| US 7,468,243 B2 | ||
| 2-aminopyrimidin-4-one nucleic acid labeling compounds | ||
| Glenn McGall, Mountain View, Calif. (US); and Anthony D. Barone, San Jose, Calif. (US) | ||
| Assigned to Affymetrix, Inc., Santa Clara, Calif. (US) | ||
| Filed on Mar. 12, 2002, as Appl. No. 10/97,113. | ||
| Claims priority of provisional application 60/275202, filed on Mar. 12, 2001. | ||
| Prior Publication US 2002/0182625 A1, Dec. 05, 2002 | ||
| This patent is subject to a terminal disclaimer. | ||
| Int. Cl. C12Q 1/68 (2006.01); C07D 239/02 (2006.01) | ||
| U.S. Cl. 435—6 [536/23.1; 536/25.1; 544/320; 544/321; 549/430] | 35 Claims |
1. A nucleic acid labeling compound having the formula:
![]() wherein A is H, monophosphate, diphosphate, triphosphate, α-thiotriphosphate, phosphoramidite, or H-phosphonate;
X is O;
Y is hydrogen, N3, F, OR9, SR9 or NHR9, wherein R9 is hydrogen, alkyl or aryl;
Z is hydrogen, N3, F, OR9, SR9 or NHR10,wherein R10 is hydrogen, alkyl or aryl;
L is a linker moiety; selected from the group consisting of —CH═CH—R11, or C═C-R11 wherein R11 comprises a moiety selected from the group consisting of alkyl, functionalized alkyl, alkenyl alkyl, amido alkyl, amino alkyl,
alkoxy, amino, aryl, and thio;
Q is selected from the group consisting of a raiolabel, 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, quatemary 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-
sulfonatonaphthanlene; 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
M is a connecting group selected from the group consisting of amino alkyl, —O(CH2)5NH—, —CO—, —CO(O)—, —CO(NH)—, —CO(CH2)5NHCO(CH2)5NH—, —NH(CH2CH2O)kNH—, NH(CH2CH2O)kCH2CH2NH— and —CO(CH2)5—, wherein k is an integer from 1 to 5, wherein m is an integer ranging from 0 to 20.
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