PeptideDB

trans-ACPD (Trans-(±)-ACP) 67684-64-4

trans-ACPD (Trans-(±)-ACP) 67684-64-4

CAS No.: 67684-64-4

trans-ACPD is a metabotropic receptor agonist (activator) that promotes calcium ion activity and generates inward curren
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trans-ACPD is a metabotropic receptor agonist (activator) that promotes calcium ion activity and generates inward current.

Physicochemical Properties


Molecular Formula C7H11NO4
Molecular Weight 173.17
Exact Mass 173.069
CAS # 67684-64-4
Related CAS # (1S,3R)-ACPD;111900-32-4;cis-ACPD;477331-06-9
PubChem CID 104766
Appearance White to off-white solid powder
LogP 0.353
Hydrogen Bond Donor Count 3
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 2
Heavy Atom Count 12
Complexity 227
Defined Atom Stereocenter Count 2
SMILES

C1C[C@](C[C@@H]1C(=O)O)(C(=O)O)N

InChi Key YFYNOWXBIBKGHB-FBCQKBJTSA-N
InChi Code

InChI=1S/C7H11NO4/c8-7(6(11)12)2-1-4(3-7)5(9)10/h4H,1-3,8H2,(H,9,10)(H,11,12)/t4-,7+/m1/s1
Chemical Name

(1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets mGluR
ln Vitro Analogs of excitatory amino acids (EAAs) stimulate receptors, which in turn cause phosphoinositides (PIs) to hydrolyze more readily. In these investigations, hippocampal slices from neonatal rats—rats that are 6–11 days old—are used to examine how EAA analogs affect these receptors. 51 μM of trans-ACPD is the concentration needed to elicit half-maximal stimulation (EC50 value). The IC50 values of DL-2-Amino-3-phosphonopropionate (DL-AP3) range from 480 to 850 μM, making it an effective inhibitor of PI hydrolysis triggered by ibotenate, quisqualate, and trans-ACPD.
ln Vivo When mice get intrathecal injections of NMDA, kainate, trans-ACPD, TNF-α, or IL-1β, their biting behavior is significantly (p<0.001) more aggressive than when mice receive intrathecal injections of saline. When compared to mice treated with saline (10 mL/kg, ip), systemic pre-treatment with GM (100 mg/kg, ip) significantly (p<0.001) reduced the biting behavior in all groups. With the following suppression percentages for pro-inflammatory cytokines and NMDA, GM has the largest effect: 92±7% for TNF-α, 91±5% for IL-1β, 69±1% for NMDA, and 71±12% for trans-ACPD. On the other hand, GM had no discernible impact on the kainate-mediated biting response at the same dosage[3].
References

[1]. Trans-ACPD, a metabotropic receptor agonist, produces calcium mobilization and an inward current in cultured cerebellar Purkinje neurons. J Neurophysiol. 1994 May;71(5):1992-8.

[2]. Multiple mechanisms for inhibition of excitatory amino acid receptors coupled to phosphoinositide hydrolysis. J Neurochem. 1992 Nov;59(5):1893-904.

[3]. Polysaccharide glucomannan isolated from Heterodermia obscurata attenuates acute and chronic pain in mice. Carbohydr Polym. 2013 Feb 15;92(2):2058-64.


Solubility Data


Solubility (In Vitro) DMSO: 50 mg/mL (288.73 mM)
H2O: 3.57 mg/mL (20.62 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.5 mg/mL (14.44 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (14.44 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 3: 5 mg/mL (28.87 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.7747 mL 28.8734 mL 57.7467 mL
5 mM 1.1549 mL 5.7747 mL 11.5493 mL
10 mM 0.5775 mL 2.8873 mL 5.7747 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.