Reagent for detecting an analyte
AssigneePrecisense A/S
InventorsJens Christian Norrild, Bo Wegge Laursen
Life of this patent
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Abstract
A reagent for use in detecting an analyte comprises a fluorescent energy donor and an energy acceptor, wherein the energy acceptor is of the general formula: and wherein the distance between the energy donor and the energy acceptor of the reagent is capable of modulation by a suitable analyte to be detected.
Claims33
A reagent for use in detecting an analyte, comprising a fluorescent energy donor, an energy acceptor and optionally a counterion, the energy donor and the energy acceptor being such that when they are sufficiently close to one another energy is non-radiatively transferred from the energy donor following excitation thereof to the energy acceptor quenching fluorescence of the energy donor, wherein the energy acceptor is of the formula:
- wherein:
- R1, R2 and R3 are each independently H, electron donating substituents, or electron withdrawing substituents or R3 is attached to a linker structure, provided that at least two of R1, R2 and R3 are electron donating groups;
- R4, R5, R6, R7, R8 and R9 are each independently H, halogen, alkyl, aryl, O-alkyl, S-alkyl and R10, R11, R12, R13, R14 and R15 are each independently hydrogen, O-alkyl, S-alkyl, alkyl, or one or more pairs of groups R1 and R4 and/or R1 and R5 and/or R2 and R6 and/or R2 and R7 and/or R3 and R8 and/or R3 and R9 and/or R4 and R10 and/or R5 and R11 and/or R6 and R12 and/or R7 and R13 and/or R8 and R14 and/or R9 and R15 is a bridging group consisting of aryl, alkylene, O-alkylene, S-alkylene or N-alkylene optionally substituted with one or more of SO3−, PO32−, OH, O-alkyl, SH, S-alkyl, COOH, COO−, ester, amide, halogen, SO-alkyl, SO2-alkyl, SO2NH2, SO2NH-alkyl, SO2N-dialkyl, SO3-alkyl, CN, secondary amine or tertiary amine, provided that not all of R10, R11, R12, R13, R14 and R15 are hydrogen and at least one of R10, R11, R12, R13, R14 and R15 is O-alkyl;
- and wherein the distance between the energy donor and the energy acceptor of the reagent is capable of modulation by a suitable analyte to be detected.
A dye compound having the formula:
- wherein:
- R4, R5, R6, R7, R8 and R9 are each independently H, halogen, alkyl, aryl, O-alkyl or S-alkyl and R10, R11, R12, R13, R14 and R15 are each independently hydrogen, O-alkyl, S-alkyl, or alkyl, or one or more pairs of groups R4 and R10 and/or R5 and R11 and/or R6 and R12 and/or R7 and R13 and/or R8 and R14 and/or R9 and R15 is a bridging group consisting of aryl, alkylene, O-alkylene, S-alkylene or N-alkylene optionally substituted with one or more of SO3−, PO32−, OH, O-alkyl, SH, S-alkyl, COOH, COO−, ester, amide, halogen, SO-alkyl, SO2-alkyl, SO2NH2, SO2NH-alkyl, SO2N-dialkyl, SO3-alkyl, CN, secondary amine or tertiary amine, provided that not all of R10, R11, R12, R13, R14 and R15 are hydrogen;
- R16, R17, R18 and R19 are each independently H, alkyl or aryl, or one or more of R16 and R17 or R18 and R19 is alkylene, optionally substituted with one or more of SO331 , PO32−, OH, O-alkyl, SH, S-alkyl, COOH, COO−, ester, amide, halogen, SO-alkyl, SO2-alkyl, SO2NH2, SO2NH-alkyl, SO2N-dialkyl, SO3-alkyl, CN, secondary amine or tertiary amine;
- or one or more of pairs of groups R6 and R16, R17 and R17, R8 and R18, and R9 and R19 is alkylene, O-alkylene, S-alkylene or N-alkylene optionally substituted with one or more of SO3−, PO32−, OH, O-alkyl, SH, S-alkyl, COOH, COO−, ester, amide, halogen, SO-alkyl, SO2-alkyl, SO2NH2, SO2NH-alkyl, SO2N-dialkyl, SO3-alkyl, CN, secondary amine or tertiary amine
- and
- R20 is a linker element selected from the group consisting of an active ester, an isothiocyanate, an acid chloride, an a-halogenated ketone, an azide and an amine of the formula:
- R21 is H or alkyl or aryl optionally substituted with one or more of SO3−, PO32−, OH, O-alkyl, SH, S-alkyl, COOH, COO−, ester, amide, halogen, SO-alkyl, SO2N-dialkyl, CN, secondary amine or tertiary amine and R22 is alkylene, O-alkylene, S-alkylene or N-alkylene or R21 and R22 are part of a ring, optionally substituted with one or more of SO3−, PO32−, OH, O-alkyl, SH, S-alkyl, COOH, COO−, ester, amide, halogen, SO-alkyl, SO2NH2, SO2NH-alkyl, SO2N-dialkyl, SO3-alkyl, CN, secondary amine or tertiary amine and
- R23 is o-succinimidyl, o-pentafluorophenyl, CI or α-halogenated alkyl;
- and optionally comprising a counterion.
Dependencies are inferred from the claim text.