Nucleic acid labeling compounds

1. A nucleic acid labeling compound having the formula:

wherein A is hydrogen, monophosphate, diphosphate, triphosphate, α-thiotriphosphate, phosphoramidite, or H-phosphonate;

wherein X 1 is O, S, NR 1 or CHR 2 , wherein R 1 and R 2 are, independently, hydrogen, alkyl or aryl;

wherein X 2 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(CH 2 ) 5 NH—, —CO—, —NH—, —CO(O)—, —CO(NH)—, —(CH 2 ) i O—, —(CH 2 ) j NH—, —C(O)(CH 2 ) h O—, —CO(CH 2 ) 5 NHCO(CH 2 ) 5 NH—, —NH(CH 2 CH 2 O) k NH—, —NH(CH 2 CH 2 O) k CH 2 CH 2 NH— and —CO(CH 2 ) 5 —, wherein k is an integer from 1 to 5, and wherein h, i, and j are independently integers from 1 to 5.

2. The nucleic acid labeling compound of claim 1 , wherein A is H or H 4 O 9 P 3 —;

wherein X 1 is O;

wherein X 2 is a bond; and

wherein G is —C(O)NR 3 —(CH 2 ) m —(CH 2 CH 2 O) n —CH 2 CH 2 —C(O)NR 3 —, wherein R 3 is hydrogen or alkyl, and wherein m and n are independently an integer from 1 to 15.

3. The nucleic acid labeling compound of claim 2 , wherein G is —C(O)NH—(CH 2 ) m —(CH 2 CH 2 O) n —CH 2 CH 2 —C(O)NH—;

wherein m is from 1 to 6; and

wherein n is from 1 to 4.

4. The nucleic acid labeling compound of claim 1 , wherein A is H or H 4 O 9 P 3 —;

wherein X 1 is O;

wherein X 2 is CH 2 ; and

wherein G is —C(O)NR 3 —(CH 2 ) m —(CH 2 CH 2 O) n —CH 2 CH 2 —C(O)NR 3 —, wherein R 3 is hydrogen or alkyl, and wherein m and n are independently an integer from 1 to 15.

5. The nucleic acid labeling compound of claim 4 , wherein G is —C(O)NH—(CH 2 ) m —(CH 2 CH 2 O) n —CH 2 CH 2 —C(O)NH—, wherein m is from 1 to 6, and wherein n is from 1 to 4.