Literature DB >> 12617898

Design, synthesis and binding affinity of 3'-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands.

Moo Hong Lim1, Hea Ok Kim, Hyung Ryong Moon, Seung Jin Lee, Moon Woo Chun, Zhan-Guo Gao, Neli Melman, Kenneth A Jacobson, Joong Hyup Kim, Lak Shin Jeong.   

Abstract

Several 3'-fluoro analogues, 1a, 1b, and 1c of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 8b with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3'-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor.

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Year:  2003        PMID： 12617898     DOI： 10.1016/s0960-894x(03)00027-1

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  8 in total

1.  Exploring human adenosine A3 receptor complementarity and activity for adenosine analogues modified in the ribose and purine moiety.

Authors:  Philippe Van Rompaey; Kenneth A Jacobson; Ariel S Gross; Zhan-Guo Gao; Serge Van Calenbergh
Journal:  Bioorg Med Chem       Date:  2005-02-15       Impact factor: 3.641

2.  Docking studies of agonists and antagonists suggest an activation pathway of the A3 adenosine receptor.

Authors:  Soo-Kyung Kim; Zhan-Guo Gao; Lak Shin Jeong; Kenneth A Jacobson
Journal:  J Mol Graph Model       Date:  2006-05-09       Impact factor: 2.518

3.  Synthesis of 3'-acetamidoadenosine derivatives as potential A3 adenosine receptor agonists.

Authors:  Moon Woo Chun; Sung Wook Choi; Tae Kyung Kang; Won Jun Choi; Hea Ok Kim; Zhan-Guo Gao; Kenneth A Jacobson; Lak Shin Jeong
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2008-04       Impact factor: 1.381

4.  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

5.  Modulation of A1 and A2B adenosine receptor activity: a new strategy to sensitise glioblastoma stem cells to chemotherapy.

Authors:  S Daniele; E Zappelli; L Natali; C Martini; M L Trincavelli
Journal:  Cell Death Dis       Date:  2014-11-27       Impact factor: 8.469

Review 6.  Partial agonists for A(3) adenosine receptors.

Authors:  Zhan-Guo Gao; Kenneth A Jacobson
Journal:  Curr Top Med Chem       Date:  2004       Impact factor: 3.295

7.  Structural determinants of efficacy at A3 adenosine receptors: modification of the ribose moiety.

Authors:  Zhan-Guo Gao; Lak Shin Jeong; Hyung Ryong Moon; Hea Ok Kim; Won Jun Choi; Dae Hong Shin; Eleonora Elhalem; Maria J Comin; Neli Melman; Liaman Mamedova; Ariel S Gross; Juan B Rodriguez; Kenneth A Jacobson
Journal:  Biochem Pharmacol       Date:  2004-03-01       Impact factor: 5.858

8.  Versatile synthesis and biological evaluation of novel 3'-fluorinated purine nucleosides.

Authors:  Hang Ren; Haoyun An; Paul J Hatala; William C Stevens; Jingchao Tao; Baicheng He
Journal:  Beilstein J Org Chem       Date:  2015-12-09       Impact factor: 2.883
  8 in total

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