Delta9-tetrahydrocannabinol immunochemical studies: haptens, monoclonal antibodies, and a convenient synthesis of radiolabeled delta9-tetrahydrocannabinol

J Med Chem. 2005 Nov 17;48(23):7389-99. doi: 10.1021/jm050442r.

Abstract

Immunopharmacotherapy as an approach to combat drugs of abuse has become an active area of investigation. Marijuana is the most commonly used illicit drug in the U.S. The main active chemical in marijuana is delta9-tetrahydrocannabinol (delta9-THC); hence, monoclonal antibodies with high affinity and specificity for delta9-tetrahydrocannabinol could be valuable immunopharmacotherapeutic intervention and diagnostic tools. We have synthesized immunoconjugates that induce an effective immune response to delta9-THC and describe a convenient synthesis of radiolabeled delta9-THC. We demonstrate the value and use of this probe to select anti-delta9-THC antibodies that bind delta9-THC with good affinity. The synthetic route to radiolabeled delta9-THC has enabled the correct assessment of the affinity of these antibodies to their ligand and may facilitate future binding studies between delta9-THC and its analogues and the cannabinoid receptors.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antibodies, Monoclonal / immunology
  • Antibodies, Monoclonal / metabolism*
  • Dronabinol / chemical synthesis*
  • Dronabinol / chemistry
  • Dronabinol / immunology*
  • Haptens / chemistry*
  • Haptens / immunology
  • Hemocyanins / chemistry
  • Immunoconjugates / chemistry*
  • Immunoconjugates / immunology
  • Isotope Labeling
  • Ligands
  • Mice
  • Serum Albumin, Bovine / chemistry
  • Tritium
  • Vaccination

Substances

  • Antibodies, Monoclonal
  • Haptens
  • Immunoconjugates
  • Ligands
  • Tritium
  • Serum Albumin, Bovine
  • Dronabinol
  • Hemocyanins
  • keyhole-limpet hemocyanin