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Defining proximity relationships in the tertiary structure of the dopamine transporter -: Identification of a conserved glutamic acid as a third coordinate in the endogenous Zn²⁺-binding site

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JOURNAL OF BIOLOGICAL CHEMISTRY 1999年第52期274卷 36928-36934页

作者： Loland, CJ Norregaard, L Gether, U Univ Copenhagen Panum Inst Dept Med Physiol 12522 Div Cellular& Mol Physiol DK-2200 Copenhagen N Denmark

Recently, we have described a distance constraint in the unknown tertiary structure of the human dopamine transporter (hDAT) by identification of two histidines, His(193) in the second extracellular loop and His(375) at the top of transmembrane (TM) 7, that form two coordinates in an endogenous, high affinity Zn2+-binding site. To achieve further insight into the tertiary organization of hDAT, we set out to identify additional residues involved in Zn2+ binding and subsequently to engineer artificial Zn2+-binding sites. Ten aspartic acids and glutamic acids, predicted to be on the extracellular side, were mutated to asparagine and glutamine, respectively. Mutation of Glu(396) (E396Q) at the top of TM 8 increased the IC50 value for Zn2+ inhibition of [H-3]dopamine uptake from 1.1 to 530 mu M and eliminated Zn2+ induced potentiation of [H-3]WIN 35,428 binding. These data suggest that Glu(396) is involved in Zn2+ binding to hDAT, Importantly, Zn2+ sensitivity was preserved following substitution of Glu(396) with histidine, indicating that the effect of mutating Glu(396) is not an indirect effect because of the removal of a negatively charged residue. The common participation of Glu(396), His(193), and His(375) in binding the small Zn2+ ion implies their proximity in the unknown tertiary structure of hDAT, The close association between TM. 7 and 8 was further established by engineering of a Zn2+-binding site between His(375) and a cysteine inserted in position 400 in TM 8, Summarized, our data define an important set of proximity relationships in hDAT that should prove an important template for further exploring the molecular architecture of Na+/Cl--dependent neurotransmitter transporters.

关键词：氨基酸序列结合部位 COS细胞载体蛋白质类/化学可卡因/类似物和衍生物可卡因/代谢多巴胺/代谢多巴胺质膜转运蛋白质类膜糖蛋白类膜转运蛋白质类分子序列数据诱变定点神经组织蛋白质类蛋白质结构三级构效关系锌/代谢动物人类

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CoMFA study of novel phenyl ring-substituted 3α-(diphenylmethoxy)tropane analogues at the dopamine transporter

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JOURNAL OF MEDICINAL CHEMISTRY 1999年第18期42卷 3502-3509页

作者： Newman, AH Izenwasser, S Robarge, MJ Kline, RH NIDA Psychobiol Sect Intramural Res Program NIH Baltimore MD 21224 USA

A series of phenyl ring-substituted analogues of 3 alpha-(diphenylmethoxy)tropane (benztropine) has been prepared as novel probes for the dopamine transporter. Cross-validated comparative molecular field analysis (CoMFA) models of the binding domain on the dopamine transporter were constructed using 37 geometry-optimized structures of these compounds and their corresponding binding affinities (Ki values) for the displacement of [H-3]WIN 35,428 or potency of [H-3]dopamine uptake inhibition (IC50 values) in rat caudate putamen tissue. The most predictive model (q(2) = 0.78) correlated the steric component of CoMFA to the dependent variable of [H-3]WIN 35,428 binding affinities. A novel series of seven phenyl ring-substituted analogues of 3a-(diphenylmethoxy)tropane was prepared, and our best molecular model was used to accurately predict their binding affinities. This study is the first to provide a CoMFA model for this class of dopamine uptake inhibitors. This model represents an advancement in the design of novel dopamine transporter ligands, based on 3a-(diphenylmethoxy)tropane, and further substantiates structure-activity relationships that have previously been proposed for this class of compounds. This CoMFA model can now be used to predict the binding affinities of novel 3a-(diphenylmethoxy)tropane analogues at the dopamine transporter and will be useful in the design of molecular probes within this class of dopamine uptake inhibitors.

