Barbituric acid antigenic conjugates, their preparation, antibodies and use
AssigneeBiological Developments, Inc.
InventorJames R. Soares
Life of this patent
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Abstract
Antigenic barbituric acid conjugates are produced by coupling the hapten acid through its 3-position to an immunogenic carrier. The antigens thus produced can be used to raise antibodies in animals, the antibodies being specific to the barbituric acid hapten compound employed. The antibodies are useful in assaying for the barbituric acid hapten compounds.
Claims25
A synthetic antigen comprising a hapten coupled to a carrier which has the following formula:
- ##STR13## where Q is selected from the class consisting of O and S;
- R.sub.1 has from 1 to 3 carbon atoms and is selected from the class consisting of saturated and unsaturated hydrocarbon groups, monohalo substituted hydrocarbon groups, ether groups, thioether groups;
- R.sub.2 is selected from the class consisting of hydrocarbon groups containing from 1 to 6 carbon atoms;
- R.sub.3 is selected from the class consisting of H and CH.sub.3 ;
- --CH.sub.2 --Y-- is a residue from a linking agent which has been coupled to the hapten and to the carrier and Y comprises a member selected from the class consisting of a direct bond, saturated and unsaturated straight and branched chain alkylene groups having from 1 to 6 carbon atoms and aromatic groups having from 6 to 14 carbon atoms;
- and the carrier is macromolecule which confers antigenicity.
A synthetic antigen comprising a plurality of identical haptens coupled to a protein carrier by a linking agent residue through the three position nitrogen atom of the hapten, wherein the hapten is selected from the class consisting of barbital, phenobarbital, propallylonal, hexobarbital, secobarbital and methitural and the linking agent is selected from the class consisting of methyleneamide and ethylenephenylazo, the ethylene portion of the residue being bonded to the nitrogen atom.
Protein-amidoethylene-N,5,5-phenylethyl barbituric acid.
A process of preparing a synthetic antigen which is a barbiturate hapten coupled to a carrier which confers antigenicity which comprises the steps of reacting a barbituric acid of formula:
- ##STR14## where Q is selected from the class consisting of O and S;
- R.sub.1 has from 1 to 3 carbon atoms and is selected from the class consisting of saturated and unsaturated hydrocarbon groups, monohalo substituted hydrocarbon groups, ether groups, tioether groups;
- R.sub.2 is selected from the class consisting of hydrocarbon groups containing from 1 to 6 carbon atoms;
- and R.sub.3 is selected from the class consisting of H and CH.sub.3 ;
- with a linking agent of a formula selected from the class consisting of Z--CH.sub.2 --R.sub.4 --X.sub.1 and CH.sub.2 =CH--X.sub.2, where Z is a leaving group displaceable in a substitution reaction, R.sub.4 is selected from the class consisting of a direct bond, saturated and unsaturated straight and branched chain alkylene groups having from 1 to 6 carbon atoms and aromatic groups having from 6 to 14 carbon atoms, and X.sub.1 and X.sub.2 each include a moiety that can be directly coupled to the carrier, with X.sub.2 being an electron withdrawing group, whereby in the reaction Z in the linking agent is substituted into the barbituric acid with a direct bond to the nitrogen atom in the three position;
- and the step of coupling the product of the foregoing reaction to a carrier through said moiety.
Dependencies are inferred from the claim text.