A-ring reduced derivatives of two synthetic progestins induce anxiolytic effects in ovariectomized rats

Brain Research

Volumn 796, Issue 1-2, 1998, Pages 45-52

  Picazo, O ^a   Fernandez Guasti A ^b   Lemus, A E ^c   Garcia G A ^d  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^b Secc de Terap Experimental   (Mexico)

^c DEPARTAMENTO DE QUÍMICA   (Mexico)

^d UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Allopregnanolone; Anxiety; Burying behavior; Levonorgestrel; Neuroactive steroid; Norethisterone; Rat

Indexed keywords

GESTAGEN; LEVONORGESTREL; NORETHISTERONE; PROGESTERONE DERIVATIVE;

ANIMAL EXPERIMENT; ANXIETY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG POTENCY; DRUG STRUCTURE; FEMALE; MOBILIZATION; NONHUMAN; OVARIECTOMY; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; SUBCUTANEOUS DRUG ADMINISTRATION; TRANQUILIZING ACTIVITY;

EID: 0032527053     PISSN: 00068993     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-8993(98)00314-X     Document Type: Article

References (38)

1. Atkinson R.M., Davis B., Pratt M.A., Sharpe H.M., Tomich E.G. Action of some steroids on the central nervous system of the mouse. J. Med. Chem. 8:1965;426-432.
2. Belleli D., Gee K.W. 5α-pregnan-3α,20α-diol behaves like a partial agonist in the modulation of GABA-stimulated chloride ion uptake by synaptoneurosomes. Eur. J. Pharmacol. 167:1989;173-176.
3. A receptor. Brain Res. 561:1991;157-161.
4. Bitran D., Shiekh M., McLeod M. Anxiolytic effect of progesterone is mediated by the neurosteroid allopregnanolone at brain GABA(A) receptors. J. Neuroendocrinol. 7:1995;171-177.
5. Bowers A., Ringold H.J., Denot E. Steroids. CI. 19-Nordihydrotestosterone derivatives. J. Am. Chem. Soc. 80:1958;6115-6121.
6. Braselton W.E., Lin T.J., Ellegood J.O., Mills T.M., Mahesh V.B. Accumulation of norethisterone and individual metabolites in human plasma during short- and long-term administration of contraceptive dosage. Am. J. Obstet. Gynecol. 133:1979;154-160.
7. Brot M.D., Akwa Y., Purdy R.H., Koob G.F., Britto K.T. The anxiolytic-like effects of the neurosteroid allopregnanolone: interactions with GABA(A) receptors. Eur. J. Pharmacol. 325:1997;1-7.
8. Brown H.C., Krifhnamurthy S. Lithium tri-sec-butyl borohydride. A new reagent for the reduction of cyclic and bicyclic ketones with superstereo selectivity. A remarkably simple and practical procedure for the conversion of ketones to alcohols in exceptionally high stereochemical purity. J. Am. Chem. Soc. 94:1972;7159-7161.
9. Carboni E., Wieland S., Lan N.C., Gee K.W. Anxiolytic properties of endogenously occurring pregnanediols in two rodent models of anxiety. Psychopharmacology. 126:1996;173-178.
10. Fernández-Guasti A., Picazo O. The actions of diazepam and serotonergic anxiolytics vary according to the gender and to the oestrous cycle phase. Pharmacol. Biochem. Behav. 36:1990;77-81.
11. Fernández-Guasti A., Picazo O. Changes in burying behavior during the estrous cycle: effect of estrogen and progesterone. Psychoneuroendocrinology. 17:1992;681-689.
12. Fernández-Guasti A., Picazo O. Flumazenil blocks the anxiolytic action of allopregnanolone. Eur. J. Pharmacol. 281:1995;113-115.
13. Figdor S.K., Kodet M.J., Bloom B.M., Agnello E.J., Plan S.Y., Laubach G.D. Central activity and structure in a series of water-soluble steroids. J. Pharmacol. Ther. 119:1957;299-309.
14. Gee K.W., Bolger M.B., Brinton R.E., Coirini H., McEwen B.S. Steroid modulation of the chloride ionophore in rat brain: structure-activity requirements, regional dependence and mechanisms of action. J. Pharmacol. Exp. Ther. 246:1988;803-812.
