195209-04-2

Basic information

• Product Name: ACPT-II
• Synonyms: (1R,3R,4S)-1-AMINOCYCLOPENTANE-1,3,4-TRICARBOXYLIC ACID;4-AMINO-1ALPHA,2ALPHA,4BETA-CYCLOPENTANETRICARBOXYLIC ACID;ACPT-II
• CAS NO: 195209-04-2
• Molecular Formula: C8H11NO6
• Molecular Weight: 217.17604
• Mol File: 195209-04-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Desiccate at -20°C
• CAS DataBase Reference: ACPT-II(CAS DataBase Reference)
• NIST Chemistry Reference: ACPT-II(195209-04-2)
• EPA Substance Registry System: ACPT-II(195209-04-2)

Safety Data

• Hazardous Substances Data: 195209-04-2(Hazardous Substances Data)

Usage

Uses

ACPT-II is a metabotropic glutamate receptor agonist, which exerts neuroprotective effects against kainate-induced excitotoxicity in primary neuronal cell and the dorsal hippocampus of rats.

Biological Activity

Competitive metabotropic receptor antagonist (K b values are 115, 88 and 77 μ M at mGlu 1a , mGlu 2 and mGlu 4a respectively).

Upstream product

• 115794-30-4 (+)-(1S,2S)-dimethyl-4-oxocyclopentane 1,2-dicarboxylate 
• 151-50-8 potassium cyanide 
• 506-87-6 ammonium carbonate 
• 6453-07-2 (+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) 
• 194918-80-4 2,4-Dioxo-1,3-diaza-spiro[4.4]nonane-7,8-dicarboxylic acid 
• 35079-19-7 trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane 
• 28269-02-5 cis-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) 

Relevant articles and documents

Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: New tools to discriminate between metabotropic glutamate receptor subtypes

The four stereoisomers of 1-aminocyclopentane-1,3,4-tricarboxylic acid {ACPT-I (18) and -II (19), (3R,4R)-III [(-)-20], and (3S,4S)-III [(+)-20]} have been synthesized and evaluated for their effects at glutamate receptors subtypes. ACPTs are ACPD analogues in which a third carboxylic group has been added at position 4 in the cyclopentane ring. None of the ACPT isomers showed a significant effect on ionotropic NMDA, KA, and AMPA receptors. On the other hand, ACPT-III (19) was found to be a general competitive antagonist for metabotropic receptors (mGluRs) and exhibited a similar affinity for mGluR1a (K(B) = 115 ± 2 μM), mGluR2 (K(B) = 88 ± 21 μM), and mGluR4a (K(B) = 77 ± 9 μM), the representative members of group I, II and III mGluRs, respectively. Two other isomers, ACPT-I (18) and (+)-(3S,4S)-ACPT-III [(+)- 20], were potent agonist at the group III receptors mGluR4a (EC50 = 7.2 ± 2.3 and 8.8 ± 3.2 μM) and competitive antagonists with low affinity for mGluR1a and mGluR2 (K(B) > 300 μM). Finally, (-)-(3R,4R)-ACPT-III [(-)-20] was a competitive antagonist with poor but significant affinity for mGluR4a (K(B) = 220 μM). These results demonstrate that the addition of a third carboxylic group to ACPD can change its activity (from agonist to antagonist) and either increase or decrease its selectivity and/or affinity for the various mGluR subtypes.