title: The Essential Medicinal Chemistry of Curcumin.
abstract: Curcumin is a constituent (up to ∼5%) of the traditional medicine known as turmeric. Interest in the therapeutic use of turmeric and the relative ease of isolation of curcuminoids has led to their extensive investigation. Curcumin has recently been classified as both a PAINS (pan-assay interference compounds) and an IMPS (invalid metabolic panaceas) candidate. The likely false activity of curcumin in vitro and in vivo has resulted in >120 clinical trials of curcuminoids against several diseases. No double-blinded, placebo controlled clinical trial of curcumin has been successful. This manuscript reviews the essential medicinal chemistry of curcumin and provides evidence that curcumin is an unstable, reactive, nonbioavailable compound and, therefore, a highly improbable lead. On the basis of this in-depth evaluation, potential new directions for research on curcuminoids are discussed.
authors.affiliation: Department of Medicinal Chemistry, Institute for Therapeutics Discovery and Development, University of Minnesota , Minneapolis, Minnesota 55414, United States.
authors.forename: Kathryn M
authors.identifier: 0000-0001-8274-2064
authors.initials: KM
authors.lastname: Nelson
authors.affiliation: Department of Pathology, Brigham and Women's Hospital , Boston, Massachusetts 02115, United States.
authors.forename: Jayme L
authors.initials: JL
authors.lastname: Dahlin
authors.affiliation: Center for Natural Product Technologies, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Bisson
authors.affiliation: Center for Natural Product Technologies, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: James
authors.initials: J
authors.lastname: Graham
authors.affiliation: Center for Natural Product Technologies, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.|Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Guido F
authors.identifier: 0000-0003-1022-4326
authors.initials: GF
authors.lastname: Pauli
authors.affiliation: Department of Medicinal Chemistry, Institute for Therapeutics Discovery and Development, University of Minnesota , Minneapolis, Minnesota 55414, United States.
authors.forename: Michael A
authors.initials: MA
authors.lastname: Walters
mesh_terms: D000818:Animals; D002626:Chemistry, Pharmaceutical; D003474:Curcumin / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D006801:Humans
chemical_list: D003474:Curcumin