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1-Aminoindan-1,5-dicarboxylic Acid: A Novel Antagonist at Phospholipase C-Linked Metabotropic Glutamate Receptors

Cite this: J. Med. Chem. 1995, 38, 19, 3717–3719
Publication Date (Print):September 1, 1995
https://doi.org/10.1021/jm00019a002
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    13. Karen J. Gregory, Cyril Goudet, . International Union of Basic and Clinical Pharmacology. CXI. Pharmacology, Signaling, and Physiology of Metabotropic Glutamate Receptors. Pharmacological Reviews 2021, 73 (1) , 521-569. https://doi.org/10.1124/pr.119.019133
    14. Tao Ju, Qiang Fu, Jian‐Heng Ye, Zhen Zhang, Li‐Li Liao, Si‐Shun Yan, Xing‐Yang Tian, Shu‐Ping Luo, Jing Li, Da‐Gang Yu. Selective and Catalytic Hydrocarboxylation of Enamides and Imines with CO 2 to Generate α,α‐Disubstituted α‐Amino Acids. Angewandte Chemie International Edition 2018, 57 (42) , 13897-13901. https://doi.org/10.1002/anie.201806874
    15. Tao Ju, Qiang Fu, Jian‐Heng Ye, Zhen Zhang, Li‐Li Liao, Si‐Shun Yan, Xing‐Yang Tian, Shu‐Ping Luo, Jing Li, Da‐Gang Yu. Selective and Catalytic Hydrocarboxylation of Enamides and Imines with CO 2 to Generate α,α‐Disubstituted α‐Amino Acids. Angewandte Chemie 2018, 130 (42) , 14093-14097. https://doi.org/10.1002/ange.201806874
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    17. Andrea Carotti, Federica Ianni, Emidio Camaioni, Lucia Pucciarini, Maura Marinozzi, Roccaldo Sardella, Benedetto Natalini. N -Decyl- S -trityl-( R )-cysteine, a new chiral selector for “green” ligand-exchange chromatography applications. Journal of Pharmaceutical and Biomedical Analysis 2017, 144 , 31-40. https://doi.org/10.1016/j.jpba.2017.02.009
    18. Juan Zou, Jason Jiang, Jenny Yang. Molecular Basis for Modulation of Metabotropic Glutamate Receptors and Their Drug Actions by Extracellular Ca2+. International Journal of Molecular Sciences 2017, 18 (3) , 672. https://doi.org/10.3390/ijms18030672
    19. S. Pal Choudhuri, R.J. Delay, E.R. Delay. Metabotropic glutamate receptors are involved in the detection of IMP and l-amino acids by mouse taste sensory cells. Neuroscience 2016, 316 , 94-108. https://doi.org/10.1016/j.neuroscience.2015.12.008
    20. Jun Shimokawa, Koji Chiyoda, Hirotatsu Umihara, Tohru Fukuyama. Antiproliferative Activity of Amathaspiramide Alkaloids and Analogs. CHEMICAL & PHARMACEUTICAL BULLETIN 2016, 64 (8) , 1239-1241. https://doi.org/10.1248/cpb.c16-00256
    21. Maris Vilums, Jules Heuberger, Laura H. Heitman, Adriaan P. IJzerman. Indanes-Properties, Preparation, and Presence in Ligands for G Protein Coupled Receptors. Medicinal Research Reviews 2015, 35 (6) , 1097-1126. https://doi.org/10.1002/med.21352
    22. Matthew O'Connor, Chunrui Sun, Daesung Lee. Synthesis of Amathaspiramides by Aminocyanation of Enoates. Angewandte Chemie International Edition 2015, 54 (34) , 9963-9966. https://doi.org/10.1002/anie.201503982
    23. Matthew O'Connor, Chunrui Sun, Daesung Lee. Synthesis of Amathaspiramides by Aminocyanation of Enoates. Angewandte Chemie 2015, 127 (34) , 10101-10104. https://doi.org/10.1002/ange.201503982
