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Definition of a pharmacophore for partial agonists of serotonin 5-HT₃ receptors

JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES 1999年第2期39卷 362-369页

作者： Daveu, C Bureau, R Baglin, I Prunier, H Lancelot, JC Rault, S Univ Caen Ctr Etud & Rech Medicament Normandie F-14032 Caen France

A definition of a partial agonists serotonin 5-HT3 pharmacophore was carried out by considering a three-dimensional model which correlates the chemical structures of series of piperazinopyrrolothienopyrazines, piperazinopyridopyrrolopyrazines, piperazinopyrroloquinolaxines, piperazinopyridopyrroloquinoxalines, aminoalkyloximinopyrroloindoles, aminoalkyloximinothienopyrrolizines, and aminoalkyloxopyrrolizines with the biological affinities. The model is formed by five features corresponding to two hydrogen bond accepters, one aromatic ring, one hydrophobic group, and one positive ionizable site (quaternary ammonium ions). The nature of the features and the distances between them explain the partial agonist activities of these compounds.

关键词：药物评价临床前静电学模型分子受体血清素/药物作用受体血清素 5-HT3 血清素激动药/化学血清素激动药/药理学软件构效关系

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The effects of the 5-hydroxytryptamine_1A agonist 8-hydroxy-2-(di-n-propylamino) tetralin on spontaneous activity, cocaine-induced hyperactivity and behavioral sensitization:: A microanalysis of locomotor activity

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第2期292卷 610-617页

作者： De la Garza, R Cunningham, KA Univ Texas Med Branch Dept Pharmacol & Toxicol Galveston TX 77555 USA

The influence of the 5-hydroxytryptamine(1A) agonist 8-hydroxy-2-(di-n-propylamino)tetralin (DPAT) on locomotor hyperactivity induced by the acute and chronic administration of cocaine was assessed. Horizontal activity was measured in the periphery and center of an open field test enclosure equipped with photobeams;vertical activity was also recorded. Peripheral hyperactivity induced by an acute administration of cocaine (10 or 20 mg/kg) was significantly enhanced by 0.2 mg/kg DPAT. In contrast, central and vertical activities were reduced in a dose-related manner by DPAT (0.1 and 0.2 mg/kg);DPAT also suppressed central (0.2 mg/kg) and vertical (0.1 and 0.2 mg/ kg) activities when administered alone. Similar observations were made on day 1 of chronic treatment with DPAT (0, 0.1, or 0.2 mg/kg) injected 15 min before an injection of cocaine (0, 10, or 15 mg/kg) administered twice daily for 7 days. By day 7 of repeated DPAT treatment, sensitization of DPAT-evoked peripheral activity developed, which contrasted with tolerance to the central and vertical hypoactivity evoked by DPAT. Sensitization developed to the repeated treatment with 15 mg/ kg cocaine but not 10 mg/kg cocaine. Interestingly, enhancements of all activity measures were observed between days 1 and 7 in rats cotreated with DPAT plus either dose of cocaine. This sensitization to DPAT plus cocaine was expressed on challenge with DPAT and cocaine but not with cocaine alone. The present study implies that the stimulation of 5-hydroxytryptamine(1A) receptors is capable of modulating the hyperactivity evoked by cocaine, possibly via modulation of the mesoaccumbens dopamine circuit thought to mediate the behavioral effects of cocaine.

关键词：行为动物/药物作用可卡因/药理学剂量效应关系药物药物相互作用运动过度/化学诱导行走/药物作用大鼠 Sprague-Dawley 血清素激动药/投药和剂量血清素激动药/药理学时间因素动物男(雄)性大鼠

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Reversal of morphine-induced apnea in the anesthetized rat by drugs that activate 5-hydroxytryptamine_1A receptors

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第2期292卷 704-713页

作者： Sahibzada, N Ferreira, M Wasserman, AM Taveira-Dasilva, AM Gillis, RA Georgetown Univ Med Ctr Dept Pharmacol Washington DC 20007 USA Univ Dist Columbia Dept Psychol Washington DC USA

