DCG-IV

DCG-IV
Identifiers
	IUPAC name (1R,2R)-3-[(1S)-1-amino-2-hydroxy-2-oxoethyl]cyclopropane-1,2-dicarboxylic acid;
CAS Number	147782-19-2 ;
PubChem CID	5310979;
ChemSpider	4470521 ;
CompTox Dashboard (EPA)	DTXSID00933208 ;
ECHA InfoCard	100.161.971
Chemical and physical data
Formula	C7H9NO6
Molar mass	203.150 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [C@@H]1([C@@H](C1[C@@H](C(=O)O)N)C(=O)O)C(=O)O;
	InChI InChI=1S/C7H9NO6/c8-4(7(13)14)1-2(5(9)10)3(1)6(11)12/h1-4H,8H2,(H,9,10)(H,11,12)(H,13,14)/t2-,3-,4+/m1/s1 ; Key:MATPZHBYOVDBLI-JJYYJPOSSA-N ;
	(what is this?) (verify)

DCG-IV is a research drug which acts as a group-selective agonist for the group II metabotropic glutamate receptors (mGluR₂_/₃).[1] It has potent neuroprotective and anticonvulsant effects in animal studies,[2][3][4][5] as well as showing anti-Parkinsonian effects,[6][7] but also impairs the formation of memories.[8][9]

References

Ishida M, Saitoh T, Shimamoto K, Ohfune Y, Shinozaki H (August 1993). "A novel metabotropic glutamate receptor agonist: marked depression of monosynaptic excitation in the newborn rat isolated spinal cord". British Journal of Pharmacology. 109 (4): 1169–77. doi:10.1111/j.1476-5381.1993.tb13745.x. PMC 2175774. PMID 8401927.
Bruno V, Copani A, Battaglia G, Raffaele R, Shinozaki H, Nicoletti F (April 1994). "Protective effect of the metabotropic glutamate receptor agonist, DCG-IV, against excitotoxic neuronal death". European Journal of Pharmacology. 256 (1): 109–12. doi:10.1016/0014-2999(94)90624-6. PMID 7517889.
Yoshioka H, Sugita M, Kinouchi H (September 2009). "Neuroprotective effects of group II metabotropic glutamate receptor agonist DCG-IV on hippocampal neurons in transient forebrain ischemia". Neuroscience Letters. 461 (3): 266–70. doi:10.1016/j.neulet.2009.06.056. PMID 19549561.
Attwell PJ, Singh Kent N, Jane DE, Croucher MJ, Bradford HF (September 1998). "Anticonvulsant and glutamate release-inhibiting properties of the highly potent metabotropic glutamate receptor agonist (2S,2'R, 3'R)-2-(2',3'-dicarboxycyclopropyl)glycine (DCG-IV)". Brain Research. 805 (1–2): 138–43. doi:10.1016/S0006-8993(98)00698-2. PMID 9733953.
Fei Z, Zhang X, Bai HM, Jiang XF, Wang XL (December 2006). "Metabotropic glutamate receptor antagonists and agonists: potential neuroprotectors in diffuse brain injury". Journal of Clinical Neuroscience. 13 (10): 1023–7. doi:10.1016/j.jocn.2005.11.042. PMID 17113985.
Dawson L, Chadha A, Megalou M, Duty S (February 2000). "The group II metabotropic glutamate receptor agonist, DCG-IV, alleviates akinesia following intranigral or intraventricular administration in the reserpine-treated rat". British Journal of Pharmacology. 129 (3): 541–6. doi:10.1038/sj.bjp.0703105. PMC 1571875. PMID 10711353.
Venero JL, Santiago M, Tomás-Camardiel M, Matarredona ER, Cano J, Machado A (2002). "DCG-IV but not other group-II metabotropic receptor agonists induces microglial BDNF mRNA expression in the rat striatum. Correlation with neuronal injury". Neuroscience. 113 (4): 857–69. doi:10.1016/S0306-4522(02)00232-4. PMID 12182892.
Huang LQ, Rowan MJ, Anwyl R (February 1997). "mGluR II agonist inhibition of LTP induction, and mGluR II antagonist inhibition of LTD. induction, in the dentate gyrus in vitro". NeuroReport. 8 (3): 687–93. doi:10.1097/00001756-199702100-00022. PMID 9106748.
Sato T, Tanaka K, Ohnishi Y, Teramoto T, Irifune M, Nishikawa T (February 2004). "Inhibitory effects of group II mGluR-related drugs on memory performance in mice". Physiology & Behavior. 80 (5): 747–58. doi:10.1016/j.physbeh.2003.12.010. PMID 14984810.

