Literature DB >> 18811138

Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists.

Lak Shin Jeong1, Shantanu Pal, Seung Ah Choe, Won Jun Choi, Kenneth A Jacobson, Zhan-Guo Gao, Athena M Klutz, Xiyan Hou, Hea Ok Kim, Hyuk Woo Lee, Sang Kook Lee, Dilip K Tosh, Hyung Ryong Moon.   

Abstract

Novel D- and l-4'-thioadenosine derivatives lacking the 4'-hydroxymethyl moiety were synthesized, starting from d-mannose and d-gulonic gamma-lactone, respectively, as potent and selective species-independent A 3 adenosine receptor (AR) antagonists. Among the novel 4'-truncated 2-H nucleosides tested, a N(6)-(3-chlorobenzyl) derivative 7c was the most potent at the human A 3 AR (K i = 1.5 nM), but a N(6)-(3-bromobenzyl) derivative 7d showed the optimal species-independent binding affinity.

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Year:  2008        PMID： 18811138      PMCID： PMC3616494          DOI： 10.1021/jm8008647

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


  28 in total

1.  Evidence for involvement of Wnt signaling pathway in IB-MECA mediated suppression of melanoma cells.

Authors:  Pnina Fishman; Lea Madi; Sara Bar-Yehuda; Faina Barer; Luis Del Valle; Kamel Khalili
Journal:  Oncogene       Date:  2002-06-06       Impact factor: 9.867

2.  A modification of a protein-binding method for rapid quantification of cAMP in cell-culture supernatants and body fluid.

Authors:  C Nordstedt; B B Fredholm
Journal:  Anal Biochem       Date:  1990-09       Impact factor: 3.365

3.  Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.

Authors:  K N Klotz; J Hessling; J Hegler; C Owman; B Kull; B B Fredholm; M J Lohse
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  1998-01       Impact factor: 3.000

Review 4.  Pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine ligands, new tools to characterize A3 adenosine receptors in human tumor cell lines.

Authors:  Pier Giovanni Baraldi; Mojgan Aghazadeh Tabrizi; Romeo Romagnoli; Francesca Fruttarolo; Stefania Merighi; Katia Varani; Stefania Gessi; Pier Andrea Borea
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

5.  N6-substituted D-4'-thioadenosine-5'-methyluronamides: potent and selective agonists at the human A3 adenosine receptor.

Authors:  Lak Shin Jeong; Dong Zhe Jin; Hea Ok Kim; Dae Hong Shin; Hyung Ryong Moon; Prashantha Gunaga; Moon Woo Chun; Yong-Chul Kim; Neli Melman; Zhan-Guo Gao; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2003-08-28       Impact factor: 7.446

6.  Modulation of adenosine receptor affinity and intrinsic efficacy in adenine nucleosides substituted at the 2-position.

Authors:  Michihiro Ohno; Zhan-Guo Gao; Philippe Van Rompaey; Susanna Tchilibon; Soo-Kyung Kim; Brian A Harris; Ariel S Gross; Heng T Duong; Serge Van Calenbergh; Kenneth A Jacobson
Journal:  Bioorg Med Chem       Date:  2004-06-01       Impact factor: 3.641

7.  2-Substituted adenosine derivatives: affinity and efficacy at four subtypes of human adenosine receptors.

Authors:  Zhan-Guo Gao; Liaman K Mamedova; Peiran Chen; Kenneth A Jacobson
Journal:  Biochem Pharmacol       Date:  2004-11-15       Impact factor: 5.858

8.  2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.

Authors:  H O Kim; X D Ji; S M Siddiqi; M E Olah; G L Stiles; K A Jacobson
Journal:  J Med Chem       Date:  1994-10-14       Impact factor: 7.446

9.  Structure-activity relationships of 9-alkyladenine and ribose-modified adenosine derivatives at rat A3 adenosine receptors.

Authors:  K A Jacobson; S M Siddiqi; M E Olah; X D Ji; N Melman; K Bellamkonda; Y Meshulam; G L Stiles; H O Kim
Journal:  J Med Chem       Date:  1995-05-12       Impact factor: 7.446

10.  Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary.