The purpose of our study was to test the hypothesis that 5-hydroxytryptamine (5-HT)(1A) receptor agonists counteract morphine-induced respiratory depression. Studies were conducted in anesthetized rats, and respiratory activity was monitored with diaphragm electromyography. Morphine was administered i.v. in doses that produce apnea. Once apnea was established, i.v. administration of the 5-HT1A receptor agonist drug 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT) at 10 or 100 mg/kg restored normal breathing in each animal (n = 24). This antagonistic effect of 8-OH-DPAT on morphine-induced respiratory depression was observed in both spontaneously breathing and artificially ventilated animals. Results obtained with 8-OH-DPAT were mimicked by buspirone (50 mg/kg i.v.), another 5-HT1A receptor agonist drug. Pretreatment with 4-(2'-methoxyphenyl)-1-[2'[N-(2'-pyridinyl]-p-iodo-benzamido]ethyl]piperazine, an antagonist of 5-HT1A receptors, prevented 8-OH-DPAT from counteracting morphine-induced apnea. These results indicate that activation of central nervous system 5-HT1A receptors is an effective way of reversing morphine-induced respiratory depression. Most important, this is the third model of disturbed respiratory function in which drugs that stimulate 5-HT1A receptors have been shown to restore breathing to near-normal levels.

关键词： 8-羟-2-(二-n-丙胺)四氢萘/药理学氨基吡啶类/药理学呼吸暂停/化学诱导丁螺环酮/药理学膈/药物作用药物相互作用肌电描记术吗啡/药理学肌收缩/药物作用哌嗪类/药理学大鼠 Sprague-Dawley 受体血清素/分类受体血清素/药物作用血清素激动药/药理学血清素拮抗药/药理学动物男(雄)性大鼠

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NEW APPROACHES TO EVALUATE SYMPATHOADRENAL SYSTEM ACTIVITY IN EXPERIMENTS ON EARTH AND IN-SPACE

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ACTA ASTRONAUTICA 1994年第C期34卷 243-254页

作者： KVETNANSKY, R NOSKOV, VB BLAZICEK, P MACHO, L GRIGORIEV, AI GOLDSTEIN, DS KOPIN, IJ National Institutes of Health NINDS Bethesda Maryland USA

In previous studies the activity of the sympathoadrenal system (SAS) in cosmonauts during space flights was evaluated by measuring plasma catecholamines (CA) levels and urinary CA and their metabolites concentrations. Plasma CA levels are accepted indicators of SAS activity, however, they are determined by the plasma clearances as well as the rates of CA release (spillover-SO) into the bloodstream. Nowadays methods are available which evaluate not only plasma levels of CA but also their release, spillover, uptake, reuptake, degradation and also CA synthesis in vivo measured by plasma levels of dihydroxyphenylalanine (DOPA). Plasma concentrations of DOPA, the CA noradrenaline (NE), adrenaline (ADR), and dopamine (DA), the deaminated catechol metabolites dihydroxyphenylglycol (DHPG) and dihydroxyphenylacetic acid (DOPAC), and the O-methylated metabolites methoxyhydroxyphenylglycol (MHGP) and homovanillic acid (HVA) were measured during immobilization stress (IMO) in conscious rats. Radiotracer methods were used to measure NE SO. IMO markedly increased arterial NE levels but NE SO was less elevated because the NE clearance was slightly reduced in IMO rats. Simultaneous measurements of plasma CA and their metabolites provide another means to obtain information about SAS function. For instance, dissociation between changes of plasma DHPG and NE levels can indicate changes in neuronal reuptake of NE. We found marked parallel increases in plasma NE and DHPG levels during acute IMO;however after repeated IMO, plasma NE levels were increased but DHPG responses were less pronounced suggesting a reduced NE reuptake. DOPA, the CA precursor, circulates in plasma at a concentration higher than NE. During stress, increased sympathoneural outflow stimulates DOPA synthesis and release into the circulation supporting the view that changes in plasma DOPA levels during stress reflect in vivo changes in the rate of CA synthesis. We propose to measure the new plasma indicators of SAS act

