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Method for labeling and detecting materials employing arylsulfonate cyanine dyes

  • US 5,268,486 A
  • Filed: 05/15/1992
  • Issued: 12/07/1993
  • Est. Priority Date: 04/18/1986
  • Status: Expired due to Term
First Claim
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1. A water soluble luminescent dye consisting of:

  • a cyanine having the structure ##STR12## wherein;

    the dotted lines each represent carbon atoms necessary for the formation of one ring to three fused rings having 5 to 6 atoms in each ring and said R3, R4, R8 and R9 groups are attached to said rings;

    X and Y are each CH3 --C--CH3 ;

    m is an integer selected from the grouping consisting of 1, 2 and 3;

    at least one of said R1, R2, R3, R4 and R7 groups reacts with amino, hydroxy or sulfhydryl nucleophiles and is a reactive moiety selected from the group consisting of ##STR13## wherein Q is Br or Cl, and n=0, 1, 2, 3, 4, 5, 6, 7 or 8 for R3, R4 and R7, and n=1, 2, 3, 4, 5, 6, 7 or 8 for R1 and R2 ;

    and when any one of said R3, R4, and R7 groups is not selected from one said reactive moiety, said remaining R3, R4, and R7 are hydrogen or E--F, a polar group wherein E is a spacer group having the structure --(CH2)n -- and n of said spacer group=0, 1, 2, 3, or 4, and F is hydroxy, sulfonate, sulfate, carboxylate, or a lower alkyl substituted amino;

    and when any one of said R1 and R2 groups is not selected from one said reactive moiety, said remaining R1 or R2 are a lower alkyl or said E--F and n of said spacer group=1, 2, 3, or 4;

    at least one said R8 and R9 groups is selected from the group consisting of a sulfonic acid and a sulfonate moiety attached directly to said ring for conferring improved luminescence to said dye when in use as compared to a dye which does not have said at least one sulfonic acid or sulfonate moiety;

    and when one of said R8 or R9 group is not a sulfonic acid or a sulfonate, said remaining R8 or R9 group is a hydrogen.

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