Literature DB >> 20036561

Comparative molecular field analysis of fenoterol derivatives: A platform towards highly selective and effective beta(2)-adrenergic receptor agonists.

Krzysztof Jozwiak1, Anthony Yiu-Ho Woo, Mary J Tanga, Lawrence Toll, Lucita Jimenez, Joseph A Kozocas, Anita Plazinska, Rui-Ping Xiao, Irving W Wainer.   

Abstract

PURPOSE: To use a previously developed CoMFA model to design a series of new structures of high selectivity and efficacy towards the beta(2)-adrenergic receptor.
RESULTS: Out of 21 computationally designed structures 6 compounds were synthesized and characterized for beta(2)-AR binding affinities, subtype selectivities and functional activities.
CONCLUSION: the best compound is (R,R)-4-methoxy-1-naphthylfelnoterol with K(i)beta(2)-AR=0.28microm, K(i)beta(1)-AR/K(i)beta(2)-AR=573, EC(50cAMP)=3.9nm, EC(50cardio)=16nm. The CoMFA model appears to be an effective predictor of the cardiomocyte contractility of the studied compounds which are targeted for use in congestive heart failure. Copyright 2009 Elsevier Ltd. All rights reserved.

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Year:  2009        PMID: 20036561      PMCID: PMC2832585          DOI: 10.1016/j.bmc.2009.11.062

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  17 in total

Review 1.  Subtype-specific beta-adrenoceptor signaling pathways in the heart and their potential clinical implications.

Authors:  Rui-Ping Xiao; Weizhong Zhu; Ming Zheng; Khalid Chakir; Richard Bond; Edward G Lakatta; Heping Cheng
Journal:  Trends Pharmacol Sci       Date:  2004-07       Impact factor: 14.819

2.  Agonist binding: a multistep process.

Authors:  Brian Kobilka
Journal:  Mol Pharmacol       Date:  2004-05       Impact factor: 4.436

3.  Three-dimensional models for agonist and antagonist complexes with beta 2 adrenergic receptor.

Authors:  M Kontoyianni; C DeWeese; J E Penzotti; T P Lybrand
Journal:  J Med Chem       Date:  1996-10-25       Impact factor: 7.446

4.  Study of interaction between agonists and asn293 in helix VI of human beta(2)-adrenergic receptor.

Authors:  H M Zuurmond; J Hessling; K Blüml; M Lohse; A P Ijzerman
Journal:  Mol Pharmacol       Date:  1999-11       Impact factor: 4.436

5.  Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction.

Authors:  Y Cheng; W H Prusoff
Journal:  Biochem Pharmacol       Date:  1973-12-01       Impact factor: 5.858

6.  Sequential binding of agonists to the beta2 adrenoceptor. Kinetic evidence for intermediate conformational states.

Authors:  Gayathri Swaminath; Yang Xiang; Tae Weon Lee; Jacqueline Steenhuis; Charles Parnot; Brian K Kobilka
Journal:  J Biol Chem       Date:  2003-10-14       Impact factor: 5.157

7.  CGP-12177. A hydrophilic beta-adrenergic receptor radioligand reveals high affinity binding of agonists to intact cells.

Authors:  M Staehelin; P Simons; K Jaeggi; N Wigger
Journal:  J Biol Chem       Date:  1983-03-25       Impact factor: 5.157

8.  A protein binding assay for adenosine 3':5'-cyclic monophosphate.

Authors:  A G Gilman
Journal:  Proc Natl Acad Sci U S A       Date:  1970-09       Impact factor: 11.205

9.  Involvement of Asn-293 in stereospecific agonist recognition and in activation of the beta 2-adrenergic receptor.

Authors:  K Wieland; H M Zuurmond; C Krasel; A P Ijzerman; M J Lohse
Journal:  Proc Natl Acad Sci U S A       Date:  1996-08-20       Impact factor: 11.205

10.  Functional selectivity of GPCR ligand stereoisomers: new pharmacological opportunities.

Authors:  Roland Seifert; Stefan Dove
Journal:  Mol Pharmacol       Date:  2008-11-10       Impact factor: 4.436

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  23 in total

Review 1.  β-Adrenergic receptor subtype signaling in heart: from bench to bedside.