    24. Lucyna Pomierny-Chamioło, Kinga Rup, Bartosz Pomierny, Ewa Niedzielska, Peter W. Kalivas, Małgorzata Filip. Metabotropic glutamatergic receptors and their ligands in drug addiction. Pharmacology & Therapeutics 2014, 142 (3) , 281-305. https://doi.org/10.1016/j.pharmthera.2013.12.012
    25. Seiji Shirakawa, Kenichiro Yamamoto, Takashi Tokuda, Keiji Maruoka. Phase‐Transfer‐Catalyzed Asymmetric α‐Arylation of α‐Amino Acid Derivatives. Asian Journal of Organic Chemistry 2014, 3 (4) , 433-436. https://doi.org/10.1002/ajoc.201400004
    26. . Peptidomimetic Bioisosteres. 2014, 37-73. https://doi.org/10.1002/9781118683033.ch3
    27. Kaizhi Li, Guangying Tan, Jingsheng Huang, Feijie Song, Jingsong You. Iron‐Catalyzed Oxidative CH/CH Cross‐Coupling: An Efficient Route to α‐Quaternary α‐Amino Acid Derivatives. Angewandte Chemie International Edition 2013, 52 (49) , 12942-12945. https://doi.org/10.1002/anie.201306181
    28. Kaizhi Li, Guangying Tan, Jingsheng Huang, Feijie Song, Jingsong You. Iron-Catalyzed Oxidative CH/CH Cross-Coupling: An Efficient Route to α-Quaternary α-Amino Acid Derivatives. Angewandte Chemie 2013, 125 (49) , 13180-13183. https://doi.org/10.1002/ange.201306181
    29. Yuji Odagaki, Masakazu Kinoshita, Ryoichi Toyoshima. Group II metabotropic glutamate receptor-mediated activation of G-proteins in rat hippocampal and striatal membranes. Neuroscience Letters 2013, 539 , 22-26. https://doi.org/10.1016/j.neulet.2013.01.033
    30. Roccaldo Sardella, Antonio Macchiarulo, Andrea Carotti, Federica Ianni, Maria Eugenia García Rubiño, Benedetto Natalini. Chiral mobile phase in ligand-exchange chromatography of amino acids: Exploring the copper(II) salt anion effect with a computational approach. Journal of Chromatography A 2012, 1269 , 316-324. https://doi.org/10.1016/j.chroma.2012.08.018
    31. Yuji Odagaki, Masakazu Kinoshita, Ryoichi Toyoshima. Functional Coupling between Metabotropic Glutamate Receptors and G-Proteins in Rat Cerebral Cortex Assessed by Guanosine-5′-O-(3-[35S]thio)triphosphate Binding Assay. Basic & Clinical Pharmacology & Toxicology 2011, 109 (3) , 175-185. https://doi.org/10.1111/j.1742-7843.2011.00705.x
    32. Benedetto Natalini, Nicola Giacchè, Roccaldo Sardella, Federica Ianni, Antonio Macchiarulo, Roberto Pellicciari. Computational studies for the elucidation of the enantiomer elution order of amino acids in chiral ligand-exchange chromatography. Journal of Chromatography A 2010, 1217 (48) , 7523-7527. https://doi.org/10.1016/j.chroma.2010.10.001
    33. Benedetto Natalini, Roccaldo Sardella, Nicola Giacchè, Samantha Palmiotto, Emidio Camaioni, Maura Marinozzi, Antonio Macchiarulo, Roberto Pellicciari. Chiral ligand-exchange separation and resolution of extremely rigid glutamate analogs: 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acids. Analytical and Bioanalytical Chemistry 2010, 397 (5) , 1997-2011. https://doi.org/10.1007/s00216-010-3669-9
    34. Ulf Madsen, Hans Bräuner‐Osborne, Jeremy R. Greenwood, Tommy N. Johansen, Povl Krogsgaard‐Larsen, Tommy Liljefors, Mogens Nielsen, Bente Frølund. GABA and Glutamate Receptor Ligands and their Therapeutic Potential in CNS Disorders. 2010, 1-111. https://doi.org/10.1002/9780470571224.pse019