关键词： 3 4-二羟苯酰乙酸/血液 3 4-二羟苯酰乙酸/代谢航天医学宇航员儿茶酚胺类/血液儿茶酚胺类/代谢二羟苯丙氨酸/血液二羟苯丙氨酸/代谢多巴胺/血液多巴胺/代谢肾上腺素/血液肾上腺素/代谢高香草酸/血液高香草酸/代谢甲氧基羟基苯乙二醇/类似物和衍生物甲氧基羟基苯乙二醇/血液甲氧基羟基苯乙二醇/代谢去甲肾上腺素/血液去甲肾上腺素/代谢大鼠 Sprague-Dawley 血清素激动药/药理学宇宙飞行应激/血液应激/病因学应激/代谢交感神经系统/代谢交感神经系统/生理学失重 α甲基酪氨酸/药理学动物人类男(雄)性大鼠

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The dynamin-dependent, arrestin-independent internalization of 5-hydroxytryptamine 2A (5-HT_2A) serotonin receptors reveals differential sorting of arrestins and 5-HT_2A receptors during endocytosis

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JOURNAL OF BIOLOGICAL CHEMISTRY 2001年第11期276卷 8269-8277页

作者： Bhatnagar, A Willins, DL Gray, JA Woods, J Benovic, JL Roth, BL Case Western Reserve Univ Sch Med Dept Biochem Cleveland OH 44106 USA Case Western Reserve Univ Sch Med Dept Psychiat Cleveland OH 44106 USA Case Western Reserve Univ Sch Med Dept Neurosci Cleveland OH 44106 USA Thomas Jefferson Univ Sch Med Kimmel Canc Ctr Philadelphia PA 19107 USA

5-Hydroxytryptamine 2A (5-HT2A) receptors, a major site of action of clozapine and other atypical antipsychotic medications, are, paradoxically, internalized in vitro and in vivo by antagonists and agonists, The mechanisms responsible for this paradoxical regulation of 5-HT2A receptors are unknown. In this study, the arrestin and dynamin dependences of agonist- and antagonist-mediated internalization were investigated in live cells using green fluorescent protein (GFP)-tagged 5-HT2A receptors (SR2-GFP). Preliminary experiments indicated that GFP tagging of 5-HT2A receptors had no effect on either the binding affinities of several ligands or agonist efficacy. Likewise, both the native receptor and SR2-GFP were Internalized via endosomes in vitro, Experiments with a dynamin dominant-negative mutant (dynamin K44A) demonstrated that both agonist- and antagonist-induced internalization were dynamin-dependent. By contrast, both the agonist- and antagonist-induced internalization of SR2-GFP were insensitive to three different arrestin (Arr) dominant-negative mutants (Arr-2 V53D, Arr-2-(319-418), and Arr-3-(284-409)), Interestingly, 5-HT2A receptor activation by agonists, but not antagonists, induced greater Arr-3 than Arr-2 translocation to the plasma membrane. Importantly, the agonist-induced internalization of 5-HT2A receptors was accompanied by differential sorting of Arr-2, Arr-3, and 5-HT2A receptors into distinct plasma membrane and intracellular compartments. The agonist-induced redistribution of Arr-2 and Arr-3 into intracellular vesicles and plasma membrane compartments distinct from those involved in 5-HT2A receptor internalization implies novel roles for Arr-2 and Arr-3 independent of 5-HT2A receptor internalization and desensitization.

关键词：抑制蛋白/生理学氯氮平/药理学动力蛋白质类胞吞作用 GTP磷酸水解酶类/生理学受体血清素 5-HT2A 受体血清素/代谢血清素激动药/药理学血清素拮抗药/药理学动物人类大鼠

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Rats selectively bred for responsiveness to 5-Hydroxytryptamine_1A receptor stimulation:: Differences in differential reinforcement of low rate 72-second performance and response to serotonergic drugs

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第1期292卷 104-113页

作者： Cousins, MS Vosmer, G Overstreet, DH Seiden, LS Univ Chicago Dept Pharmacol Chicago IL 60637 USA Univ Chicago Dept Physiol Sci Chicago IL 60637 USA Univ N Carolina Sch Med Ctr Alcohol Studies Chapel Hill NC 27599 USA Univ N Carolina Sch Med Dept Psychiat Chapel Hill NC 27599 USA

