Position 4 analogues of [deamino-Cys1] arginine vasopressin exhibit striking species differences for human and rat V2/V1b receptor selectivity

Journal of Peptide Science

Volumn 12, Issue 3, 2006, Pages 190-198

  Guillon, Gilles ^a   Pena, Ana ^a   Murat, Brigitte ^a   Derick, Sylvain ^a   Trueba, Miguel ^a   Ventura, Maria A ^b   Szeto, Hazel H ^c   Wo, Nga ^c   Stoev, Stoytcho ^d   Cheng, Ling Ling ^d   Manning, Maurice ^d  

^a INSTITUT DE GÉNOMIQUE FONCTIONNELLE   (France)

^b INSTITUT COCHIN   (France)

^c WEILL CORNELL MEDICAL COLLEGE   (United States)

^d MEDICAL COLLEGE OF OHIO   (United States)

Author keywords

OT; Receptors; Selectivity; V1a; V1b; V2; Vasopressin agonists

Indexed keywords

ARGIPRESSIN DERIVATIVE; HORMONE RECEPTOR STIMULATING AGENT; MAGNESIUM ION; OXYTOCIN RECEPTOR; UNCLASSIFIED DRUG; VASOPRESSIN RECEPTOR; VASOPRESSIN V1 RECEPTOR; VASOPRESSIN V1A RECEPTOR; VASOPRESSIN V1B RECEPTOR; VASOPRESSIN V1B RECEPTOR STIMULATING AGENT; VASOPRESSIN V2 RECEPTOR;

ANIMAL TISSUE; ARTICLE; BIOASSAY; CONTROLLED STUDY; DIURESIS; DRUG DESIGN; DRUG MECHANISM; DRUG SELECTIVITY; DRUG SYNTHESIS; HORMONE ACTION; HORMONE STRUCTURE; HUMAN; HUMAN VERSUS ANIMAL COMPARISON; IN VITRO STUDY; NONHUMAN; PEPTIDE SYNTHESIS; PRESSOR RESPONSE; PRIORITY JOURNAL; PROTEIN FUNCTION; RAT; RAT STRAIN; RECEPTOR AFFINITY; SPECIES DIFFERENCE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIDIURETIC AGENTS; ARGININE VASOPRESSIN; CHO CELLS; CRICETINAE; FEMALE; HUMANS; OXYTOCICS; RATS; RECEPTORS, VASOPRESSIN; SPECIES SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP; VASOCONSTRICTOR AGENTS;

ANIMALIA;

EID: 33644793117     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.710     Document Type: Article

References (72)