    35. E. D. Matveeva, T. A. Podrugina, I. N. Kolesnikova, N. S. Zefirov. Benzoylhydrazones in catalytic hydrophosphorylation. Russian Chemical Bulletin 2010, 59 (2) , 411-417. https://doi.org/10.1007/s11172-010-0094-3
    36. E. D. Matveeva, T. A. Podrugina, M. V. Prisyazhnoi, S. O. Bachurin, N. S. Zefirov. Synthesis of a “memory tripeptide” (Arg—Glu—Arg, RER) and the Kabachnik—Fields reaction with di- and tripeptides as a method for the synthesis of phosphorus-containing peptide analogs. Russian Chemical Bulletin 2010, 59 (1) , 200-208. https://doi.org/10.1007/s11172-010-0063-x
    37. Lai-Hong Yan, Jun-Feng Hou, Ming-Gang Liu, Meng-Meng Li, Xiu-Yu Cui, Zhuo-Min Lu, Fu-Kang Zhang, Yang-Yuan An, Lin Shi, Jun Chen. Imbalance between excitatory and inhibitory amino acids at spinal level is associated with maintenance of persistent pain-related behaviors. Pharmacological Research 2009, 59 (5) , 290-299. https://doi.org/10.1016/j.phrs.2009.01.012
    38. Benedetto Natalini, Roccaldo Sardella, Giovanni Carbone, Antonio Macchiarulo, Roberto Pellicciari. The effect of the copper(II) salt anion in the Chiral Ligand-Exchange Chromatography of amino acids. Analytica Chimica Acta 2009, 638 (2) , 225-233. https://doi.org/10.1016/j.aca.2009.02.031
    39. Milan Stoiljkovic, Miodrag Radulovacki, David W. Carley. Local antagonism of intertrigeminal region metabotropic glutamate receptors exacerbates apneic responses to intravenous serotonin. Respiratory Physiology & Neurobiology 2009, 165 (2-3) , 137-142. https://doi.org/10.1016/j.resp.2008.10.019
    40. Francesco Ferraguti, Luca Crepaldi, Ferdinando Nicoletti. Metabotropic Glutamate 1 Receptor: Current Concepts and Perspectives. Pharmacological Reviews 2008, 60 (4) , 536-581. https://doi.org/10.1124/pr.108.000166
    41. Benedetto Natalini, Antonio Macchiarulo, Roccaldo Sardella, Alberto Massarotti, Roberto Pellicciari. Descriptive structure–separation relationship studies in chiral ligand‐exchange chromatography. Journal of Separation Science 2008, 31 (13) , 2395-2403. https://doi.org/10.1002/jssc.200800102
    42. Roccaldo Sardella, Michael Lämmerhofer, Benedetto Natalini, Wolfgang Lindner. Enantioselective HPLC of potentially CNS‐active acidic amino acids with a cinchona carbamate based chiral stationary phase. Chirality 2008, 20 (3-4) , 571-576. https://doi.org/10.1002/chir.20529
    43. M. Raiteri. Presynaptic Metabotropic Glutamate and GABA B Receptors. 2008, 373-407. https://doi.org/10.1007/978-3-540-74805-2_12
    44. Prantik Maity, Burkhard König. Enantio‐ and diastereoselective syntheses of cyclic C α ‐tetrasubstituted α‐amino acids and their use to induce stable conformations in short peptides. Peptide Science 2008, 90 (1) , 8-27. https://doi.org/10.1002/bip.20902
    45. Katja Naie, Marian Tsanov, Denise Manahan‐Vaughan. Group I metabotropic glutamate receptors enable two distinct forms of long‐term depression in the rat dentate gyrus in vivo. European Journal of Neuroscience 2007, 25 (11) , 3264-3275. https://doi.org/10.1111/j.1460-9568.2007.05583.x
    46. Dafydd R. Owen, Peter G. Dodd, Simon Gayton, Ben S. Greener, Gareth W. Harbottle, Simon J. Mantell, Graham N. Maw, Simon A. Osborne, Huw Rees, Tracy J. Ringer, Margarita Rodriguez-Lens, Graham F. Smith. Structure–activity relationships of novel non-competitive mGluR1 antagonists: A potential treatment for chronic pain. Bioorganic & Medicinal Chemistry Letters 2007, 17 (2) , 486-490. https://doi.org/10.1016/j.bmcl.2006.10.015
