Vinyl sulfide cyclized analogues of angiotensin II with high affinity and full agonist activity at the AT1 receptor

Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2002, Pages 1767-1777

  Johannesson, Petra ^a   Lindeberg, Gunnar ^a   Johansson, Anja ^a   Nikiforovich, Gregory V ^b   Gogoll, Adolf ^a   Synnergren, Barbro ^a   Le Grèves, Madeleine ^a   Nyberg, Fred ^a   Karlén, Anders ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN II DERIVATIVE; ANGIOTENSIN RECEPTOR; CYSTEINE; DISULFIDE; LYSINE; SULFIDE; VINYL DERIVATIVE;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONFORMATION; CONTROLLED STUDY; CYCLIZATION; LIVER MEMBRANE; MALE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RABBIT; RAT; RECEPTOR BINDING; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ACTIVITY RELATION;

ANGIOTENSIN II; ANIMALS; AORTA; BINDING, COMPETITIVE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LIVER; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MUSCLE CONTRACTION; MUSCLE, SMOOTH, VASCULAR; PEPTIDE FRAGMENTS; PEPTIDES, CYCLIC; RABBITS; RADIOLIGAND ASSAY; RATS; RECEPTOR, ANGIOTENSIN, TYPE 1; RECEPTORS, ANGIOTENSIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES; VINYL COMPOUNDS;

EID: 0037171723     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm011063a     Document Type: Article

References (73)

1. Conformational restrictions of biologically active peptides via amino acid side chain groups
2. Conformationally restricted peptides through short-range cyclizations
3. The synthesis of cyclic peptides
4. Application of ring-closing metathesis to the synthesis of rigidified amino acids and peptides
5. Synthesis of novel cyclic protease inhibitors using grubbs olefin metathesis
6. Ring closing metathesis in organic synthesis: Evolution of a high speed, solid phase method for the preparation of β-turn mimetics
7. Design, synthesis, and conformational analysis of a proposed type I β-turn mimic
8. Synthesis of cyclic peptides by ring-closing metathesis
9. Synthesis of cyclic peptides as mimics for the constrained conformation of structural analogues of HIV protease inhibitors
10. Synthesis of an eight-membered cyclic pseudo-dipeptide using ring closing metathesis
11. A Biologically active analogue of oxytocin not containing a disulfide group
12. Coutts efficient method for the syntheses of thioether cyclic peptides
13. N2 macrocyclization reactions to form β-turn mimics
14. Synthesis, conformational analysis and bioactivity of Lan-7, a lanthionine analog of TT-232
15. Synthesis, conformational analysis and biological activities of lanthionine analogs of a cell adhesion modulator
16. Dithioether-containing cyclic peptides
17. Synthesis and biological activity of new conformationally restricted analogues of pepstatin
18. 8]-vasopressin methylenedithioether
19. 2-S bond formation and its application to a djenkolic acid-containing cyclic enkephalin analog
20. Synthesis, receptor binding affinities and conformational properties of cyclic methylenedithioether analogues of angiotensin II
21. General method for the synthesis of cyclic peptidomimetic compounds
22. Highly potent side-chain to side-chain cyclized enkephalin analogues containing a carbonyl bridge: Synthesis, biology and conformation
23. α sites: Design, synthesis, and unexpected conformational properties of an i,(i + 4)-linked peptide
24. 8]angiotensin II
25. Patton cyclic analogs having high potency
26. Multiple binding modes for the receptor-bound conformations of cyclic AII agonists
27. Novel synthesis of cyclic amide-linked analogues and angeotensins II and III
28. 5]ANG II
29. Novel cyclic analogs of angiotensin II with cyclization between positions 5 and 7: Conformational and biological implications
30. Bicyclic tripeptide mimetics with reverse turn inducing properties
31. Angiotensin II analogues encompassing 5,9- and 5,10-fused thiazabicycloalkane tripeptide mimetics
32. The design and synthesis of a potent angiotensin II cyclic analogue confirms the ring cluster receptor conformation of the hormone angiotensin II
33. 1 non-peptide antagonists
34. Refinement of a molecular model of angiotensin II (AII) employed in the discovery of potent nonpeptide antagonists
35. Three-dimensional recognition requirements for angiotensin agonists: A novel solution for an old problem
36. Conformational analysis of two cyclic analogs of angiotensin: Implications for the biologically active conformation
37. Proposals for the angiotensin II receptor-bound conformation by comparative computer modeling of aII and cyclic analogs
38. Conformational analysis of cyclic angiotensin II analogs
39. The octapeptide angiotensin II adopts a well-defined structure in a phospholipid environment
40. 1 receptor as a ligand contact point: Receptor-bound angiotensin II adopts an extended structure
41. Cross-linking in collagen and elastin
42. Allysine peptides and derivatives
43. Reactivity of the allysine aldehyde group
44. New and efficient route to pipecolic acid derivatives by means of Rh-catalyzed intramolecular cyclohydrocarbonylation
45. Reaction of acylamino acids with paraformaldehyde
46. E.COSY a simple Alternative to E.COSY
47. Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy
48. Structure determination of a tetrasaccharide: Transient nuclear overhauser effects in the rotating frame
49. Semianalytical treatment of solvation for molecular mechanics and dynamics
50. MacroModel - An integrated software system for modeling organic and bioorganic molecules using molecular mechanics
51. Energy parameters in polypeptides. 9. Updating of geometrical parameters, nonbonded interactions, and hydrogen bond interactions for the naturally occurring amino acids
52. Energy parameters in polypeptides. 8. Empirical potential energy algorithm for the conformational analysis of large molecules
53. Subclasses of angiotensin II binding sites and their functional significance
54. Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics
55. Dual metalloprotease inhibitors: Mercaptoacetyl-based fused heterocyclic dipeptide mimetics as inhibitors of angiotensin-converting enzyme and neutral endopeptidase
56. Synthesis of constrained bicyclic dipeptide mimetics
57. PXP
58. L-leucyl-glycinamide
59. Cyclic dipeptides. 3. Synthesis of methyl (R)-6-[(tert-butoxycarbonyl)amino]-4,5,6, 7-tetrahydro-2-methyl-5-oxo-1,4-thiazepine-3-carboxylate and its hexahydro analogues: Elaboration of a novel dual ACE/NEP inhibitor
60. 5] enkephalin by NMR spectroscopy and conformational energy calculations
61. Preparation of the enantiomers of 2-Carbobenzyloxyaminoadipic acid and their 1-Benzylesters
62. Synthesis of thyrotropin-releasing hormone analogs. 2. tripeptides structurally greatly different from TRH with high central nervous system activity
63. An unbounded systematic search of conformational space