Literature DB >> 16640326

Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytisine derivatives. Nicotinic ligands of enhanced subtype selectivity.

Sheela K Chellappan1, Yingxian Xiao, Werner Tueckmantel, Kenneth J Kellar, Alan P Kozikowski.   

Abstract

We report the synthesis and pharmacological properties of several cytisine derivatives. Among them, two 10-substituted derivatives showed much higher selectivities for the alpha4beta2 nAChR subtype in binding assays than cytisine. The 9-vinyl derivative was found to have a very similar agonist activity profile to that of cytisine.

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Year:  2006        PMID： 16640326      PMCID： PMC2504867          DOI： 10.1021/jm051196m

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  52 in total

1.  Pharmacology of neuronal nicotinic acetylcholine recceptors: effects of acute and chronic nicotine.

Authors:  K J Kellar; M I Dávila-García; Y Xiao
Journal:  Nicotine Tob Res       Date:  1999       Impact factor: 4.244

2.  Effects of nicotine in the dopaminergic system of mice lacking the alpha4 subunit of neuronal nicotinic acetylcholine receptors.

Authors:  L M Marubio; A M Gardier; S Durier; D David; R Klink; M M Arroyo-Jimenez; J M McIntosh; F Rossi; N Champtiaux; M Zoli; J-P Changeux
Journal:  Eur J Neurosci       Date:  2003-04       Impact factor: 3.386

3.  Cytisine derivatives as high affinity nAChR ligands: synthesis and comparative molecular field analysis.

Authors:  O Nicolotti; C Canu Boido; F Sparatore; A Carotti
Journal:  Farmaco       Date:  2002-06

Review 4.  Assembly and subunit diversity of nicotinic acetylcholine receptors.

Authors:  N S Millar
Journal:  Biochem Soc Trans       Date:  2003-08       Impact factor: 5.407

Review 5.  Cytisine derivatives as ligands for neuronal nicotine receptors and with various pharmacological activities.

Authors:  Caterina Canu Boido; Bruno Tasso; Vito Boido; Fabio Sparatore
Journal:  Farmaco       Date:  2003-03

Review 6.  Desensitization of neuronal nicotinic receptors.

Authors:  Michael W Quick; Robin A J Lester
Journal:  J Neurobiol       Date:  2002-12

7.  Agonist regulation of rat alpha 3 beta 4 nicotinic acetylcholine receptors stably expressed in human embryonic kidney 293 cells.

Authors:  E L Meyer; Y Xiao; K J Kellar
Journal:  Mol Pharmacol       Date:  2001-09       Impact factor: 4.436

8.  Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2',3'-disubstituted 5'-pyridinyl)-7-azabicyclo[2.2.1]heptanes: epibatidine analogues.

Authors:  F Ivy Carroll; Jeffrey R Lee; Hernán A Navarro; Wei Ma; Lawrence E Brieaddy; Philip Abraham; M I Damaj; Billy R Martin
Journal:  J Med Chem       Date:  2002-10-10       Impact factor: 7.446

9.  Synthesis of a [2-pyridinyl-18F]-labelled fluoro derivative of (-)-cytisine as a candidate radioligand for brain nicotinic alpha4beta2 receptor imaging with PET.

Authors:  Gaëlle Roger; Béatrice Lagnel; Jacques Rouden; Laurent Besret; Héric Valette; Stéphane Demphel; JaganMohan Gopisetti; Christine Coulon; Michele Ottaviani; Lori A Wrenn; Sharon R Letchworth; Georg A Bohme; Jesus Benavides; Marie-Claire Lasne; Michel Bottlaender; Frédéric Dollé
Journal:  Bioorg Med Chem       Date:  2003-12-01       Impact factor: 3.641

10.  Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.

Authors:  J Brek Eaton; Jian-Hong Peng; Katherine M Schroeder; Andrew A George; John D Fryer; Chandra Krishnan; Lori Buhlman; Yen-Ping Kuo; Ortrud Steinlein; Ronald J Lukas
Journal:  Mol Pharmacol       Date:  2003-12       Impact factor: 4.436
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  6 in total

1.  Chemistry and pharmacology of nicotinic ligands based on 6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol (AMOP-H-OH) for possible use in depression.

Authors:  Alan P Kozikowski; J Brek Eaton; Krishna Mohan Bajjuri; Sheela K Chellappan; Yihua Chen; Sudhakar Karadi; Rong He; Barbara Caldarone; Michael Manzano; Po-Wai Yuen; Ronald J Lukas
Journal:  ChemMedChem       Date:  2009-08       Impact factor: 3.466

2.  Development of fluorescence imaging probes for nicotinic acetylcholine α4β2∗ receptors.

Authors:  Gurleen K Samra; Irakli Intskirveli; Anitha P Govind; Christopher Liang; Ronit Lazar; William N Green; Raju Metherate; Jogeshwar Mukherjee
Journal:  Bioorg Med Chem Lett       Date:  2017-12-17       Impact factor: 2.823

3.  Competition, Selectivity and Efficacy of Analogs of A-84543 for Nicotinic Acetylcholine Receptors with Repositioning of Pyridine Nitrogen.

Authors:  Adebowale E Ogunjirin; Joseph M Fortunak; LaVerne L Brown; Yingxian Xiao; Martha I Dávila-García
Journal:  Neurochem Res       Date:  2015-10-27       Impact factor: 3.996

4.  Structural characterization of binding mode of smoking cessation drugs to nicotinic acetylcholine receptors through study of ligand complexes with acetylcholine-binding protein.

Authors:  Prakash Rucktooa; Claire A Haseler; René van Elk; August B Smit; Timothy Gallagher; Titia K Sixma
Journal:  J Biol Chem       Date:  2012-05-02       Impact factor: 5.157

Review 5.  Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.

Authors:  Li-Fang Yu; Han-Kun Zhang; Barbara J Caldarone; J Brek Eaton; Ronald J Lukas; Alan P Kozikowski
Journal:  J Med Chem       Date:  2014-07-02       Impact factor: 7.446

6.  Fluorescence activation mechanism and imaging of drug permeation with new sensors for smoking-cessation ligands.

Authors:  Aaron L Nichols; Zack Blumenfeld; Chengcheng Fan; Laura Luebbert; Annet E M Blom; Bruce N Cohen; Jonathan S Marvin; Philip M Borden; Charlene H Kim; Anand K Muthusamy; Amol V Shivange; Hailey J Knox; Hugo Rego Campello; Jonathan H Wang; Dennis A Dougherty; Loren L Looger; Timothy Gallagher; Douglas C Rees; Henry A Lester
Journal:  Elife       Date:  2022-01-04       Impact factor: 8.140
  6 in total

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