A new strategy for improved nicotine vaccines using conformationally constrained haptens

Michael M Meijler; Masayuki Matsushita; Laurence J Altobell 3rd; Peter Wirsching; Kim D Janda

doi:10.1021/ja034805t

A new strategy for improved nicotine vaccines using conformationally constrained haptens

J Am Chem Soc. 2003 Jun 18;125(24):7164-5. doi: 10.1021/ja034805t.

Authors

Michael M Meijler¹, Masayuki Matsushita, Laurence J Altobell 3rd, Peter Wirsching, Kim D Janda

Affiliation

¹ Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

PMID: 12797775
DOI: 10.1021/ja034805t

Abstract

Constrained nicotine analogues were synthesized and coupled to the carrier protein KLH. The immunogenic effects were compared to those using our previously designed flexible nicotine hapten. Immunization of mice with the constrained hapten conjugates resulted in highly increased antibody titers and affinity for nicotine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Enzyme-Linked Immunosorbent Assay
Haptens / chemistry*
Haptens / immunology*
Hemocyanins / chemistry
Hemocyanins / immunology
Immunoconjugates / chemistry
Immunoconjugates / immunology
Kinetics
Models, Molecular
Molecular Conformation
Nicotine / analogs & derivatives
Nicotine / chemistry*
Nicotine / immunology*
Pyridines / chemistry
Pyridines / immunology
Vaccines / chemistry*
Vaccines / immunology

Substances

Haptens
Immunoconjugates
Pyridines
Vaccines
Nicotine
Hemocyanins
keyhole-limpet hemocyanin