15. Gyermek L., Iriarte J., Crabbé P. Structure-activity relationship of some steroidal hypnotic agents. J. Med. Chem. 11:1968;117-125.
16. A receptor function Mol. Pharmacol. 46:1994;977-985.
17. A receptor complex. J. Pharmacol. Exp. Ther. 241:1987;346-353.
18. Kokate T.G., Svensson B.E., Rogawski M.A. Anticonvulsant activity of neurosteroids: correlation with γ-aminobutyric acid-evoked chloride current potentiation. J. Pharmacol. Exp. Ther. 270:1994;1223-1229.
19. Lan N.C., Bolger M.B., Gee K.W. Identification and characterization of a pregnane steroid recognition site that is functionally coupled to an expressed GABAA receptor. Neurochem. Res. 16:1991;347-356.
20. Lemus A.E., Vilchis F., Damsky R., Chávez B.A., García G.A., Grillasca I., Pérez-Palacios G. Mechanism of action of levonorgestrel: in vitro metabolism and specific interactions with steroid receptors in target organs. J. Steroid Biochem. Mol. Biol. 41:1992;888-890.
21. Majewska M.D., Harrison N.L., Schwartz R.D., Barker J.L., Paul S.M. Steroid hormone metabolites are barbiturate-like modulators of the GABA receptor. Science. 232:1986;1004-1007.
22. 3H ]flunitrazepam binding by natural and synthetic progestational agents Pharmacol. Biochem. Behav. 45:1993;77-83.
23. A receptor complex in rat brain. Mol. Pharmacol. 47:1995;354-362.
24. Orchinik M., McEwen B. Novel and classical actions of neuroactive steroids. Neurotransmissions. 9:1993;1-6.
25. Picazo O., Fernández-Guasti A. Antianxiety effects of progesterone and some of its reduced metabolites: an evaluation using the burying behavior test. Brain Res. 680:1995;135-141.
26. Pinel J.P.J., Treit D. Burying as a defensive response in rats. J. Comp. Physiol. Psychol. 92:1978;708-712.
27. A receptor complex. Neurosci. Lett. 135:1992;273-275.
28. Purdy R.H., Morrow A.L., Blinn J.R., Paul S.M. Synthesis, metabolism, and pharmacological activity of 3α-hydroxy steroids which potentiate GABA-receptor-mediated chloride ion uptake in rat cerebral cortical synaptosomes. J. Med. Chem. 33:1990;1572-1581.
29. Rodríguez-Sierra J.F., Howard J.L., Pollard G.T., Hendricks S.E. Effect of ovarian hormones on conflict behavior. Psychoneuroendocrinology. 9:1984;293-300.
30. Rupprecht R., Hauser C.A.E., Trapp T., Holsboer F. Neurosteroids: molecular mechanisms of action and psychopharmacological significance. J. Steroid Biochem. Mol. Biol. 56:1996;163-168.
31. A agonists on hippocampal slices. Cell. Mol. Neurobiol. 16:1996;427-431.
32. Still W.C., Kahan M., Mitra A. Rapid chromatographic technique for preparative separation with moderate resolution. J. Org. Chem. 43:1978;2923-2925.
33. Stillwell W.G., Horning E.C., Horning M.G., Stillwell K.N., Zlatkis A. Characterization of metabolites of steroid contraceptives by gas chromatography and mass spectrometry. J. Steroid Biochem. 3:1972;699-706.
34. Treit D. The inhibitory effect of diazepam on defensive burying: anxiolytic vs. analgesic effects. Pharmacol. Biochem. Behav. 22:1985;47-52.
35. Treit D. Animal models for the study of antianxiety agents: a review. Neurosci. Biobehav. Rev. 9:1985;203-222.
36. Treit D., Pinel J.P.J., Fibiger H.C. Conditioned defensive burying: a new paradigm for the study of anxiolytic agents. Pharmacol. Biochem. Behav. 15:1981;619-626.
37. Vilchis F., Chávez B., Pérez A.E., García G.A., Angeles A., Pérez-Palacios G. Evidence that a non-aromatizable metabolite of norethisterone induces estrogen-dependent pituitary progestin receptors. J. Steroid Biochem. 24:1986;525-531.
38. Wieland S., Lan N.C., Mirasedeghi S., Gee K.W. Anxiolytic activity of the progesterone metabolite 5α-pregnan-3α-ol-20-one. Brain Res. 565:1991;263-268.