Literature DB >> 11392549

Ring-Constrained (N)-methanocarba nucleosides as adenosine receptor agonists: independent 5'-uronamide and 2'-deoxy modifications.

K Lee1, G Ravi, X D Ji, V E Marquez, K A Jacobson.   

Abstract

Novel methanocarba adenosine analogues, having the pseudo-ribose northern (N) conformation preferred at adenosine receptors (ARs), were synthesized and tested in binding assays. The 5'-uronamide modification preserved [N6-(3-iodobenzyl)] or enhanced (N6-methyl) affinity at A3ARs, while the 2'-deoxy modification reduced affinity and efficacy in a functional assay.

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Year:  2001        PMID： 11392549      PMCID： PMC4957017          DOI： 10.1016/s0960-894x(01)00213-x

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


  14 in total

1.  Towards a revised nomenclature for P1 and P2 receptors.

Authors:  B B Fredholm; M P Abbracchio; G Burnstock; G R Dubyak; T K Harden; K A Jacobson; U Schwabe; M Williams
Journal:  Trends Pharmacol Sci       Date:  1997-03       Impact factor: 14.819

2.  Interaction of full and partial agonists of the A1 adenosine receptor with receptor/G protein complexes in rat brain membranes.

Authors:  A Lorenzen; L Guerra; H Vogt; U Schwabe
Journal:  Mol Pharmacol       Date:  1996-05       Impact factor: 4.436

3.  Characterization of adenosine receptors in rat brain by (-)[3H]N6-phenylisopropyladenosine.

Authors:  U Schwabe; T Trost
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  1980-09       Impact factor: 3.000

4.  Mechanism-based pharmacokinetic-pharmacodynamic modeling of the effects of N6-cyclopentyladenosine analogs on heart rate in rat: estimation of in vivo operational affinity and efficacy at adenosine A1 receptors.

Authors:  P H Van Der Graaf; E A Van Schaick; R A Math-ot; A P Ijzerman; M Danhof
Journal:  J Pharmacol Exp Ther       Date:  1997-11       Impact factor: 4.030

5.  Selective A2A adenosine receptor activation reduces ischemia-reperfusion injury in rat kidney.

Authors:  M D Okusa; J Linden; T Macdonald; L Huang
Journal:  Am J Physiol       Date:  1999-09

6.  125I-4-aminobenzyl-5'-N-methylcarboxamidoadenosine, a high affinity radioligand for the rat A3 adenosine receptor.

Authors:  M E Olah; C Gallo-Rodriguez; K A Jacobson; G L Stiles
Journal:  Mol Pharmacol       Date:  1994-05       Impact factor: 4.436

7.  The synthesis of new adenosine A3 selective ligands containing bioisosteric isoxazoles.

Authors:  J P Mogensen; S M Roberts; A N Bowler; C Thomsen; L J Knutsen
Journal:  Bioorg Med Chem Lett       Date:  1998-07-07       Impact factor: 2.823

8.  A physiological role of the adenosine A3 receptor: sustained cardioprotection.

Authors:  B T Liang; K A Jacobson
Journal:  Proc Natl Acad Sci U S A       Date:  1998-06-09       Impact factor: 11.205

9.  Synthesis, biological activity, and molecular modeling of ribose-modified deoxyadenosine bisphosphate analogues as P2Y(1) receptor ligands.

Authors:  E Nandanan; S Y Jang; S Moro; H O Kim; M A Siddiqui; P Russ; V E Marquez; R Busson; P Herdewijn; T K Harden; J L Boyer; K A Jacobson
Journal:  J Med Chem       Date:  2000-03-09       Impact factor: 8.039

10.  Adenosine A3 receptor stimulation and cerebral ischemia.

Authors:  D K Von Lubitz; R C Lin; P Popik; M F Carter; K A Jacobson
Journal:  Eur J Pharmacol       Date:  1994-09-22       Impact factor: 4.432
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  24 in total

1.  Adenine nucleotide analogues locked in a Northern methanocarba conformation: enhanced stability and potency as P2Y(1) receptor agonists.

Authors:  R Gnana Ravi; Hak Sung Kim; Jörg Servos; Herbert Zimmermann; Kyeong Lee; Savitri Maddileti; José L Boyer; T Kendall Harden; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2002-05-09       Impact factor: 7.446

2.  Identification by site-directed mutagenesis of residues involved in ligand recognition and activation of the human A3 adenosine receptor.

Authors:  Zhan-Guo Gao; Aishe Chen; Dov Barak; Soo-Kyung Kim; Christa E Müller; Kenneth A Jacobson
Journal:  J Biol Chem       Date:  2002-03-12       Impact factor: 5.157

3.  Chapter 13. A3 Adenosine Receptors.

Authors:  Kenneth A Jacobson; Susanna Tchilibon; Bhalchandra V Joshi; Zhan-Guo Gao
Journal:  Annu Rep Med Chem       Date:  2003       Impact factor: 1.059

4.  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

5.  Methanocarba modification of uracil and adenine nucleotides: high potency of Northern ring conformation at P2Y1, P2Y2, P2Y4, and P2Y11 but not P2Y6 receptors.

Authors:  Hak Sung Kim; R Gnana Ravi; Victor E Marquez; Savitri Maddileti; Anna-Karin Wihlborg; David Erlinge; Malin Malmsjö; José L Boyer; T Kendall Harden; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2002-01-03       Impact factor: 7.446

Review 6.  Medicinal chemistry of the A3 adenosine receptor: agonists, antagonists, and receptor engineering.

Authors:  Kenneth A Jacobson; Athena M Klutz; Dilip K Tosh; Andrei A Ivanov; Delia Preti; Pier Giovanni Baraldi
Journal:  Handb Exp Pharmacol       Date:  2009

7.  Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists.

Authors:  Artem Melman; Zhan-Guo Gao; Deepmala Kumar; Tina C Wan; Elizabeth Gizewski; John A Auchampach; Kenneth A Jacobson
Journal:  Bioorg Med Chem Lett       Date:  2008-04-04       Impact factor: 2.823

8.  Methanocarba ring as a ribose modification in ligands of G protein-coupled purine and pyrimidine receptors: synthetic approaches.

Authors:  Dilip K Tosh; Kenneth A Jacobson
Journal:  Medchemcomm       Date:  2013-12-17       Impact factor: 3.597

9.  p53-Independent induction of Fas and apoptosis in leukemic cells by an adenosine derivative, Cl-IB-MECA.

Authors:  Seong Gon Kim; Gnana Ravi; Carsten Hoffmann; Yun Jin Jung; Min Kim; Aishe Chen; Kenneth A Jacobson
Journal:  Biochem Pharmacol       Date:  2002-03-01       Impact factor: 5.858

10.  Synthesis and pharmacological characterization of [(125)I]MRS1898, a high-affinity, selective radioligand for the rat A(3) adenosine receptor.

Authors:  Zhan-Guo Gao; Bao Teng; Haitao Wu; Bhalchandra V Joshi; Gary L Griffiths; Kenneth A Jacobson
Journal:  Purinergic Signal       Date:  2008-06-05       Impact factor: 3.765
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