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Synthesis and pharmacology of the baclofen homologues 5-amino-4-(4-chlorophenyl)pentanoic acid and the R- and S-enantiomers of 5-amino-3-(4-chlorophenyl)pentanoic acid

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JOURNAL OF MEDICINAL CHEMISTRY 1999年第11期42卷 2053-2059页

作者： Karla, R Ebert, B Thorkildsen, C Herdeis, C Johansen, TN Nielsen, B Krogsgaard-Larsen, P Royal Danish Sch Pharm NeuroSci PharmaBiotec Res Ctr Dept Pharmacol DK-2100 Copenhagen Denmark Royal Danish Sch Pharm Dept Med Chem DK-2100 Copenhagen Denmark Univ Wurzburg Inst Pharm & Lebensmittelchem Wurzburg Germany

(RS)-5-Amino-4-(4-chlorophenyl)pentanoic acid (10) and the R-form (11) and S-form (12) of (RS)-5-amino-3-(4-chlorophenyl)pentanoic acid, which are homologues of the 4-aminobutanoic acid(B) (gaba(B)) receptor agonist (RS)-4-amino-3-(4-chlorophenyl)butanoic acid (baclofen), were synthesized. Compound 10 was synthesized by homologation at the carboxyl end of baclofen using a seven-step reaction sequence. N-Boc-protected (4R,5R)-4-(4-chlorophenyl)-5-hydroxy-2-piperidone (18) was deoxygenated via a modified Barton-McCombie reaction to give N-Boc-protected (R)-4-(4-chlorophenyl)-2-piperidone (20), which was ring opened and deprotected to give ***. The corresponding S-enantiomer, ***, was synthesized analogously from the 4S,5S-enantiomer of 18, compound 21. The enantiomeric purities of *** (ee = 99.8%) and *** (ee = 99.3%) were determined by chiral HPLC. Compound 10 did not show detectable affinity for gaba(A) or gaba(B) receptor sites and was inactive as an agonist or an antagonist at gaba(B) receptors in the guinea pig ileum. Like the enantiomers of baclofen, neither 11 nor 12 showed detectable affinity for gaba(A) receptor sites, and in agreement with the findings far (S)-baclofen, 12 did not interact significantly with gaba(B) receptor sites. Compound 11 (IC50 = 7.4 +/- 0.6 mu M), a homologue of (R)-baclofen (2), was shown to be some 50 times weaker than 2 (IC50 = 0.14 +/- 0.01 mu M) as an inhibitor of gaba(B) binding. Accordingly, 11 (EC50 = 150 +/- 23 mu M) was shown to be weaker than 2 (EC50 = 11 +/- 1 mu M) as an inhibitor of electrically induced contractions of the guinea pig ileum. However, whereas this effect of 2 was sensitive to the gaba(B) antagonist, CGP35348 (4), the inhibition by 11 was not significantly affected. Furthermore, 12 (EC50 = 310 +/- 16 mu M) was shown to be one-half as potent as 11 in this test system, and this effect of 12 also was insensitive to 4. The dissimilarities of the pharmacological effects of 2 and compounds 11 and 12 we

关键词：巴氯芬/化学结合竞争性脑/代谢脑/超微结构 gaba类药/化学合成 gaba类药/化学 gaba类药/代谢 gaba类药/药理学回肠/药物作用回肠/生理学肌收缩/药物作用肌平滑/药物作用肌平滑/生理学戊酸类/化学合成戊酸类/化学戊酸类/代谢戊酸类/药理学放射配体测定大鼠 Sprague-Dawley 受体 gaba-a/药物作用受体 gaba-A/代谢受体 gaba-B/药物作用受体 gaba-B/代谢立体异构现象构效关系突触膜/代谢动物豚鼠男(雄)性大鼠

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Effects of chronic ethanol treatment on γ-aminobutyric acid_A and glycine receptors in mouse glycinergic spinal neurons

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第1期295卷 423-429页

作者： Van Zundert, B Albarran, FA Aguayo, LG Univ Concepcion Dept Physiol Neurophysiol Lab Concepcion Chile