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[pmid8401927-1] Ishida M, Saitoh T, Shimamoto K, Ohfune Y, Shinozaki H (August 1993). "A novel metabotropic glutamate receptor agonist: marked depression of monosynaptic excitation in the newborn rat isolated spinal cord". British Journal of Pharmacology. 109 (4): 1169–77. doi:10.1111/j.1476-5381.1993.tb13745.x. PMC 2175774. PMID 8401927.

[pmid7517889-2] Bruno V, Copani A, Battaglia G, Raffaele R, Shinozaki H, Nicoletti F (April 1994). "Protective effect of the metabotropic glutamate receptor agonist, DCG-IV, against excitotoxic neuronal death". European Journal of Pharmacology. 256 (1): 109–12. doi:10.1016/0014-2999(94)90624-6. PMID 7517889.

[pmid19549561-3] Yoshioka H, Sugita M, Kinouchi H (September 2009). "Neuroprotective effects of group II metabotropic glutamate receptor agonist DCG-IV on hippocampal neurons in transient forebrain ischemia". Neuroscience Letters. 461 (3): 266–70. doi:10.1016/j.neulet.2009.06.056. PMID 19549561.

[pmid9733953-4] Attwell PJ, Singh Kent N, Jane DE, Croucher MJ, Bradford HF (September 1998). "Anticonvulsant and glutamate release-inhibiting properties of the highly potent metabotropic glutamate receptor agonist (2S,2'R, 3'R)-2-(2',3'-dicarboxycyclopropyl)glycine (DCG-IV)". Brain Research. 805 (1–2): 138–43. doi:10.1016/S0006-8993(98)00698-2. PMID 9733953.

[pmid17113985-5] Fei Z, Zhang X, Bai HM, Jiang XF, Wang XL (December 2006). "Metabotropic glutamate receptor antagonists and agonists: potential neuroprotectors in diffuse brain injury". Journal of Clinical Neuroscience. 13 (10): 1023–7. doi:10.1016/j.jocn.2005.11.042. PMID 17113985.

[pmid10711353-6] Dawson L, Chadha A, Megalou M, Duty S (February 2000). "The group II metabotropic glutamate receptor agonist, DCG-IV, alleviates akinesia following intranigral or intraventricular administration in the reserpine-treated rat". British Journal of Pharmacology. 129 (3): 541–6. doi:10.1038/sj.bjp.0703105. PMC 1571875. PMID 10711353.

[pmid12182892-7] Venero JL, Santiago M, Tomás-Camardiel M, Matarredona ER, Cano J, Machado A (2002). "DCG-IV but not other group-II metabotropic receptor agonists induces microglial BDNF mRNA expression in the rat striatum. Correlation with neuronal injury". Neuroscience. 113 (4): 857–69. doi:10.1016/S0306-4522(02)00232-4. PMID 12182892.

[pmid9106748-8] Huang LQ, Rowan MJ, Anwyl R (February 1997). "mGluR II agonist inhibition of LTP induction, and mGluR II antagonist inhibition of LTD. induction, in the dentate gyrus in vitro". NeuroReport. 8 (3): 687–93. doi:10.1097/00001756-199702100-00022. PMID 9106748.

[pmid14984810-9] Sato T, Tanaka K, Ohnishi Y, Teramoto T, Irifune M, Nishikawa T (February 2004). "Inhibitory effects of group II mGluR-related drugs on memory performance in mice". Physiology & Behavior. 80 (5): 747–58. doi:10.1016/j.physbeh.2003.12.010. PMID 14984810.