bis-pyridinium cyclophanes: Novel ligands with high affinity for the blood-brain barrier choline transporter

Title

bis-pyridinium cyclophanes: Novel ligands with high affinity for the blood-brain barrier choline transporter

Creator

Zhang Z F; Lockman P R; Mittapalli R K; Allen D D; Dwoskin L P; Crooks P A

Publisher

Bioorganic & Medicinal Chemistry Letters

Date

2008
2008-10

Description

A series of bis-pyridinium cyclophane analogs designed as conformationally restricted bis-quaternary ammonium compounds were evaluated for their affinity for the blood-brain barrier (BBB) choline transporter. All the cyclophanes investigated exhibited high affinity compared to choline. Of these compounds, N, N'-(1,10-decanediyl)3,3'-(1,9-decadiyn-1,10-diyl)-bis-pyridinium diiodide (5c) and N, N'-(1,9-nonanediyl) 3,3'-(1,9-decadiyn-1,10-diyl)-bis-pyridinium dibromide (5b) exhibited highest affinity with K(i) values of 0.8 mu M and 1.4 mu M, respectively, and constitute some of the most potent BBB choline transporter ligands reported. (C) 2008 Elsevier Ltd. All rights reserved.

Subject

12-diyl-bis-3-picolinium dibromide; acetylcholine receptor; ammonium-salts; blood-brain barrier choline transporter; carrier-mediated transport; Chemistry; drug delivery; evoked dopamine release; extracellular dopamine; hyperactivity; inhibition; n; n-alkylnicotinium analogs; n'-dodecane-1; nicotinic; nicotinic receptor antagonists; Pharmacology & Pharmacy; quaternary; quaternary ammonium

Format

Journal Article

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Rights

Article information provided for research and reference use only. All rights are retained by the journal listed under publisher and/or the creator(s).

Pages

5622-5625

Issue

20

Volume

18

Citation

Zhang Z F; Lockman P R; Mittapalli R K; Allen D D; Dwoskin L P; Crooks P A, “bis-pyridinium cyclophanes: Novel ligands with high affinity for the blood-brain barrier choline transporter,” NEOMED Bibliography Database, accessed September 26, 2021, https://neomed.omeka.net/items/show/7651.

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