Five-day-old cultures of mouse glycinergic spinal interneurons were chronically treated with 100 mM ethanol and the glycine and gamma-aminobutyric acid (gaba)(A) receptors were assayed using whole-cell recordings and fluorescence-imaging techniques. Control neurons displayed a glycine(50) of 19 +/- 0.6 mu M and a Hill coefficient of 3.1 +/- 0.3. Chronic ethanol treatment did not significantly change these parameters. The maximal responses were 310 +/- 80 pA/pF in control and 440 +/- 19 pA/pF in treated cells, and the fluorescence intensity associated to a monoclonal glycine receptor antibody was unchanged. Strychnine inhibited the glycine current with smaller potency (29%) in treated neurons, thus the IC(50) increased from 14 +/- 2 nM in control to 18 +/- 6 nM in treated neurons. Zn(2+) (10 mu M) potentiated the glycine current by 43 +/- 33% in control, but only by 18 +/- 13% in treated neurons. Interestingly, no change on the inhibition produced by a high concentration of Zn(2+) was found in treated neurons. The inhibitory effect of picrotoxin on the glycine receptor, associated to a homomeric receptor, was eliminated with chronic ethanol, suggesting a faster switch to beta-subunit-containing receptors. Unlike glycine receptors, the sensitivity of gaba(A) receptors to gaba, pentobarbital, diazepam, and Zn(2+), as well as the fluorescence intensity associated to a high-affinity benzodiazepine analog was unchanged by chronic ethanol. In conclusion, we found that glycine receptors in spinal interneurons were altered by chronic ethanol treatment and this may reflect the expression of different subunits in control and treated neurons. gaba(A) receptors were resistant to the treatment.

关键词：细胞培养的乙醇/毒性中间神经元/药物作用小鼠近交C57BL 印防己毒素/药理学受体 gaba-a/药物作用受体甘氨酸/药物作用脊髓/药物作用士的宁/药理学锌/药理学动物小鼠

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IMMUNOENHANCING EFFECTS OF ALPRAZOLAM, A BENZODIAZEPINE RECEPTOR AGONIST

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ANNALS OF THE NEW YORK ACADEMY OF SCIENCES 1992年第1期650卷 132-139页

作者： FRIDE, E MENG, R SKOLNICK, P ARORA, PK NIDDK NEUROSCI LAB ROOM 111 BLDG 8 BETHESDA MD 20892 USA

The effects of alprazolam (ALP), a triazolobenzodiazepine with high affinity for 'central' benzodiazepine receptors, were examined on several parameters of immune function in mice. NK, MLR, and mitogen-induced lymphocyte proliferation were all significantly increased 2 hr after administration of low doses (0.02-1.0 mg/kg) of ALP. Twenty four hr later, similar but less robust immunoenhancing effects were observed. These measures of immune functions were not affected by higher doses of ALP (5-10 mg/kg). The immunoenhancing effects of ALP did not appear related to serum corticosterone levels. These and other findings demonstrate that the gaba/benzodiazepine receptor chloride channel complex can bidirectionally modulate immune function.

关键词：阿普唑仑/投药和剂量细胞毒性免疫/药物作用剂量效应关系药物免疫/药物作用免疫细胞/药物作用杀伤细胞天然/免疫学淋巴细胞活化/药物作用受体 gaba-a/药物作用时间因素动物男(雄)性小鼠

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The in vitro ethanol sensitivity of hippocampal synaptic γ-aminobutyric acid_A responses differs in lines of mice and rats genetically selected for behavioral sensitivity or insensitivity to ethanol

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第2期295卷 741-746页

作者： Poelchen, W Proctor, WR Dunwiddie, TV Univ Colorado Hlth Sci Ctr Dept Pharmacol C236 Denver CO 80262 USA Dept Vet Affairs Med Ctr Denver CO USA