1. Barberis C, Mouillac B, Durroux T. Structural bases of vasopressin/oxytocin receptor function. J. Endocrinol. 1998; 156: 223-229.
2. Jard S. Vasopressin receptors. A historical survey. In Advances in Experimental Medicine and Biology, Zingg HH, Bourque CW, Bichet DG (eds). Plenum Press: New York, 1998; 1-13.
3. Ring RH. The central vasopressinergic system: examining the opportunities for psychiatric drug development. Curr. Pharm. Des. 2005: 11: 205-225.
4. Barberis C, Morin D, Durroux T, Mouillac B, Guillon G, Seyer R, Hibert M, Tribollet E, Manning M. Molecular pharmacology of AVP and OT receptors and therapeutic potential. Drug News Perspect. 1999; 12: 279-292.
5. Antoni FA. Novel ligand specificity of pituitary vasopressin receptors in the rat. Neuroendocrinology 1984; 39: 186-188.
6. 1b vasopressin receptor in rat adrenal medulla. Endocrinology 1996; 137: 3906-3914.
7. 1b receptors: characterization in In-R1-G9 cells and localization in human pancreas. Am. J. Physiol. Endocrinol. Metab. 2003; 285: E566-E576.
8. Andres M, Pena A, Derick S, Raufaste D, Trojnar J, Wisniewski K, Trueba M, Serradeil-Le Gal C, Guillon G. Comparative pharmacology of bovine, human and rat vasopressin receptor isoforms. Eur. J. Pharmacol. 2004; 501: 59-69.
9. 1b receptor in the rat brain and pituitary gland: anatomical support for its involvement in the central effects of vasopressin. Endocrinology 2001; 142: 1659-1668.
10. Jard S, Gaillard RC, Guillon G, Marie J, Schoenenberg P, Muller AF, Manning M, Sawyer WH. Vasopressin antagonists allow demonstration of a novel type of vasopressin receptor in the rat adenohypophysis. Mol. Pharmacol. 1986; 30: 171-177.
11. 1b receptors. Am. J. Physiol: Endocrinol. Metab. 1995; 269: E1095-E1100.
12. 1b receptor critically regulates hypothalamic-pituitary-adrenal axis activity under both stress and resting conditions. J. Clin. Invest. 2004; 113: 302-309.
13. Yibchok-Anun S, Cheng H, Heine PA, Hsu WH. Characterization of receptors mediating AVP- and OT-induced glucagons release from the rat pancreas. Am. J. Physiol. Endocrinol. Metab. 1999; 277: E56-E62.
14. Alonso R, Griebel G, Pavone G, Stemmelin J, Le Fur G, Soubrie P. Blockade of CRF(1) or V(1b) receptors reverses stress-induced suppression of neurogenesis in a mouse model of depression. Mol. Psychiatry 2004; 9: 278-286.
15. 1b receptor antagonist, SSR149415, suggest an innovative approach for the treatment of stress-related disorders. Proc. Nail. Acad. Sci U.S.A. 2002; 99: 6370-6375.
16. Ma S, Shipston MJ, Morilak D, Russell JA. Reduced hypothalamic vasopressin secretion underlies attenuated adrenocorticotropin stress responses in pregnant rats. Endocrinology 2005; 146: 1626-1637.
17. Dinan TG, Lavelle E, Scott LV, Newell-Price J, Medbak S, Grossman AB. Desmopressin normalizes the blunted adrenocorticotropin response to corticotropin-releasing hormone in melancholic depression: evidence of enhanced vasopressinergic responsivity. J. Clin. Endocrinol. Metab. 1999; 84: 2238-2240.
18. 3 receptor responses in melancholic depression. Psychol. Med. 2004; 34: 169-172.
19. Scott LV, Dinan TG. Vasopressin as a target for antidepressant development: an assessment of the available evidence. J. Affect. Disord. 2002; 72: 113-124.
20. Birnbaumer M, Seibold A, Gilbert S, Ishido M, Barberis C, Antaramian A, Brabet P, Rosenthal W. Molecular cloning of the receptor for human antidiuretic hormone. Nature 1992; 357: 333-335.
21. 3 pituitary vasopressin receptor. FEBS Lett. 1994; 356: 215-220.
22. 2 [8-lysine] vasopressin and oxytocin receptors from a pig kidney cell line. Eur. J. Biochem. 1993: 215:1-7.
23. Kimura T, Tanizawa O, Mori K, Brownstein MJ, Okayama H. Structure and expression of a human oxytocin receptor. Nature 1992; 356: 526-529.
24. 1a arginine vasopressin receptor. Nature 1992; 356: 523-526.
25. 1b, vasopressin receptor. J. Blot. Chem. 1994; 269: 27088-27092.
