioactive atom; W is an alkylene group having 1 to 12 carbon atoms; an alkenylene group of 2 to 12 carbon atoms and 1 or 2 olefinic bonds; an alkynylene group of 2 to 12 carbon atoms and 1 or 2 acetylenic bonds; --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy-substituted alkylene group having 1 to 12 carbon atoms, --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy-substituted alkenylene group of 2 to 12 carbon atoms and 1 or 2 olefinic bonds, or --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy-substituted alkynylene group of 2 to 12 carbon atoms and 1 or 2 acetylenic bonds, said W forming a linking group between a and B wherein the --O--, --S--, --NH-- --CO--, --NHCO--, --NHCH 2 CO-- or hydroxy groups are remote from B; A is an intercalator, a crosslinking agent, an antibody having a binding site specific for double-stranded DNA, a reporter group, or a biotin residue and A either is the same in all said nucleotide units where t is 1, or varies among said nucleotide units; and t is zero or 1, and either is the same in all said nucleotide units or varies among said nucleotide units.
Claim 3
Dependent Claim
20 words
An oligonucleotide in accordance with claim 1 in which t is 1 on at least one of said nucleotide units.
Claim 4
Dependent Claim
18 words
An oligonucleotide in accordance with claim 1 in which t is zero on all of said nucleotide units.
Claim 5
Dependent Claim
12 words
An oligonucleotide in accordance with claim 1 in which R is monophosphate.
Claim 6
Dependent Claim
22 words
An oligonucleotide in accordance with claim 1 in which W includes an aliphatic chain of at least three carbon atoms in length.
Claim 7
Dependent Claim
33 words
An oligonucleotide in accordance with claim 1 in which W is an aliphatic chain of at least three carbon atoms in length, terminating with a nucleophilic group at the end adjacent to A.
Claim 8
Dependent Claim
36 words
An oligonucleotide in accordance with claim 1 in which W is an aliphatic chain of at least three carbon atoms in length, terminating with an amino or an amido group at the end adjacent to A.
Claim 9
Dependent Claim
24 words
An oligonucleotide in accordance with claim l..in which B is a member selected from the group consisting of purines, pyrimidines, 3-deazapurines, 7-deazapurines, and pyrazolo{3,4-d}pyrimidines.
Claim 10
Dependent Claim
25 words
An oligonucleotide in accordance with claim 1 in which B is a member selected from the group consisting of adenine, guanine, thymine, cytosine and uracil.
Claim 11
Dependent Claim
90 words
An oligonucleotide in accordance with claim 1 in which B is a member selected from the group consisting of: purines, at whose 8-position W is joined in nucleotide units where t is 1, pyrimidines, at whose 5-position W is joined in nucleotide units where t is 1, 3-deazapurines, at whose 3-position W is joined in nucleotide units where t is 1, 7-deazapurines, at whose 7-position W is joined in nucleotide units where t is 1, and pyrazolo{3,4-d}pyrimidines, at whose 3-position W is joined in nucleotide units where t is 1.
Claim 12
Dependent Claim
89 words
An oligonucleotide in accordance with claim 1 in which B is a member selected from the group consisting of: adenine, at whose 8-position W is joined in nucleotide units where t is 1; guanine, at whose 8-position W is joined in nucleotide units where t is 1; thymine, and t is zero in all nucleotide units where B is thymine; cytosine, at whose 5-position W is joined in nucleotide units where t is 1; and uracil, at whose 5-position W is joined in nucleotide units where t is 1.
Claim 13
Dependent Claim
24 words
An oligonucleotide in accordance with claim 1 in which the number of nucleotide units in said chain is from about 5 to about 2000.
Claim 14
Dependent Claim
24 words
An oligonucleotide in accordance with claim 1 in which the number of nucleotide units in said chain is from about 10 to about 100.
Claim 15
Dependent Claim
31 words
An oligonucleotide in accordance with claim 1 in which A is a member selected from the group consisting of intercalators, signal-producing reporter groups, and ligands capable of binding to signal-producing anti-ligands.
References Cited (Backward Citations)
EP0227459A2
Cited
US4760017A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-01-05 | 1996-07-06 | 1997-01-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-01-05 | 2000-07-06 | 2001-01-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-01-05 | 2004-07-06 | 2005-01-05 | $7700.00 | Window Closed / Lapsed |