Previous work has demonstrated that in the hippocampal CA1 region of Sprague-Dawley rats, there are ethanol-sensitive and ethanol-insensitive populations of gabaergic synapses on pyramidal neurons. The present experiments characterized the ethanol sensitivity of these pathways in lines of rats and mice genetically selected for sensitivity or insensitivity to the behavioral effects of ethanol. In ethanol-sensitive inbred long sleep mice, gaba(A) IPSCs induced by stimulation of proximal (probably somatic) synapses were enhanced by 80 mM ethanol, whereas the distal (i.e., dendritic) pathway was unaffected. Thus, the relative sensitivity of these pathways (proximal. distal) is the same in both Sprague-Dawley rats and in inbred long sleep mice. However, in the ethanol-insensitive inbred short sleep mice, neither proximal nor distal IPSCs were affected by 80 mM ethanol. The ethanol sensitivity of the proximal pathway was also examined in replicate lines of rats selected for either high ethanol sensitivity or low ethanol sensitivity. gaba(A) IPSCs in the high ethanol sensitivity lines were significantly enhanced by 80 mM ethanol, whereas IPSCs in the low ethanol sensitivity lines were unaffected. Thus, IPSCs evoked via the proximal pathway were enhanced by ethanol in all the sensitive mouse and rat lines, and unaffected in all the insensitive lines. These experiments demonstrate that gaba(A) synapses in brain differ in their sensitivity to enhancement by ethanol, and the sensitivity to such enhancement is under the control of genes that can be selected for using classical genetic selective breeding based on a behavioral phenotype.

关键词：行为动物/药物作用行为动物/生理学中枢神经系统抑制药/药理学乙醇/药理学海马/药物作用海马/生理学小鼠近交系神经抑制/药物作用大鼠近交系受体 gaba-a/药物作用受体 gaba-A/生理学突触/药物作用突触/生理学突触传递/药物作用突触传递/生理学 γ氨基丁酸/生理学动物小鼠大鼠

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Effects of γ-aminobutyric acid_A receptor manipulation on migrating gonadotropin-releasing hormone neurons through the entire migratory route in vivo and in vitro

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ENDOCRINOLOGY 2000年第3期141卷 1254-1262页

作者： Bless, EP Westaway, WA Schwarting, GA Tobet, SA Eunice Kennedy Shriver Ctr Mental Retardat Inc Div Biomed Sci Waltham MA 02452 USA

GnRH neurons originate in the nasal compartment and migrate along vomeronasal fibers over the cribiform plate to the forebrain. Previously, we found gamma-aminobutyric acid (gaba) present in GnRH neurons during development. To clarify the influence of gaba across the entire GnRH migration route, we examined the effects of muscimol and bicuculline (gaba(A) agonist and antagonist) in vivo and in vitro, maintaining the integrity of the nasal-forebrain connection. For in vivo experiments, mice were administered muscimol, bicuculline, or vehicle on days 10-15 of pregnancy and were killed on embryonic day 15 (E15). For in vitro experiments, 250-mu m parasagittal slices of whole heads of E13 mice were incubated with muscimol, bicuculline, or vehicle for 2 days. Muscimol inhibited GnRH cell migration and decreased extension of GnRH fibers. Bicuculline treatment led to a disorganized distribution of GnRH cells in the forebrain and a concomitant dissociation of GnRH cells from fibers of guidance. These results suggest that gaba's influence on GnRH development changes as the cells move out of the nasal compartment and extend processes toward the median eminence.

关键词：荷包牡丹碱/药理学细胞计数细胞运动/药物作用 gaba激动剂/药理学 gaba拮抗剂/药理学促性腺素释放激素/生理学免疫组织化学小鼠近交C57BL 显微镜检查共焦蝇蕈醇/药理学神经纤维/代谢神经元/生理学垂体/细胞学垂体/药物作用垂体/代谢前脑/细胞学前脑/药物作用前脑/代谢受体 gaba-A/激动剂受体 gaba-A/拮抗剂和抑制剂受体 gaba-a/药物作用动物女(雌)性小鼠妊娠

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Calcineurin-mediated LTD of gabaergic inhibition underlies the increased excitability of CA1 neurons associated with LTP

