Dopamine Agonists

Effects of Charged and Uncharged Analogues of Dopamine

Yu An Chang, Jeffrey Ares, Karen Anderson, Brian Sabol, Raye Ann Wallace, Tahira Farooqui, Norman Uretsky, Duane Miller

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Dopamine, at physiological pH, may exist as either an uncharged amine or a charged ammonium species. In order to gain insight as to which species is better suited for interaction with the dopamine receptor, we have synthesized dopamine analogues in which the nitrogen atom is replaced with a neutral methyl sulfide, a neutral methyl selenide, a charged dimethylsulfonium iodide, and a charged dimethylselenonium iodide. These analogues were tested for their ability to inhibit the K+-stimulated release of [3H] acetylcholine from striatal slices. At 30 μM concentration, the charged sulfonium and selenonium salts possessed significant agonist activity while the corresponding neutral species were inactive, suggesting that a charged species is optimal for dopamine agonist activity. In addition, the methyl sulfide was converted into the corresponding sulfoxide and sulfone; however, neither of these oxidation products possessed significant activity as dopaminergic agonists.

Original languageEnglish (US)
Pages (from-to)214-218
Number of pages5
JournalJournal of Medicinal Chemistry
Volume30
Issue number1
DOIs
StatePublished - Jan 1 1987
Externally publishedYes

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Dopamine Agents
sulfoxide
Dopamine Agonists
Iodides
Sulfides
Dopamine
Corpus Striatum
Sulfones
Dopamine Receptors
Ammonium Compounds
Acetylcholine
Amines
Nitrogen
Salts

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Chang, Y. A., Ares, J., Anderson, K., Sabol, B., Wallace, R. A., Farooqui, T., ... Miller, D. (1987). Dopamine Agonists: Effects of Charged and Uncharged Analogues of Dopamine. Journal of Medicinal Chemistry, 30(1), 214-218. https://doi.org/10.1021/jm00384a038

Dopamine Agonists : Effects of Charged and Uncharged Analogues of Dopamine. / Chang, Yu An; Ares, Jeffrey; Anderson, Karen; Sabol, Brian; Wallace, Raye Ann; Farooqui, Tahira; Uretsky, Norman; Miller, Duane.

In: Journal of Medicinal Chemistry, Vol. 30, No. 1, 01.01.1987, p. 214-218.

Research output: Contribution to journalArticle

Chang, YA, Ares, J, Anderson, K, Sabol, B, Wallace, RA, Farooqui, T, Uretsky, N & Miller, D 1987, 'Dopamine Agonists: Effects of Charged and Uncharged Analogues of Dopamine', Journal of Medicinal Chemistry, vol. 30, no. 1, pp. 214-218. https://doi.org/10.1021/jm00384a038
Chang YA, Ares J, Anderson K, Sabol B, Wallace RA, Farooqui T et al. Dopamine Agonists: Effects of Charged and Uncharged Analogues of Dopamine. Journal of Medicinal Chemistry. 1987 Jan 1;30(1):214-218. https://doi.org/10.1021/jm00384a038
Chang, Yu An ; Ares, Jeffrey ; Anderson, Karen ; Sabol, Brian ; Wallace, Raye Ann ; Farooqui, Tahira ; Uretsky, Norman ; Miller, Duane. / Dopamine Agonists : Effects of Charged and Uncharged Analogues of Dopamine. In: Journal of Medicinal Chemistry. 1987 ; Vol. 30, No. 1. pp. 214-218.
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