Structure-activity relationships of a series of analogs of the endozepine octadecaneuropeptide (ODN11-18) on neurosteroid biosynthesis by hypothalamic explants

Journal of Medicinal Chemistry

Volumn 50, Issue 13, 2007, Pages 3070-3076

  Do Rego, Jean Luc ^a   Leprince, Jérôme ^a   Luu The, Van ^b   Pelletier, Georges ^b   Tonon, Marie Christine ^a   Vaudry, Hubert ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

17 HYDROXYPREGNENOLONE; ALANINE; ARGININE; DIAZEPAM BINDING INHIBITOR; HYDROXYPROGESTERONE; NEUROSTEROID; OCTADECANEUROPEPTIDE; PRASTERONE; PROGESTERONE; PROLINE;

AMINO ACID SUBSTITUTION; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; HYPOTHALAMUS; NONHUMAN; STEROIDOGENESIS; STRUCTURE ACTIVITY RELATION;

17-ALPHA-HYDROXYPREGNENOLONE; 17-ALPHA-HYDROXYPROGESTERONE; 3-HYDROXYSTEROID DEHYDROGENASES; AMINO ACID SEQUENCE; ANIMALS; DEHYDROEPIANDROSTERONE; DIAZEPAM BINDING INHIBITOR; ENZYME ACTIVATION; HYPOTHALAMUS; MALE; NEUROPEPTIDES; PEPTIDE FRAGMENTS; PEPTIDES, CYCLIC; PROGESTERONE; RANA ESCULENTA; STEROID 17-ALPHA-HYDROXYLASE; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34347250496     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0610548     Document Type: Article

References (50)