Authors:  Zhan-Guo Gao; Soo-Kyung Kim; Thibaud Biadatti; Wangzhong Chen; Kyeong Lee; Dov Barak; Seong Gon Kim; Carl R Johnson; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2002-09-26       Impact factor: 8.039
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  15 in total

Review 1.  Recent developments in adenosine receptor ligands and their potential as novel drugs.

Authors:  Christa E Müller; Kenneth A Jacobson
Journal:  Biochim Biophys Acta       Date:  2010-12-23

2.  Discovery of New Human A(2A) Adenosine Receptor Agonists: Design, Synthesis, and Binding Mode of Truncated 2-Hexynyl-4'-thioadenosine.

Authors:  Xiyan Hou; Hea Ok Kim; Varughese Alexander; Kyunglim Kim; Sun Choi; Seul-Gi Park; Jin Hee Lee; Lena S Yoo; Zhan-Guo Gao; Kenneth A Jacobson; Lak Shin Jeong
Journal:  ACS Med Chem Lett       Date:  2010-09-01       Impact factor: 4.345

3.  Functionalized congeners of A3 adenosine receptor-selective nucleosides containing a bicyclo[3.1.0]hexane ring system.

Authors:  Dilip K Tosh; Moshe Chinn; Andrei A Ivanov; Athena M Klutz; Zhan-Guo Gao; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2009-12-10       Impact factor: 7.446

4.  Probing biased/partial agonism at the G protein-coupled A(2B) adenosine receptor.

Authors:  Zhan-Guo Gao; Ramachandran Balasubramanian; Evgeny Kiselev; Qiang Wei; Kenneth A Jacobson
Journal:  Biochem Pharmacol       Date:  2014-05-20       Impact factor: 5.858

5.  Truncated Nucleosides as A(3) Adenosine Receptor Ligands: Combined 2-Arylethynyl and Bicyclohexane Substitutions.

Authors:  Dilip K Tosh; Silvia Paoletta; Khai Phan; Zhan-Guo Gao; Kenneth A Jacobson
Journal:  ACS Med Chem Lett       Date:  2012-06-11       Impact factor: 4.345

6.  Truncated (N)-Methanocarba Nucleosides as A(1) Adenosine Receptor Agonists and Partial Agonists: Overcoming Lack of a Recognition Element.

Authors:  Dilip K Tosh; Khai Phan; Francesca Deflorian; Qiang Wei; Zhan-Guo Gao; Kenneth A Jacobson
Journal:  ACS Med Chem Lett       Date:  2011-08-11       Impact factor: 4.345

7.  Polypharmacology of N6-(3-Iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA) and Related A3 Adenosine Receptor Ligands: Peroxisome Proliferator Activated Receptor (PPAR) γ Partial Agonist and PPARδ Antagonist Activity Suggests Their Antidiabetic Potential.

Authors:  Jinha Yu; Seyeon Ahn; Hee Jin Kim; Moonyoung Lee; Sungjin Ahn; Jungmin Kim; Sun Hee Jin; Eunyoung Lee; Gyudong Kim; Jae Hoon Cheong; Kenneth A Jacobson; Lak Shin Jeong; Minsoo Noh
Journal:  J Med Chem       Date:  2017-08-28       Impact factor: 7.446

8.  Design, synthesis, and binding of homologated truncated 4'-thioadenosine derivatives at the human A3 adenosine receptors.

Authors:  Hyuk Woo Lee; Hea Ok Kim; Won Jun Choi; Sun Choi; Jin Hee Lee; Seul-gi Park; Lena Yoo; Kenneth A Jacobson; Lak Shin Jeong
Journal:  Bioorg Med Chem       Date:  2010-08-14       Impact factor: 3.641

Review 9.  Structure-based approaches to ligands for G-protein-coupled adenosine and P2Y receptors, from small molecules to nanoconjugates.

Authors:  Kenneth A Jacobson
Journal:  J Med Chem       Date:  2013-05-09       Impact factor: 7.446

10.  Structural sweet spot for A1 adenosine receptor activation by truncated (N)-methanocarba nucleosides: receptor docking and potent anticonvulsant activity.

Authors:  Dilip K Tosh; Silvia Paoletta; Francesca Deflorian; Khai Phan; Steven M Moss; Zhan-Guo Gao; Xiaohui Jiang; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2012-09-10       Impact factor: 7.446
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