发明名称 MONOAZO DYES WITH CYCLIC AMINE AS FLUORESCENCE QUENCHERS
摘要 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.
申请公布号 US2016289779(A1) 申请公布日期 2016.10.06
申请号 US201514672944 申请日期 2015.03.30
申请人 Enzo Biochem, Inc. 发明人 LI ZAIGUO;PANDE PRAVEEN;RAJU NATARAJAN
分类号 C12Q1/70;C12Q1/68;C09B56/00 主分类号 C12Q1/70
代理机构 代理人
主权项 1. A compound of formula I: wherein R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently selected from H, F, Cl, Br, I, CN, nitro, 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; or one or more of R1 in combination with R2, R2 in combination with R3, R3 in combination with R4, R4 in combination with R5, R6 in combination with R7, and R8 in combination with R9, form a 5- to 10-member ring that is saturated or unsaturated, unsubstituted or optionally substituted with one or more of alkyl, aryl, alkenyl, alkynyl, alkoxy, aroxyl, hydroxyl, F, Cl, Br, I, CN, nitro, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, arylsulfinyl, (thio)carbonyl, (thio)carboxylic acid, (thio)carboxylic acid ester, nitro, amino, (thio)amide, azido, hydrazino, or (thio)phosphonate, wherein the alkyl or alkoxy groups are saturated or unsaturated, linear or branched, substituted or unsubstituted, and the aryl group is optionally substituted with F, Cl, Br, I, CN, OH, alkyl, alkenyl, alkynyl, alkoxy, aryoxy, alkylthio, arylthio, nitro, azido, hydrazino, carboxyl, thiocarboxyl, carbonyl, thiocarbonyl, carboxylic acid ester, thiocarboxylic acid ester, unsubstituted or substituted amino, amide, thioamide, or Q; Q is selected from 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), its thioanalogue (PSNR12R13NR15R16), a phosphoramide (PONR12R13NR15R16), its thioanalogue (PSNR12R13NR14NR15R16), a phosphoramidite (PO2R15NR12R13) or its thioanalogue (POSR15NR12R13), wherein E is independently O or S; R10 and R11 are each independently selected from 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; or at least one of R7 in combination with R10 , or R9 in combination with R11 forms a 5- to 10-member saturated or unsaturated ring optionally further substituted with one or more saturated or unsaturated, linear or branched, substituted or unsubstituted alkyl, aryl, alkenyl, alkynyl, saturated or unsaturated, linear or branched, substituted or unsubstituted alkoxy, aroxyl, hydroxyl, F, Cl, Br, I, CN, nitro, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, arylsulfinyl, (thio)carbonyl, (thio)carboxylic acid, (thio)carboxylic acid ester, nitro, amino, (thio)amide, azido, hydrazino, or (thio)phosphonate; wherein the aryl group is optionally substituted with one or more of F, Cl, Br, I, CN, OH, alkyl, alkenyl, alkynyl, alkoxy, aryoxy, alkylthio, arylthio, nitro, azido, hydrazino, carboxyl, thiocarboxyl, carbonyl, thiocarbonyl, carboxylic acid ester, thiocarboxylic acid ester, unsubstituted or substituted amino, amide, thioamide, or Q; and wherein R12, R13, R14, R15 and R16 are independently selected from 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.
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