Abstract：
:In our effort to develop imaging agents for brain glucocorticoid receptors, we have prepared several novel glucocorticoids possessing a 2-methylsulfanyl-acetyl side chain. The synthesis was accomplished via a Mitsunobu reaction with thiobenzoic acid starting from cortisol, prednisolone, dexamethasone and triamcinolone acetonide to give the corresponding S-thiobenzoates in 75-82% yield. Subsequent saponification and reaction with methyl iodide afforded C-21 methylthioethers in 68-82% yield. All compounds were tested in an in vitro glucocorticoid receptor-binding assay. Triamcinolone acetonide-based compound 12 showed promising binding affinity of 144% relative to dexamethasone (100%). Compound 12 was selected for radiolabeling with the short-lived positron emitter carbon-11. The radiolabeling was carried out starting from S-thiobenzoate 8 and in situ formation of the corresponding sodium thiolate, which was further reacted with [(11)C]methyl iodide. The obtained radiochemical yield was 20-30%. The specific activity was determined to be 20-40GBq/micromol at the end-of-synthesis, and the radiochemical purity exceeded 98%.
journal_name
Steroidsjournal_title
Steroidsauthors
Wuest F,Carlson KE,Katzenellenbogen JAdoi
10.1016/j.steroids.2007.08.013subject
Has Abstractpub_date
2008-01-01 00:00:00pages
69-76issue
1eissn
0039-128Xissn
1878-5867pii
S0039-128X(07)00159-6journal_volume
73pub_type
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