1. Guidotti, A.; Forchetti, C. M.; Corda, M. G.; Kondel, D.; Bennett, C. D.; Costa, E. Isolation, characterization and purification to homogeneity of an endogenous polypeptide with agonistic action on benzodiazepine receptors. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 3531-3535.
2. Tonon, M. C.; Leprince, J.; Gandolfo, P.; Compère, V.; Pelletier, G.; Malagon, M.; Vaudry, H. Endozepines. In Handbook of Biologically Active Peptides; Kastin, A. J., Ed.; Elsevier: New York, 2006; pp 833-839.
3. Ferrero, P.; Santi, M. R.; Conti-Tronconi, B.; Costa, E.; Guidotti, A. Study of an octadecaneuropeptide derived from diazepam binding inhibitor (DBI): Biological activity and presence in rat brain. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 827-831.
4. Alho, H.; Bovolin, P.; Slobodyansky, E. Diazepam-binding inhibitor (DBI) processing: Immunohistochemical studies in the brain. Neurochem. Res. 1990, 15, 209-216.
5. Slobodyansky, E.; Guidotti, A.; Wambebe, C.; Berkovich, A.; Costa, E. Isolation and characterization of a triakontatetraneuropeptide (TTN) a post-translational product of diazepam binding inhibitor: Specific action at the Ro5-4864 recognition sites. J. Neurochem. 1989, 53, 1276-1284.
6. 39-75, and characterization of its binding site in the rat brain. Regul. Pept. 1994, 50, 29-35.
7. A receptor subtypes: a role for the neuronal posttranslational processing products of rat brain DBI. In GABA and Benzodiazepine Receptor Subtypes; Biggio, G., Costa, E., Eds.; Raven Press: New York, 1990; pp 51-60.
8. Berkovich, A.; McPhie, P.; Campagnone, M.; Guidotti, A.; Hensley, P. A natural processing product of rat diazepam-binding inhibitor, triakontatetraneuroeptide diazepam-binding inhibitor (17-50) contains an α-helix, which allows discrimination between benzodiazepine binding site subtypes. Mol. Pharmacol. 1990, 37, 164-172.
9. Patte, C.; Vaudry, H.; Desrues, L.; Gandolfo, P.; Srijdveen, I.; Lamacz, M.; Tonon, M. C. The endozepine ODN stimulates polyphosphoinositide metabolism in rat astrocytes. FEBS Lett. 1995, 362, 106-110.
10. 2+ in rat astrocytes is not mediated through classical benzodiazepine receptors. Eur. J. Pharmacol. 1997, 322, 275-281.
11. Chen, Z. W.; Agerberth, B.; Gell, K.; Andersson, M.; Mutt, V.; Östenson, C. G.; Efendic, S.; Barros-Soderling, J.; Persson, B.; Jörnvall, H. Isolation and characterization of porcine diazepam-binding inhibitor, a polypeptide not only of cerebral occurrence but also common in intestinal tissues and with effects on regulation of insulin release. Eur. J. Biochem. 1988, 174, 239-245.
12. Alho, H.; Fremeau, R. T.; Tiedge, H.; Wilcox, J.; Bovolin, P.; Brosius, J.; Roberts, J. L.; Costa, E. Diazepam-binding inhibitor gene expression: Location in brain and peripheral tissues of the rat. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 7018-7022.
13. Tonon, M. C.; Désy, L.; Nicolas, P.; Vaudry, H.; Pelletier, G. Immunocytochemical localization of the endogenous benzodiazepine ligand octadecaneuropeptide (ODN) in the rat brain. Neuropeptides 1990, 15, 17-24.
14. Malagon, M.; Vaudry, H.; Vallarino, M.; Gracia-Navarro, F.; Tonon, M. C. Distribution and characterization of endozepine-like immunoreactivity in the central nervous system of the frog Rana ridibunda. Peptides 1992, 13, 99-107.
15. Malagon, M.; Vallarino, M.; Tonon, M. C.; Vaudry, H. Localization and characterization of endozepine-like peptides in the brain of the trout (Salmo gairdneri). Brain Res. 1992, 576, 208-217.
16. Malagon, M.; Vaudry, H.; Van, Strien, F.; Pelletier, G.; Gracia-Navarro, F.; Tonon, M. C. Ontogeny of diazepam-binding inhibitor-related peptides (endozepines) in the rat brain. Neuroscience 1993, 57, 777-786.
17. Östenson, C. G.; Ahren, B.; Karlsson, S.; Knudsen, J.; Efendic, S. Inhibition by rat diazepam-binding inhibitor/acyl-CoA-binding protein of glucose-induced insulin secretion in the rat. Eur. J. Endocrinol. 1994, 131, 143-151.
