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US5658731A
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2'-O-alkylnucleotides as well as polymers which contain such nucleotides
Assignee: European Molecular Biology Laboratory
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Filing: 1995-01-23
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Granted: 1997-08-19
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Expires: 2015-01-23
Abstract
Abstract Oligonucleotides having the general formula, <IMAGE> in which B denotes an arbitrary nucleobase, A equals 0 or CH2; X or Z equals O, S, NH or denotes CH2 whereby X and Z can be the same or different, V and W denote O, S, Se, NH2 or an alkyloxy residue, or OH or SH whereby V and W can be the same or different in a monomer unit and L is a H atom or a partner of a binding pair and C equals -O-R and R is an alkyl group with at least 1 C atom which may be modified if desired, or it denotes an alkenyl or alkynyl group with at least 2 C atoms which may be modified if desired, whereby the modification consists of a substitution by one or several halogen, cyano, carboxy, hydroxy, nitro or/and mercapto residues, and n is an arbitrary whole number, are stable antisense probes which bind specifically. Such oligonucleotides and polynucleotides may be used for the regulation of gene expression and as pharmaceutical agents. They are synthesized from the corresponding 2'-substituted monomers according to well-known methods, preferably on a solid phase.
Inventors
- 👤 Brian Sproat
- 👤 Angus Lamond
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 18:34
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C07H21/00
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
112 words
A nucleotide of formula I, ##STR6## wherein B is a purine or pyrimidine base A is oxygen C is --O--R wherein R is an alkyl group with a total of at least 2 C atom or an alkenyl group or an alkynyl group having at least 2 C atoms wherein the alkyl, alkenyl or alkynyl groups are unsubstituted or substituted by at least one halogen, cyano, carboxy, hydroxy, nitro or mercapto, group and D and E are groups selected from the group consisting of OH, --PO 4 H 2 , --P 2 O 7 H 3 , --P 3 O 10 H 4 , and reactive groups which form 3'-5' internucleotide bonds.
Claim 2
Dependent Claim
112 words
A nucleotide of formula I, ##STR6## wherein B is a purine or pyrimidine base A is oxygen C is --O--R wherein R is an alkyl group with a total of at least 2 C atom or an alkenyl group or an alkynyl group having at least 2 C atoms wherein the alkyl, alkenyl or alkynyl groups are unsubstituted or substituted by at least one halogen, cyano, carboxy, hydroxy, nitro or mercapto, group and D and E are groups selected from the group consisting of OH, --PO 4 H 2 , --P 2 O 7 H 3 , --P 3 O 10 H 4 , and reactive groups which form 3'-5' internucleotide bonds.
Claim 3
Dependent Claim
36 words
The nucleotide claim 1 wherein D and E are selected from the group consisting of OH, --PO 4 H 2 , P 2 O 7 H 3 , and --P 3 O 10 H 4 .
Claim 4
Dependent Claim
12 words
The nucleotide of claim 1 wherein the reactive group is a phosphoramidite.
Claim 5
Dependent Claim
8 words
The nucleotide of claim 1 which is 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-propargyl-4-O-(2,6-dichlorophenyl)uridine.
Claim 6
Dependent Claim
25 words
The nucleotide of claim 1, wherein the purine or pyrimidine base is selected from the group consisting of adenine-9-yl, cytosine-1-yl, guanine-9-yl, uracil-1-yl, hypoxanthine-9-yl and thymine-1-yl.
Claim 7
Dependent Claim
15 words
The nucleotide of claim 1, wherein the purine or pyrimidine base is a 2-aminoadenine-9-yl residue.
Claim 8
Dependent Claim
15 words
The nucleotide of claims 1 or 5, wherein the alkenyl residue is an alk-2-enyl residue.
Claim 9
Dependent Claim
15 words
The nucleotide of claims 1 or 5 wherein the alkenyl residue is an allyl residue.
Claim 10
Dependent Claim
12 words
The nucleotide monomer of claims 1 or 5 consisting of 2'-O-allyl-4-0(2,6-dichlorophenyl) uridine.
