Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands

Xiaobo Gu; Sari Izenwasser; Dean Wade; Amy Housman; Gerard Gulasey; Jill B. Rhoden; Christopher D. Savoie; David L. Mobley; Stacey A. Lomenzo; Mark L. Trudell

doi:10.1016/j.bmc.2010.09.060

Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands

Xiaobo Gu, Sari Izenwasser, Dean Wade, Amy Housman, Gerard Gulasey, Jill B. Rhoden, Christopher D. Savoie, David L. Mobley, Stacey A. Lomenzo, Mark L. Trudell

Psychiatry & Behavioral Sciences

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

3 Scopus citations

Abstract

A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (K_i values <2 nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).

Original language	English (US)
Pages (from-to)	8356-8364
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	23
DOIs	https://doi.org/10.1016/j.bmc.2010.09.060
State	Published - Dec 1 2010

Keywords

Depression
Dopamine transporters
Meperidine
Norepinephrine transporters
Normeperidine
Serotonin transporter

ASJC Scopus subject areas

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

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10.1016/j.bmc.2010.09.060

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Gu, X., Izenwasser, S., Wade, D., Housman, A., Gulasey, G., Rhoden, J. B., Savoie, C. D., Mobley, D. L., Lomenzo, S. A., & Trudell, M. L. (2010). Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. Bioorganic and Medicinal Chemistry, 18(23), 8356-8364. https://doi.org/10.1016/j.bmc.2010.09.060

Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. / Gu, Xiaobo; Izenwasser, Sari; Wade, Dean; Housman, Amy; Gulasey, Gerard; Rhoden, Jill B.; Savoie, Christopher D.; Mobley, David L.; Lomenzo, Stacey A.; Trudell, Mark L.

In: Bioorganic and Medicinal Chemistry, Vol. 18, No. 23, 01.12.2010, p. 8356-8364.

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

Gu, X, Izenwasser, S, Wade, D, Housman, A, Gulasey, G, Rhoden, JB, Savoie, CD, Mobley, DL, Lomenzo, SA & Trudell, ML 2010, 'Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands', Bioorganic and Medicinal Chemistry, vol. 18, no. 23, pp. 8356-8364. https://doi.org/10.1016/j.bmc.2010.09.060

Gu, Xiaobo ; Izenwasser, Sari ; Wade, Dean ; Housman, Amy ; Gulasey, Gerard ; Rhoden, Jill B. ; Savoie, Christopher D. ; Mobley, David L. ; Lomenzo, Stacey A. ; Trudell, Mark L. / Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. In: Bioorganic and Medicinal Chemistry. 2010 ; Vol. 18, No. 23. pp. 8356-8364.

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title = "Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands",

abstract = "A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (Ki values <2 nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).",

keywords = "Depression, Dopamine transporters, Meperidine, Norepinephrine transporters, Normeperidine, Serotonin transporter",

author = "Xiaobo Gu and Sari Izenwasser and Dean Wade and Amy Housman and Gerard Gulasey and Rhoden, {Jill B.} and Savoie, {Christopher D.} and Mobley, {David L.} and Lomenzo, {Stacey A.} and Trudell, {Mark L.}",

note = "Funding Information: This research was supported by the National Institute on Drug Abuse (DA11528, MLT) and the Louisiana Optical Network Initiative Institute (DLM), supported by the Louisiana Board of Regents Post-Katrina Support Fund Initiative grant LEQSF (2007-12)-ENH-PKSFI-PRS-01.",

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doi = "10.1016/j.bmc.2010.09.060",

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AU - Gu, Xiaobo

AU - Izenwasser, Sari

AU - Wade, Dean

AU - Housman, Amy

AU - Gulasey, Gerard

AU - Rhoden, Jill B.

AU - Savoie, Christopher D.

AU - Mobley, David L.

AU - Lomenzo, Stacey A.

AU - Trudell, Mark L.

N1 - Funding Information: This research was supported by the National Institute on Drug Abuse (DA11528, MLT) and the Louisiana Optical Network Initiative Institute (DLM), supported by the Louisiana Board of Regents Post-Katrina Support Fund Initiative grant LEQSF (2007-12)-ENH-PKSFI-PRS-01.

PY - 2010/12/1

Y1 - 2010/12/1

N2 - A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (Ki values <2 nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).

AB - A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (Ki values <2 nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).

KW - Depression

KW - Dopamine transporters

KW - Meperidine

KW - Norepinephrine transporters

KW - Normeperidine

KW - Serotonin transporter

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Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands

Abstract

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