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Aza-Benzazolium Containing Cyanine Dyes

  • US 20080044811A1
  • Filed: 06/01/2007
  • Published: 02/21/2008
  • Est. Priority Date: 04/30/1999
  • Status: Active Grant
First Claim
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1. A method for determining the presence of an analyte of interest in a sample, wherein said method comprises:

  • a) combining said sample with a staining solution, wherein said staining solution comprises one or more dyes having formula wherein A represents the atoms necessary to form one to two fused aromatic rings having 6 atoms in each ring, at least one of which is a nitrogen atom, said ring or rings being optionally further substituted one or more times by C1-C6 alkyl, C1-C6 alkoxy trifluoromethyl, halogen, BRIDGE, -L-Rx or -L-Sc;

    wherein Rx is a reactive group;

    Sc is a conjugated substance; and

    L and BRIDGE are independently a single covalent bond, or a covalent linkage;

    X is O, S, Se, NR15, or CR16R17, where R15 is H or an alkyl group having 1-6 carbons; and

    R16 and R17, which may be the same or different, are independently alkyl groups having 1-6 carbons, or R16 and R17 taken in combination complete a five or six membered saturated ring;

    R2 is selected from the group consisting of -L-Rx, -L-Sc, TAIL, BRIDGE and an alkyl group having 1-6 carbons that is optionally substituted by sulfo, carboxy, amino, substituted amino or substituted ammonium, wherein α

    is 0 or 1; and

    TAIL is a heteroatom-containing moiety;

    Y is —

    CR3

    CR4

    wherein p and m=0 or 1, such that p+m=1;

    R3, R4, R6, and R7 are independently selected from the group consisting of hydrogen, a C1-C6 alkyl, a halogen, a CYCLIC SUBSTITUENT, —

    OR8, —

    SR8, —

    (NR8R9), TAIL;

    BRIDGE, -L-Rx and -L-Sc;

    where R8 and R9 are independently a C1-C6 alkyl group, 1-2 alicyclic or aromatic rings;

    or R8 and R9 taken in combination are —

    (CH2)2-V-(CH2)2

    where V is a single bond, —

    O—

    , —

    CH2

    , or —

    NR10

    , where R10 is H or an alkyl having 1-6 carbons;

    wherein CYCLIC SUBSTITUENT is a substituted or unsubstituted aryl, heteroaryl or C3-C10 cycloalkyl;

    or R6 and R7 form a fused aromatic ring —

    R11

    R12

    R13

    R14

    wherein R11, R12, R13, and R14 are independently selected from the group consisting of hydrogen, C1-C6 alkyl group, —

    OR8, —

    SR8, —

    (NR8R9), a CYCLIC SUBSTITUENT, TAIL, BRIDGE, -L-Rx and -L-Sc;

    R5 is independently selected from the group consisting of a C1-C6 alkyl group, a CYCLIC SUBSTITUENT, TAIL, BRIDGE, -L-Rx and -L-Sc;

    or R5 is absent;

    R30, R31, and R32 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C3-C10 cycloalkyl, aryl, and heteroaryl, wherein n=0, 1 or 2;

    wherein, BRIDGE, when present, is bound to a compound having formula I or another unsymmetrical cyanine dye b) incubating said sample and said staining solution for a sufficient amount of time to form a dye-analyte complex;

    c) illiminating said complex with an appropriate wavelength whereby the presence of said analyte is determined.

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