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.

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Abdellatif KR, Velazquez CA, Huang Z, Chowdhury MA, Knaus EE

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.

Bioorg Med Chem Lett. 2010 Sep 1;20(17):5245-50. doi: 10.1016/j.bmcl.2010.06.155. Epub 2010 Jul 23.

PubMed ID

20655211 [ View in PubMed

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Abstract

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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Celecoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	65	N/A	N/A	Details