Synthesis of (nor)tropeine (di)esters and allosteric modulation of glycine receptor binding

G. Maksay, Péter Nemes, Zoltán Vincze, Timea Bíró

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

(Hetero)aromatic mono- and diesters of tropine and nortropine were prepared. Modulation of [3H]strychnine binding to glycine receptors of rat spinal cord was examined with a ternary allosteric model. The esters displaced [3H]strychnine binding with nano- or micromolar potencies and strong negative cooperativity. Coplanarity and distance of the ester moieties of diesters affected the binding affinity being nanomolar for isophthaloyl-bistropane and nortropeines. Nortropisetron had the highest affinity (KA ∼ 10 nM). Two esters displayed negative cooperativity with glycine in displacement, while three esters of low-affinity and nortropisetron exerted positive cooperativity with glycine.

Original languageEnglish
Pages (from-to)2086-2092
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number4
DOIs
Publication statusPublished - Feb 15 2008

Fingerprint

Glycine Receptors
Esters
Modulation
Strychnine
Glycine
Rats
Spinal Cord

Keywords

  • Glycine displacement
  • Glycine receptors
  • Ternary allosteric model
  • Tropeines

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis of (nor)tropeine (di)esters and allosteric modulation of glycine receptor binding. / Maksay, G.; Nemes, Péter; Vincze, Zoltán; Bíró, Timea.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 4, 15.02.2008, p. 2086-2092.

Research output: Contribution to journalArticle

Maksay, G. ; Nemes, Péter ; Vincze, Zoltán ; Bíró, Timea. / Synthesis of (nor)tropeine (di)esters and allosteric modulation of glycine receptor binding. In: Bioorganic and Medicinal Chemistry. 2008 ; Vol. 16, No. 4. pp. 2086-2092.
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