US2001018514A1PendingUtilityA1
Nucleic acid labeling compounds
Priority: Jul 31, 1998Filed: Jul 31, 1998Published: Aug 30, 2001
Est. expiryJul 31, 2018(expired)· nominal 20-yr term from priority
C07H 19/12C07H 19/06C07H 19/04C07H 19/052C07H 21/00C07H 19/10
34
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Claims
Abstract
Nucleic acid labeling compounds containing heterocyclic derivatives are disclosed. The heterocyclic derivative containing compounds are synthesized by condensing a heterocyclic derivative with a cyclic group (e.g. a ribofuranose derivative). The labeling compounds are suitable for enzymatic attachment to a nucleic acid, either terminally or internally, to provide a mechanism of nucleic acid detection.
Claims
exact text as granted — not AI-modified1 . A nucleic acid labeling compound of the following structure:
wherein A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid; X is O, S, NR 1 or CHR 2 , wherein R 1 and R 2 are, independently, H, alkyl or aryl; Y is H, N 3 , F, OR 1 , SR 1 or NHR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is amido alkyl; Q is a detectable moiety; and, M is a connecting group, wherein m is an integer ranging from 0 to about 3.
2 . A nucleic acid labeling compound according to claim 1 , wherein A is H or H 4 O 9 P 3 —; X is O; Y is H or OR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is —C(O)NH(CH 2 ) n NH—, wherein n is an integer ranging from about 2 to about 10; Q is biotin or a carboxyfluorescein; and, M is —CO(CH 2 ) 5 NH—, wherein m is 1 or 0.
3 . A nucleic acid labeling compound according to claim 2 , wherein Y is H or OH; Z is H or OH; L is —C(O)NH(CH 2 ) 4 NH—; Q is biotin; and, M is —CO(CH 2 ) 5 NH, wherein m is 1.
4 . A nucleic acid labeling compound according to claim 2 , wherein Y is H or OH; Z is H or OH; L is —C(O)NH(CH 2 ) 4 NH—; Q is 5-carboxyfluorescein; and m is 0.
5 . A nucleic acid labeling compound of the following structure:
wherein A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid; X is O, S, NR 1 or CHR 2 , wherein R 1 and R 2 are, independently, H, alkyl or aryl; Y is H, N 3 , F, OR 1 , SR 1 or NHR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is amino alkyl; Q is a detectable moiety; and, M is a connecting group, wherein m is an integer ranging from 0 to about 3.
6 . A nucleic acid labeling compound according to claim 5 , wherein A is H or H 4 O 9 P 3 —; X is O; Y is H or OR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is —NH(CH 2 ) n NH—, wherein n is an integer ranging from about 2 to about 10; Q is biotin or carboxyfluorescein; and, M is —CO(CH 2 ) 5 NH— or —CO(CH 2 ) 5 NHCO(CH 2 ) 5 NH—, wherein m is 1 or 0.
7 . A nucleic acid labeling compound according to claim 6 , wherein Y is H or OH; Z is H or OH; L is —NH(CH 2 ) 4 NH—; Q is biotin; and, m is 0.
8 . A nucleic acid labeling compound according to claim 6 , wherein Y is H or OH; Z is H or OH; L is —NH(CH 2 ) 4 NH—; Q is 5-carboxyfluorescein; and, m is 0.
9 . A nucleic acid labeling compound of the following structure:
wherein A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid; X is O, S, NR 1 or CHR 2 , wherein R 1 and R 2 are, independently, H, alkyl or aryl; Y is H, N 3 , F, OR 1 , SR 1 or NHR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is alkynyl alkyl; Q is a detectable moiety; and, M is a connecting group, wherein m is an integer ranging from 0 to about 3.
10 . A nucleic acid labeling compound according to claim 9 , wherein A is H or H 4 O 9 P 3 —; X is O; Y is H or OR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is —C≡C(CH 2 ) n NH—, wherein n is an integer ranging from about 1 to about 10; Q is biotin or carboxyfluorescein; and, M is —CO(CH 2 ) 5 NH—, wherein m is 1 or 0.
11 . A nucleic acid labeling compound according to claim 10 , wherein Y is H or OH; Z is H or OH; L is —C≡CCH 2 NH—; Q is biotin; and, m is 1.
12 . A nucleic acid labeling compound according to claim 10 , wherein Y is H or OH; Z is H or OH; L is —C≡CCH 2 NH—; Q is 5-carboxyfluorescein; and, m is 1.
13 . A nucleic acid labeling compound of the following structure:
wherein A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid; X is O, S, NR 1 or CHR 2 , wherein R 1 and R 2 are, independently, H, alkyl or aryl; Y is H, N 3 , F, OR 1 , SR 1 or NHR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is amino alkyl; Q is a detectable moiety; and, M is a connecting group, wherein m is an integer ranging from 0 to about 3.
14 . A nucleic acid labeling compound according to claim 13 , wherein A is H or H 4 O 9 P 3 —; X is O; Y is H or OR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is —NH(CH 2 ) n NH—, wherein n is an integer ranging from about 2 to about 10; Q is biotin or carboxyfluorescein; and, M is —CO(CH 2 ) 5 NH— or —CO(CH 2 ) 5 NHCO(CH 2 ) 5 NH—, wherein m is 1 or 0.