High (+/-)-8-hydroxy-dipropylaminotetralin HBr (8-OH-DPAT) sensitive (HDS) rats and low 8-OH-DPAT-sensitive (LDS) rats were selectively bred for differences in sensitivity to the hypothermic effect of the 5-hydroxytryptamine(1A) (5-HT1A) receptor agonist 8-OH-DPAT in 30 to 35-day-old rat pups. These rats were trained on the differential reinforcement of low rate 72-s operant schedule. On this schedule, LDS rats had a higher response rate and a lower reinforcement rate than HDS rats. Drugs with primary action on the 5-HT system, 8-OH-DPAT, ketanserin, and fluoxetine, decreased response rate of HDS and LDS rats but increased the reinforcement rate of only the LDS rats. However, a drug with primary action on the norepinephrine system, desipramine, decreased response rate and increased reinforcement rate of HDS and LDS rats, suggesting that norepinephrine function was similar in the two lines of rats. The finding with desipramine indicates that increases in reinforcers on the differential reinforcement of low rate 72-s task are not simply dependent on baseline response or reinforcement rate. We also observed that 8-OH-DPAT engenders a greater hypothermic response in adult (90-day-old) HDS rats than in adult LDS rats. The 5-HT1A receptor antagonist WAY-100635 antagonized the hypothermic response. Tissue levels of 8-OH-DPAT from several brain regions in LDS and HDS rats did not differ from each other at either 15- or 30-min postinjection. Because the LDS and HDS rats have different responses to 5-HT-acting drugs, these rats may be useful for studying the role of the serotonergic system in depression.

关键词： 8-羟-2-(二-n-丙胺)四氢萘/分析 8-羟-2-(二-n-丙胺)四氢萘/药理学肾上腺素能摄取抑制剂/药理学年龄因素行为动物/药物作用生物源单胺类/分析脑化学/药物作用条件反射操作式地昔帕明/药理学剂量效应关系药物药物相互作用氟西汀/药理学低温/化学诱导酮色林/药理学受体血清素/分类受体血清素/药物作用强化分级表血清素激动药/药理学血清素拮抗药/药理学血清素摄取抑制药/药理学时间因素动物男(雄)性大鼠

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Mechanisms of 5-hydroxytryptamine_2A receptor activation of the mitogen-activated protein kinase pathway in vascular smooth muscle

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 1999年第3期291卷 1179-1187页

作者： Banes, A Florian, JA Watts, SW Michigan State Univ Dept Pharmacol & Toxicol E Lansing MI 48824 USA

5-Hydroxytryptamine (5-HT) activates the extracellular signal-regulated kinase (Erk) mitogen-activated protein kinases (MAPKs) in the vasculature, resulting in contraction. The mechanisms by which this occurs are unclear. G protein-coupled receptors can activate Erk MAPK pathways through a variety of mechanisms, including stimulation of Src, phosphoinositide-3 kinase (PI-3-K), protein kinase C (PKC), or the epidermal growth factor (EGF) receptor tyrosine kinase. We hypothesize that 5-HT uses one or more of these pathways. In isolated strips of rat aorta, the MAPK/Erk kinase inhibitor U0126 (50 mu M), Src inhibitor PP1 (0.5 mu M), PKC inhibitors calphostin C (1 mu M) and chelerythrine (10 mu M), and the PI-3-K inhibitor LY294002 (1-20 mu M) reduced 5-HT- induced contraction. The EGF receptor tyrosine kinase inhibitor AG1478 (0.25-1 mu M) was without effect. Thus, 5-HT activates PKC, Src, and possibly PI-3-K to result in contraction. In rat aortic myocytes, 5-HT (1 mu M) activated Erk MAPK proteins 2- to 3-fold over basal values;activation was reduced by U0126, PP1, and LY294002 and unaffected by calphostin C or chelerythrine, wortmannin, or AG1478. The lack of effect of EGF receptor tyrosine kinase and PI-3-K inhibitors was confirmed in that the EGF receptor immunoprecipitated from 5-HT-exposed cells did not display an increase in autophosphorylation, nor did 5-HT significantly increase activation of Akt/protein kinase B, a downstream substrate for PI-3-K. These data suggest that the rat aortic 5-HT2A receptor uses Src but not PKC, PI-3-K, or the EGF receptor tyrosine kinase in stimulating Erk MAPK activation.

