title: Modulating cocaine vaccine potency through hapten fluorination.
abstract: Cocaine addiction is a long-lasting relapsing illness characterized by cycles of abuse, abstinence, and reinstatement, and antibody-based therapies could be a powerful therapeutic approach. Herein, we explored the possibility of using halogenated cocaine haptens to enhance the immunological properties of anti-cocaine vaccines. Three fluorine-containing cocaine haptens (GNF, GNCF and GN5F) and one chlorine-containing cocaine hapten (GNCl) were designed and synthesized, based upon the chemical scaffold of the only hapten that has reached clinical trials, succinyl norcocaine (SNC). Hapten GNF was found to retain potent cocaine affinity, and also elicit antibodies in a higher concentration than the parent structure SNC. Our data suggests that not only could strategic hapten fluorination be useful for improving upon the current cocaine vaccine undergoing clinical trials, but it may also be a valuable new approach, with application to any of the vaccines being developed for the treatment of drugs of abuse.
authors: Department of Chemistry, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors: Xiaoqing
authors: X
authors: Cai
authors: Kyoji
authors: K
authors: Tsuchikama
authors: Kim D
authors: KD
authors: Janda
mesh_terms: D003042:Cocaine / Q000276:immunology*; D005461:Fluorine / Q000737:chemistry*; D006241:Haptens; D014612:Vaccines / Q000276:immunology*
chemical_list: D006241:Haptens; D014612:Vaccines; D005461:Fluorine; D003042:Cocaine
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