关键词：结合部位脑/药物作用脑/代谢载体蛋白质类/化学载体蛋白质类/代谢可卡因/类似物和衍生物可卡因/化学多巴胺/化学多巴胺质膜转运蛋白质类多巴胺摄取抑制剂/化学膜糖蛋白类膜转运蛋白质类模型分子神经组织蛋白质类蛋白质结合大鼠 Sprague-Dawley 托烷类/化学托烷类/药理学动物男(雄)性大鼠

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GAS-LIQUID-CHROMATOGRAPHIC DETERMINATION OF COCAINE AND BENZOYLECGONINE IN URINE

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ANALYTICAL CHEMISTRY 1976年第1期48卷 34-38页

作者： WALLACE, JE HAMILTON, HE KING, DE BASON, DJ SCHWERTNER, HA HARRIS, SC UNIV TEXAS HLTH SCI CTRDEPT PATHOLSAN ANTONIOTX 78284

Cocaine and Its principal metabolite, benzoylecgonine (BE), are determined by gas-liquid chromatography (3% OV-17, FID) following extraction from urine into chloroform-ethanol (80/20, v/v) and methylation of BE to cocaine. The recovery from biologic specimens of 93 and 65 % for cocaine and BE, respectively, and 72% conversion of BE to cocaine provide detection limits of <0.1 and 0.2 μg/ml for cocaine and BE, respectively. Separate simultaneous determinations of cocaine and benzoylecgonine are achieved by analyzing both a methylated (combined cocaine and BE) and nonmethylated (cocaine only) aliquot of the specimen extract. Data on drug levels in urine specimens from post-surgery patients receiving cocaine anesthesia are presented. © 1976, American Chemical Society. All rights reserved.

关键词：色谱法气相可卡因/类似物和衍生物可卡因/尿人类

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Simultaneous GC-MS analysis of meta- and para-hydroxybenzoylecgonine and norbenzoylecgonine:: A secondary method to corroborate cocaine ingestion using nonhydrolytic metabolites

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JOURNAL OF ANALYTICAL TOXICOLOGY 2000年第7期24卷 482-488页

作者： Klette, KL Poch, GK Czarny, R Lau, CO USN Drug Screening Lab San Diego CA 92134 USA Inst Sci & Forens Med Dept Sci Serv Singapore Singapore

Positive benzoylecgonine (BZE) urinalysis results are sometimes challenged in legal and administrative proceedings on the grounds that the presence of BZE is due to the addition of cocaine to the urine sample with subsequent in vitro hydrolysis to BZE. Consequently, counsel for the respondent or defendant may move that an ecgonine methyl ester (EME) analysis be preformed because EME is presumed to be solely an in vivo cocaine metabolite. For these reasons, a sensitive and rapid gas chromatographic–mass spectrometric procedure was developed for the simultaneous analysis of m-hydroxybenzoylecgonine (m-OHBZE), p-hydroxybenzoylecgonine (p-OHBZE), and N-desmethyl benzoyl ecgonine (norBZE), all of which are cocaine metabolites believed to arise exclusively via in vivo metabolism. Analysis of human urine specimens previously reported positive for BZE using GC–MS at the Department of Defense cutoff of 100 ng/mL demonstrated that at least one of the three metabolites was present in 79 of the 82 specimens studied (96.3%). Thus, the simultaneous analysis of m-OHBZE, p-OHBZE, and norBZE could be used to substantiate that the presence of BZE in urine specimens is the result of cocaine ingestion. Additionally, the premise that EME is a “true” in vivo cocaine metabolite was investigated by assessing the stability of cocaine in unpreserved urine samples at several pHs ranging from 5.0 to 9.0.