    47. Nerijus Lamanauskas, Andrea Nistri. Persistent rhythmic oscillations induced by nicotine on neonatal rat hypoglossal motoneurons in vitro. European Journal of Neuroscience 2006, 24 (9) , 2543-2556. https://doi.org/10.1111/j.1460-9568.2006.05137.x
    48. Roberto Pellicciari, Rosanna Filosa, Maria Carmela Fulco, Maura Marinozzi, Antonio Macchiarulo, Clemens Novak, Benedetto Natalini, Mette Brunsgaard Hermit, Søren Nielsen, Thomas Nikolaj Sager, Tine Bryan Stensbøl, Christian Thomsen. Synthesis and Preliminary Biological Evaluation of 2′‐Substituted 2‐(3′‐Carboxybicyclo[1.1.1]pentyl)glycine Derivatives as Group I Selective Metabotropic Glutamate Receptor Ligands. ChemMedChem 2006, 1 (3) , 358-365. https://doi.org/10.1002/cmdc.200500071
    49. Yunkyung Park, Jihoon Jo, John T.R. Isaac, Kwangwook Cho. Long-Term Depression of Kainate Receptor-Mediated Synaptic Transmission. Neuron 2006, 49 (1) , 95-106. https://doi.org/10.1016/j.neuron.2005.11.035
    50. James N. C. Kew, John A. Kemp. Ionotropic and metabotropic glutamate receptor structure and pharmacology. Psychopharmacology 2005, 179 (1) , 4-29. https://doi.org/10.1007/s00213-005-2200-z
    51. Vicky W. -W. Tsai, Heather L. Scott, Richard J. Lewis, Peter R. Dodd. The role of group I metabotropic glutamate receptors in neuronal excitotoxicity in alzheimer’s disease. Neurotoxicity Research 2005, 7 (1-2) , 125-141. https://doi.org/10.1007/BF03033782
    52. Aigars Jirgensons, Maura Marinozzi, Roberto Pellicciari. Conformationally constrained amino acids: enantiodivergent synthesis of all four stereoisomers of 2-(tetrahydrofuran-2-yl)glycine. Tetrahedron 2005, 61 (2) , 373-377. https://doi.org/10.1016/j.tet.2004.10.091
    53. Caroline Rae, Charbel El‐Hajj Moussa, Julian L. Griffin, William A. Bubb, Trent Wallis, Vladimir J. Balcar. Group I and II metabotropic glutamate receptors alter brain cortical metabolic and glutamate/glutamine cycle activity: a 13 C NMR spectroscopy and metabolomic study. Journal of Neurochemistry 2005, 92 (2) , 405-416. https://doi.org/10.1111/j.1471-4159.2004.02880.x
    54. Udo Meyer, Elke Breitling, Philippe Bisel, August W. Frahm. Asymmetric Strecker synthesis of enantiopure 2,4-ethanothreonines. Tetrahedron: Asymmetry 2004, 15 (13) , 2029-2037. https://doi.org/10.1016/j.tetasy.2004.06.003
    55. Laura A. Schrader, Stephen P. Perrett, Lan Ye, Michael J. Friedlander. Substrates for Coincidence Detection and Calcium Signaling for Induction of Synaptic Potentiation in the Neonatal Visual Cortex. Journal of Neurophysiology 2004, 91 (6) , 2747-2764. https://doi.org/10.1152/jn.00908.2003
    56. Gabriele Costantino, Maura Marinozzi, Emidio Camaioni, Benedetto Natalini, Iran Sarichelou, Fabrizio Micheli, Paolo Cavanni, Stefania Faedo, Christian Noe, Flavio Moroni, Roberto Pellicciari. Stereoselective synthesis and preliminary evaluation of (+)- and (–)-3-methyl-5-carboxy-thien-2-yl-glycine (3-MATIDA): identification of (+)-3-MATIDA as a novel mGluR1 competitive antagonist. Il Farmaco 2004, 59 (2) , 93-99. https://doi.org/10.1016/j.farmac.2003.11.008