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NEURON 2000年第1期26卷 197-205页

作者： Lu, YM Mansuy, IM Kandel, ER Roder, J Columbia Univ Coll Phys & Surg Ctr Neurobiol & Behav Howard Hughes Med Inst New York NY 10032 USA Univ Toronto Mt Sinai Hosp Samuel Lunenfeld Res Inst Dept Mol & Med Genet Toronto ON M5S 1A8 Canada

Coincident pre- and postsynaptic activity generates long-term potentiation (LTP), a possible cellular model of learning and memory. LTP has two components: (1) an increase in the excitatory postsynaptic potential (EPSP), and (2) an increase in the ability of the EPSP to generate a spike (ES coupling of LTP). We have used pharmacological and genetic approaches to address the molecular nature of E-S coupling in CA1 pyramidal neurons. Blockade of the Ca2+-sensitive phosphatase, calcineurin, prevents induction of ES coupling without interfering with LTP of the EPSP. Calcineurin produces its effect on E-S coupling by inducing a long-lasting depression (LTD) of the gaba,mediated inhibitory postsynaptic potentials (IPSPs). This LTD of the IPSP was prevented by blockade of NMDA receptors. Thus, the tetanus that elicits NMDA-dependent LTP mediates a coordinately regulated double function. It produces LTP of the EPSP and, concomitantly, LTD of the IPSP that leads to enhancement of E-S coupling.

关键词：荷包牡丹碱/药理学钙神经素/药物作用钙神经素/生理学酶抑制剂/药理学兴奋性突触后电位/药物作用兴奋性突触后电位/生理学 gaba拮抗剂/药理学免疫抑制剂/药理学长时程增强/药物作用长时程增强/生理学小鼠转基因黑软海绵素A/药理学锥体细胞/药物作用锥体细胞/生理学大鼠 Sprague-Dawley 受体 gaba-a/药物作用受体 gaba-A/生理学受体 N-甲基-D-天冬氨酸/药物作用受体 N-甲基-D-天冬氨酸/生理学他罗利姆/药理学动物小鼠大鼠

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Treatment of epilepsy in the elderly

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PROGRESS IN NEUROBIOLOGY 1999年第5期58卷 389-407页

作者： Gareri, P Gravina, T Ferreri, G De Sarro, G Univ Catanzaro Dept Clin & Expt Med Policlin Materdomini I-88100 Catanzaro Italy

Management of epilepsy in the elderly involves many challenges, including the presence of concomitant diseases, polypharmacy and changes in body physiology. Age-related changes in pharmacokinetics and pharmacodynamics have to be tal;en into account in order to avoid potentially severe adverse drug reactions in elderly people. The present study reviews the most commonly used antiepileptic drugs (AEDs) in the elderly. Because some AEDs may induce the metabolism of other agents and reduce the effectiveness of several drugs, the physicians have tct carefully evaluate concomitant drugs being administered. Moreover, the main problems appear to be: when beginning therapy, the first choice drug, the appropriate dosage and pharmacologic compliance. Elderly patients must be screened for hepatic and renal functions before beginning a treatment with an AED, carefully interviewed To reduce complaints for drug side-effects which may negatively influence compliance and monitored for total and free blood levels. Besides the 'classic' AEDs, such as phenytoin. phenobarbital, carbamazepine, valproic acid. primidone and benzodiazepines, the review shows the possible advantages of new AEDs, such as felbamate, gabapentin, lamotrigine, oxcarbazepine and gamma-vinyl-gaba, which may be used in the elderly too for their good tolerability. A careful control of drug assumption is requested in the elderly, especially when it is difficult to achieve seizure control. (C) 1999 Elsevier Science Ltd. All rights reserved.

