MGS-0039

MGS-0039 Alerta sobre risco à saúde

Nome IUPAC	(1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid
Outros nomes	MGS-0039
Identificadores
Número CAS	569686-87-9
PubChem	9886034
ChemSpider	8061707
SMILES	`F[C@@]2(C(=O)O)[C@H]3[C@@](C(=O)O)(N)[C@H](OCc1ccc(Cl)c(Cl)c1)C[C@@H]23`
Propriedades
Fórmula química	C₁₅H₁₄Cl₂NO₅
Massa molar	359.15 g mol^-1
Farmacologia
Página de dados suplementares
Estrutura e propriedades	n, ε_r, etc.
Dados termodinâmicos	Phase behaviour Solid, liquid, gas
Dados espectrais	UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a materiais sob condições normais de temperatura e pressão Referências e avisos gerais sobre esta caixa. Alerta sobre risco à saúde.

MGS-0039 é um fármaco usado em pesquisas neurocientíficas que atua como um antagonista potente e seletivo do grupo II dos receptores metabotrópicos de glutamato (mGluR_2/3).^[1]^[2] Em estudos com animais, produziu efeitos antidepressivos e ansiolíticos,^[3]^[4]^[5]^[6] e estimulou a liberação de dopamina e serotonina em regiões específicas do cérebro.^[7]^[8] As pesquisas sugerem que isso pode ocorrer por meio de um mecanismo semelhante ao da cetamina, droga glutamatérgica semelhante.^[9]^[10]

Referências

↑ Chaki S, Yoshikawa R, Hirota S, Shimazaki T, Maeda M, Kawashima N, et al. (março de 2004). «MGS0039: a potent and selective group II metabotropic glutamate receptor antagonist with antidepressant-like activity». Neuropharmacology. 46: 457–67. PMID 14975669. doi:10.1016/j.neuropharm.2003.10.009
↑ Nakazato A, Sakagami K, Yasuhara A, Ohta H, Yoshikawa R, Itoh M, et al. (agosto de 2004). «Synthesis, in vitro pharmacology, structure-activity relationships, and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists». Journal of Medicinal Chemistry. 47: 4570–87. PMID 15317467. doi:10.1021/jm0400294
↑ Shimazaki T, Iijima M, Chaki S (outubro de 2004). «Anxiolytic-like activity of MGS0039, a potent group II metabotropic glutamate receptor antagonist, in a marble-burying behavior test». European Journal of Pharmacology. 501: 121–5. PMID 15464070. doi:10.1016/j.ejphar.2004.08.016
↑ Yasuhara A, Nakamura M, Sakagami K, Shimazaki T, Yoshikawa R, Chaki S, et al. (junho de 2006). «Prodrugs of 3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (MGS0039): a potent and orally active group II mGluR antagonist with antidepressant-like potential». Bioorganic & Medicinal Chemistry. 14: 4193–207. PMID 16487713. doi:10.1016/j.bmc.2006.01.060
↑ Yoshimizu T, Shimazaki T, Ito A, Chaki S (julho de 2006). «An mGluR2/3 antagonist, MGS0039, exerts antidepressant and anxiolytic effects in behavioral models in rats». Psychopharmacology. 186: 587–93. PMID 16612616. doi:10.1007/s00213-006-0390-7
↑ Stachowicz K, Wierońska J, Domin H, Chaki S, Pilc A (2011). «Anxiolytic-like activity of MGS0039, a selective group II mGlu receptor antagonist, is serotonin- and GABA-dependent». Pharmacological Reports. 63: 880–7. PMID 22001975. doi:10.1016/S1734-1140(11)70603-X
↑ Kawashima N, Karasawa J, Shimazaki T, Chaki S, Okuyama S, Yasuhara A, Nakazato A (abril de 2005). «Neuropharmacological profiles of antagonists of group II metabotropic glutamate receptors». Neuroscience Letters. 378: 131–4. PMID 15781145. doi:10.1016/j.neulet.2004.12.021
↑ Karasawa J, Yoshimizu T, Chaki S (janeiro de 2006). «A metabotropic glutamate 2/3 receptor antagonist, MGS0039, increases extracellular dopamine levels in the nucleus accumbens shell». Neuroscience Letters. 393: 127–30. PMID 16233956. doi:10.1016/j.neulet.2005.09.058
↑ Pałucha-Poniewiera A, Wierońska JM, Brański P, Stachowicz K, Chaki S, Pilc A (dezembro de 2010). «On the mechanism of the antidepressant-like action of group II mGlu receptor antagonist, MGS0039». Psychopharmacology. 212: 523–35. PMC 2981731 . PMID 20703449. doi:10.1007/s00213-010-1978-5
↑ Koike H, Iijima M, Chaki S (dezembro de 2011). «Involvement of the mammalian target of rapamycin signaling in the antidepressant-like effect of group II metabotropic glutamate receptor antagonists». Neuropharmacology. 61: 1419–23. PMID 21903115. doi:10.1016/j.neuropharm.2011.08.034

