title: The immunogenicity of dinitrophenyl amino acids.
abstract: Numerous dinitrophenyl amino acid preparations injected intradermally induced contact hypersensitivity to dinitrochlorobenzene, delayed type skin reactions to DNP-amino acids, and anti-DNP antibodies in guinea pigs. Some DNP-amino adds induced precipitating anti-DNP antibodies in rabbits as well. Some of the DNP-ammo acids studied were regularly immunogenic, possible immunogenic impurities having been excluded by extensive purification procedures. Others were either constantly nonimmunogenic or irregularly immunogenic, e.g., their immunogenicity varying from one preparation lot to another. By means of extensive chemical analyses and the establishment of dose-response curves, we were able to demonstrate in most cases that the immunogenicity was not due to contamination with unreacted dinitrofluorobenzene or other DNP derivatives, to photodecomposition or other degradation products, or to DNP-protein contaminants. Nevertheless, the irregular immunogenicity of several DNP-amino acid preparations can only be explained by a highly immunogenic impurity (or impurities) which we were unable to detect analytically. The regular immunogenicity of some other DNP-amino acids (e.g. di-DNP-L-histidine) appears to be based on a "transconjugation" phenomenon, the DNP group being able to split off from its amino acid carrier and to conjugate secondarily with proteins in vivo and in vitro. Accordingly, the interpretation of some recent data concerning the immunogenicity of low molecular weight hapten-amino acids may have to be reevaluated.
mesh_terms: D000473:Alkanes; D000596:Amino Acids; D000818:Animals; D000941:Antigens; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D004140:Dinitrophenols; D005260:Female; D006168:Guinea Pigs; D006241:Haptens; D006968:Hypersensitivity, Delayed; D005779:Immunodiffusion; D007267:Injections; D008297:Male; D010323:Passive Cutaneous Anaphylaxis; D011817:Rabbits; D012882:Skin Tests
chemical_list: D000473:Alkanes; D000596:Amino Acids; D000941:Antigens; D004140:Dinitrophenols; D006241:Haptens