Claim 11
Dependent Claim
21 words
The nucleotide monomer of claims 1 or 5 selected from the group consisting of 2'-O-allyl-uridine-5'-monophosphate, 2'-O-allyl-adenosine-5'-monophosphate, 2'-O-allyl-guanosine-5'-monophosphate, 2'-O-ally-cytidine-5'-monophosphate, 2'-O-allyl-thymidine-5'-monophosphate, and 2'-O-allyl-inosine-5'-monophosphate.
Claim 12
Dependent Claim
25 words
A composition comprising a nucleotide oligomer or a nucleotide polymer wherein said nucleotide oligomer or said nucleotide polymer comprises the nucleotide monomer of claim 10.
Claim 13
Dependent Claim
33 words
The nucleotide monomer of claims 1 or 5 selected from the group consisting of (2'-O-allyl-uridine-5'-diphosphate or -5'-triphosphate), (2'-O-allyl-adenosine-5'-diphosphate or -5'-triphosphate), (2'-O-allyl-guanosine-5'-diphosphate or -5'-triphosphate), (2'-O-allyl-thymidine-5'-diphosphate or -5'-triphosphate), (2'-O-allyl-cytidine-5'-diphosphate or -5'-triphosphate), and (2'-O-allyl-inosine-5'-diphosphate or -5'-triphosphate).
Claim 14
Dependent Claim
25 words
A composition comprising a nucleotide oligomer or a nucleotide polymer wherein said nucleotide oligomer or said nucleotide polymer comprises the nucleotide monomer of claim 12.
Claim 15
Dependent Claim
17 words
A nucleotide polymer containing at least one of the monomers as claimed in claims 1 or 5.
Claim 16
Dependent Claim
12 words
A composition comprising the nucleotide polymer of claim 14 in a carrier.
Claim 17
Dependent Claim
83 words
A nucleotide polymer comprising at least one monomer of claim 1 and having the following formula II ##STR7## wherein X and Z are O, V and W are O or S, and wherein V and W can be the same or different in a monomer unit, L is H or a partner of an antigen-antibody or biotin-avidin or streptavidin binding pair, and B, A and C have the meaning defined in claim 1 and n denotes an arbitrary whole number greater than one.
Claim 18
Dependent Claim
17 words
The nucleotide polymer of claim 16 having a 3'-terminal end wherein the 3'-terminal end is a 3'-deoxyribonucleoside.
Claim 19
Dependent Claim
12 words
A composition comprising the nucleotide polymer of claim 16 in a carrier.
Claim 20
Dependent Claim
10 words
The nucleotide polymer of claim 16, wherein L is biotin.
Claim 21
Dependent Claim
17 words
The nucleotide polymer of claim 19 having a 3'-terminal end wherein the 3'-terminal end is a 3'-deoxyribonucleoside.
Claim 22
Dependent Claim
12 words
A composition comprising the nucleotide polymer of claim 19 in a carrier.
Claim 23
Dependent Claim
21 words
An oligonucleotide consisting of SEQ ID NO: 1, wherein said oligonucleotide comprises at least one modified nucleoside having a 2'-O-allyl moiety.
Claim 24
Dependent Claim
21 words
An oligonucleotide consisting of SEQ ID NO: 1, wherein said oligonucleotide comprises at least one modified nucleoside having a 2'-O-allyl moiety.
Claim 25
Dependent Claim
79 words
A method for detecting the presence of a nucleic acid molecule in a sample comprising: a) incubating said sample with a nucleic acid probe which hybridizes to said nucleic acid molecule and which comprises at least one nucleotide of claim 1, wherein said incubation is under conditions where hybridization takes place; and b) detecting hybridization of said nucleic acid probe to said nucleic acid molecule as an indication of the presence of said nucleic acid molecule in said sample.
References Cited (Backward Citations)
EP0260032A2
Cited
WO1989012642A1
Cited
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