关键词：可卡因/类似物和衍生物可卡因/分析可卡因/代谢可卡因/尿可卡因相关性障碍/尿气相色谱-质谱法水解作用物质滥用检测/方法人类

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In vitro studies of striatal vesicles containing the vesicular monoamine transporter (VMAT2): Rat versus mouse differences in sequestration of 1-methyl-4-phenylpyridinium

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第2期293卷 329-335页

作者： Staal, RGW Hogan, KA Liang, CL German, DC Sonsalla, PK Univ Med & Dent New Jersey Robert Wood Johnson Med Sch Dept Neurol Piscataway NJ 08854 USA Univ Texas SW Med Ctr Dept Psychiat Dallas TX USA

Significant differences exist in the sensitivity of mice and rats to the neurotoxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) that cannot be explained by differences in exposure to or uptake of 1-methyl-4-phenylpyridinium (MPP+) into dopamine (DA) neurons. MPP+ is also a substrate for the brain vesicular monoamine transporter (VMAT2), and sequestration into synaptic vesicles may be one mechanism of protection against MPP+ toxicity. A greater sequestration of MPP+ into vesicles of DA neurons in rats versus mice could explain the lower vulnerability of DA neurons in the rat to MPP+ toxicity. To test this hypothesis, the kinetics of uptake for [H-3]MPP+ and [H-3]DA as well as [H-3]dihydrotetrabenazine binding to VMAT2 were compared in vesicles isolated from the striata of rats and mice. The K-m value of [H-3]MPP+ transport was similar in the two species. In contrast, the maximal transport rate (V-max) was 2-fold greater in vesicles from rats than in those from mice. Likewise, the K-m value for [H-3]DA transport was similar in both preparations, but the V-max value was 2-fold greater in rat than in mouse vesicles. The B-max value for [H-3]dihydrotetrabenazine binding was also 2-fold greater in striatal vesicles from rats than in those from mice. Electron micrographs demonstrated that vesicles isolated from rats and mice were approximately the same size. Based on these observations, we propose that striatal vesicles from rats have more VMAT2 than vesicles from mice and that this species difference in VMAT2 density may help explain the reduced vulnerability of rat DA neurons to MPP+ neurotoxicity.

关键词： 1-甲基-4-苯基吡啶/代谢可卡因/类似物和衍生物可卡因/代谢多巴胺药/代谢多巴胺摄取抑制剂/代谢指示剂和试剂动力学膜糖蛋白类/代谢膜转运蛋白质类显微镜检查电子新纹状体/药物作用新纹状体/代谢新纹状体/超微结构神经肽类神经毒素类/代谢神经递质药/代谢大鼠 Sprague-Dawley 种特异性突触小泡/药物作用突触小泡/代谢突触小泡/超微结构囊泡生物胺转运蛋白质类囊泡单胺转运蛋白质类动物男(雄)性小鼠大鼠

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Quantitation of cocaine, benzoylecgonine, cocaethylene, methylecgonine, and norcocaine in human hair by positive ion chemical ionization (PICI) gas chromatography-tandem mass spectrometry

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JOURNAL OF ANALYTICAL TOXICOLOGY 2000年第7期24卷 489-495页

作者： Bourland, JA Hayes, EF Kelly, RC Sweeney, SA Hatab, MM Associated pathologists Labs Las Vegas NV 89119 USA