15 . A nucleic acid labeling compound according to claim 14 , wherein Y is H or OH; Z is H or OH; L is —NH(CH 2 ) 4 NH—; Q is biotin; and, M is —CO(CH 2 ) 5 NH—, wherein m is 1.
16 . A nucleic acid labeling compound according to claim 14 , wherein Y is H or OH; Z is H or OH; L is —NH(CH 2 ) 4 NH—; Q is 5-carboxyfluorescein; and, M is —CO(CH 2 ) 5 NH—, wherein m is 1.
17 . A nucleic acid labeling compound of the following structure:
wherein A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid; X is O, S, NR 1 or CHR 2 , wherein R 1 and R 2 are, independently, H, alkyl or aryl; Y is H, N 3 , F, OR 1 , SR 1 or NHR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is functionalized alkyl, alkenyl alkyl or alkynyl alkyl; Q is a detectable moiety; and, M is a connecting group, wherein m is an integer ranging from 0 to about 3.
18 . A nucleic acid labeling compound according to claim 17 , wherein A is H or H 4 O 9 P 3 —; X is O; Y is H or OR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is —CH═CH(CH 2 ) n NH—, wherein n is an integer ranging from about 1 to about 10; Q is biotin or carboxyfluorescein; and, M is —CO(CH 2 ) 5 NH— or —CO(CH 2 ) 5 NHCO(CH 2 ) 5 NH—, wherein m is 1 or 0.
19 . A nucleic acid labeling compound according to claim 18 , wherein Y is H or OH; Z is H or OH; L is —CH═CHCH 2 NH—; Q is biotin; and, m is 0.
20 . A nucleic acid labeling compound according to claim 18 , wherein Y is H or OH; Z is H or OH; L is —CH═CHCH 2 NH—; Q is 5-carboxyfluorescein; and, m is 0.
21 . A nucleic acid labeling compound of the following structure:
wherein A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid; X is O, S, NR 1 or CHR 2 , wherein R 1 and R 2 are, independently, H, alkyl or aryl; Y is H, N 3 , F, OR 1 , SR 1 or NHR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is functionalized alkyl, alkenyl alkyl or alkynyl alkyl; Q is a detectable moiety; and, M is a connecting group, wherein m is an integer ranging from 0 to about 3.
22 . A nucleic acid labeling compound according to claim 21 , wherein A is H or H 4 O 9 P 3 —; X is O; Y is H or OR 1 , wherein R 1 is H, alkyl or aryl; Z is H, N 3 , F or OR 1 , wherein R 1 is H, alkyl or aryl; L is —CH═CH(CH 2 ) n NH—, wherein n is an integer ranging from about 1 to about 10; Q is biotin or carboxyfluorescein; and, M is —CO(CH 2 ) 5 NH— or —CO(CH 2 ) 5 NHCO(CH 2 ) 5 NH—, wherein m is 1 or 0.
23 . A nucleic acid labeling compound according to claim 22 , wherein Y is H or OH; Z is H or OH; L is —CH═CHCH 2 NH—; Q is biotin; and, m is 0.
24 . A nucleic acid labeling compound according to claim 22 , wherein Y is H or OH; Z is H or OH; L is —CH═CHCH 2 NH—; Q is 5-carboxyfluorescein; and, m is 0.
25 . A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 2 with a nucleic acid.
26 . A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 6 with a nucleic acid.
27 . A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 10 with a nucleic acid.
28 . A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 14 with a nucleic acid.
29 . A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 18 with a nucleic acid.
30 . A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 22 with a nucleic acid.
31 . A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 25 bound to a complementary probe.
32 . The hybridization product according to claim 31 , wherein the probe is attached to a glass chip.
33 . A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 26 bound to a complementary probe.
34 . The hybridization product according to claim 33 , wherein the probe is attached to a glass chip.
35 . A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 27 bound to a complementary probe.
36 . The hybridization product according to claim 35 , wherein the probe is attached to a glass chip.
37 . A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 28 bound to a complementary probe.
38 . The hybridization product according to claim 37 , wherein the probe is attached to a glass chip.
39 . A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 29 bound to a complementary probe.
40 . The hybridization product according to claim 39 , wherein the probe is attached to a glass chip.
41 . A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 30 bound to a complementary probe.
42 . The hybridization product according to claim 41 , wherein the probe is attached to a glass chip.
43 . A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 2 to a nucleic acid.
44 . A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 6 to a nucleic acid.
45 . A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 10 to a nucleic acid.
46 . A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 14 to a nucleic acid.
47 . A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 18 to a nucleic acid.
48 . A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 22 to a nucleic acid.
49 . A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 25 with a probe.
50 . A method according to claim 49 , wherein the probe is attached to a glass chip.
51 . A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 26 with a probe.
52 . A method according to claim 51 , wherein the probe is attached to a glass chip.
53 . A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 27 with a probe.
54 . A method according to claim 53 , wherein the probe is attached to a glass chip.
55 . A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 28 with a probe.
56 . A method according to claim 55 , wherein the probe is attached to a glass chip.
57 . A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 29 with a probe.
58 . A method according to claim 57 , wherein the probe is attached to a glass chip.
59 . A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 30 with a probe.
60 . A method according to claim 59 , wherein the probe is attached to a glass chip.Cited by (0)
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