    57. Els J. M. Van Dam, Amer Kamal, Alain Artola, Pierre N. E. De Graan, Willem Hendrik Gispen, Geert M. J. Ramakers. Group I metabotropic glutamate receptors regulate the frequency–response function of hippocampal CA1 synapses for the induction of LTP and LTD. European Journal of Neuroscience 2004, 19 (1) , 112-118. https://doi.org/10.1111/j.1460-9568.2004.03103.x
    58. Benedetto Natalini, Maura Marinozzi, Katrin Bade, Roccaldo Sardella, Christian Thomsen, Roberto Pellicciari. Preparative resolution of 1‐aminoindan‐1,5‐dicarboxylic acid (AIDA) by chiral ligand‐exchange chromatography. Chirality 2004, 16 (5) , 314-317. https://doi.org/10.1002/chir.20027
    59. Abidali Fazal, Fred Parker, Alan M. Palmer, Martin J. Croucher. Characterisation of the actions of group I metabotropic glutamate receptor subtype selective ligands on excitatory amino acid release and sodium‐dependent re‐uptake in rat cerebrocortical minislices. Journal of Neurochemistry 2003, 86 (6) , 1346-1358. https://doi.org/10.1046/j.1471-4159.2003.01932.x
    60. A. E. Bandrowski, J. R. Huguenard, D. A. Prince. Baseline Glutamate Levels Affect Group I and II mGluRs in Layer V Pyramidal Neurons of Rat Sensorimotor Cortex. Journal of Neurophysiology 2003, 89 (3) , 1308-1316. https://doi.org/10.1152/jn.00644.2002
    61. Masaharu Kudoh, Masashi Sakai, Katsuei Shibuki. Differential Dependence of LTD on Glutamate Receptors in the Auditory Cortical Synapses of Cortical and Thalamic Inputs. Journal of Neurophysiology 2002, 88 (6) , 3167-3174. https://doi.org/10.1152/jn.00928.2001
    62. Kamalesh P. Pai Fondekar, Franz-J. Volk, S.M. Khaliq-uz-Zaman, Philippe Bisel, August W. Frahm. Carbocyclic α,β-diamino acids: asymmetric Strecker synthesis of stereomeric 1,2-diaminocyclohexanecarboxylic acids. Tetrahedron: Asymmetry 2002, 13 (20) , 2241-2249. https://doi.org/10.1016/S0957-4166(02)00610-9
    63. Claudia H. Tambeli, Carlos A. Parada, Jon D. Levine, Robert W. Gear. Inhibition of tonic spinal glutamatergic activity induces antinociception in the rat. European Journal of Neuroscience 2002, 16 (8) , 1547-1553. https://doi.org/10.1046/j.1460-9568.2002.02204.x
    64. S. Dolan, A.M. Nolan. Behavioral evidence supporting a differential role for spinal group I and II metabotropic glutamate receptors in inflammatory hyperalgesia in sheep. Neuropharmacology 2002, 43 (3) , 319-326. https://doi.org/10.1016/S0028-3908(02)00107-7
    65. S Datta, E.E Spoley, V.K Mavanji, E.H Patterson. A novel role of pedunculopontine tegmental kainate receptors: a mechanism of rapid eye movement sleep generation in the rat. Neuroscience 2002, 114 (1) , 157-164. https://doi.org/10.1016/S0306-4522(02)00250-6
    66. Andrea Cozzi, Elena Meli, Vincenzo Carlà, Roberto Pellicciari, Flavio Moroni, Domenico E Pellegrini-Giampietro. Metabotropic glutamate 1 (mGlu1) receptor antagonists enhance GABAergic neurotransmission: a mechanism for the attenuation of post-ischemic injury and epileptiform activity?. Neuropharmacology 2002, 43 (2) , 119-130. https://doi.org/10.1016/S0028-3908(02)00080-1
    67. Dawei Ma, Ke Ding, Hongqi Tian, Baomin Wang, Dongliang Cheng. Asymmetric synthesis of (S)-1-aminoindan-1,5-dicarboxylic acid and related analogues via intramolecular acylation of enantiopure α,α-disubstituted amino acids. Tetrahedron: Asymmetry 2002, 13 (9) , 961-969. https://doi.org/10.1016/S0957-4166(02)00224-0
