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Neuroprotection against ischemic/hypoxic brain damage: blockers of ionotropic glutamate receptor and voltage sensitive calcium channels.

The growing number of cellular and molecular pathways believed to be involved in mechanisms of ischemic cell death in the brain has spurred a similar growth in the number of potential neuroprotective modalities, the majority of which are pharmacological in nature. Preventing or minimizing the first few steps in the cascade of events leading to ischemic cell death would have a more profound effect on the postischemic outcome than intervention at later steps in that cascade. This logic is, of course, at the heart of the urgency in providing the stroke or cardiac arrest patient with the earliest possible neuroprotective treatment. For the purpose of assessing potential neuroprotective modalities, the use of a well-established cerebral hypoxic/ischemic model system is a prerequisite. In our studies, we have used two major approaches, in vitro and in vivo. We evaluated both agonists and antagonists of ionotropic glutamate receptor channels (IGRC) and their effects in exacerbating and attenuating, respectively, the posthypoxic/ischemic outcome. Other drugs were tested for their ability to block the L-type voltage-sensitive calcium channels (VSCC), which are responsible for calcium influx and overload upon hypoxia/ischemia. These two membrane protein entities, the IGRC and the VSCC, are believed to be involved in the early stages of the cellular cascade that leads to the demise of neurons posthypoxia/ischemia. Some of the drugs were also tested for possible interaction with each other searching for possible synergy. These and other published studies in the field are reviewed here.

Animals↗

An alternative synthesis of the NMDA antagonist CGS 19755 via free radical carbamoylation of ethyl isonicotinate.

The NMDA antagonist CGS 19755 (cis-4-phosphonomethyl-2-piperidinecarboxylic acid) has been prepared by applying Minisci reaction conditions [formamide, hydrogen peroxide, iron(II) sulfate] to ethyl isonicotinate, reduction of the ester with sodium borohydride, alcoholysis of the 2-carboxamide, formation of 4-(diethylphosphonomethyl)-2-pyridinecarboxylate, hydrogenation of the pyridine nucleus, and acid hydrolysis. The overall, unoptimized yield was around 11%. The procedure employs cheap starting materials, is practical and avoids the use of toxic and hazardous cyanotrimethylsilane which is used in the published procedure.

Free Radicals↗

Complex behavioral strategy and reversal learning in the water maze without NMDA receptor-dependent long-term potentiation.

Successful performance of the water maze task requires that rats learn complex behavioral strategies for swimming in a pool of water, searching for and interacting with a hidden platform before its spatial location can be learned. To evaluate whether NMDA receptor-dependent long-term potentiation (NMDA-LTP) is required for learning the required behavioral strategies, rats with NMDA-LTP blocked by systemic pharmacological treatment were trained in the behavioral strategies using simplified and stepwise training methods. Despite the blockade of NMDA-LTP in the dentate gyrus and hippocampal area CA1, rats learned the required behavioral strategies and used them to learn both initial and reversed platform locations. This is the first evaluation of the role of NMDA-LTP specifically in behavioral strategy learning. Although hippocampal NMDA-LTP might contribute to the water maze task, this form of LTP is not essential for learning complex behavioral strategies or multiple hidden platform locations.

Animals↗

Differential effects of N-methyl-D-aspartate receptor blockade on eticlopride-induced immediate early gene expression in the medial and lateral striatum.

The function of striatopallidal neurons is regulated by N-methyl-D-aspartate (NMDA) and dopamine D2 receptors. Previous studies show that immediate early gene induction by D2 receptor blockade is suppressed by NMDA receptor antagonists. Because the pharmacology of NMDA receptors depends on the incorporation of different NR2 subunits and NR2 subunits show regional and cellular differences in their expression in striatum, our study examined whether different NMDA receptor antagonists would have differential effects on eticlopride-induced immediate early gene expression in striatum. Male Sprague-Dawley rats were pretreated with vehicle, CGS 19755, MK-801 or ifenprodil. Rats then received injections of eticlopride and were killed 40 min later. In situ hybridization histochemistry was used to determine the expression of c-fos and zif268 in the striatum. Eticlopride increased immediate early gene expression in striatum, with the increase generally being greater in lateral than in medial striatum. Pretreatment with each of the NMDA receptor antagonists dose-dependently decreased the expression of the immediate early genes. This suppression of eticlopride-induced gene expression was significant only in the medial-central aspect of striatum. Although there was a trend toward suppression of the gene induction in lateral striatum, it did not reach statistical significance and was not typically dose dependent. The data suggest that different types of NMDA receptor antagonists do not exert differential effects on D2 dopamine receptor-mediated function in the striatum. In addition, the data indicate that eticlopride-induced gene expression in the striatum is not uniformly dependent on NMDA receptor activation.