18. Herzig, K. H.; Schon, I.; Tatemoto, K.; Ohe, Y.; Li, Y.; Folsch, U. R.; Owyang, C. Diazepam binding inhibitor is a potent cholecystokinin-releasing peptide in the intestine. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 7927-7932.
19. Gandolfo, P.; Patte, C.; Leprince, J.; Do-Rego, J. L.; Mensah-Nyagan, A. G.; Vaudry, H.; Tonon, M. C. The triakontatetraneuropeptide (TTN) stimulates thymidine incorporation in rat astrocytes through peripheral-type benzodiazepine receptors. J. Neurochem. 2000, 75, 701-707.
20. Papadopoulos, V.; Berkovich, A.; Krueger, K. E.; Costa, E.; Guidotti, A. Diazepam binding inhibitor and its processing products stimulate mitochondrial steroid biosynthesis via an interaction with mitochondrial benzodiazepine receptors. Endocrinology 1991, 129, 1481-1488.
21. Papadopoulos, V.; Berkovich, A.; Krueger, K. E. The role of diazepam binding inhibitor and its processing products at mitochondrial benzodiazepine receptors: Regulation of steroid biosynthesis. Neuropharmacology 1991, 30, 1417-1423.
22. Garnier, M.; Boujrad, N.; Oke, B. O.; Brown, A. S.; Riond, J.; Ferrara, P.; Shoyab, M.; Suarez-Quian, C. A.; Papadopoulos, V. Diazepam binding inhibitor is a paracrine/autocrine regulator of Leydig cell proliferation and steroidogenesis: action via peripheral-type benzodiazepine receptor and independent mechanisms. Endocrinology 1993, 132, 444-458.
23. Lesouhaitier, O.; Feuilloley, M.; Vaudry, H. Effect of the triakontatetraneuropeptide (TTN) on corticosteroid secretion by the frog adrenal gland. J. Mol. Endocrinol. 1998, 20, 45-53.
24. Leprince, J.; Gandolfo, P.; Thoumas, J. L.; Patte, C.; Fauchère, J. L.; Vaudry, H.; Tonon, M. C. Structure-activity relationships of a series of analogues of the octadecaneuropeptide ODN on calcium mobilization in rat astrocytes. J. Med. Chem. 1998, 41, 4433-4438.
25. Schumacher, M.; Weill-Engerer, S.; Liere, P.; Robert, F.; Franklin, R. J. M.; Garcia-Segura, L. M.; Lambert, J. J.; Mayo, W.; Melcangi, R. C.; Parducz, A.; Suter, U.; Carelli, C.; Baulieu, E. E.; Akwa, Y. Steroid hormones and neurosteroids in normal and pathological aging of the nervous system. Prog. Neurobiol. (Oxford) 2003, 71, 3-29.
26. Dubrovsky, B. O. Steroids, neuroactive steroids and neurosteroids in psychopathology. Prog. Neuro. Psychopharmacol. Biol. Psychiatry 2005, 29, 169-192.
27. Strous, R. D.; Maayan, R.; Weizman, A. The relevance of neurosteroids to clinical psychiatry: From the laboratory to the bedside. Eur. Neuropsychopharmacol. 2006, 16, 155-169.
28. Mensah-Nyagan, A. G.; Do-Rego, J. L.; Beaujean, D.; Luu-The, V.; Pelletier, G.; Vaudry, H. Neurosteroids: Expression of steroidogenic enzymes and regulation of steroid biosynthesis in the central nervous system. Pharmacol. Rev. 1999, 51, 63-81.
29. Tsutsui, K.; Ukena, K.; Takase, M.; Kohchi, C.; Lea, R. W. Neurosteroid biosynthesis in vertebrate brains. Comp. Biochem. Physiol., Part C: Pharmacol., Toxicol. Endocrinol. 1999, 124, 121-129.
30. Compagnone, N. A.; Mellon, S. H. Neurosteroids: Biosynthesis and function of these novel neuromodulators. Front. Neuroendocrinol. 2000, 21, 1-56.
31. Mellon, S.; Vaudry, H. Biosynthesis of neurosteroids and regulation of their synthesis. Int. Rev. Neurobiol. 2001, 46, 33-78.
32. Mensah-Nyagan, A. G.; Feuilloley, M.; Dupont, E.; Do Rego, J. L.; Leboulenger, F.; Pelletier, G.; Vaudry, H. Immunocytochemical localization and biological activity of 3β-hydroxysteroid dehydrogenase in the central nervous system of the frog. J. Neurosci. 1994, 14, 7306-7318.
33. Do Rego, J. L.; Mensah-Nyagan, A. G.; Feuilloley, M.; Ferrara, P.; Pelletier, G.; Vaudry, H. The endozepine triakontatetraneuropeptide diazepam-binding inhibitor [17-50] stimulates neurosteroid biosynthesis in the frog hypothalamus. Neuroscience 1998, 83, 555-570.