A total of 30 human head-hair samples were analyzed for cocaine (COC), cocaethylene (CE), benzoylecgonine (BE), methylecgonine (EME), and norcocaine (NCOC) using a sensitive positive ion chemical ionization gas chromatography–tandem mass spectrometry (GC–MS–MS) method. All 30 hair samples had been previously submitted to the laboratory and had confirmed positive for cocaine. Hair samples (20 mg each) were cut into small segments (2–5 mm) and incubated overnight at 45°C in 0.1N HCl after the addition of 50 μL of an internal standard mix of COC-d3 (1.0 ng/mg), BE-d3 (0.5 ng/mg), EME-d3 (0.25 ng/mg), and NCOC-3 (0.25 ng/mg). The samples were then extracted with Clean Screen? extraction columns from United Chemical Technologies, Inc. The final extract was evaporated to dryness and derivatized with 50 μL of 1,1,1,3,3,3-hexafluoro-2-propanol and 50 μL of trifluoroacetic anhydride at 90°C for 15 min. The derivatized samples were allowed to cool to room temperature, evaporated to dryness, and then reconstituted in 50 μL of ethyl acetate. Parent set masses (unbolded ions) and product ions were m/z 304 and m/z 182 and 82 (COC), m/z 307 and m/z 185 and 85 (COC-d3), m/z 318 and m/z 196 and 82 (CE), m/z 440 and m/z 318 and 105 (BE), m/z 443 and m/z 321 and 105 (BE-d3), m/z 296 and m/z 182, and 82 (EME), m/z 299 and m/z 185 and 85 (EME-d3), m/z 403 and m/z 386 and 105 (NCOC), m/z 406 and m/z 389 and 105 (NCOC-d3). Quantitation was accomplished by calculating the area ratio of the higher mass product ion (underlined ions) of analyte to the respective internal standard based on multilevel calibrations from 0.01 to 10.0 ng/mg. The GC–MS–MS method had a limit of detection of 0.01 ng/mg and a limit of quantitation of 0.05 ng/mg for all five analytes. COC, BE, and EME were detected in all 30 samples, and CE and NCOC were found in 19 and 29 samples, respectively. The average relative percentages of each metabolite normalized to the cocaine concentrations were 12.8%, 15.4%, 1.8%, and 2.5

关键词：生物转化可卡因/类似物和衍生物可卡因/分析可卡因/代谢可卡因相关性障碍/诊断可卡因相关性障碍/代谢精制可卡因/分析气相色谱-质谱法/方法毛发/化学结果可重复性物质滥用检测/方法人类

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Toward development of an in vitro model of methamphetamine-induced dopamine nerve terminal toxicity

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第2期293卷 625-633页

作者： Kim, S Westphalen, R Callahan, B Hatzidimitriou, G Yuan, J Ricaurte, GA Johns Hopkins Bayview Med Ctr Dept Neurol Baltimore MD USA

To develop an in vitro model of methamphetamine (METH) induced dopamine (DA) neurotoxicity, striatal synaptosomes were incubated at 37 degrees C with METH for different periods of time (10-80 min), washed once, then tested for DA transporter function at 37 degrees C. METH produced time- and dose-dependent reductions in the V-max of DA uptake, without producing any change in K-m. Incubation of synaptosomes with the DA neurotoxins 1-methyl-4-phenyl-pyridinium ion, 6-hydroxydopamine, and amphetamine under similar conditions produced comparable effects. In contrast, incubation with fenfluramine, a serotonin neurotoxin, did not. METH-induced decreases in DA uptake were selective, insofar as striatal glutamate uptake was unaffected. Various DA transporter blockers (cocaine, methylphenidate, and bupropion) afforded complete protection against METH-induced decreases in DA uptake, without producing any effect themselves. METH's effects were also temperature dependent, with greater decreases in DA uptake occurring at higher temperatures. Tests for residual drug revealed small amounts (0.1-0.2 mu M) of remaining METH, but kinetic studies indicated that decreases in DA uptake were not likely to be due to METH acting as a competitive inhibitor of DA uptake. Decreases in the V-max of DA uptake were not accompanied by decreases in B-max of [H-3]WIN 35,428 binding, possibly because there is no mechanism for removing damaged DA nerve endings from the in vitro preparation Collectively, these results give good support to the development of a valid in vitro model that may prove helpful for elucidating the mechanisms underlying METH-induced DA neurotoxicity.