Authors:  Anthony Yiu Ho Woo; Rui-ping Xiao
Journal:  Acta Pharmacol Sin       Date:  2012-01-30       Impact factor: 6.150

2.  {Beta}2-adrenergic receptor agonists inhibit the proliferation of 1321N1 astrocytoma cells.

Authors:  L Toll; L Jimenez; N Waleh; K Jozwiak; A Y-H Woo; R-P Xiao; M Bernier; I W Wainer
Journal:  J Pharmacol Exp Ther       Date:  2010-11-11       Impact factor: 4.030

3.  Cannabinoid receptor activation correlates with the proapoptotic action of the β2-adrenergic agonist (R,R')-4-methoxy-1-naphthylfenoterol in HepG2 hepatocarcinoma cells.

Authors:  Rajib K Paul; Anuradha Ramamoorthy; Jade Scheers; Robert P Wersto; Lawrence Toll; Lucita Jimenez; Michel Bernier; Irving W Wainer
Journal:  J Pharmacol Exp Ther       Date:  2012-07-09       Impact factor: 4.030

Review 4.  Advances in receptor conformation research: the quest for functionally selective conformations focusing on the β2-adrenoceptor.

Authors:  Anthony Yiu-Ho Woo; Ying Song; Weizhong Zhu; Rui-Ping Xiao
Journal:  Br J Pharmacol       Date:  2015-02-27       Impact factor: 8.739

5.  Concurrent activation of β2-adrenergic receptor and blockage of GPR55 disrupts pro-oncogenic signaling in glioma cells.

Authors:  Artur Wnorowski; Justyna Such; Rajib K Paul; Robert P Wersto; Fred E Indig; Krzysztof Jozwiak; Michel Bernier; Irving W Wainer
Journal:  Cell Signal       Date:  2017-05-08       Impact factor: 4.315

6.  Interaction of fenoterol stereoisomers with β2-adrenoceptor-G sα fusion proteins: antagonist and agonist competition binding.

Authors:  Michael T Reinartz; Solveig Kälble; Irving W Wainer; Roland Seifert
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2015-01-31       Impact factor: 3.000

Review 7.  Effect of fenoterol stereochemistry on the β2 adrenergic receptor system: ligand-directed chiral recognition.

Authors:  Krzysztof Jozwiak; Anita Plazinska; Lawrence Toll; Lucita Jimenez; Anthony Yiu-Ho Woo; Rui-Ping Xiao; Irving W Wainer
Journal:  Chirality       Date:  2011-05-26       Impact factor: 2.437

8.  The stereoselective sulfate conjugation of 4'-methoxyfenoterol stereoisomers by sulfotransferase enzymes.

Authors:  Lalitha V Iyer; Anuradha Ramamoorthy; Ewelina Rutkowska; Anna M Furimsky; Liang Tang; Paul Catz; Carol E Green; Krzysztof Jozwiak; Irving W Wainer
Journal:  Chirality       Date:  2012-06-29       Impact factor: 2.437

9.  Structure-bias relationships for fenoterol stereoisomers in six molecular and cellular assays at the β2-adrenoceptor.

Authors:  Michael T Reinartz; Solveig Kälble; Timo Littmann; Takeaki Ozawa; Stefan Dove; Volkhard Kaever; Irving W Wainer; Roland Seifert
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2014-10-24       Impact factor: 3.000

10.  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β₂-adrenergic receptor.

Authors:  Anita Plazinska; Karolina Pajak; Ewelina Rutkowska; Lucita Jimenez; Joseph Kozocas; Gary Koolpe; Mary Tanga; Lawrence Toll; Irving W Wainer; Krzysztof Jozwiak
Journal:  Bioorg Med Chem       Date:  2013-11-23       Impact factor: 3.641

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