High affinity ligands for 'diazepam-insensitive' benzodiazepine receptors.

Structurally diverse compounds have been shown to possess high affinities for benzodiazepine receptors in their 'diazepam-sensitive' (DS) conformations. In contrast, only the imidazobenzodiazepinone Ro 15-4513 has been shown to exhibit a high affinity for the 'diazepam-insensitive' (DI) conformation of benzodiazepine receptors. We examined a series of 1,4-diazepines containing one or more annelated ring systems for their affinities at DI and DS benzodiazepine receptors, several 1,4-diazepinone carboxylates including Ro 19-4603, Ro 16-6028 and Ro 15-3505 were found to possess high affinities (Ki approximately 2.6-20 nM) for DI. Nonetheless, among the ligands examined, Ro 15-4513 was the only substance with a DI/DS potency ratio approximately 1; other substances had ratios ranging from 13 to greater than 1000. Ligands with high to moderate affinities at DI were previously classified as partial agonists, antagonists, or partial inverse agonists at DS benzodiazepine receptors, but behaved as 'GABA neutral' (antagonist) substances at DI. The identification of several additional high affinity ligands at DI benzodiazepine receptors may be helpful in elucidating the pharmacological and physiological importance of these sites.

[1]  G. Carcangiu,et al.  An Electrophysiological Analysis , 2004 .

[2]  S. Kulkarni,et al.  Molecular interactions of ethanol with GABAergic system and potential of RO15–4513 as an ethanol antagonist , 1988, Pharmacology Biochemistry and Behavior.

[3]  S. Paul,et al.  Effects of Ro15-4513 and other benzodiazepine receptor inverse agonists on alcohol-induced intoxication in the rat. , 1988, The Journal of pharmacology and experimental therapeutics.

[4]  H. M. Geller,et al.  Electrophysiological studies on benzodiazepine antagonists , 1984, Brain Research.

[5]  Glowa,et al.  A selective imidazobenzodiazepine antagonist of ethanol in the rat. , 1986, Science.

[6]  C. Gardner Pharmacological profiles in vivo of benzodiazepine receptor ligands , 1988 .

[7]  W. Sieghart,et al.  Photoaffinity labeling of benzodiazepine receptors with a partial inverse agonist. , 1984, European journal of pharmacology.

[8]  W. Sieghart,et al.  Photoaffinity Labeling of Benzodiazepine Receptor Proteins with the Partial Inverse Agonist [3H]Ro 15–4513: A Biochemical and Autoradiographic Study , 1987, Journal of neurochemistry.

[9]  P. Skolnick Is Receptor Heterogeneity Relevant to the Anxiolytic Actions of Benzodiazepine Receptor Ligands , 1991 .

[10]  P. Skolnick,et al.  Differences in the Biophysical Properties of the Benzodiazepine/γ‐Aminobutyric Acid Receptor Chloride Channel Complex in the Long‐Sleep and Short‐Sleep Mouse Lines , 1988, Journal of neurochemistry.

[11]  P. Skolnick,et al.  Differential responsiveness of cerebellar Purkinje neurons to GABA and benzodiazepine receptor ligands in an animal model of hepatic encephalopathy , 1988, The Journal of neuroscience : the official journal of the Society for Neuroscience.

[12]  Y. Cheng,et al.  Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. , 1973, Biochemical pharmacology.

[13]  E. Korpi,et al.  Diazepam-insensitive [3H]Ro 15-4513 binding in intact cultured cerebellar granule cells. , 1989, European journal of pharmacology.

[14]  Willy Haefely,et al.  Recent advances in the molecular pharmacology of Benzodiazepine receptors and in the structure-activity relationships of their agonists and antagonists , 1985 .

[15]  K F Koehler,et al.  Synthetic and computer-assisted analyses of the pharmacophore for the benzodiazepine receptor inverse agonist site. , 1990, Journal of medicinal chemistry.

[16]  R. Olsen,et al.  The benzodiazepine/alcohol antagonist Ro 15-4513: binding to a GABAA receptor subtype that is insensitive to diazepam. , 1991, The Journal of pharmacology and experimental therapeutics.

[17]  Hannah Monyer,et al.  Cerebellar GABAA receptor selective for a behavioural alcohol antagonist , 1990, Nature.

[18]  K. Koehler,et al.  Synthetic and computer assisted analysis of the pharmacophore for agonists at benzodiazepine receptors. , 1991, Life sciences.

[19]  W. Haefely,et al.  Novel anxiolytics that act as partial agonists at benzodiazepine receptors. , 1990, Trends in pharmacological sciences.

[20]  H. Lal,et al.  Central nervous system effects of the imidazodiazepine Ro 15‐4513 , 1988 .

[21]  R. Lister,et al.  Antagonism of the intoxicating effects of ethanol by the potent benzodiazepine receptor ligand Ro 19-4603 , 1989, Brain Research.

[22]  J. Tainer,et al.  Enzyme motifs in antibodies , 1990, Nature.

[23]  L. Pieri,et al.  Selective antagonists of benzodiazepines , 1981, Nature.

[24]  P. Seeburg,et al.  Type I and type II GABAA-benzodiazepine receptors produced in transfected cells. , 1989, Science.

[25]  E. Korpi,et al.  Diazepam Sensitivity of the Binding of an Imidazobenzodiazepine, [3H]Ro 15‐4513, in Cerebellar Membranes from Two Rat Lines Developed for High and Low Alcohol Sensitivity , 1990, Journal of neurochemistry.