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US 8,026,057 B2Granted
Nucleic acid labeling compounds
AssigneeAffymetrix, Inc.
InventorsGlenn Hugh McGall, Anthony Dale Barone
Life of this patent
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Abstract
Nucleic acid labeling compounds are disclosed. The 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.
Claims5
A nucleic acid labeling compound having the formula:
- wherein A is hydrogen, monophosphate, diphosphate, triphosphate, α-thiotriphosphate, phosphoramidite, or H-phosphonate;
- wherein X1 is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, hydrogen, alkyl or aryl;
- wherein X2 is a bond or alkylene;
- wherein Q is selected from the group consisting of a radiolabel, a magnetic particle, colloidal gold, fluorescein, texas red, rhodamine, green fluorescent protein, luminal lophine, acridine salts, luciferin, vanadium spin labels, copper spin labels, iron spin labels, manganese spine labels, nitroxide free radicals, quinoline dyes, triarlmethane dyes, acridine dyes, colored glass beads, polystyrene beads, polypropylene beads, latex beads, biotin, horseradish peroxidase, alkaline phosphatase, 1-aminonapthalene, 2-aminonapthalene, p,p′-diaminostilbenes, pyrenes, quaternary phenanthridine salts, 9-aminoacridines, p,p′-diaminobenzophenone imines, anthracenes, oxacarbocyanines, marocyanine, 3-amino aminoequilenin, perylene, bisbenzoxazole, bis-p-oxazolyl benzene, 1,2-benzophenazin, retinol, bis-3-aminopridinium salts, hellebrigenin, tetracyline, sterophenol, benzimidazolyl phenylamine, 2-oxo-3-chromen, indole, xanthen, 7-hydroxycoumarin, phenoxazine, salycilate, strophanthidin, porphyrins, triarylmethanes, flavin, xanthene dyes, rhodamine dyes, cyanine dyes, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene dyes, phycobiliprotein, dansyl chloride, 3,6-dihydroxy-9-phenylxanthhydrol;
- rhodamineisothiocyanate;
- N-phenyl-1-amino-8-sulfonatonaphthalene;
- N-phenyl-2-amino-6-sulfonatonaphthalene;
- 4-acetamido-4-isothiocyanatostilbene-2,2′-disulfonic acid;
- pyrene-3-sulfonic acid;
- 2-toluidinonapththalene-6-sulfonate;
- N-phenyl, N-methyl 2-aminonaphthalene-6-sulfonate;
- ethidium bromide;
- stebrine;
- auromine-0,2-(9′-anthroyl)palmitate;
- dansyl phosphatidylethanolamin;
- N,N′-dioctadecyl oxacarbocycanine;
- N,N′-dihexyl oxacarbocyanine;
- merocyanine, 4-(3′-pyrenyl)butryate;
- d-3-aminodesoxy-equilenin;
- 12-(9′-anthroyl)stearate;
- 2-methylanthracene;
- 9-vinylanthracene;
- 2,2′-(vinylene-p-phenylene)bisbenzoxazole;
- p-bis[2-(4-methyl-5-phenyl oxazolyl)]benzene;
- 6-dimethylamino-1,2-benzophenzin;
- retinol;
- bis(3′-aminopyridinium)-1,10-decandiyl diiodide;
- sulfonaphthylhydrazone of hellibrienin;
- chlorotetracycline;
- N-(7-dimethylamino-4-methyl-2-oxo-3-chromenyl)maleimide;
- N-[p-(2-benzimidazolyl)phenyl]maleimide;
- N-(4-fluoranthyl)maleimide;
- bis(homovanillic acid);
- resazarin;
- 4-chloro-7-nitro-2,1,3-benzooxadizole;
- merocyanine 540;
- resorufin;
- rose_bengal and 2,4-diphenyl-3(2H)-furanone;
- and
- wherein G is -L-(M)m, wherein L is a linker moiety selected from the group consisting of amido alkyl groups, functionalized alkyl groups, alkenyl alkyl groups, alkanoyl groups, and N-alkyl amido groups, wherein m is an integer from 0 to 20 and each M is a connecting group selected from the group consisting of amino alkyl, —O(CH2)5NH—, —CO—, —NH—, —CO(O)—, —CO(NH)—, —(CH2)iO—, —(CH2)jNH—, —C(O)(CH2)hO—, —CO(CH2)5NHCO(CH2)5NH—, —NH(CH2CH2O)kNH—, —NH(CH2CH2O)kCH2CH2NH— and —CO(CH2)5—, wherein k is an integer from 1 to 5, and wherein h, i, and j are independently integers from 1 to 5.
37 more elements
Dependencies are inferred from the claim text.