关键词：可卡因/类似物和衍生物可卡因/代谢多巴胺/代谢多巴胺/生理学多巴胺拮抗剂/药理学多巴胺摄取抑制剂/分析多巴胺摄取抑制剂/代谢多巴胺摄取抑制剂/毒性剂量效应关系药物芬氟拉明/药理学谷氨酸/代谢动力学甲基苯丙胺/分析甲基苯丙胺/代谢甲基苯丙胺/毒性新纹状体/细胞学新纹状体/药物作用新纹状体/代谢突触前末梢/药物作用突触前末梢/代谢突触前末梢/生理学蛋白激酶C/拮抗剂和抑制剂蛋白激酶C/代谢大鼠 Sprague-Dawley 血清素摄取抑制药/药理学突触体/药物作用突触体/代谢温度时间因素动物男(雄)性大鼠

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C-fos and egr-1 immediate-early gene induction by cocaine and cocaethylene in rat brain -: A comparative study

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NEUROBIOLOGICAL MECHANISMS OF DRUGS OF ABUSE: COCAINE, IBOGAINE, AND SUBSTITUTED AMPHETAMINES 2000年第1期914卷 46-57页

作者： Thiriet, N Aunis, D Zwiller, J Unite INSERM U338 Ctr Neurochim F-67084 Strasbourg France

The induction of immediate-early genes can now be considered as a tool to study neuronal activation in different brain structures. These genes, which are rapidly and transiently induced in response to diverse extracellular stimulation, coordinate alterations in gene expression underlying neuronal plasticity. Using in situ hybridization, we found that acute i.p. cocaine (20 mg/kg) injection produced a strong expression of egr-1 and c-fos genes in the nucleus accumbens, caudate-putamen, and frontal cortex in the rat. Cocaethylene is an active metabolite of cocaine that is formed when cocaine is consumed together with ethyl alcohol. Injection of cocaethylene at a dose equivalent to cocaine induced the expression of the two immediate-early genes in the same brain structures, but to a lesser extent. A high dose of ethanol increased egr-1 and c-fos expression in the frontal cortex and in the lateral part of the caudate-putamen. Since cocaine is known to potently inhibit both dopamine and serotonin transporters, whereas cocaethylene only inhibits the dopamine transporter, our results strongly suggest that the serotonergic system participates in the mode of action of cocaine in its ability to trigger immediate-early gene transcription.

关键词：放射自显影术/方法脑/解剖学和组织学脑/药物作用中枢神经系统抑制药/药理学可卡因/类似物和衍生物可卡因/药理学多巴胺摄取抑制剂/药理学早期生长反应蛋白质1/遗传学早期生长反应蛋白质1/代谢乙醇/药理学基因表达调控/药物作用原位杂交/方法原癌基因蛋白质c-fos/遗传学原癌基因蛋白质c-fos/代谢大鼠 Wistar 转录激活动物男(雄)性大鼠

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Cocaine, cocaine metabolite, and ethanol concentrations in postmortem blood and vitreous humor

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JOURNAL OF ANALYTICAL TOXICOLOGY 2000年第1期24卷 59-65页

作者： Mackey-Bojack, S Kloss, J Apple, F Hennepin Cty Med Ctr Clin Labs Minneapolis MN 55415 USA

The use of postmortem cocaine and metabolite concentrations is a complex subject. This study was undertaken to determine (1) the usefulness of vitreous humor as a specimen, compared with blood, to quantitate cocaine and cocaine metabolites; (2) whether there is a preferential site of disposition for cocaethylene between vitreous humor and blood; and (3) if the presence of cocaethylene influences the concentration of benzoylecgonine in postmortem specimens. Cocaine, benzoylecgonine, and cocaethylene were quantitated in blood and vitreous humor by gas chromatography-mass spectrometry, and ethanol was quantitated by gas chromatography in 62 medical examiner cases. No differences were found between mean concentrations of vitreous cocaine 0.613 mg/L (standard deviation [SD] 0.994 mg/L), cocaethylene 0.027 mg/L (SD 0.59 mg/L), and ethanol 0.092 g/dL (SD 0.13 g/dL) compared to blood cocaine 0.489 mg/L (SD 1.204 mg/L), cocaethylene 0.022 mg/L (SD 0.055 mg/L), and ethanol 0.058 g/dL (SD 0.91 g/dL), respectively. However, a statistical difference was found between mean benzoylecgonine concentrations in vitreous 0.989 mg/L (SD 1.597 mg/L) and blood 1.941 mg/L (SD 2.912 mg/L) (p = 0.0004). Regression analysis demonstrated that linear relationships were present between concentrations of vitreous and blood cocaine (r = 0.854) and benzoylecgonine (r = 0.763). However, the correlation coefficients were lower for cocaethylene (r = 0.433) and ethanol (r = 0.343). There were variations between the concentrations of cocaine and metabolites both in terms of magnitude and also direction of change. Mean concentrations of benzoylecgonine in blood and vitreous were higher in cases where ethanol was absent, 2.593 mg/L (SD 3.195 mg/L) and 1.431 mg/L (SD 2.021 mg/L), compared to when ethanol was present, 1.199 mg/L (SD 2.396 mg/L) and 0.469 mg/L (SD 0.553 mg/L). This study demonstrates that vitreous humor may be used to quantitate cocaine and cocaine metabolites; however, because the concentra

