Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane.

Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane. Research Abstract Details 

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Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane. Abstract Text:

Amy Hauck Newman,Joo Hwan Cha,Jianjing Cao,Theresa Kopajtic,Jonathan L Katz,M Laura Parnas,Roxanne Vaughan,John R Lever,

Tropane-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.

Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane. Publishing Authors By Initials

AH Newman,JH Cha,J Cao,T Kopajtic,JL Katz,ML Parnas,R Vaughan,JR Lever,

For similar biochemical phenomena, metabolism, and nutrition: biochemical phenomena: structure-activity relationship research abstracts see: biochemical phenomena, metabolism, and nutrition: biochemical phenomena: structure-activity relationship research

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Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Journal of medicinal chemistry

VOLUME: 49

Page Numbers: 6621-5

Journal Abbreviation: J. Med. Chem.

ISSN: 0022-2623

DAY: 2

MONTH: Nov

YEAR: 2006

Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 9716531

Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane. Keywords Mesh Terms:

KEYWORDS: Structure-Activity Relationship

MESH TERMS: chemistry

Chemical & Substance for Abstract: Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane. Information

Substance Name: Cocaine

Registry Number: 50-36-2

Grant and Affiliation Information for Design and synthesis of a novel photoaffinity ligand for the dopamine and serotonin transporters based on 2beta-carbomethoxy-3beta-biphenyltropane.

AFFILIATION: Medicinal Chemistry and Psychobiology Sections, National Institute on Drug Abuse-Intramural Research Program, National Institutes of Health/DHHS, Baltimore, MD, USA. anewman@intra.nida.nih.gov

Country: United States

AGENCY: United States NIDA

GRANT: DA 15175

ACRONYM: DA

MEDLINETA: J Med Chem

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