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pubmed-article:17064081pubmed:abstractTextTropane-based photoaffinity ligands covalently bind to discrete points of attachment on the dopamine transporter (DAT). To further explore structure-activity relations, a ligand in which the photoactivated group was extended from the 3-position of the tropane ring was synthesized from cocaine via a Stille or Suzuki coupling strategy. 3-(4'-Azido-3'-iodo-biphenyl-4-yl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester (11; K(i) = 15.1 +/- 2.2 nM) demonstrated high binding affinity for the DAT. Moreover, this compound showed moderate binding affinity for the serotonin transporter (SERT, K(i) = 109 +/- 14 nM), suggesting the potential utility of [(125)I]11 in both DAT and SERT protein structure studies.lld:pubmed
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pubmed-article:17064081pubmed:dateRevised2007-12-3lld:pubmed
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pubmed-article:17064081pubmed:articleTitleDesign and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane.lld:pubmed
pubmed-article:17064081pubmed:affiliationMedicinal Chemistry and Psychobiology Sections, National Institute on Drug Abuse-Intramural Research Program, National Institutes of Health/DHHS, Baltimore, MD, USA. anewman@intra.nida.nih.govlld:pubmed
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