Structure-Activity Relationship Studies of N-Sulfonyl Analogs of Cocaine: Role of Ionic Interaction in Cocaine Binding

Alan P. Kozikowski; M. K.Eddine Saiah; John S. Bergmann; Kenneth M. Johnson

doi:10.1021/jm00046a029

Structure-Activity Relationship Studies of N-Sulfonyl Analogs of Cocaine: Role of Ionic Interaction in Cocaine Binding

Alan P. Kozikowski, M. K.Eddine Saiah, John S. Bergmann, Kenneth M. Johnson

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

43 Scopus citations

Abstract

Six new N-sulfonylated analogs of cocaine have been prepared, and these compounds have been evaluated for their ability to inhibit[³H]mazindol binding and [³H]dopamine uptake into striatal synaptosomes. The N-sulfonyl compounds still inhibited binding and uptake at low micromolar concentrations despite the neutral character of the tropane nitrogen, thus suggesting that the binding of cocaine to the dopamine transporter may not require protonation of its nitrogen and ionic interaction with its recognition site.

Original language	English (US)
Pages (from-to)	3440-3442
Number of pages	3
Journal	Journal of medicinal chemistry
Volume	37
Issue number	20
DOIs	https://doi.org/10.1021/jm00046a029
State	Published - Sep 1 1994
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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AU - Johnson, Kenneth M.

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N2 - Six new N-sulfonylated analogs of cocaine have been prepared, and these compounds have been evaluated for their ability to inhibit[3H]mazindol binding and [3H]dopamine uptake into striatal synaptosomes. The N-sulfonyl compounds still inhibited binding and uptake at low micromolar concentrations despite the neutral character of the tropane nitrogen, thus suggesting that the binding of cocaine to the dopamine transporter may not require protonation of its nitrogen and ionic interaction with its recognition site.

AB - Six new N-sulfonylated analogs of cocaine have been prepared, and these compounds have been evaluated for their ability to inhibit[3H]mazindol binding and [3H]dopamine uptake into striatal synaptosomes. The N-sulfonyl compounds still inhibited binding and uptake at low micromolar concentrations despite the neutral character of the tropane nitrogen, thus suggesting that the binding of cocaine to the dopamine transporter may not require protonation of its nitrogen and ionic interaction with its recognition site.

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Structure-Activity Relationship Studies of N-Sulfonyl Analogs of Cocaine: Role of Ionic Interaction in Cocaine Binding

Abstract

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