    68. Flavio Moroni, Sabina Attucci, Andrea Cozzi, Elena Meli, Roberta Picca, Mark A Scheideler, Roberto Pellicciari, Christian Noe, Iran Sarichelou, Domenico E Pellegrini-Giampietro. The novel and systemically active metabotropic glutamate 1 (mGlu1) receptor antagonist 3-MATIDA reduces post-ischemic neuronal death. Neuropharmacology 2002, 42 (6) , 741-751. https://doi.org/10.1016/S0028-3908(02)00033-3
    69. Ornella Valenti, P. Jeffrey Conn, Michael J. Marino. Distinct physiological roles of the Gq‐coupled metabotropic glutamate receptors co‐expressed in the same neuronal populations. Journal of Cellular Physiology 2002, 191 (2) , 125-137. https://doi.org/10.1002/jcp.10081
    70. Boris S. Gafurov, Albert K. Urazaev, Robert M. Grossfeld, Edward M. Lieberman. Mechanism of NMDA receptor contribution to axon‐to‐glia signaling in the crayfish medial giant nerve fiber. Glia 2002, 38 (1) , 80-86. https://doi.org/10.1002/glia.10042
    71. John J. Renger, Kenichi N. Hartman, Yoshiko Tsuchimoto, Mineto Yokoi, Shigetada Nakanishi, Takao K. Hensch. Experience-dependent plasticity without long-term depression by type 2 metabotropic glutamate receptors in developing visual cortex. Proceedings of the National Academy of Sciences 2002, 99 (2) , 1041-1046. https://doi.org/10.1073/pnas.022618799
    72. Gabriele Costantino, Roberto Pellicciari, Antonio Macchiarulo. Metabotropic glutamate receptors: targets for therapy of cerebral ischaemia. Expert Opinion on Therapeutic Targets 2001, 5 (6) , 669-683. https://doi.org/10.1517/14728222.5.6.669
    73. Antonio Macchiarulo, Antonio Entrena Guadix, Gabriele Costantino. Conformational analysis of carboxyphenylglycine (CPG) derivatives: insight into bioactive and bioselective conformations of group-I mGluRs antagonists. Il Farmaco 2001, 56 (11) , 891-898. https://doi.org/10.1016/S0014-827X(01)01155-7
    74. Ki-Wug Sung, Sukwoo Choi, David M. Lovinger. Activation of Group I mGluRs Is Necessary for Induction of Long-Term Depression at Striatal Synapses. Journal of Neurophysiology 2001, 86 (5) , 2405-2412. https://doi.org/10.1152/jn.2001.86.5.2405
    75. James Monn, Darryle Schoepp. Pharmacology of metabotropic glutamate receptors. 2001, 151-186. https://doi.org/10.1201/9780203299388.ch7
    76. Valeria Bruno, Giuseppe Battaglia, Agata Copani, Mara D'Onofrio, P. Di Iorio, Antonio De Blasi, Daniela Melchiorri, Peter J. Flor, Ferdinando Nicoletti. Metabotropic Glutamate Receptor Subtypes as Targets for Neuroprotective Drugs. Journal of Cerebral Blood Flow & Metabolism 2001, 21 (9) , 1013-1033. https://doi.org/10.1097/00004647-200109000-00001
    77. Silvarosa Grassi, Vito Enrico Pettorossi. Synaptic plasticity in the medial vestibular nuclei: role of glutamate receptors and retrograde messengers in rat brainstem slices. Progress in Neurobiology 2001, 64 (6) , 527-553. https://doi.org/10.1016/S0301-0082(00)00070-8
    78. Laddawan Karachot, Yoshinori Shirai, Réjan Vigot, Tetsuo Yamamori, Masao Ito. Induction of Long-Term Depression in Cerebellar Purkinje Cells Requires a Rapidly Turned Over Protein. Journal of Neurophysiology 2001, 86 (1) , 280-289. https://doi.org/10.1152/jn.2001.86.1.280
