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US 7,737,281 B2Granted
Purine based fluorescent dyes
AssigneeEnzo Life Sciences, Inc. C/O Enzo Biochem, Inc.
InventorMaciej Szczepanik
Life of this patent
Estimating the term…
Abstract
The present invention provides novel purine-based fluorescent dyes that may be used for staining, localizing and otherwise labeling target molecules, such as nucleic acids, for detection, amplification and quantification.
Claims23
A dye having the formula:
- wherein n is 0, 1 or 2;
- wherein Y comprises CR10R11, NR10, O, S or Se where R10 and R11 independently comprise hydrogen, a halogen, an amino group, an alkyl group wherein said alkyl group is saturated or unsaturated, linear or branched, substituted or unsubstituted, an alkoxy group wherein said alkoxy group is saturated or unsaturated, branched or linear, substituted or unsubstituted, or when taken together, R10 and R11 form a 5 or 6 membered ring;
- wherein at least one of R1, R2, R3, R5, R6, R7, R8, R16, R17 or R18 comprises Q;
- wherein Q comprises a sulfonate ester (SO2ER13), a sulfoxide (SOR13), a sulfone (SO2CR13R14R15), a sulfonamide (SO2NR13R14), a phosphate (PO4=), a phosphate monoester (PO3−ER13), a phosphate diester (PO2ER13ER14), a phosphonate (PO3=), a phosphonate monoester (PO2−ER—), a phosphonate diester (POER13ER14), a thiophosphate (PSO3=), a thiophosphate monoester (PSO2−ER13), a thiophosphate diester (PSOER13ER14), a thiophosphonate (PSO2=), a thiophosphonate monoester (PSO−ER13), a thiophosphonate diester (PSER13ER14), a phosphonamide (PONR13R14NR19R20), its thioanalogue (PSNR13R14NR19R20), a phosphoramide (PONR13R14NR15NR19R20), its thioanalogue (PSNR13R14NR15NR19R20), a thioanalogue of phosphoramidite (POSR19NR13R14), wherein any of E can independently comprise O or S;
- wherein Q is attached directly, or indirectly through a linker arm comprising carbon, sulfur, oxygen, nitrogen, or any combinations thereof, and wherein said linker arm may be saturated or unsaturated, linear or branched, substituted or unsubstituted, or any combinations thereof;
- wherein the remaining R1, R2, R3, R5, R6, R7, R8, R16, R17 and R18 independently comprise hydrogen, Z, an alkyl group wherein said alkyl group is saturated or unsaturated, linear or branched, substituted or unsubstituted, an alkoxy group wherein said alkoxy group is saturated or unsaturated, branched or linear, substituted or unsubstituted, or when taken together, R16 and R3, R3 and R8, R8 and R7, R7 and R6, R6 and R5, R5 and R10, R16 and R17, R10 and R16, and R17 and R18 may form a 5 or 6 membered ring;
- wherein Z comprises a carboxyl group (CO2−), a carbonate ester (COER13), a sulfonate (SO3−), a sulfonate ester (SO2ER13), a sulfoxide (SOR13), a sulfone (SO2CR13R14R15), a sulfonamide (SO2NR13R14), a phosphate (PO4=), a phosphate monoester (PO3−ER13), a phosphate diester (PO2ER13ER14), a phosphonate (PO3=), a phosphonate monoester (PO2−ER13), a phosphonate diester (PO2ER13ER14), a thiophosphate (PSO3=), a thiophosphate monoester (PSO2−ER13), a thiophosphate diester (PSOER13ER14), a thiophosphonate (PSO2=), a thiophosphonate monoester (PSO−ER13), a thiophosphonate diester (PSER13ER14), a phosphonamide (PONR13R14NR19R20), its thioanalogue (PSNR13R14NR19R20), a phosphoramide (PONR13R14NR15NR19R20), its thioanalogue (PSNR13R14NR15NR19R20), a phosphoramidite (PO2R19NR13R14) or its thioanalogue (POSR19NR13R14), wherein any of E can independently comprise O or S;
- wherein Z is attached directly, or indirectly through a linker arm comprising carbon, sulfur, oxygen, nitrogen, or any combinations thereof, and wherein said linker arm may be saturated or unsaturated, linear or branched, substituted or unsubstituted, or any combinations thereof;
- and wherein any of R1, R2, R3, R5, R6, R7, R8, R16, R17 and R18 may independently further comprise a heteroatom containing side chain wherein said side chain is joined to said R group by a linkage which comprises an ether linkage (—OR25), a thioether linkage (—SR25), or an amine linkage (—NR25R26 or —N+R25R26R27), and wherein R25, R26 and R27 independently comprise hydrogen, Z, an alkyl group wherein said alkyl group is saturated or unsaturated, linear or branched, substituted or unsubstituted, an alkoxy group that is saturated or unsaturated, branched or linear, substituted or unsubstituted, or when taken together, R25 and R26, and R26 and R27 independently comprise a five or six membered ring, and wherein any of R25, R26 or R27 may further comprise said heteroatom containing side chain.
6 more elements
A dye having the formula
- or
A dye having the formula
Dependencies are inferred from the claim text.