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US 10,131,789 B2Granted
Monoazo dyes with cyclic amine as fluorescence quencers
AssigneeEnzo Biochem, Inc.
InventorsZaiguo Li, Praveen Pande, Natarajan Raju
Life of this patent
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Abstract
The present disclosure provides reactive quencher dyes that can be used in the detection and/or quantification of desirable target molecules, such as proteins, nucleic acids and various cellular organelles. These dyes are essentially non-fluorescent but are efficient quenchers of various fluorescent dyes. Also, provided are methods of using the dyes, bio-probes incorporating dyes and methods of using the bio-probes. The quencher dyes described herein are modified to provide beneficial properties.
Claims8
A compound having the formula:
- wherein R1 and R8 are each independently H, F, Cl, Br, I, CN, nitro (NO2), azido, hydroxyl, amino, hydrazino, aryl, substituted aryl, aroxyl, 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, wherein the alkyl or alkoxy groups are saturated or unsaturated, linear or branched, unsubstituted or optionally substituted by F, Cl, Br, I, CN, OH, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q, and the aryl group is optionally substituted by F, Cl, Br, I, CN, OH, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q;
- Q is a carboxyl group (CO2−), a carbonate ester (COER12), a sulfonate ester (SO2ER12), a sulfoxide (SOR12), a sulfone (SO2CR12R13R14), a sulfonamide (SO2NR12R13), a phosphate (PO4=), a phosphate monoester (PO3−ER12), a phosphate diester (PO2ER12ER13), a phosphonate (PO3=) a phosphonate monoester (PO2−ER12) a phosphonate diester (POER12ER13), a thiophosphate (PSO3=), a thiophosphate monoester (PSO2−ER12) a thiophosphate diester (PSOER12ER13), a thiophosphonate (PSO2=), a thiophosphonate monoester (PSO−ER12), a thiophosphonate diester (PSER12ER13), a phosphonamide (PONR12R13NR15R16) or its thioanalogue (PSNR12R13NR15R16), a phosphoramide (PONR12R13NR14NR15R16) or its thioanalogue (PSNR12R13NR14NR15R16), or a phosphoramidite (PO2R15NR12R13) or its thioanalogue (POSR15NR12R13), wherein E is independently O or S;
- R10 is H, a saturated or unsaturated, linear or branched, unsubstituted or further substituted alkyl group, aryl group, alkylcarbonyl, aryl carbonyl, alkylthiocarbonyl, arylthiocarbonyl, alkoxycarbonyl, aroxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, alkyl(aryl)aminocarbonyl, arylcarboxamido, or Q, the alkyl or alkoxy portions of which are, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q, or the aryl portions of which are optionally substituted by F, Cl, Br, I, CN, OH, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q;
- R12, R13, R14, R15 and R16 are each independently hydrogen, a halogen, an amino group, a saturated or unsaturated, linear or branched, substituted or unsubstituted alkyl group, a saturated or unsaturated, branched or linear, substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or
- R12 in combination with R13, R14 in combination with R16, R12 in combination with R14, R12 in combination with R15, R13 in combination with R16, and R14 in combination with R15, one or more of which, form a 5- to 10-member ring;
- R3 is nitro;
- R5 is H or OCH3;
- and
- R6 is H or OCH3.
6 more elements
A compound having the formula:
- wherein
- R10 is H, a saturated or unsaturated, linear or branched, unsubstituted or further substituted alkyl group, aryl group, alkylcarbonyl, aryl carbonyl, alkylthiocarbonyl, arylthiocarbonyl, alkoxycarbonyl, aroxycarbonyl, alkyl aminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, alkyl (aryl)aminocarbonyl, arylcarboxamido, or Q, the alkyl or alkoxy portions of which are, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q, or the aryl portions of which are optionally substituted by F, Cl, Br, I, CN, OH, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q,
- wherein Q is a carboxyl group (CO2−), a carbonate ester (COER12), a sulfonate ester (SO2ER12), a sulfoxide (SOR12), a sulfone (SO2CR12R13R14), a sulfonamide (SO2NR12R13), a phosphate (PO4=), a phosphate monoester (PO3−ER12), a phosphate diester (PO2ER12ER13), a phosphonate (PO3=) a phosphonate monoester (PO2−ER12) a phosphonate diester (POER12ER13), a thiophosphate (PSO3=), a thiophosphate monoester (PSO2−ER12) a thiophosphate diester (PSOER12ER13), a thiophosphonate (PSO2=), a thiophosphonate monoester (PSO−ER12), a thiophosphonate diester (PSER12ER13), a phosphonamide (PONR12R13NR15R16) or its thioanalogue (PSNR12R13NR15R16), a phosphoramide (PONR12R13NR14NR15R16) or its thioanalogue (PSNR12R13NR14NR15R16), or a phosphoramidite (PO2R15NR12R13) or its thioanalogue (POSR15NR12R13), wherein E is independently O or S;
- R12, R13, R14, R15 and R16 are each independently hydrogen, a halogen, an amino group, a saturated or unsaturated, linear or branched, substituted or unsubstituted alkyl group, a saturated or unsaturated, branched or linear, substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or
- R12 in combination with R13, R14 in combination with R16, R12 in combination with R14, R12 in combination with R15, R13 in combination with R16, and R14 in combination with R15, one or more of which, form a 5- to 10-member ring;
- R1 is CN or H;
- and
- R5, R6 and R8 are each independently H, CH3, or OCH3.