    79. Bruce G. Lyeth, Qin-Zhi Gong, Shannon Shields, J.Paul Muizelaar, Robert F. Berman. Group I Metabotropic Glutamate Antagonist Reduces Acute Neuronal Degeneration and Behavioral Deficits after Traumatic Brain Injury in Rats. Experimental Neurology 2001, 169 (1) , 191-199. https://doi.org/10.1006/exnr.2001.7643
    80. Sergei Karnup, Armin Stelzer. Seizure‐like activity in the disinhibited CA1 minislice of adult guinea‐pigs. The Journal of Physiology 2001, 532 (3) , 713-730. https://doi.org/10.1111/j.1469-7793.2001.0713e.x
    81. Roberto Pellicciari, Gabriele Costantino, Maura Marinozzi, Antonio Macchiarulo, Emidio Camaioni, Benedetto Natalini. Metabotropic glutamate receptors: structure and new subtype-selective ligands. Il Farmaco 2001, 56 (1-2) , 91-94. https://doi.org/10.1016/S0014-827X(01)01006-0
    82. Daniel D Savage, Rafael Galindo, Susan A Queen, Linda L Paxton, Andrea M Allan. Characterization of electrically evoked [3H]-d-aspartate release from hippocampal slices. Neurochemistry International 2001, 38 (3) , 255-267. https://doi.org/10.1016/S0197-0186(00)00077-2
    83. Gabriele Costantino, Katiuscia Maltoni, Maura Marinozzi, Emidio Camaioni, Laurent Prezeau, Jean-Philippe Pin, Roberto Pellicciari. Synthesis and biological evaluation of 2-(3′-(1 H -tetrazol-5-yl)bicyclo[1.1.1]pent-1-yl)glycine ( S -TBPG), a novel mGlu1 receptor antagonist. Bioorganic & Medicinal Chemistry 2001, 9 (2) , 221-227. https://doi.org/10.1016/S0968-0896(00)00270-4
    84. Daniel L Small. Ion channels involved in stroke. Emerging Therapeutic Targets 2001, 5 (1) , 59-86. https://doi.org/10.1517/14728222.5.1.59
    85. Lianna R. Orlando, Stephen A. Alsdorf, John B. Penney, Anne B. Young. The Role of Group I and Group II Metabotropic Glutamate Receptors in Modulation of Striatal NMDA and Quinolinic Acid Toxicity. Experimental Neurology 2001, 167 (1) , 196-204. https://doi.org/10.1006/exnr.2000.7542
    86. Masaaki Hirouchi, Michiko Oka, Yoshinori Itoh, Yojiro Ukai, Kiyoshi Kimura. Role of metabotropic glutamate receptor subclasses in modulation of adenylyl cyclase activity by a nootropic NS-105. European Journal of Pharmacology 2000, 387 (1) , 9-17. https://doi.org/10.1016/S0014-2999(99)00785-2
    87. V Bruno, I Ksiazek, G Battaglia, S Lukic, T Leonhardt, D Sauer, F Gasparini, R Kuhn, F Nicoletti, P.J Flor. Selective blockade of metabotropic glutamate receptor subtype 5 is neuroprotective. Neuropharmacology 2000, 39 (12) , 2223-2230. https://doi.org/10.1016/S0028-3908(00)00079-4
    88. S. Grassi, V.E. Pettorossi. Role of nitric oxide in long-term potentiation of the rat medial vestibular nuclei. Neuroscience 2000, 101 (1) , 157-164. https://doi.org/10.1016/S0306-4522(00)00334-1
    89. Jeong-Hoon Kim, Jeff A Beeler, Paul Vezina. Group II, but not group I, metabotropic glutamate receptors in the rat nucleus accumbens contribute to amphetamine-induced locomotion. Neuropharmacology 2000, 39 (10) , 1692-1699. https://doi.org/10.1016/S0028-3908(99)00252-X
    90. Jeffrey R. Cottrell, Gilles R. Dubé, Christophe Egles, Guosong Liu. Distribution, Density, and Clustering of Functional Glutamate Receptors Before and After Synaptogenesis in Hippocampal Neurons. Journal of Neurophysiology 2000, 84 (3) , 1573-1587. https://doi.org/10.1152/jn.2000.84.3.1573
