title: Facile synthesis of deuterated and [(14) C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools.
abstract: Curcumin is a dietary diphenol with antioxidant, antinflammatory, and antitumor activity. We describe facile procedures for the synthesis of [(14) C2 ]curcumin (4 mCi/mmol), [d6 ]curcumin, [d3 ]curcumin, [(13) C5 ]curcumin, and [d6 ]bicyclopentadione, the major oxidative metabolite of curcumin. We also describe synthesis of the labeled building blocks [(14) C]vanillin, [d3 ]vanillin, and [(13) C5 ]acetylacetone. The overall molar yields of the labeled products were 52 ([(14) C]) and 47% ([d3 ]) for vanillin and 25 ([(14) C2 ]) and 27% ([d6 ]) for curcumin. The compounds can be used as radiotracers in biotransformation studies and as isotopic standards for mass spectrometry-based quantification in pharmacokinetic analyses.
authors: Division of Clinical Pharmacology, Department of Pharmacology, Vanderbilt Institute of Chemical Biology, Vanderbilt University Medical School, Nashville, TN, 37232, USA.
authors: Odaine N
authors: ON
authors: Gordon
authors: Leigh A
authors: LA
authors: Graham
authors: Claus
authors: C
authors: Schneider
mesh_terms: D001547:Benzaldehydes / Q000138:chemical synthesis*; D002250:Carbon Radioisotopes / Q000737:chemistry*; D003474:Curcumin / Q000138:chemical synthesis*; D007553:Isotope Labeling / Q000379:methods*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*
chemical_list: D001547:Benzaldehydes; D002250:Carbon Radioisotopes; D019275:Radiopharmaceuticals; C100058:vanillin; D003474:Curcumin
keywords: acetylacetone; bicyclopentadione; biotransformation; dietary; methyliodide; oxidative metabolism; polyphenol