US4950744A
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Photochemical nucleic acid-labeling reagent having a polyalkylamine spacer
Assignee: MILES INC. A CORP. OF INDIANA
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Filing: 1987-03-18
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Granted: 1990-08-21
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Expires: 2007-03-18
Abstract
Abstract A photochemical nucleic acid-labeling reagent of the formula <IMAGE> wherein Q is a photoreactive residue of a nucleic acid-binding ligand; L is a detectable label residue; R is hydrogen, C1 to C7-alkyl, aryl, hydroxy, or C1 to C7-alkoxy; x is an integer from 2 through 7; and y is an integer from 3 through 10; wherein R and x, respectively, can be the same or different each time they appear in the formula. The reagent is useful in the highly efficient labeling of nucleic acids for the purpose of detection in hybridization assays.
Inventors
- 👤 Nanibhushan Dattagupta
- 👤 James P. Albarella
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 03:59
CPC Classifications
C; C12; C12Q; C12Q1/00; C12Q1/68; C12Q1/6813; C12Q1/6816; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; G01N33/532; Y; Y10; Y10T; Y10T436/00; Y10T436/14; Y10T436/142222; Y10T436/143333
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
60 words
A photochemical nucleic acid-labeling reagent of the formula ##STR11## wherein Q is a photoreactive residue of a nucleic acid-binding ligand; L is a detectable label residue; R is hydrogen, C 1 to C 7 -alkyl, aryl, hydroxy, or C 1 to C 7 -alkoxy; and wherein R can be the same or different each time R appears in the formula.
Claim 2
Dependent Claim
60 words
A photochemical nucleic acid-labeling reagent of the formula ##STR11## wherein Q is a photoreactive residue of a nucleic acid-binding ligand; L is a detectable label residue; R is hydrogen, C 1 to C 7 -alkyl, aryl, hydroxy, or C 1 to C 7 -alkoxy; and wherein R can be the same or different each time R appears in the formula.
Claim 3
Dependent Claim
17 words
A reagent according to claim 1, wherein R is hydrogen or C 1 to C 4 -alkyl.
Claim 4
Dependent Claim
10 words
A reagent according to claim 1 of the formula ##STR12##
Claim 5
Dependent Claim
23 words
A reagent according to claim 1, wherein the photoreactive residue of a nucleic acid-binding ligand is a photoreactive residue of an intercalator compound.
Claim 6
Dependent Claim
26 words
A reagent according to claim 4, wherein the intercalator compound is selected from the group consisting of acridine dyes, phenanthridines, phenazines, furocoumarins, phenothiazines, quinolines and antracyclines.
Claim 7
Dependent Claim
20 words
A reagent according to claim 4, wherein the intercalator compound is selected from the group consisting of furocoumarins and phenanthridines.
Claim 8
Dependent Claim
67 words
A reagent according to claim 4, wherein the intercalator compound is of the formula ##STR13## in which R 1 , R 2 and R 3 each independently is hydrogen or C 1 -C 7 -alkyl; and R 4 is hydrogen, C 1 -C 7 -alkyl or C 1 -C 7 -alkyl substituted with hydroxy, C 1 -C 7 -alkoxy, amino, halo, or is of the formula ##STR14##
Claim 9
Dependent Claim
12 words
A reagent according to claim 4, wherein the intercalator compound is 4'-aminomethyl-4,5'-dimethylangelicin.
Claim 10
Dependent Claim
88 words
A reagent according to claim 4, wherein the intercalator compound is of the formula ##STR15## in which R 1 , R 3 and R 6 each independently is hydrogen or C 1 -C 7 -alkyl; R 4 is hydrogen, C 1 -C 7 -alkyl or C 1 -C 7 -alkyl substituted with hydroxy, C 1 -C 7 -alkoxy, amino, halo, or is of the formula ##STR16## R 2 and R 5 each independently is hydrogen, hydroxy, carboxy, carbo-C 1 -C 7 -alkoxy or C 1 -C 7 -alkoxy.
Claim 11
Dependent Claim
12 words
A reagent according to claim 4, wherein the intercalator compound is 4'-aminomethyl-4,5',8-trimethylpsoralen.
Claim 12
Dependent Claim
35 words
A reagent according to claim 1, wherein the detectable label residue is a residue of a moiety selected from the group consisting of biotin, a hapten, an enzyme, a fluorescent molecule and a luminescent molecule.