    91. Alessandra Sistiaga, José Sánchez-Prieto. Protein phosphatase 2B inhibitors mimic the action of arachidonic acid and prolong the facilitation of glutamate release by group I mGlu receptors. Neuropharmacology 2000, 39 (9) , 1544-1553. https://doi.org/10.1016/S0028-3908(00)00034-4
    92. Lisa S. Thomas, David E. Jane, John R. Harris, Martin J. Croucher. Metabotropic glutamate autoreceptors of the mGlu5 subtype positively modulate neuronal glutamate release in the rat forebrain in vitro. Neuropharmacology 2000, 39 (9) , 1554-1566. https://doi.org/10.1016/S0028-3908(99)00223-3
    93. Astrid G Chapman, Karl Nanan, Martin Williams, Brian S Meldrum. Anticonvulsant activity of two metabotropic glutamate Group I antagonists selective for the mGlu5 receptor: 2-methyl-6-(phenylethynyl)-pyridine (MPEP), and (E)-6-methyl-2-styryl-pyridine (SIB 1893). Neuropharmacology 2000, 39 (9) , 1567-1574. https://doi.org/10.1016/S0028-3908(99)00242-7
    94. Sharron Dolan, Andrea M Nolan. Behavioural evidence supporting a differential role for group I and II metabotropic glutamate receptors in spinal nociceptive transmission. Neuropharmacology 2000, 39 (7) , 1132-1138. https://doi.org/10.1016/S0028-3908(99)00200-2
    95. J W Allen, S M Knoblach, A I Faden. Activation of group I metabotropic glutamate receptors reduces neuronal apoptosis but increases necrotic cell death in vitro. Cell Death & Differentiation 2000, 7 (5) , 470-476. https://doi.org/10.1038/sj.cdd.4400678
    96. Christian Hansel, David J. Linden. Long-Term Depression of the Cerebellar Climbing Fiber–Purkinje Neuron Synapse. Neuron 2000, 26 (2) , 473-482. https://doi.org/10.1016/S0896-6273(00)81179-4
    97. Inna Lieb, Mary Chebib, Benedict Cooper, Leonora S. Dias, Vladimir J. Balcar. Quantitative autoradiography of Na+-dependent [3H]l-aspartate binding to l-glutamate transporters in rat brain: structure-activity studies using l-trans-pyrrolidine-2,4-dicarboxylate (l-t-PDC) and 2-(carboxycyclopropyl)-glycine (CCG). Neurochemistry International 2000, 36 (4-5) , 319-327. https://doi.org/10.1016/S0197-0186(99)00140-0
    98. L. Pastorino, F. Colciaghi, F. Gardoni, S. Albani‐Torregrossa, D. E. Pellegrini‐Giampietro, F. Moroni, P. N. E. De Graan, F. Cattabeni, M. Di Luca. (+)‐MCPG induces PKCε translocation in cortical synaptosomes through a PLD‐coupled mGluR. European Journal of Neuroscience 2000, 12 (4) , 1310-1318. https://doi.org/10.1046/j.1460-9568.2000.00023.x
    99. Jane H Crawford, Anna Wainwright, Robert Heavens, Jamie Pollock, Duncan J Martin, Roderick H Scott, Guy R Seabrook. Mobilisation of intracellular Ca2+ by mGluR5 metabotropic glutamate receptor activation in neonatal rat cultured dorsal root ganglia neurones. Neuropharmacology 2000, 39 (4) , 621-630. https://doi.org/10.1016/S0028-3908(99)00167-7
    100. Roberto Pellicciari, Gabriele Costantino, Antonio Macchiarulo. Metabotropic glutamate receptors: a structural view point. Pharmaceutica Acta Helvetiae 2000, 74 (2-3) , 231-237. https://doi.org/10.1016/S0031-6865(99)00055-2
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