26. 1b receptor: evidence for its expression in extra-pituitary tissues. Biochem. Biophys. Res. Commun. 1995; 212: 751-757.
27. 1a vasopressin receptor. J. Biol. Chen-L 1994; 269: 3304-3310.
28. Sawyer WH. Biologic assays for oxytocin and vasopressin. Methods Med. Res. 1961; 9: 210-219.
29. Dekanski J. The quantitative assay of vasopressin. Br. J. Pharmacol. 1952; 7: 567-572.
30. Munsick RA Effect of magnesium ion on the response of the rat uterus to neurohypophysial hormones and analogues. Endocrinology 1960; 66: 451-457.
31. Berde B, Boissonnas PA. Basic pharmacological properties of synthetic analogues and homologues of the neurohypophyseal hormones. In Handbook of Experimental Pharmacology, Vol. 23, Berde B (ed.). Springer-Verlag: New York, 1968; 802-870.
32. Lebl M. Analogs with inhibitory properties; Lebl M, Jost K, Brtnik F. Tables of analogs. In Handbook of Neurohypophyseal Hormone Analogs, Vol. II, Jost K, Lebl M, Brtnik F (eds). CRC Press: Boca Raton, 1988: Part 1: 17-74; Part 2: 127-267.
33. Hruby VJ, Smith CJ Structure-activity relationships of neurohypophyseal peptides. In The Peptides, Udenfriend S, Meienhofer J. (eds), Vol. 8: Chemistry, Biology and Medicine of Neurohypophyseal Hormones and their Analogs, Smith CW (ed.). Academic Press: Orlando, 1987; 177-207.
34. Manning M, Bankowski K, Sawyer WH. Selective agonists and antagonists of vasopressin. In Vasopressin: Principles and Properties, Gash DM, Boer GJ (eds). Plenum Press: New York, 1987; 335-368.
35. Manning M, Sawyer WH. Design, synthesis and some uses of receptor-specific agonists and antagonists of vasopressin and oxytocin.J. Recept. Res. 1993; 13: 195-214.
36. 1b receptor antagonist. J. Pharmacol. Exp. Ther. 2002: 300: 1122-1130.
37. 1b receptors. Endocrinology 2002; 143: 4655-4664.
38. 1b receptor in mammals. Stress 2003; 6: 199-220.
39. 1b receptor ligands for pharmacological, functional and structural investigations. J. Neuroendocrinol. 2004; 16: 356-361.
40. 1]arginine vasopressin at position 4. J. Med. CheTrL 2004; 47: 2375-2388.
41. 8]-vasopressin, two analogues possessing an antidiuretic activity more elevated and selective than that of the natural vasopressin). Helv. Chim. Acta 1966; 49: 695-705.
42. Zaoral M, Kolc J, Sorm F. Amino acid and peptides. LXXI. Synthesis of 1-deamino-8-D-γ-aminobutyrine-vasopressin, 1-deamino-8-D-lysine-vasopressin, and 1-deamino-8-D-arginine-vasopressin. Collect. Czech. Chern. Commun. 1967; 32: 1250-1257.
43. 1b vasopressin receptor. Biochem. Pharmacol. 1997; 53: 1711-1717.
44. du Vigneaud V, Gish DT, Katsoyannis PG. A synthetic preparation possessing biological properties associated with arginine-vasopressin. J. Am. Chem. Soc. 1954; 76: 4751-4752.
45. Manning M, Coy EJ, Acosta M, Sawyer WH. Solid-phase synthesis and some pharmacological properties of deamino-4-threonine analogs of the vasopressins and vasotocin and [deamino]arginine-vasotocin. J. Med. Chem. 1973; 16: 836-839.
46. Manning M, Balaspiri L, Moehring J, Haldar J, Sawyer WH. Synthesis and some pharmacological properties of deamino[4-threonine, 8-D-arginine]vasopressin and deamino[8-D-arginine]vasopressin, highly potent and specific antidiuretic peptides, and [8-D-arginine]vasopressin and deamino-arginine-vasopressin. J. Med. Chem. 1976: 19: 842-845.
47. 4] arginine-vasopressin and two related analogues. Acta Chem. Scand. 1985; B39: 453-457.
48. Sawyer WH, Acosta M, Balaspiri L, Judd J, Manning M. Structural changes in the arginine vasopressin molecule that enhance antidiuretic activity and specificity. Endocrinology 1974; 94: 1106-1115.
49. Gillessen D, du Vigneaud V. Synthesis and pharmacological properties of 4-decarboxamido-8-arginine-vasopressin and its 1-deamino analog. J. Med. Chem. 1970; 13: 346-349.
50. 1a receptors reveal surprising species differences. In Peptides 2000, Martinez J, Fehrentz J-A (eds). EDK, Editions Medicales et Scientifiques: Paris, 2001; 589-590.
