Fluorescent dyes containing phosphorus or arsenic
AssigneeEnzo Life Sciences, Inc.
InventorsZaiguo Li, Praveen Pande
Life of this patent
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Abstract
The present invention provides a fluorescent dye that incorporates a pentavalent phosphorus or arsenic into its ring structure. Also provided is a fluorescence energy transfer system that comprises the above fluorescent dye and a second dye, where the second dye is capable of energy transfer with the fluorescent dye. Additionally provided is a kit for labeling a target molecule. In further embodiments, another kit for labeling a target molecule is provided. A target molecule labeled with the above-described fluorescent dye is also provided. In additional embodiments, methods of labeling a target molecule are provided.
Claims20
A fluorescent dye comprising Structure I, II, III or IV:
- wherein
- R1, R2, R3, R4, R5, R6, R7 and R8 are independently H, F, Cl, Br, I, CN, nitro, azido, hydroxyl, amino, hydrazino, (substituted) aryl, (substituted) aroxyl, alkenyl, alkynyl, alkyl, alkoxy, alkylamino, dialkylamino, arylamino, diarylamino, alkyl(aryl)amino, alkanoylamino, alkylthio, alkylcarbonyl, aryl carbonyl, alkylthiocarbonyl, arylthiocarbonyl, alkyloxycarbonyl, aroxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, alkyl(aryl)aminocarbonyl, arylcarboxamido, or Q, the alkyl or alkoxy portions of which are saturated or unsaturated, linear or branched, and unsubstituted or substituted;
- wherein Q comprises a carboxyl group (CO2−), a carbonyl halide, a carbonate ester or thioester (COSR9) or amide (COER9), a thiocarboxylic acid, a thiocarbonyl halide, a thiocarbonate ester or amide (CSER9), a sulfonate acid or halide or ester (SO2ER9), a sulfoxide (SOR9), a sulfone (SO2CR9R10R11), a sulfonamide (SO2NR9R10), a phosphate (PO4=), a phosphoryl halide, a phosphate monoester or monoamide (PO3−ER9), a phosphate diester or diamide (PO2ER9ER10), a phosphonate (PO3=), a phosphonyl halide, a phosphonate monoester or monoamide (PO2−ER9), a phosphonate diester or diamide (POER9ER10), a thiophosphate (PSO3=), a thiophosphate monoester or monoamide (PSO2−ER9), a thiophosphate diester or diamide (PSOER9ER10), a thiophosphonate (PSO2=), a thiophosphonyl halide, a thiophosphonate monoester or monoamide (PSO−ER9), a thiophosphonate diester or diamide (PSER9ER10), a phosphonamide (PONR9R10NR12R13), a phosphonamide thioanalogue (PSNR9R10NR12R13), a phosphoramide (PONR9R10NR11NR12R13), a phosphoramide thioanalogue (PSNR9R10NR11NR12R13), a phosphoramidite (PO2R12NR9R10) or a phosphoramidite thioanalogue (POSR12NR9R10), where each E is independently N, NH, O or S;
- R1 in combination with R2, R2 in combination with R3, R3 in combination with R4, R3 in combination with R7, R4 in combination with R7, or R4 in combination with R5 can independently form a 5-10 member ring structure which is saturated, unsaturated or aromatic, unsubstituted or comprising a heteroatom, and/or further substituted;
- R9, R10, R11, R12 and R13 are independently a hydrogen, a halogen, an amino group, an alkyl group wherein said alkyl group is saturated or unsaturated, linear or branched, or substituted or unsubstituted, an alkoxy group wherein said alkoxy group is saturated or unsaturated, branched or linear, or substituted or unsubstituted, an aryl group wherein said aryl group is unsubstituted or substituted;
- wherein R9 in combination with R10, R12 in combination with R13, R9 in combination with R11, R9 in combination with R12, R10 in combination with R13, or R11 in combination with R12 can independently form a 5-10 member ring;
- X is O, OR14, S, SR15, CR16R17, NR16R17 or N+R16R17;
- Y is O, OR14, S, SR15, CR18R19, NR18R19 or N+R18R19, wherein
- R14, R15, R16, R17, R18 and R19 are independently H, alkyl, aryl, alkylcarbonyl, arylcarbonyl, or Q, in which the alkyl or aryl potions are unsubstituted or substituted, saturated or unsaturated, or
- R16 in combination with R17, or R18 in combination with R19 can independently form an unsubstituted or substituted 5-10 member ring structure, and R16 in combination with R1, R17 in combination with R2, R18 in combination with R5, or R19 in combination with R6, can independently form a 5- to 10-member ring structure that is saturated or unsaturated and substituted or unsubstituted;
- Z is a pentavalent P or As;
- A and B are substituents that link to Z through single or double bonds and are independently H, O, S, NH, F, Cl, Br, I, CN, nitro, azido, hydroxyl, amino, imino, hydrazino, (substituted) aryl, (substituted) aroxyl, alkenyl, alkynyl, alkyl, alkoxy, alkylamino, dialkylamino, arylamino, diarylamino, alkyl(aryl)amino, alkanoylamino, alkylthio, alkylcarbonyl, aryl carbonyl, alkylthiocarbonyl, arylthiocarbonyl, alkyloxycarbonyl, aroxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, alkyl(aryl)aminocarbonyl, arylcarboxamido, or Q, the alkyl or alkoxy portions of which are saturated or unsaturated, linear or branched, and substituted or unsubstituted;
- A in combination with B, A in combination with a ring formed by R1 and R2, B in combination with a ring formed by R4 and R5 of structures I or II, A in combination with R1, B in combination with R6, A in combination with R6, or B in combination with R7, can independently form a 5- to 10-member ring structure that is saturated or unsaturated, and unsubstituted or substituted;
- and
- D1, D2, D3 and D4 are either C or N, wherein only 1 or none of D1, D2, D3 or D4 are N.
Dependencies are inferred from the claim text.