Triaryl (Z)-olefins suitable for radiolabeling with carbon-11 or fluorine-18 radionuclides for positron emission tomography imaging of cyclooxygenase-2 expression in pathological disease.
A group of (Z)-1,1-diphenyl-2-(4-methylsulfonylphenyl)alk-1-enes were synthesized using methodologies that will allow incorporation of a [(11)C]OCH(3) substituent at the para-position of the C-1 phenyl ring, a [(11)C]SO(2)CH(3) substituent at the para-position of the C-2 phenyl ring, a [(18)F]OCH(2)CH(2)F substituent at the para-position of the C-1 phenyl ring, and a [(18)F]CH(2)CH(2)F substituent at the C-2 position of the olefinic bond. The [(11)C] and [(18)F] radiotracers are designed as potential radiopharmaceuticals to image cyclooxygenase-2 (COX-2) expression in any organ where COX-2 is upregulated. The COX-1/COX-2 inhibition data acquired suggest that compounds having a [(11)C]OMe or [(18)F]OCH(2)CH(2)F substituent at the para-position of the C-1 phenyl ring may be more suitable for imaging COX-2 expression in view of their ability to exclusively inhibit the COX-2 isozyme.
Abdellatif
Khaled R A
KR
Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, Canada.
Velázquez
Carlos A
CA
Huang
Zhangjian
Z
Chowdhury
Morshed A
MA
Knaus
Edward E
EE
D000475:Alkenes / Q000737:chemistry*; D002250:Carbon Radioisotopes; D051546:Cyclooxygenase 2 / Q000378:metabolism*; D004194:Disease; D005462:Fluorine Radioisotopes; D006801:Humans; D049268:Positron-Emission Tomography
D000475:Alkenes; D002250:Carbon Radioisotopes; D005462:Fluorine Radioisotopes; D051546:Cyclooxygenase 2