51. Manning M, Balaspiri L, Acosta M, Sawyer WH. Solid phase synthesis of [1-deamino,4-valine]-8-D-arginine-vasopressin (DVDAVP). A highly potent and specific antidiuretic agent possessing protracted effects. J. Med. Chem. 1973; 16: 975-978.
52. Schwartz J, Derdowska I, Sobocinska M, Kupryszewski G. A potent new synthetic analog of vasopressin with relative agonist specificity for the pituitary. Endocrinology 1991; 129: 1107-1109.
53. 1b receptor are potent antidiuretic agonists in the rat. In American Peptide Symposium, San Diego, 2005; abstract #292.
54. Merrifield RB. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963: 85: 2149-2154.
55. Merrifield RB. Solid-phase peptide synthesis. Biochemistry 1964; 2: 1385-1390.
56. Stewart JM, Young JD. Solid Phase Synthesis. Pierce Chemical Company: Rockford, 1984.
57. Holton P. A modification of the method of Dale and Laidlaw for standardization of posterior pituitary extract. Br. J. Pharmacol. 1948: 3: 328-334.
58. 2 vasopressin receptor. J. Biol. Chem. 1998; 273: 29462-29468.
59. Aizawa T, Yasuda N, Greer MA, Sawyer WH. In vivo adrenocorticotropin-releasing activity of neurohypophyseal hormones and their analogs. Endocrinology 1982; 110: 98-104.
60. Knepel W, Homolka L, Vlaskovska M, Nutto D. In vitro adrenocorticotropin/beta-endorphin-releasing activity of vasopressin analogs is related neither to pressor nor to antidiuretic activity. Endocrinology 1984; 114: 1797-1804.
61. Williams TDM, Lightman SL, Leadbearer MJ. Hormonal and cardiovascular responses to DDAVP in man. Clin. Endocrinol. 1986; 24:89-96.
62. Derdowska I, Prahl A, Kowalczyk W, Janecki M, Melhem S, Trzeciak HI, Lammek B. Influence of enantiomers of 1-naphthylalanine in position 2 of VAVP and dVAVP on their pharmacological properties. Eur. J. Med. Chem. 2005; 40: 63-68.
63. Jastrzebska B, Derdowska I, Kowalczyk W, Machova A, Slaninova J, Lammek B. Influence of 1-aminocyclohexane-1-carboxylic acid in position 2 or 3 of AVP and its analogues on their pharmacological properties. J. Pept. Res. 2003; 62: 70-77.
64. 2 agonists of arginine vasopressin. J. Med. Chem. 2004; 47: 6020-6024.
65. Kowalczyk W, Derdowska I, Dawidowska O, Prahl A, Hartrodt B, Neubert K, Slaninova J, Lammek B. Analogues of arginine vasopressin modified in the N-terminal part of the molecule with enantiomers of N-methylphenylalanine. J Pept. Res. 2004; 63: 420-425.
66. Lammek B, Bankowski K, Misicka A, Manning M, Seto J, Sawyer WH. 2-O-alkyltyrosine derivatives of 1-deamino-arginine-vasopressin: highly specific and potent antidiuretic agonists. J Med. Chem. 1989: 32: 244-247.
67. Lammek B, Czaja M, Derdowska I, Rekowski P, Trzeciak HI, Sikora P, Szkrobka W, Stojko R, Kupryszewski G. Influence of L-naphthylalanine in position 3 of AVP and its analogues on their pharmacological properties. J. Pept. Res. 1997: 49: 261-268.
68. Stoev S, Cheng LL, Olma A, Klis WA, Manning M, Sawyer WH, Wo NC, Chan WY. An investigation of position 3 in arginine vasopressin with aliphatic, aromatic, conformationally-restricted, polar and charged amino acids. J. Pept. ScL 1999; 5: 141-153.
69. Guillon G, Gaillard RC, Kehrer P, Schoenenberg P, Muller AF, Jard S. Vasopressin and angiotensin induce mositol lipid breakdown in rat adenohypophysial cells in primary culture. Regul. Pept. 1987; 18: 119-129.
70. 1b receptor. In American Peptide Symposium, San Diego, 2005; abstract #352.
71. Tahara A, Saito M, Sugimoto T, Tomura Y, Wada K, Kusayama T, Tsukada J, Ishii N, Yatsu T, Uchida W, Tanaka A. Pharmacological characterization of the human vasopressin receptor subtypes stably expressed in Chinese hamster ovary cells. Br.J Pharmacol. 1998; 125: 1463-1470.
72. Tahara A, Tsukada J, Ishii N, Tomura Y, Wada. K, Kusayama T, Yatsu T, Uchida W, Tanaka A. Characterization of rodent liver and kidney AVP receptors: pharmacologic evidence for species differences. Regul. Pept. 1999: 84: 13-19.