关键词：丝裂原激活蛋白激酶类/拮抗剂和抑制剂丝裂原激活蛋白激酶类/代谢肌平滑血管/药物作用肌平滑血管/酶学磷酰化沉淀素试验蛋白激酶C/拮抗剂和抑制剂蛋白激酶C/代谢蛋白酪氨酸激酶类/拮抗剂和抑制剂蛋白酪氨酸激酶类/代谢大鼠 Sprague-Dawley 受体蛋白质酪氨酸激酶类/拮抗剂和抑制剂受体蛋白质酪氨酸激酶类/代谢受体血清素 5-HT2A 受体血清素/药物作用血清素激动药/药理学信号传导/药物作用大鼠

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5-Hydroxytryptamine_1A receptor activation enhances norepinephrine release from nerves in the rabbit saphenous vein

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 1999年第3期290卷 1195-1201页

作者： Cohen, ML Schenck, KW Henirick-Luecke, SH Eli Lilly & Co Lilly Corp Ctr Lilly Res Labs Indianapolis IN 46285 USA

Although serotonergic receptor agonists are known to modulate release of central serotonin, less is known about the ability of serotonin to alter neurotransmission in peripheral adrenergic nerves. The present study used field stimulation (40V, 0.7 ms duration, 1-16 Hz) to contract the rabbit saphenous vein, an effect that was abolished in the presence of tetrodotoxin and prazosin (10(-6) M), consistent with stimulation of neuronal norepinephrine release. Furthermore, the field-stimulated contraction was not altered by the 5-hydroxytryptamine (5-HT)(1B/1D) receptor antagonist GR127935 (10(-6) M), but was markedly inhibited by the 5-HT(1A) receptor antagonist WAY 100635 (10(-6) M). GR127935 (10(-8) M) inhibited contraction to sumatriptan, documenting that the concentration used was sufficient to block 5-HT(1B/1D-like) vascular receptors in this tissue. Likewise, WAY 100635 (10-6 M) inhibited contraction to the 5-HT(1A) receptor agonists (+/-)-8-hydroxydipropylaminotetralin hydrobromide (8-OH-DPAT) and LY238729, without altering contraction to norepinephrine or sumatriptan. Furthermore, both 8-OH-DPAT and LY228729 enhanced the contractile response to field stimulation (1.0-8.0 Hz) and activated norepinephrine release in the absence of field stimulation. Contractile responses of the rabbit saphenous vein to both 5-HT(1A) receptor agonists were markedly inhibited by prazosin and dextrally shifted by WAY 100635, supporting the idea that the 5-HT(1A) receptor agonists were activating presynaptic 5-HT(1A) receptors to enhance norepinephrine release even in the absence of field stimulation. Thus, in the rabbit saphenous vein, 5-HT(1A) but not 5-HT(1B/1D) receptors enhanced neurotransmitter release from adrenergic nerves. These observations suggested that serotonergic nerves or other cell types in the saphenous vein are activated by field stimulation to release serotonin, which in turn activates presynaptic 5HT(1A) receptors on adrenergic neurons to effect norepinephrine rele

关键词： 8-羟-2-(二-n-丙胺)四氢萘/药理学肾上腺素能纤维/药物作用肾上腺素能纤维/生理学肾上腺素能纤维/分泌肾上腺素能α激动剂/药理学电刺激麦角林类/药理学肌收缩/药物作用肌收缩/生理学去甲肾上腺素/代谢去甲肾上腺素/药理学去甲肾上腺素/分泌恶二唑类/药理学哌嗪类/药理学吡啶类/药理学受体血清素/生理学受体血清素 5-HT1 隐静脉/药物作用隐静脉/神经支配隐静脉/代谢隐静脉/生理学血清素激动药/药理学血清素拮抗药/药理学舒马普坦/药理学突触传递/药物作用突触传递/生理学动物男(雄)性兔

