Open channel block of NMDA receptors by conformationally restricted analogs of milnacipran and their protective effect against NMDA-induced neurotoxicity

Synapse

Volumn 31, Issue 2, 1999, Pages 87-96

  Noguchi, Tomohiro ^a   Ishii, Kyoko ^a   Ohtubo, Yoshitaka ^a   Shuto, Satoshi ^b   Ono, Shizuka ^b   Matsuda, Akira ^b   Yoshii, Kiyonori ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Excitotoxicity; Hippocampus; Kinetics; Rate constants; Voltage clamp; Xenopus

Indexed keywords

MILNACIPRAN; N METHYL DEXTRO ASPARTIC ACID;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; DRUG CONFORMATION; DRUG EFFECT; HIPPOCAMPUS; NERVE CELL MEMBRANE POTENTIAL; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; VOLTAGE CLAMP; XENOPUS;

EID: 0032925130     PISSN: 08874476     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2396(199902)31:2<87::AID-SYN1>3.0.CO;2-H     Document Type: Article

References (35)

1. Adams PR. 1976. Drug blockade of open end-plate channels. J Physiol (Lond) 260:531-552.
2. Armstrong CM. 1971. Interaction of tetraethylammonium ion derivatives with the potassium channels of giant axons. J Gen Physiol 58:413-437.
3. Barone P, Moret C, Briley M, Fillion G. 1994. Autoradiographic characterization of binding sites for [3 H]milnacipran, a new antidepressant drug, and their relationship to the serotonin transporter in rat brain. Brain Res 668:129-143.
4. Bear MF. 1996. A synaptic basis for memory storage in the cerebral cortex. Proc Natl Acad Sci USA 93:13453-13459.
5. Bonnaud B, Cousse H, Mouzin G, Briley M, Stenger A, Fauran F, JP C. 1987. 1-Aryl-2-(aminomethyl) cyclopropane-carboxylic acid derivatives. A new series of potential antidepressants. J Med Chem 38:2964-2968.
6. Bresink I, Danysz W, Parsons CG, Mutschler E. 1995. Different binding affinities of NMDA receptor channel blockers in various brain regions - indication of NMDA receptor heterogeneity. Neuropharmacology 34:533-540.
7. Brewer GJ, Cotman CW. 1989. Survival and growth of hippocampal neurons in defined medium at low density: Advantages of a sandwich culture technique or low oxygen. Brain Res 494:65-74.
8. Choi DW. 1988. Glutamate neurotoxicity and diseases of the nervous system. Neuron 1:623-634.
9. Dumont JN. 1972. Oogenesis in Xenopus laevis (Daudin). 1. Stages of aocytes development in laboratory maintained animals. J Morphol 136:153-180.
10. Erdo SL, Schafer M. 1991. Memantine is highly potent in protecting cortical cultures against excitotoxic cell death evoked by glutamate and N-methyl-D-aspartate. Eur J Pharmacol 198:215-217.
11. Ford LM, Sanberg PR, Norman AB, Fogelson MH. 1989. MK-801 prevents hippocampal neurodegeneration in neonatal hypoxicischemic rats. Arch Neurol 46:1090-1096.
12. Foster AC, Wong EH. 1987. The novel anticonvulsant MK-801 binds to the activated state of the N-methyl-D-aspartate receptor in rat brain. Br J Pharmacol 91:403-409.
13. Foster AC, Gill R, Woodruff GN. 1988. Neuroprotective effects of MK-801 in vivo: Selectivity and evidence for delayed degeneration mediated by NMDA receptor activation. J Neurosci 8:4745-4754.
14. Furue H, Fudamato N, Ohtubo Y, Yoshii K. 1997. Phenytoin protected mouse cortical cell cultures against neurotoxicity induced by kainate but not by NMDA. Amino Acids 12:179-184.
15. Hamill OP, Marty A, Neher E, Sakmann B, Sigworth FJ. 1981. Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches. Pflugers Arch 391:85-100.
16. Hirsch SR, Das I, Garey LJ, de Belleroche J. 1997. A pivotal role for glutamate in the pathogenesis of schizophrenia, and its cognitive dysfunction. Pharmacol Biochem Behav 56:797-802.
17. Huettner JE, Bean BP. 1988. Block of N-methyl-D-aspartate-activated current by the anticonvulsant MK-801: Selective binding to open channels. Proc Natl Acad Sci USA 85:1307-1311.