关键词：衰老/生理学抗惊厥药/血液抗惊厥药/药代动力学抗惊厥药/治疗应用药物相互作用癫痫/药物疗法癫痫/病因学癫痫/代谢癫痫/病理生理学受体 gaba-a/药物作用受体谷氨酸/药物作用成年人老年人老年人 80以上女(雌)性人类男(雄)性中年人

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Incorporation of the π subunit into functional γ-aminobutyric acid_A receptors

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MOLECULAR PHARMACOLOGY 1999年第3期56卷 598-610页

作者： Neelands, TR Macdonald, RL Univ Michigan Sch Med Neurosci Program Ann Arbor MI 48104 USA Univ Michigan Dept Neurol Ann Arbor MI USA Univ Michigan Dept Physiol Ann Arbor MI 48109 USA

mRNA encoding the recently cloned gamma-aminobuytyric acid, receptor (gabaR) pi subunit is expressed in the hippocampus and in several non-neuronal tissues including the uterus and ovaries. Whereas native gabaRs are pentamers composed primarily of alpha beta gamma, alpha beta delta, or alpha beta epsilon subunits, it has not been demonstrated clearly that the pi subunit incorporates into functional gabaRs to form cup rr receptors and, if so, with what properties. We provide electrophysiological evidence that the rr subunit can coassemble with either alpha 5 beta 3 or alpha 5 beta 3 gamma 3 subunits to produce recombinant gabaRs with distinct pharmacological and biophysical properties. Compared with alpha 5 beta 3 receptors, gabaRs produced by coexpression of alpha 5 beta 3 pi subunits had a lower gaba EC50 value, were enhanced to a lesser extent by loreclezole, had different IC50 values for pregnenolone sulfate and lanthanum, and were insensitive to benzodiazepines. Incorporation of both pi and gamma 3 subunits into an alpha 5 beta 3 gamma 3 pi isoform was suggested by reduced enhancement by diazepam and a high zinc IC50 value. Current-voltage relations for the alpha 5 beta 3 pi subunit combination outwardly rectified more than currents from alpha 5 beta 3 gamma 3 but less than alpha 5 beta 3 combination gabaRs. Single-channel alpha 5 beta 3 gabaR currents had a main conductance state of 15.2 picoSeimens (pS). Coexpression of the pi subunit with alpha 5 beta 3 subtypes increased the conductance level to 23.8 pS, similar to the conductance level of alpha 5 beta 3 gamma 3 gabaRs (26.9 pS). We conclude that the rr subunit coassembles with alpha, beta, and gamma subunits to form functional alpha beta pi or alpha beta gamma pi gabaRs and, thus, could have a significant impact on the function of native gabaRs expressed in the brain or non-neuronal tissue.

关键词：巴比妥酸盐类/药理学苯二氮|艹卓|类/药理学细胞培养的剂量效应关系药物电生理学镧/药理学受体 gaba-A/化学受体 gaba-a/药物作用受体 gaba-A/遗传学受体 gaba-A/代谢重组融合蛋白质类/遗传学重组融合蛋白质类/代谢甾类/药理学三唑类/药理学锌/药理学 γ氨基丁酸/代谢动物小鼠大鼠

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Chlormethiazole: Effectiveness against toxic effects of cocaine in mice

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第1期295卷 153-161页

作者： Gasior, M Ungard, JT Witkin, JM NIDA Drug Dev Grp Behav Neurosci Branch Addict Res CtrNIH Baltimore MD 21224 USA Med Univ Sch Dept Pharmacol Lublin Poland

Chlormethiazole positively modulates the gamma-aminobutyric acid (gaba)(A) receptor complex and is primarily used to treat certain life-threatening neurological events (e.g., refractory seizures and ethanol withdrawal syndrome). On account of several experimental and clinical studies reporting effectiveness against the toxic effects of heroin and methamphetamine, chlormethiazole was systematically tested in the present study for its effectiveness against cocaine-induced seizures and lethality in mice. The protective effects of chlormethiazole were evaluated against single, submaximal convulsive (75 mg/kg) or lethal (110 mg/kg) doses of cocaine. Chlormethiazole also was tested against the expression (anticonvulsant effect) and development (antiepileptogenic effect) of cocaine- kindled seizures, and against fully developed kindled seizures. Cocaine-kindled seizures were produced by a total of five daily treatments with 60 mg/kg cocaine. The inverted-screen test was used to assess behavioral side effects of chlormethiazole. Chlormethiazole protected against acute cocaine- induced convulsions (ED50 = 7.0 mg/kg) and lethality (ED50 = 21.8 mg/kg) with a robust separation [protective index (PI) = TD50/ED50 = 22.3 and 7.2, respectively] from doses producing behavioral side effects (TD50 = 156 mg/kg). Chlormethiazole suppressed the behavioral expression of cocaine-kindled seizures and prevented the development of sensitization to the convulsant effects of cocaine. It was also effective in suppressing fully developed kindled seizures. Relative to cocaine seizures in naive mice, chlormethiazole was equieffective, less potent (ED50 = 22.3 mg/kg), and had a reduced protective index (PI = 3.7) against cocaine-induced seizures in kindled mice. The protective profile and protective index of chlormethiazole were superior to those of the benzodiazepines clonazepam and diazepam, which were of limited efficacy and had low protective indices (PI = similar to 1). The results of this stud