34. Do Rego, J. L.; Acharjee, S.; Seong, J. Y.; Galas, L.; Alexandre, D.; Bizet, P.; Burlet, A.; Kwon, H. B.; Luu-The, V.; Pelletier, G.; Vaudry, H. Vasotocin and mesotocin stimulate the biosynthesis of neurosteroids in the frog brain. J. Neurosci. 2006, 26, 6749-6760.
35. Do Rego, J. L.; Mensah-Nyagan, A. G.; Beaujean, D.; Leprince, J.; Tonon, M. C.; Luu-The, V.; Pelletier, G.; Vaudry, H. The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors. J. Neurochem. 2001, 76, 128-138.
36. Leprince, J.; Oulyadi, H.; Vaudry, D.; Masmoudi, O.; Gandolfo, P.; Patte, C.; Costentin, J.; Fauchère, J. L.; Davoust, D.; Vaudry, H.; Tonon, M. C. Synthesis, conformational analysis and biological activity of cyclic analogs of the octadecaneuropeptide ODN. Design of a potent endozepine antagonist. Eur. J. Biochem. 2001, 268, 6045-6057.
37. Tong, Y.; Toranzo, D.; Pelletier, G. Localization of diazepam-binding inhibitor (DBI) mRNA in the rat brain by high resolution in situ hybridization. Neuropeptides 1991, 20, 33-40.
38. Lihrmann, I.; Plaquevent, J. C.; Tostivint, H.; Raijmakers, R.; Tonon, M. C.; Conlon, J. M.; Vaudry, H. Frog diazepam-binding inhibitor: Peptide sequence, cDNA cloning and expression in the brain. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6899-6903.
39. Bürgi, B.; Lichtensteiger, W.; Lauber, M. E.; Schlumpf, M. Ontogeny of diazepam binding inhibitor/Acyl-CoA binding protein mRNA and peripheral benzodiazepine receptor mRNA expression in the rat. J. Neuroendocrinol. 1999, 11, 85-100.
40. Mocchetti, I.; Einstein, R.; Brosius, J. Putative diazepam binding inhibitor peptide: cDNA clones from rat. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 7221-7225.
41. Mocchetti, I.; Santi, M. R. Diazepam binding inhibitor peptide: Cloning and gene expression. Neuropharmacology 1991, 30, 1365-1371.
42. Costa, E.; Guidotti, A. Diazepam-binding inhibitor (DBI): A peptide with multiple biological actions. Life Sci. 1991, 49, 325-344.
43. Do Rego, J. L.; Mensah-Nyagan, A. G.; Beaujean, D.; Vaudry, D.; Sieghart, W.; Luu-The, V.; Pelletier, G.; Vaudry, H. Gamma-aminobutyric acid, acting through gamma-aminobutyric acid type A receptors, inhibits the biosynthesis of neurosteroids in the frog hypothalamus. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 13925-13930.
44. Garcia de Mateos-Verchere, J.; Leprince, J.; Tonon, M. C.; Vaudry, H.; Costentin, J. The octadecaneuropeptide [diazepam-binding inhibitor (33-50)] exerts potent anorexigenic effects in rodents. Eur. J. Pharmacol. 2001, 414, 225-231.
45. Ferrero, P.; Guidotti, A.; Conti-Tronconi, B. A brain octadecaneuropeptide generated by tryptic digestion of DBI (diazepam binding inhibitor) functions as a proconflict ligand of benzodiazepine recognition sites. Neuropharmacology 1984, 23, 1359-1362.
46. Garcia de Mateos-Verchere, J.; Leprince, J.; Tonon, M. C.; Vaudry, H.; Costentin, J. The octadecaneuropeptide ODN induces anxiety in rodents: Possible involvement of a shorter biologically active fragment. Peptides 1998, 19, 841-848.
47. Garcia de Mateos-Verchere, J.; Leprince, J.; Tonon, M. C.; Vaudry, H.; Costentin, J. Reduction of pentylenetetrazol-induced convulsions by the octadecaneuropeptide ODN. Peptides 1999, 20, 1431-1436.
48. Lacor, P.; Gandolfo, P.; Tonon, M. C.; Brault, E.; Schumacher, M.; Benavides, J.; Ferzaz, B. Regulation of the expression of peripheral benzodiazepine receptors and their endogenous ligands during rat sciatic nerve degeneration and regeneration: A role for PBR in neurosteroidogenesis. Brain Res. 1999, 815, 70-80.
49. Akwa, Y.; Young, J.; Kabbadj, K.; Sancho, M. J.; Zucman, D.; Vourc'h, C.; Jung-Testas, I.; Hu, Z. Y.; Le Goascogne, C.; Jo, D. H.; Corpéchot, C.; Simon, P.; Baulieu, E. E.; Robel, P. Neurosteroids: Biosynthesis, metabolism and function of pregnenolone and dehydroepiandrosterone in the brain. J. Steroid Biochem. Mol. Biol. 1991, 40, 71-81.
50. C17) in the frog brain and pituitary. J. Neurochem. 2007, 100, 251-268.