Adenine nucleotide analogues locked in a Northern methanocarba conformation: Enhanced stability and potency as P2Y1 receptor agonists

Journal of Medicinal Chemistry

Volumn 45, Issue 10, 2002, Pages 2090-2100

  Ravi, R Gnana ^a   Kim, Hak Sung ^a   Servos, Jörg ^b   Zimmermann, Herbert ^b   Lee, Kyeong ^a   Maddileti, Savitri ^c   Boyer, José L ^c   Harden, T Kendall ^c   Jacobson, Kenneth A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b GOETHE UNIVERSITY   (Germany)

^c UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLOROMONOPHOSPHATE DERIVATIVE; 5' ECTONUCLEOTIDASE; ADENINE NUCLEOTIDE DERIVATIVE; ADENOSINE TRIPHOSPHATE; BETA,GAMMA METHYLENE METHANOCARBA ADENOSINE TRIPHOSPHATE; METHANOCARBA 2 METHYLTHIO ADENINE NUCLEOTIDE DERIVATIVE; METHANOCARBA 2 METHYLTHIO DERIVATIVE; NUCLEOTIDASE; PHOSPHATE; PHOSPHOLIPASE C; PURINE P2 RECEPTOR; PURINE P2Y RECEPTOR; PURINERGIC RECEPTOR STIMULATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; ASTROCYTOMA CELL; DRUG CONFORMATION; DRUG HYDROLYSIS; DRUG POTENCY; DRUG STABILITY; DRUG SYNTHESIS; ENZYME ACTIVATION; ERYTHROCYTE;

ADENINE NUCLEOTIDES; ADENOSINE TRIPHOSPHATASES; ANIMALS; ANTIGENS, CD; APYRASE; CHO CELLS; CRICETINAE; ERYTHROCYTE MEMBRANE; HUMANS; HYDROLYSIS; INOSITOL PHOSPHATES; MOLECULAR CONFORMATION; PHOSPHOLIPASE C; RATS; RECEPTORS, PURINERGIC P2; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION; TUMOR CELLS, CULTURED; TURKEY;

EID: 0037046516     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010538v     Document Type: Article

References (53)

1. Toward a revised nomenclature for P1 and P2 receptors
2. Recombinant P2Y receptors: The UCL experience
3. Identification of a novel human ADP receptor coupled to Gi
4. Identification of the platelet ADP receptor targeted by antithrombotic drugs
5. ADP is the cognate ligand for the orphan G protein-coupled receptor SP1999
6. 12 receptor: A novel member of the P2Y family of receptors activated by extracellular nucleotides
7. A G protein-coupled receptor for UDP-glucose
8. P2 purine and pyrimidine receptors: Emerging superfamilies of G protein and ligandgated ion channel receptors
9. Therapeutic applications of ATP-(P2) receptors agonists and antagonists
10. P1 and P2 purine and pyrimidine receptors
11. 5 receptor subunits reveals a novel ATP-gated ion channel
12. Heteromeric association creates a P2Y-like adenosine receptor
13. 1 and P2cyc receptors
14. 1 receptor ligands
15. The stable pyrimidines UDPβS and UTPγS discriminate between the P2 receptors that mediate vascular contraction and relaxation of the rat mesenteric artery
16. 2T receptor: A novel approach to antithrombotic therapy
17. 1 receptors
18. Agonists and antagonists acting at P2X receptors: Selectivity profiles and functional implications
19. 7 nucleotide receptor: High selectivity for the human versus rat receptor homologues
20. Pharmacological characterization of P2 (nucleotide) receptors
21. 1 receptor
22. 2Y-subtypes
23. 2Y purinoceptor agonists that are derivatives of adenosine 5′-monophosphate
24. 12 receptor
25. Oxygen-induced pulmonary vasodilation is mediated by adenosine triphosphate in newborn lambs
26. P2 purinoceptor agonists: New insulin secretagogues potentially useful in the treatment of non-insulin-dependent diabetes mellitus
27. P2 receptor agonists stimulate insulin release from human pancreatic islets
28. 1 receptor of platelets without effect on the adenylyl cyclase linked P2Y receptor
29. 1 and P2YT receptors in the morphological changes of platelet aggregation
30. 2-Thioether 5′-O-(1-thiotriphosphate)adenosine derivatives as new insulin secretagogues acting through P2Y-receptors
31. 1 receptor on bone cells
32. 1 purinergic receptor in Alzheimer's disease
33. Cloning and functional expression of a brain G-protein-coupled ATP receptor
34. 1 purinergic receptor in the human brain: Striking neuronal localisation
35. 1 receptor stimulate mitogen-activated protein kinases and induce apoptosis
36. Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides?
37. (1S,2R)-[(benzyloxy)-methyl]cyclopent-3-enol. A versatile synthon for the preparation of 4′,1′a-methano and 1′,1′a-methano carbocyclic nucleosides
38. Synthesis, conformational analysis, and biological activity of a rigid carbocyclic analogue of 2′-deoxyaristeromycin built on a bicyclo[3.1.0]hexane template
39. 6 receptors
40. Identification of potent, selective P2Y-purinoceptor agonists. Structure-activity-relationships for 2-thioether derivatives of adenosine 5′-triphosphate
41. Synthesis of nucleoside triphosphates
42. Use of adenine nucleotide derivatives to assess the potential of exo-active-site-directed reagents as species- or isozyme-specific enzyme inactivators. 3. Synthesis of adenosine 5′-triphosphate derivatives with N6- or 8-substituents bearing iodoacetyl groups
43. Synthesis using ring closure metathesis and effect on nucleoside transport of a (N)-methanocarba S-(4-nitrobenzyl)thioinosine derivative
44. Di-tert-butyl N,N-diethylphosphoramidite. A new phosphitylating agent for the efficient phosphorylation of alcohols
45. Ring-constrained (N)methanocarba-nucleosides as adenosine receptor agonists: Independent 5′-uronamide and 2′-deoxy modifications
46. 1-purinoceptor
47. Kinetics of activation of phospholipase C by P2Y purinergic receptor agonists and guanine nucleotides
48. Catalytically active soluble ecto-5′-nucleotidase purified after heterologous expression as a tool for drug screening
49. Functional characterization of rat ecto-ATPase and ecto-ATP diphosphohydrolase after heterologous expression in CHO cells
50. 4 receptor
51. An improved assay for nanomole amounts of inorganic phosphate
52. An ecto-ATPase and an ecto-ATP diphosphohydrolase are expressed in rat brain
53. Phosphoinositide hydrolysis by guanosine 5′-(gammathio]triphosphate-activated phospholipase C of turkey erythrocyte membranes