18. Jahr CE. 1992. High probability opening of NMDA receptor channels by L-glutamate. Science 255:470-472.
19. Kawano H, Sashihara S, Ohno K, Mita T, Kawamura M, Yoshii K. 1994. Phenytoin, an antiepileptic drug, competitively blocked non-NMDA receptors produced by Xenopus oocytes. Neurosci Lett 166:183-186.
20. Keilhoff G, Wolf G. 1992. Memantine prevents quinolinic acid-induced hippocampal damage. Eur J Pharmacol 219:451-454.
21. Koh JY, Choi DW. 1987. Quantitative determination of glutamate mediated cortical neuronal injury in cell culture by lactate dehydrogenase efflux assay. J Neurosci Methods 20:83-90.
22. Moret C, Charveron M, Finberg JP, Couzinier JP, Briley M. 1985. Biochemical profile of midalcipran (F 2207), 1-phenyl-1-diethyl-aminocarbonyl-2-aminomethyl-cyclopropane (Z) hydrochloride, a potential fourth generation antidepressant drug. Neuropharmacology 24:1211-1219.
23. Muller WE, Mutschler E, Riederer P. 1995. Noncompetitive NMDA receptor antagonists with fast open-channel blocking kinetics and strong voltage-dependency as potential therapeutic agents for Alzheimer's dementia. Pharmacopsychiatry 28:113-124.
24. Olney J, Price M, Salles KS, Labruyere J, Frierdich G. 1987. MK-801 powerfully protects against N-methyl aspartate neurotoxicity. Eur J Pharmacol 141:357-361.
25. Parsons CG, R, G, Rozental J, Millar J, Lodge D. 1993. Patch clamp studies on the kinetics and selectivity of N-methyl-D-aspartate receptor antagonism by memantine (1-amino-3,5-dimethyladamantan). Neuropharmacology 32:1351-1358.
26. Parsons CG, Quack G, Bresink I, Baran L, Przegalinski E, Kostowski W, Krzascik P, S, H, Danysz W. 1995. Comparison of the potency, kinetics and voltage-dependency of a series of uncompetitive NMDA receptor antagonists in vitro with anticonvulsive and motor impairment activity in vivo. Neuropharmacology 34:1239-1258.
27. Scheetz AJ, Constantine PM. 1994. Modulation of NMDA receptor function: Implications for vertebrate neural development. Faseb J 8:745-752.
28. Seeburg PH. 1993. The TINS/TiPS Lecture. The molecular biology of mammalian glutamate receptor channels. Trends Neurosci 16:359-365.
29. Shuto S, Takada H, Mochizuki D, Tsujita R, Hase Y, Ono S, Shibuya N, Matsuda A. 1995. (±)-(Z)-2-(Aminomethyl)-1-phenylcyclopropanecarboxamide derivatives as a new prototype of NMDA receptor antagonists. J Med Chem 38:2964-2968.
30. Shuto S, Ono S, Hase Y, Kamiyama N, Takada H, Yamashita K, Matsuda A. 1996a. Conformational restriction by repulsion between adjacent substituents on a cyclopropane ring: Design and enantioselective synthesis of 1-phenyl-2-(1-aminoalkyl)cyclopropane-N,N-diethylcarboxamides as potent NMDA receptor antagonists J Org Chem 61:915-923.
31. Shuto S, Ono S, Hase Y, Ueno Y, Noguchi T, Yoshii K, Matsuda A. 1996b. Synthesis and biological activity of conformationally restricted analogs of milnacipran: (1S, 1R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide, an efficient noncompetitive N-methyl-D-aspartic acid receptor antagonist. J Med Chem 39:4844-4852.
32. Wong EH, Kemp JA, Priestley T, Knight AR, Woodruff GN, Iversen LL. 1986. The anticonvulsant MK-801 is a potent N-methyl-D-aspartate antagonist. Proc Natl Acad Sci USA 83:7104-7108.
33. Yoshii K, Kurihara K. 1989. Inward rectifier produced by Xenopus oocyte injected with mRNA extracted from carp olfactory epithelium. Synapse 3:234-238.
34. Yoshii K, Yu L, Mixtera-Mayne K, Davidson N, Lester HA. 1987. Equilibrium properties of mouse-torpedo acetylcholine receptor hybrids expressed in Xenopus oocytes. J Gen Physiol 90:553-573.
35. Yoshii K, Noguchi T, Ohtubo Y, Imoto H, Tanaka E. 1996. Block of NMDA receptor by a milnacipran analog. Soc Neurosci Abst 22:65.