Animals↗

P2 purinoceptor blocker suramin antagonises NMDA receptors and protects against excitatory behaviour caused by NMDA receptor agonist (RS)-(tetrazol-5-yl)-glycine in rats.

It has been reported that suramin, an anthelminthic, trypanocidal agent and an inhibitor of P2 receptors, may antagonise N-methyl-D-aspartate (NMDA) subtype of the excitatory amino acid receptors. Both NMDA receptors and P2X subclass of P2 receptors are ligand-gated Ca2+-selective channels and, since the increased influx of Ca2+ into neurons has been linked to neurotoxicity, simultaneous inhibition of P2X and NMDA receptors in vivo by suramin could represent an effective neuroprotective treatment. We have found that suramin inhibited the binding of [3H]CGP 39653 to NMDA receptor binding sites in vitro and reduced the frequency of NMDA channel openings in patch-clamp studies. Suramin (1 mM) had no effect on [3H]kainate binding in vitro. In vivo, intracerebroventricular (I.C.V.) injections of suramin (70 nmol/brain) antagonised convulsive effects of the NMDA agonist (RS)-(tetrazol-5-yl)-glycine (TZG, LY 285265). Suramin, however, did not prevent neurotoxic lesions in the hippocampus caused by I.C.V. administration of TZG. Increasing the dose of suramin resulted in death from severe respiratory depression.

Animals↗

Effect of up-regulation of NMDA receptors on cerebral O2 consumption and blood flow in rat.

We tested the hypothesis that cerebrocortical blood flow and O2 consumption would be proportional to an up-regulated number of functional N-methyl-D-aspartate (NMDA) receptors. Previous work had shown a relationship between cerebral metabolism and NMDA receptor activity. We increased the specific binding to NMDA receptors in the cerebral cortex, from 2.2 +/- 0.9 to 4.5 +/- 0.8 (density units) in male Long-Evans rats by daily giving two intraperiotoneal injections (30 mg/kg) of CGS-19755, an NMDA receptor inhibitor, for 7 consecutive days (discontinued for 20 h before experiment). Twelve up-regulated (CGS treated) and 12 control rats were used in this study. Under isoflurane anesthesia and after topical stimulation of the right cerebral cortex with 10(-2) M NMDA, the blood flow (14C-iodoantipyrine method) increased from 98 +/- 11 ml/min/100 g in the unstimulated cortex of the control rats to 161 +/- 37 ml/min/100 g in the stimulated cortex. The unstimulated value for blood flow (95 +/- 7 ml/min/100 g) did not change in the upregulated group but it doubled (194 +/- 69 ml/min/100 g) in the stimulated, upregulated cortex. Similarly, O2 consumption (cryomicrospectrophotometrically determined) in normal rats increased 46%, from 9.3 +/- 1 ml/min/100 g to 13.6 +/- 4 after NMDA stimulation. While in the upregulated animals, O2 consumption increased 103% from 7.9 +/- 0.6 to 16 +/- 6.5 after NMDA stimulation. In conclusion, NMDA receptor upregulation does not alter basal cerebrocortical blood flow or O2 consumption but in the NMDA-stimulated cortex, the blood flow and O2 consumption increase is dependent on the number of NMDA receptors present.

Animals↗

Effects of antagonism of NMDA receptors on transient lower esophageal sphincter relaxations in the dog.

Transient lower esophageal sphincter relaxation is the major cause of gastroesophageal reflux. Mechanisms underlying transient lower esophageal sphincter relaxation are poorly understood although gastric mechanosensitive vagal afferent pathways play a central role. Glutamate is a key transmitter of vagal afferents acting partly on NMDA receptors. The aim of this work was to study the effects on transient lower esophageal sphincter relaxation in awake dogs (n=5) of the competitive NMDA receptor antagonist cis-4-phosphonomethyl-2-piperidine carboxylic acid (CGS 19755; 0.3 and 3 mg/kg i.v., the high dose was given at two separate occasions to each dog). Transient lower esophageal sphincter relaxations were evoked by intragastric infusion of a liquid meal followed by air insufflation and were scored during a 45-min period. Neither dose produced any significant effect on the group average number of transient lower esophageal sphincter relaxations. Synchronous contractions of the esophagus were commonly seen during transient lower esophageal sphincter relaxation and CGS 19755 at both doses greatly reduced their occurrence. The findings indicate that NMDA receptor antagonism selectively inhibits the esophageal component of transient lower esophageal sphincter relaxation although the rate of transient lower esophageal sphincter relaxations is not consistently affected.

