Design, synthesis and pharmacological characterization of a potent radioiodinated and photoactivatable peptidic oxytocin antagonist

Journal of Medicinal Chemistry

Volumn 44, Issue 18, 2001, Pages 3022-3030

  Carnazzi, E ^a,b   Aumelas, A ^c   Mouillac, B ^d   Breton, C ^b,d   Guillou, L ^a   Barberis, C ^d   Seyer, R ^a  

^a CNRS UPR 9023   (France)

^b CNRS   (France)

^c UNIV MONTPELLIER   (France)

^d CCIPE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OXYTOCIN ANTAGONIST; OXYTOCIN RECEPTOR; PHOSPHOLIPASE C;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING SITE; CHO CELL; DISSOCIATION CONSTANT; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; MASS SPECTROMETRY; NONHUMAN; PHOTOACTIVATION; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOIODINATION; RECEPTOR BINDING; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ANIMALS; BINDING, COMPETITIVE; CHO CELLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRICETINAE; DRUG DESIGN; HUMANS; INOSITOL PHOSPHATES; IODINE RADIOISOTOPES; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES, CYCLIC; PHOTOLYSIS; RADIOLIGAND ASSAY; RECEPTORS, OXYTOCIN; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035974702     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010125u     Document Type: Article

References (51)

1. Molecular tinkering of G protein-coupled receptors: An evolutionary success
2. Structure and expression of a human oxytocin receptor
3. Molecular cloning and functional characterization of V2 [8-lysine] vasopressin and oxytocin receptors from a pig kidney cell line
4. Structure, characterization, and expression of the rat oxytocin receptor gene
5. Molecular pharmacology of AVP and OT receptors and therapeutic potential
6. Docking of linear peptide antagonists into the human V1a vasopressin receptor. Identification of binding domains by photoaffinity labeling
7. Progress in the development of oxytocin antagonists for use in preterm labor
8. Oxytocin receptor antagonists. Update
9. Discovery and design of novel and selective vasopressin and oxytocin agonists and antagonists: The role of bioassays
10. Two aromatic residues regulate the response of the human oxytocin receptor to the partial agonist arginine vasopressin
11. Separate agonist and peptide antagonist binding sites of the oxytocin receptor defined by their transfer into the V2 vasopressin receptor
12. Using photolabile ligands in drug discovery and development
13. Synthesis and characterization of 2-nitro-5-azidobenzoylglycyloxytocin, an oxytocin photoaffinity label
14. Identification of the V1 vasopressin receptor by chemical cross-linking and ligand affinity blotting
15. Identification and enzymatic deglycosylation of the myometrial oxytocin receptor using a radioiodinated photoreactive antagonist
16. Characterization of oxytocin receptors in rabbit amnion involved in the production of prostaglandin E2
17. Molecular size characterization of oxytocin receptors in rabbit amnion
18. Carboxy terminus of vasopressin required for activity but not binding
19. [1-Beta-mercapto-beta,beta-pentamethylenepropionic acid]oxytocin, a potent inhibitor of oxytocin
20. 7]oxytocin), and [7-glycine]oxytocin, peptides with high oxytocic-antidiuretic selectivity
21. Design of potent antagonists of the vasopressor response to arginine-vasopressin
22. Design and synthesis of potent in vivo antagonists of oxytocin
23. 9]OVT: A selective oxytocin receptor ligand
24. 7]OT: A highly selective ligand for central and peripheral OT receptors
25. Comparison of the photochemical behavior of four different photoactivatable probes
26. Exploratory photochemistry of iodinated aromatic azides
27. Aryl azides as photolabels. Retention of iodine during photochemical ring expansion of an iodinated tyrosine derivative
28. Photoaffinity labeling the beta-adrenergic receptor with an iodoazido derivative of norepinephrine
29. Synthesis of azidotubulin: A photoaffinity label for tubulin-binding proteins
30. 12-[(5-iodo-4-azido-2-hydroxybenzoyl)amino]dodecanoic acid: Biological recognition by cholesterol esterase and acyl-CoA: Cholesterol O-acyltransferase
31. PyBOP: A new peptide reagent devoid of toxic byproduct
32. Synthesis of biotinylated and photoreactive probes for angiotensin receptors
33. 125I]iodo-azidophenpyramine, an irreversible specific photoaffinity probe
34. Characterization of a novel, linear radioiodinated vasopressin antagonist: An excellent radioligand for vasopressin V1a receptors
35. The binding site of neuropeptide vasopressin V1a receptor. Evidence for a major localization within transmembrane regions
36. A new series of photoactivatable and iodinatable linear vasopressin antagonists
37. +-ATPase from chloroplasts and 2-nitreno-ADP. Modification of the catalytic site 1 (tight) and catalytic sites 1 and 2 together impairs both uni-site and multisite catalysis of ATP synthesis and ATP hydrolysis
38. 7 amide cis-isomer population
39. Direct identification of human oxytocin receptor-binding domains using a photoactivatable cyclic peptide antagonist: Comparison with the human V1a vasopressin receptor
40. An efficient procedure for the synthesis of cristalline aryldiazonium trifluoroacetates. Synthetic applications
41. Recent trends in photoaffinity labeling
42. 1H NMR spectra of proteins via double quantum filtering
43. Improved techniques for homonuclear rotating-frame and isotropic mixing experiments
44. Two-dimensional chemical chemical exchange and cross relaxation spectroscopy of coupled nuclear spins
45. Influence of matrix solution conditions on the MALDI-MS analysis of peptides and proteins
46. Ligand: A versatile computerized approach for characterization of ligand-binding systems