Claim 13
Dependent Claim
24 words
A reagent according to claim 1, wherein the detectable label residue is selected from the group consisting of a biotin and a hapten residue.
Claim 14
Dependent Claim
73 words
A labeled nucleic acid comprising (a) a nucleic acid component, (b) a nucleic acid-binding ligand photochemically linked to the nucleic acid component, (c) a label, and (d) a spacer chemically linking (b) and (c) and being of the formula ##STR17## wherein R is hydrogen, C 1 -C 7 alkyl, aryl, hydroxy, or C 1 -C 7 alkoxy; and wherein R can be the same or different each time R appears in the formula.
Claim 15
Dependent Claim
73 words
A labeled nucleic acid comprising (a) a nucleic acid component, (b) a nucleic acid-binding ligand photochemically linked to the nucleic acid component, (c) a label, and (d) a spacer chemically linking (b) and (c) and being of the formula ##STR17## wherein R is hydrogen, C 1 -C 7 alkyl, aryl, hydroxy, or C 1 -C 7 alkoxy; and wherein R can be the same or different each time R appears in the formula.
Claim 16
Dependent Claim
18 words
A labeled nucleic acid according to claim 13, wherein R is hydrogen or C 1 -C 4 alkyl.
Claim 17
Dependent Claim
16 words
A labeled nucleic acid according to claim 13, wherein the spacer is of the formula ##STR18##
Claim 18
Dependent Claim
17 words
A labeled nucleic acid according to claim 13, wherein the nucleic acid-binding ligand is an intercalator compound.
Claim 19
Dependent Claim
28 words
A labeled nucleic acid according to claim 16, wherein the intercalator compound is selected from the group consisting of acridine dyes, phenanthridines, phenazines, furocoumarins, phenothiazines, quinolines and anthracyclines.
Claim 20
Dependent Claim
22 words
A labeled nucleic acid according to claim 16, wherein the intercalator compound is selected from the group consisting of furocoumarins and phenanthridines.
Claim 21
Dependent Claim
66 words
A labeled nucleic acid according to claim 16, wherein the intercalator compound is of the formula ##STR19## in which R 1 , R 2 and R 3 each independently is hydrogen or lower alkyl; and R 4 is hydrogen, C 1 -C 7 -alkyl or C 1 -C 7 -alkyl substituted with hydroxy, C 1 -C 7 -alkoxy, amino, halo, or is of the formula ##STR20##
Claim 22
Dependent Claim
14 words
A labeled nucleic acid according to claim 16, wherein the intercalator compound is 4'-aminomethyl-4,5'-dimethylangelicin.
Claim 23
Dependent Claim
90 words
A labeled nucleic acid according to claim 16, wherein the intercalator compound is of the formula ##STR21## in which R 1 , R 3 and R 6 each independently is hydrogen or C 1 -C 7 -alkyl; R 4 is hydrogen, C 1 -C 7 -alkyl or C 1 -C 7 -alkyl substituted with hydroxy, C 1 -C 7 -alkoxy, amino, halo, or is of the formula ##STR22## R 2 and R 5 each independently is hydrogen, hydroxy, carboxy, carbo-C 1 -C 7 -alkoxy or C 1 -C 7 -alkoxy.
Claim 24
Dependent Claim
14 words
A labeled nucleic acid according to claim 16, wherein the intercalator compound is 4'-aminomethyl-4,5'-8-trimethylpsoralen.
Claim 25
Dependent Claim
30 words
A labeled nucleic acid according to claim 13, wherein the label is selected from the group consisting of biotin, a hapten, an enzyme, a fluorescent molecule and a luminescent molecule.
Claim 26
Dependent Claim
22 words
A labeled nucleic acid according to claim 13, wherein the label is selected from the group consisting of biotin and a hapten.
Claim 27
Dependent Claim
15 words
A labeled nucleic acid according to claim 13, wherein the nucleic acid component is DNA.
Claim 28
Dependent Claim
15 words
A labeled nucleic acid according to claim 13, wherein the nucleic acid component is RNA.
Claim 29
Dependent Claim
16 words
A labeled nucleic acid according to claim 13, wherein the nucleic acid component is an oligonucleotide.
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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) | 1993-08-20 | 1994-02-19 | 1994-08-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-08-20 | 1998-02-19 | 1998-08-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-08-20 | 2002-02-19 | 2002-08-21 | $7700.00 | Window Closed / Lapsed |