Animals↗

Neuroprotection by the alpha2-adrenoceptor agonist, dexmedetomidine, in rat focal cerebral ischemia.

The present study was undertaken to explore the possible neuroprotective effect of the selective alpha2-adrenoceptor agonist, dexmedetomidine in a rat model of focal cerebral ischemia. The effect of dexmedetomidine (9 microg kg(-1)) on infarct volume was assessed and compared to that of glutamate receptor antagonists cis-4(phosphonomethyl)-2-piperidine carboxylic acid (CGS-19755) (20 mg kg(-1)) or 2,3-dihydro-6-nitro-7-sulfamoyl-benzo(F)quinoxaline (NBQX) (50 mg kg(-1)). Dexmedetomidine decreased total ischemic volume by 40% in the cortex (P<0.05) compared to NaCl-treated control rats, whereas NBQX reduced the infarct by 73% in the cortex (P<0.001) and by 43% in the striatum (P<0.01). Dexmedetomidine infusion was associated with some minor degree of hyperglycemia and hypotension. Drug-induced kidney changes were only seen in NBQX-treated rats. These results suggest that dexmedetomidine reduced ischemic volume despite causing a minor increase in blood glucose concentrations and hypotension. Its neuroprotective efficacy was better than that produced by CGS-19775, and dexmedetomidine was safer with respect to kidney toxicity when compared to NBQX.

Adrenergic alpha-Agonists↗

Cycloalliin, a cyclic sulfur imino acid, reduces serum triacylglycerol in rats.

Allium species such as onions and garlic are used as foodstuff, condiment, flavoring, and folk medicine. Onions may decrease hyperlipidemia and improve atherosclerosis. However, the ingredients in onion that are responsible for this phenomenon are not known. In the present study, we investigated the effects of cycloalliin, a sulfur-containing imino acid in onions, on lipid metabolism in Sprague-Dawley rats. When supplemented at the 0.1% and 0.3% levels to the atherogenic diet, cycloalliin reduced serum triacylglycerol (TAG) concentration by approximately 40% compared to the control. Serum cholesterol ester level also showed a tendency to decrease in cycloalliin groups. Hepatic lipid levels were comparable among the groups, although TAG and phospholipid contents were slightly higher in both cycloalliin groups. Dietary cycloalliin had no significant effect on hepatic enzyme activities responsible for TAG synthesis (phosphatidate phosphohydrolase, malic enzyme, and glucose-6-phosphate dehydrogenase (G6PDH)). In conclusion, dietary cycloalliin has serum TG-lowering effect without affecting hepatic TAG synthesis and content in rats, suggesting an alteration of lipoprotein assembly and secretion processes in the liver.

Animals↗

Two non-racemic preparations of a piperidine-based NMDA antagonist with analgesic activity.

(2R,3S,1'R)-3-(1-Hydroxy-2-phosphonoethyl)-2-piperidinecarboxyl ic acid 1 has been synthesized by two different methods. The NMDA receptor binding affinities (Ki values) are 74 nM for compound 1, and 64 nM for the corresponding ketone 2. The analgesic effects were evaluated using the mouse hot-plate test and the mouse formalin model. The ED50 values for the racemates of compounds 1 and 2, using the mouse hotplate and intrathecal injection, were 0.53 and 0.51 nmol, respectively.

Analgesics↗

Characterization of the rod photoresponse isolated from the dark-adapted primate ERG.

The a-wave of the human dark-adapted ERG is thought to derive from activity of rod photoreceptors. However, other sources within the retina could potentially perturb this simple equation. We investigated the extent to which the short-latency dark-adapted rod a-wave of the primate ERG is dominated by the rod photoresponse and the applicability of the phototransduction model to fit the rod a-wave. Dark-adapted Ganzfeld ERGs were elicited over a 5-log-unit intensity range using short bright xenon flashes, and the light-adapted cone responses were subtracted to isolate the rod ERG a-wave. Intravitreal 4-phosphono-butyric acid (APB) and cis-2,3-piperidine-dicarboxylic acid (PDA) were applied to isolate the photoreceptor response. The Hood and Birch version of the phototransduction model, Rmax[1 - e(-I x S x (t-t(eff)))2], was fitted to the a-wave data while allowing Rmax and S to vary. Three principle observations were made: (1) At flash intensities > or =0.77 log sc-td-s the leading edge of the normalized rod ERG a-wave tracks the isolated photoreceptor response across the first 20 ms or up to the point of b-wave intrusion. The rod ERG a-wave was essentially identical to the isolated receptor response for all intensities that produce peak responses within 14 ms after the flash. (2) The best fit of sensitivity (S) was not affected by APB and/or PDA, suggesting that the inner retina contributes very little to the dark-adapted a-wave. (3) APB always reduced the maximum dark-adapted a-wave amplitude (by 15-30%), and PDA always increased it (by 7-15%). Using the phototransduction model, both events can be interpreted as a scaling of the photoreceptor dark current. This suggests that activity of postreceptor cells somehow influences the rod dark current, possibly by feedback through horizontal cells (although currently not demonstrated for the rod system), or by altering the ionic concentrations near the photoreceptors, or by neuromodulator effects mediated by dopamine or melatonin.