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[1] Chaki S, Yoshikawa R, Hirota S, Shimazaki T, Maeda M, Kawashima N, et al. (março de 2004). «MGS0039: a potent and selective group II metabotropic glutamate receptor antagonist with antidepressant-like activity». Neuropharmacology. 46: 457–67. PMID 14975669. doi:10.1016/j.neuropharm.2003.10.009

[2] Nakazato A, Sakagami K, Yasuhara A, Ohta H, Yoshikawa R, Itoh M, et al. (agosto de 2004). «Synthesis, in vitro pharmacology, structure-activity relationships, and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists». Journal of Medicinal Chemistry. 47: 4570–87. PMID 15317467. doi:10.1021/jm0400294

[3] Shimazaki T, Iijima M, Chaki S (outubro de 2004). «Anxiolytic-like activity of MGS0039, a potent group II metabotropic glutamate receptor antagonist, in a marble-burying behavior test». European Journal of Pharmacology. 501: 121–5. PMID 15464070. doi:10.1016/j.ejphar.2004.08.016

[4] Yasuhara A, Nakamura M, Sakagami K, Shimazaki T, Yoshikawa R, Chaki S, et al. (junho de 2006). «Prodrugs of 3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (MGS0039): a potent and orally active group II mGluR antagonist with antidepressant-like potential». Bioorganic & Medicinal Chemistry. 14: 4193–207. PMID 16487713. doi:10.1016/j.bmc.2006.01.060

[5] Yoshimizu T, Shimazaki T, Ito A, Chaki S (julho de 2006). «An mGluR2/3 antagonist, MGS0039, exerts antidepressant and anxiolytic effects in behavioral models in rats». Psychopharmacology. 186: 587–93. PMID 16612616. doi:10.1007/s00213-006-0390-7

[6] Stachowicz K, Wierońska J, Domin H, Chaki S, Pilc A (2011). «Anxiolytic-like activity of MGS0039, a selective group II mGlu receptor antagonist, is serotonin- and GABA-dependent». Pharmacological Reports. 63: 880–7. PMID 22001975. doi:10.1016/S1734-1140(11)70603-X

[7] Kawashima N, Karasawa J, Shimazaki T, Chaki S, Okuyama S, Yasuhara A, Nakazato A (abril de 2005). «Neuropharmacological profiles of antagonists of group II metabotropic glutamate receptors». Neuroscience Letters. 378: 131–4. PMID 15781145. doi:10.1016/j.neulet.2004.12.021

[8] Karasawa J, Yoshimizu T, Chaki S (janeiro de 2006). «A metabotropic glutamate 2/3 receptor antagonist, MGS0039, increases extracellular dopamine levels in the nucleus accumbens shell». Neuroscience Letters. 393: 127–30. PMID 16233956. doi:10.1016/j.neulet.2005.09.058

[9] Pałucha-Poniewiera A, Wierońska JM, Brański P, Stachowicz K, Chaki S, Pilc A (dezembro de 2010). «On the mechanism of the antidepressant-like action of group II mGlu receptor antagonist, MGS0039». Psychopharmacology. 212: 523–35. PMC 2981731 . PMID 20703449. doi:10.1007/s00213-010-1978-5

[10] Koike H, Iijima M, Chaki S (dezembro de 2011). «Involvement of the mammalian target of rapamycin signaling in the antidepressant-like effect of group II metabotropic glutamate receptor antagonists». Neuropharmacology. 61: 1419–23. PMID 21903115. doi:10.1016/j.neuropharm.2011.08.034

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