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Probes comprising fluorescent nucleosides and uses thereof

  • US 5,652,099 A
  • Filed: 08/18/1994
  • Issued: 07/29/1997
  • Est. Priority Date: 02/12/1992
  • Status: Expired due to Fees
First Claim
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1. A fluorescent nucleoside, or structural analog thereof, having either of the following structures:

  • ##STR2## wherein X1, X2, X3, X4, X5, and X6 =N, O, C, S, or Si, wherein at least one of X1, X2, X3, X4, X5, or X6 =N;

    R4 is a reactive group derivatizable with a detectable label wherein said reactive group is selected from the group consisting of NH2, SH, ═

    O, and optionally, a linking moiety selected from the group consisting of an amide, a thioether, a disulfide, a combination of an amide a thioether or a disulfide, R1 --(CH2)x --R2 and R1 -R2 --(CH2)x --R3 wherein x is an integer from 1 to 25 inclusive, and R1, R2, and R3 are H, OH, alkyl, acyl, amide, thioether, or disulfide, and wherein said detectable label is selected from the group consisting of radioisotopes, fluorescent or chemiluminescent reporter molecules, antibodies, haptens, biotin, photobiotin, digoxigenin, fluorescent aliphatic amino groups, avidin, enzymes, and acridinium;

    R5 is H or part of an etheno linkage with R4 ;

    R6 is H, NH2, SH, or ═

    O;

    R8 and R9 are hydrogen, methyl, bromine, fluorine, or iodine;

    alkyl or aromatic substituents, or an optional linking moiety selected from the group consisting of an amide, a thioether, a disulfide linkage, and a combination thereof;

    R10 is hydrogen, an acid-sensitive/base-stable blocking group, or a phosphorous derivative;

    R11 =R13 =H;

    R12 is hydrogen, OH, 3'"'"' amino, 3'"'"'-azido, 3'"'"'-thiol, 3'"'"'-unsaturated or a 3'"'"'-phosphorous derivative; and

    R14 is H, OH, or OR3 where R3 is a reactive group, protecting group, or additional fluorophore;

    provided that excluded from such compound is any purine-like compound in which;

    (i) X1=X4=C;

    X2=X3=N;

    R4=NH2;

    R5=R8 which is absent;

    R6=H;

    R9 is H or is absent;

    R10=H; and

    R12=R14=OH;

    or(ii) X1=C;

    X2=X3=X4=N;

    R4=NH2 or H;

    R5=R8 which is absent;

    R6=NH2;

    R9 is H or is absent;

    R10=H; and

    R12=R14=OH;

    or(iii) R4 and R5 in combination form an etheno linkage;

    R6=R8=H;

    R9 is absent;

    X1=X3=C; and

    X2=X4=N;

    or(iv) X1=X2=C;

    X3=X4=N;

    R4=halogen or --S(CH2)nR with n being an integer between 1-6 and R is lower alkoxy, alkylthio, phenoxy, phenylthio, unsubstituted or substituted phenyl, --C═

    C--R'"'"' wherein R'"'"' is unsubstituted or mono-, di- or trisubstituted phenyl;

    R9=R10=H; and

    R12=R14=acyloxy;

    or(v) R4=NH2 or OH;

    R5 is absent;

    R9 is --COOH, --CONH2, --C(S)NH2, --C(NH)NH2, or --C(N--NH2)NH2;

    X1=X2=X3=C; and

    X4=N.

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