关键词：尸体解剖色谱法气相可卡因/类似物和衍生物可卡因/分析可卡因/血液乙醇/分析乙醇/血液气相色谱-质谱法回归分析物质滥用检测/方法玻璃体/化学女(雌)性人类男(雄)性

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Comparative behavioral pharmacology of cocaine and the selective dopamine uptake inhibitor RTI-113 in the squirrel monkey

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JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 2000年第2期292卷 521-529页

作者： Howell, LL Czoty, PW Kuhar, MJ Carrol, FI Emory Univ Yerkes Reg Primate Res Ctr Atlanta GA 30322 USA Emory Univ Dept Psychiat & Behav Sci Atlanta GA 30322 USA Emory Univ Dept Pharmacol Atlanta GA 30322 USA Res Triangle Inst Res Triangle Pk NC 27709 USA

The behavioral effects of 3 beta-(4-chlorophenyl)tropane-2 beta-carboxylic acid phenyl ester hydrochloride (RTI-113;0.03-1.0 mg/ kg), a selective dopamine uptake inhibitor, were compared with those of cocaine (0.03-3.0 mg/kg) and 1-{2-[bis(4-fluorophenyl) methoxy]ethyl}-4-(3-phenylpropyl)piperazine dihydrochloride (GBR 12909;0.03-3.0 mg/ kg) in squirrel monkeys. Intermediate doses of each drug produced significant increases in response rate maintained by a fixed-interval (FI) 300-s schedule of stimulus termination, but RTI-113 was less effective than cocaine or GBR 12909. The order of potency for increasing response rate was RTI-113 greater than or equal to cocaine. GBR 12909. In drug time course determinations, RTI-113 and GBR 12909 had longer durations of action than cocaine. RTI-113 substituted completely for cocaine in subjects trained to discriminate cocaine and saline under a two-lever drug-discrimination procedure maintained by food delivery. RTI-113 also reliably maintained self-administration behavior in subjects trained under a second-order FI 900-s schedule of i.v. cocaine delivery. Pretreatment with RTI-113 significantly decreased responding for cocaine at the highest pretreatment dose, but RTI-113 had similar effects on responding maintained by a second-order FI 900-s schedule of stimulus termination. The results indicate that the behavioral pharmacology of RTI-113 is similar to that of cocaine, further implicating a prominent role for dopamine uptake inhibition in the behavioral effects of cocaine. Its longer duration of action in conjunction with less pronounced behavioral-stimulant effects are desirable properties for a substitute pharmacotherapy for cocaine abuse. RTI-113 effectively decreased cocaine self-administration behavior, although its direct rate-altering effects may have contributed to the interactions obtained.

关键词：行为动物/药物作用可卡因/类似物和衍生物可卡因/药理学多巴胺摄取抑制剂/药理学剂量效应关系药物药物相互作用哌嗪类/药理学松鼠猴属自我遵嘱服药/心理学统计数据时间因素动物男(雄)性

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