Aminobutyrates↗

4-(Tetrazolylalkyl)piperidine-2-carboxylic acids. Potent and selective N-methyl-D-aspartic acid receptor antagonists with a short duration of action.

We have prepared a series of cis-4-(tetrazolylakyl)piperidine-2-carboxylic acids as potent and selective N-methyl-D-aspartic acid (NMDA) receptor antagonists. NMDA antagonists may prove to be useful therapeutic agents, for instance, as anticonvulsants, in the treatment of neurodegenerative disorders such as Alzheimer's disease and in the prevention of neuronal damage that occurs during cerebral ischemia. The compounds prepared were evaluated in vitro in both receptor binding assays [( 3H]CGS-19755, [3H]AMPA, and [3H]kainic acid) and in a cortical-wedge preparation (versus NMDA, quisqualic acid, and kainic acid) to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. The most potent compound of this series, 15 (LY233053), selectively displaced [3H]CGS-19755 binding with an IC50 of 107 +/- 7 nM and selectively antagonized responses due to NMDA in a cortical-wedge preparation with an IC50 of 4.2 +/- 0.4 microM. Compound 15 blocked both NMDA-induced convulsions in neonatal rats (minimum effective dose (MED) = 20 mg/kg ip) and NMDA-induced lethality in mice (MED = 5 mg/kg ip). This is the first example of an NMDA receptor antagonist that incorporates a tetrazole moiety as an omega-acid bioisostere. These amino acid antagonists are also unique from their phosphonic acid counterparts in that they have a shorter duration of action in vivo. For the treatment of acute disorders such as stroke, where an NMDA antagonist would be administered parenterally, the shorter duration of action may be beneficial, e.g., allowing for better dosage control. The combination of potent NMDA receptor antagonism and a short duration of action may make these compounds useful therapeutic agents in the treatment of a variety of neurological disorders.

Animals↗

Enantioselective synthesis of N(alpha)-Fmoc protected (2S,3R)-3-phenylpipecolic acid. A constrained phenylalanine analogue suitably protected for solid-phase peptide synthesis.

Reported herein is the first enantioselective preparation of (2S,3R)-3-phenylpipecolic acid as a conformationally constrained phenylalanine analogue bearing N(alpha)-protection suitable for solid-phase peptide synthesis. Stereochemistries at both the 2- and 3-positions are derived inductively from a single chiral center provided by the commercially available Evans chiral auxiliary, (4S)-4-benzyl-1,3-oxazolidin-2-one. By constraining phi and chi(1) torsion angles, this novel amino acid analogue can serve as a useful tool for the induction of defined geometry in phenylalanine-containing peptides.

Carboxylic Acids↗

NMDA receptors in rat cerebellum and forebrain: subtle differences in pharmacology and modulation.

Binding of [3H]glutamate, [3H]glycine, and the glutamate antagonist [3H]CGS-19755 to NMDA-type glutamate receptors was examined in homogenates of rat forebrain and cerebellum. Most glutamate agonists had a higher affinity at the [3H]glutamate binding site of cerebellar NMDA receptors as compared with forebrain, whereas all the glutamate antagonists examined showed the reverse relationship. The [3H]glycine binding site of forebrain and cerebellar NMDA receptors showed a similar pharmacology in both brain regions. In the cerebellum, however, [3H]glycine bound to a second site with a 10-fold lower affinity and with a pharmacology that resembled that of the glycine/strychnine chloride channel. [3H]-Glutamate binding was not affected by glycine agonists or antagonists, nor was [3H]glycine binding affected by glutamate agonists in either forebrain or cerebellum. Both CGS-19755 and 3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid, glutamate antagonists, reduced [3H]-glycine binding in cerebellum, whereas only CGS-19755 was effective in forebrain. Glycine agonists and antagonists modulated [3H]CGS-19755 binding in forebrain and cerebellum to different extents in the two brain regions. From these studies we conclude that the cerebellar NMDA receptor has a different pattern of modulation at glutamate and glycine sites and that glycine may play a more important role in the control of NMDA function in the cerebellum as compared with forebrain.

Animals↗