关键词：抗惊厥药/药理学氯美噻唑/药理学氯硝西泮/药理学可卡因/毒性可卡因相关性障碍/药物疗法剂量效应关系药物 gaba调节剂/药理学点燃效应神经病学/药物作用运动活动/药物作用受体 gaba-a/药物作用动物男(雄)性小鼠

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Modulation of neuronal and recombinant gaba_A receptors by redox reagents

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JOURNAL OF PHYSIOLOGY-LONDON 1999年第1期517卷 35-50页

作者： Amato, A Connolly, CN Moss, SJ Smart, TG Univ London Sch Pharm Dept Pharmacol London WC1N 1AX England UCL MRC Inst Mol Cell Biol London WC1E 6BT England UCL Dept Pharmacol London WC1E 6BT England

1. The functional role played by the postulated disulphide bridge in gamma-aminobutyric acid type A (gaba(A)) receptors and its susceptibility to oxidation and reduction were studied using recombinant (murine receptor subunits expressed in human embryonic kidney cells) and rat neuronal gaba(A) receptors in conjunction with whole-cell and single channel patch-clamp techniques. 2. The reducing agent dithiothreitol (DTT) reversibly potentiated gaba-activated responses (I(gaba)) of alpha 1 beta 1 or alpha 1 beta 2 receptors while the oxidizing reagent 5,5'-dithio-bis-(2-nitrobenzoic acid) (DTNB) caused inhibition. Redox modulation of I(gaba) was independent of gaba concentration, membrane potential and the receptor agonist and did not affect the gaba EC(50) or Hill coefficient. The endogenous antioxidant reduced glutathione (GSH) also potentiated I(gaba) in alpha 1 beta 2 receptors, while both the oxidized form of DTT and glutathione (GSSG) caused small inhibitory effects. 3. Recombinant receptors composed of alpha 1 beta 1 gamma 2S or alpha 1 beta 2 gamma 2S were considerably less sensitive to DTT and DTNB. 4. For neuronal gaba(A) receptors, I(gaba) was enhanced flurazepam and relatively unaffected by redox reagents. However, in cultured sympathetic neurones, nicotinic acetylcholine-activated responses were inhibited by DTT whilst in cerebellar granule neurones, NMDA-activated currents were potentiated by DTT and inhibited by: DTNB. 5. Single gaba-activated ion channel currents exhibited a conductance of 16 pS for alpha 1 beta 1 constructs. DTT did not affect the conductance or individual open time constants determined from dwell time histograms, but increased the mean open time by affecting the channel open probability without increasing the number of cell surface receptors. 6. A kinetic model of the effects of DTT and DTNB suggested that the receptor existed in equilibrium between oxidized and reduced forms. DTT increased the rate of entry into reduced receptor forms

关键词：细胞系细胞培养的二硫硝基苯甲酸/药理学二硫苏糖醇/药理学动力学膜电位模型生物学神经元/药物作用神经元/代谢氧化还原膜片钳术蛋白质构象受体 gaba-a/药物作用受体 gaba-A/遗传学受体 gaba-A/代谢受体 N-甲基-D-天冬氨酸/药物作用受体 N-甲基-D-天冬氨酸/代谢受体烟碱/药物作用受体烟碱/代谢重组蛋白质类/化学重组蛋白质类/遗传学重组蛋白质类/代谢巯基试剂/药理学动物人类小鼠大鼠

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