5 more elements
A compound having the formula:
- wherein
- R1 is CN or H;
- R3 is nitro;
- R5 is H;
- R6 is OCH3;
- R8 is H;
- and
- R10 is H, a saturated or unsaturated, linear or branched, unsubstituted or further substituted alkyl group, aryl group, alkylcarbonyl, aryl carbonyl, alkylthiocarbonyl, arylthiocarbonyl, alkoxycarbonyl, aroxycarbonyl, alkylaminocarbonyl, apylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, alkyl(aryl)aminocarbonyl, arylcarboxamido, or Q, the alkyl or alkoxy portions of which are, alkenyl, alkynyl, alkycarbonyl, amide, thioamide, or Q, or the aryl portions of which are optionally substituted by F, Cl, Br, I, CN, OH, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q,
- wherein Q is a carboxyl group (CO2−), a carbonate ester (COER12), a sulfonate ester (SO2ER12), a sulfoxide (SOR12), a sulfone (SO2CR12R13R14), a sulfonamide (SO2NR12R13), a phosphate (PO4=), a phosphate monoester (PO3−ER12), a phosphate diester (PO2ER12ER13), a phosphonate (PO3=) a phosphonate monoester (PO2−ER12) a phosphonate diester (POER12ER13), a thiophosphate (PSO3=), a thiophosphate monoester (PSO2−ER12) a thiophosphate diester (PSOER12ER13), a thiophosphonate (PSO2=), a thiophosphonate monoester (PSO−ER12), a thiophosphonate diester (PSER12ER13), a phosphonamide (PONR12R13NR15R16) or its thioanalogue (PSNR12R13NR15R16), a phosphoramide (PONR12R13NR14NR15R16) or its thioanalogue (PSNR12R13NR14NR15R16), or a phosphoramidite (PO2R15NR12R13) or its thioanalogue (POSR15NR12R13), wherein E is independently O or S.
6 more elements
A compound having the formula:
- wherein
- R1 is CN or H;
- R3 is nitro;
- R5 is H;
- R6 is OCH3;
- R8 is H;
- and
- R10 is H, a saturated or unsaturated, linear or branched, unsubstituted or further substituted alkyl group, aryl group, alkylcarbonyl, aryl carbonyl, alkylthiocarbonyl, arylthiocarbonyl, alkoxycarbonyl, aroxycarbonyl, alkylaminocarbonyl, apylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, alkyl(aryl)aminocarbonyl, arylcarboxamido, or Q, the alkyl or alkoxy portions of which are, alkenyl, alkynyl, alkycarbonyl, amide, thioamide, or Q, or the aryl portions of which are optionally substituted by F, Cl, Br, I, CN, OH, alkenyl, alkynyl, alkylcarbonyl, amide, thioamide, or Q,
- wherein Q is a carboxyl group (CO2−), a carbonate ester (COER12), a sulfonate ester (SO2ER12), a sulfoxide (SOR12), a sulfone (SO2CR12R13R14), a sulfonamide (SO2NR12R13), a phosphate (PO4=), a phosphate monoester (PO3−ER12), a phosphate diester (PO2ER12ER13), a phosphonate (PO3=) a phosphonate monoester (PO2−ER12) a phosphonate diester (POER12ER13), a thiophosphate (PSO3=), a thiophosphate monoester (PSO2−ER12) a thiophosphate diester (PSOER12ER13), a thiophosphonate (PSO2=), a thiophosphonate monoester (PSO−ER12), a thiophosphonate diester (PSER12ER13), a phosphonamide (PONR12R13NR15R16) or its thioanalogue (PSNR12R13NR15R16), a phosphoramide (PONR12R13NR14NR15R16) or its thioanalogue (PSNR12R13NR14NR15R16), or a phosphoramidite (PO2R15NR12R13) or its thioanalogue (POSR15NR12R13), wherein E is independently O or S.
6 more elements
Dependencies are inferred from the claim text.