A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy]tropane

Gregory E. Agoston; Roxanne Vaughan; John R. Lever; Sari Izenwasser; Phyllis D. Terry; Amy Hauck Newman

doi:10.1016/S0960-894X(97)10139-1

A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy]tropane

Gregory E. Agoston, Roxanne Vaughan, John R. Lever, Sari Izenwasser, Phyllis D. Terry, Amy Hauck Newman

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy] tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the ¹²⁵I analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT.

Original language	English (US)
Pages (from-to)	3027-3032
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	7
Issue number	23
DOIs	https://doi.org/10.1016/S0960-894X(97)10139-1
State	Published - Dec 2 1997
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(97)10139-1

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title = "A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy]tropane",

abstract = "A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy] tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the 125I analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT.",

author = "Agoston, {Gregory E.} and Roxanne Vaughan and Lever, {John R.} and Sari Izenwasser and Terry, {Phyllis D.} and Newman, {Amy Hauck}",

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doi = "10.1016/S0960-894X(97)10139-1",

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T1 - A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy]tropane

AU - Agoston, Gregory E.

AU - Vaughan, Roxanne

AU - Lever, John R.

AU - Izenwasser, Sari

AU - Terry, Phyllis D.

AU - Newman, Amy Hauck

N1 - Funding Information: "Psychobiology Section and bMolecular Neurobiology Branch, National Institute on Drug Abuse, Intramural Research Program, National Institutes of Health, 5500 Nathan Shock Drive, Baltimore, MD 21224, U. S. A. CDepartment of Environmental Health Sciences, The Johns Hopkins Universi~ School of Public Health, Baltimore, MD 21205, U. S. A.

PY - 1997/12/2

Y1 - 1997/12/2

N2 - A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy] tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the 125I analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT.

AB - A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy] tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the 125I analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT.

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A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4'-fluorophenyl)methoxy]tropane

Abstract

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