Artículo
Alvarez, L.D.; Veleiro, A.S.; Baggio, R.F.; Garland, M.T.; Edelsztein, V.C.; Coirini, H.; Burton, G. "Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs" (2008) Bioorganic and Medicinal Chemistry. 16(7):3831-3838
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Abstract:
Three analogs of neuroactive steroids were prepared (4-6) in which 1,11- or 11,19-oxygen bridges give a constrained conformation. Their 3D structures were obtained by ab initio calculations and in the case of 3α-hydroxy-11,19-epoxypregn-4-ene-20-one (4), confirmed by X-ray analysis. Biological activity of the synthetic steroids was assayed in vitro using t-[3H]butylbicycloorthobenzoate as radiolabeled ligand for the GABAA receptor. The activity of compound 4 was similar to that of allopregnanolone (1). 1α,11α-Epoxypregnanolone (6) was more active than pregnanolone (2). © 2008 Elsevier Ltd. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs |
| Autor: | Alvarez, L.D.; Veleiro, A.S.; Baggio, R.F.; Garland, M.T.; Edelsztein, V.C.; Coirini, H.; Burton, G. |
| Filiación: | Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina Departamento de Física (Lab. TANDAR), Comisión Nacional de Energía Atómica, Av. Gral Paz 1499, B1650KNA San Martin Pcia de Buenos Aires, Argentina Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Avda. Blanco Encalada 2008, Casilla 487-3, Santiago, Chile Instituto de Biología y Medicina Experimental (CONICET), Vuelta de Obligado 2490, C1428ADN Buenos Aires, Argentina |
| Palabras clave: | γ-Aminobutyric acid; GABA; GABAA receptor; Neurosteroids; Steroids; 3alpha hydroxy 11,19 epoxypregn 4 ene 20 one; 3alpha hydroxy 1alpha,11alpha epoxy 5beta pregnan 20 one; 3alpha hydroxy 1beta,11alpha epoxy 5alpha pregnan 20 one; 3alpha hydroxy 5alpha pregnan 20 one; 4 aminobutyric acid A receptor; eltanolone; neurosteroid; oxygen; tert butylbicycloorthobenzoate; tritium; unclassified drug; ab initio calculation; article; biological activity; controlled study; drug conformation; drug receptor binding; drug structure; in vitro study; isotope labeling; male; nonhuman; rat; X ray analysis; Animals; Male; Models, Molecular; Molecular Structure; Neurons; Oxygen; Rats; Rats, Sprague-Dawley; Receptors, GABA-A; Steroids |
| Año: | 2008 |
| Volumen: | 16 |
| Número: | 7 |
| Página de inicio: | 3831 |
| Página de fin: | 3838 |
| DOI: | http://dx.doi.org/10.1016/j.bmc.2008.01.048 |
| Título revista: | Bioorganic and Medicinal Chemistry |
| Título revista abreviado: | Bioorg. Med. Chem. |
| ISSN: | 09680896 |
| CODEN: | BMECE |
| CAS: | 3alpha hydroxy 5alpha pregnan 20 one, 516-54-1; eltanolone, 128-20-1; oxygen, 7782-44-7; tritium, 10028-17-8; Oxygen, 7782-44-7; Receptors, GABA-A; Steroids |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v16_n7_p3831_Alvarez |
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Citas:
---------- APA ----------
Alvarez, L.D., Veleiro, A.S., Baggio, R.F., Garland, M.T., Edelsztein, V.C., Coirini, H. & Burton, G. (2008) . Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs. Bioorganic and Medicinal Chemistry, 16(7), 3831-3838.http://dx.doi.org/10.1016/j.bmc.2008.01.048
---------- CHICAGO ----------
Alvarez, L.D., Veleiro, A.S., Baggio, R.F., Garland, M.T., Edelsztein, V.C., Coirini, H., et al. "Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs" . Bioorganic and Medicinal Chemistry 16, no. 7 (2008) : 3831-3838.http://dx.doi.org/10.1016/j.bmc.2008.01.048
---------- MLA ----------
Alvarez, L.D., Veleiro, A.S., Baggio, R.F., Garland, M.T., Edelsztein, V.C., Coirini, H., et al. "Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs" . Bioorganic and Medicinal Chemistry, vol. 16, no. 7, 2008, pp. 3831-3838.http://dx.doi.org/10.1016/j.bmc.2008.01.048
---------- VANCOUVER ----------
Alvarez, L.D., Veleiro, A.S., Baggio, R.F., Garland, M.T., Edelsztein, V.C., Coirini, H., et al. Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs. Bioorg. Med. Chem. 2008;16(7):3831-3838.http://dx.doi.org/10.1016/j.bmc.2008.01.048
