Immunogenic conjugates of Gram-negative bacterial autoinducer molecules

  • US 6,395,282 B1
  • Filed: 04/16/1999
  • Issued: 05/28/2002
  • Est. Priority Date: 04/16/1998
  • Status: Expired due to Fees
First Claim
Patent Images

1. An immunogenic conjugate comprising an immunogenic carrier molecule covalently conjugated to an autoinducer according to Formula (I) of a Gram negative bacterium:

  • embedded imagewhere X is O, S, N—

    (C1-C6) alkyl, NR2, N-phenyl;

    Y is C1-C6 straight or branched alkyl, C1-C6 straight or branched alkenyl, C1-C6 straight or branched alkynyl;

    Z is C═

    O, C═

    S, CHOH, C═

    N—

    NR1, C═

    N—

    OH, C1-C8 straight or branched allyl, C1-C8 straight or branched alkenyl, C1-C8 straight or branched alkynyl;

    L is C1-C18 straight or branched allyl, C1-C18 straight or branched alkenyl, C1-C18 straight branched alkynyl, or —

    CO2H, —

    CO2R1, —

    CHO, —

    C≡

    N, —

    N═

    C═

    O, —

    N═

    C═

    S, OH, OR1, —

    CH═

    CH—

    CH2Br, —

    CH═

    CH—

    CH2Cl, —

    SAc or SH where R1 is C1-C6 straight or branched alkyl, m is 0 or 1;

    z is 0 or 1;

    R2 is H, C1-C6 straight or branched alkyl, C1-C6 straight or branched alkenyl or C1-C6 straight or branched alkynyl, or CO2H; and

    Q is CH or N; and

    n is 0-3 with the proviso that when n is 0, X is N—

    (C1-C6 alkyl) or N-phenyl.

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