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Use of bioluminescent aequorin for the pharmacological characterization of 5HT receptors

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JOURNAL OF RECEPTOR AND SIGNAL TRANSDUCTION RESEARCH 1999年第6期19卷 927-938页

作者： Schaeffer, MT Cully, D Chou, M Liu, J Van der Ploeg, LHT Fong, TM Merck Res Labs Rahway NJ 07065 USA

A convenient functional assay for 5HT2a and 5HT2c receptors is reported utilizing the bioluminescent aequorin to detect intracellular calcium changes. Using this assay, the pharmacological properties of many 5HT ligands can be determined in a 96-well format. The data indicate that the aequorin detection method is superior to the inositol phosphate assay with regard to speed and scope. This system is also appropriate for kinetic studies of receptor desensitization. We showed that the human 5HT2c receptor desensitizes in a biphasic manner, with a fast desensitization of approximately 90% of the total response occurring within 15 minutes while the remaining 10% response remains for at least 3 hours.

关键词：水母荧光素钙/代谢细胞系配体发光测定法受体血清素/分析受体血清素/代谢血清素/代谢血清素/药理学血清素激动药/代谢血清素激动药/药理学信号传导/药物作用人类

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Intestinal prokinesia by two esters of 4-amino-5-chloro-2-methoxybenzoic acid: Involvement of 5-hydroxytryptamine-4 receptors and dissociation from cardiac effects in vivo

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 1999年第3期288卷 1045-1052页

作者： Crema, F Modini, C Croci, T Langlois, M De Ponti, F Univ Pavia Dept Internal Med & Therapeut Sect Pharmacol & Toxicol I-27100 Pavia PV Italy

In five fasting, conscious dogs, we compared the prokinetic action of two selective 5-hydroxytryptamine-4 (5-HT4) receptor agonists with low affinity for 5-HT3 receptors ML10302 (2-piperidinoethyl 4-amino-5-chloro-2-methoxybenzoate) and SR59768 (2-[(3S)-3-hydroxypiperidino]ethyl 4-amino-5-chloro-2-methoxybenzoate) in the duodenum and jejunum, using cisapride as a reference compound. Heart rate and rate-corrected QT (QT(c)) also were monitored to assess whether or not the cardiac effects of cisapride are shared by other 5-HT4 receptor agonists. Both ML10302 and SR59768 dose-dependently stimulated spike activity in the duodenum with similar potencies (dose range, 3-300 nmol/kg i.v.;ED50 values: 24 and 23 nmol/kg i.v., respectively);mimicking the effect of cisapride (303000 nmol/kg i.v.). The maximal effect was achieved with the dose of 100 nmol/kg i.v. for both compounds. Similar findings were obtained in the jejunum. Atropine and GR125487 (1-[2-[(methylsulfonyl)amino]ethyl]-4-piperidinyl-methyl 5-fluoro-2-methoxy-1 H-indole-3-carboxylate, selective 5-HT4 receptor antagonist), at doses having no effect per se, antagonized intestinal prokinesia by maximal doses of ML10302 and SR59768. Neither ML10302 nor SR59768 had any effect on heart rate or QT(c) at any of the doses tested, whereas cisapride, at the highest dose (3000 nmol/kg), induced tachycardia and lengthened the QT(c) (p < .01). In conclusion, ML10302 and SR59768 share with cisapride a similar prokinetic action in the canine duodenum and jejunum in vivo. This effect is mediated by pathways involving activation of 5-HT4 and muscarinic receptors. Unlike cisapride, which induces tachycardia and prolongs the QT(c) by a mechanism probably unrelated to 5-HT4 receptor activation, ML10302 and SR59768 are devoid of cardiac effects in this model.

关键词：氨基苯甲酸类/药理学阿托品/药理学西沙必利/药理学十二指肠/药物作用十二指肠/生理学心电描记术/药物作用电生理学心率/药物作用空肠/药物作用空肠/生理学肌电复合波移行/药物作用哌啶类/药理学受体血清素/药物作用受体血清素 5-HT4 血清素激动药/药理学血清素拮抗药/药理学动物狗女(雌)性

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