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MedKoo Cat#: 532124 | Name: LSP4-2022

Description:

WARNING: This product is for research use only, not for human or veterinary use.

LSP4-2022 is a novel mGlu4 selective agonist which increases behavioral despair in mouse models of antidepressant action. LSP4-2022 displaued EC(50): 0.11 ± 0.02, 11.6 ± 1.9, 29.2 ± 4.2 μM (n>19) in calcium assays on mGlu4, mGlu7, and mGlu8 receptors, respectively, with no activity at the group I and -II mGlu receptors at 100 μM. LSP4-2022 inhibits neurotransmission in cerebellar slices from wild-type but not mGlu4 receptor-knockout mice. In vivo, it possesses antiparkinsonian properties after central or systemic administration in a haloperidol-induced catalepsy test, revealing its ability to cross the blood-brain barrier. Site-directed mutagenesis and molecular modeling was used to identify the LSP4-2022 binding site, revealing interaction with both the glutamate binding site and a variable pocket responsible for selectivity.

Chemical Structure

LSP4-2022
LSP4-2022
CAS#1413405-33-0

Theoretical Analysis

MedKoo Cat#: 532124

Name: LSP4-2022

CAS#: 1413405-33-0

Chemical Formula: C13H18NO8P

Exact Mass: 347.0770

Molecular Weight: 347.26

Elemental Analysis: C, 44.96; H, 5.22; N, 4.03; O, 36.86; P, 8.92

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
1413405-33-0
Synonym
LSP4-2022; LSP4 2022; LSP42022.
IUPAC/Chemical Name
(2S)-2-amino-4-({[4-(carboxymethoxy)phenyl](hydroxy)methyl}(hydroxy)phosphoryl)butanoic acid
InChi Key
BGOFVWMHMQISHB-NKUHCKNESA-N
InChi Code
InChI=1S/C13H18NO8P/c14-10(12(17)18)5-6-23(20,21)13(19)8-1-3-9(4-2-8)22-7-11(15)16/h1-4,10,13,19H,5-7,14H2,(H,15,16)(H,17,18)(H,20,21)/t10-,13?/m0/s1
SMILES Code
O=C(O)[C@@H](N)CCP(O)(C(C1=CC=C(OCC(O)=O)C=C1)O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Metabotropic glutamate (mGlu) receptors are promising targets to treat numerous brain disorders. So far, allosteric modulators are the only subtype selective ligands, but pure agonists still have strong therapeutic potential.

Preparing Stock Solutions

The following data is based on the product molecular weight 347.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Cieślik P, Woźniak M, Rook JM, Tantawy MN, Conn PJ, Acher F, Tokarski K, Kusek M, Pilc A, Wierońska JM. Mutual activation of glutamatergic mGlu4 and muscarinic M4 receptors reverses schizophrenia- related changes in rodents. Psychopharmacology (Berl). 2018 Oct;235(10):2897-2913. doi: 10.1007/s00213-018-4980-y. Epub 2018 Jul 27. PMID: 30054675; PMCID: PMC6182605. 2: Selvam C, Lemasson IA, Brabet I, Oueslati N, Karaman B, Cabaye A, Tora AS, Commare B, Courtiol T, Cesarini S, McCort-Tranchepain I, Rigault D, Mony L, Bessiron T, McLean H, Leroux FR, Colobert F, Daniel H, Goupil-Lamy A, Bertrand HO, Goudet C, Pin JP, Acher FC. Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites. J Med Chem. 2018 Mar 8;61(5):1969-1989. doi: 10.1021/acs.jmedchem.7b01438. Epub 2018 Feb 14. PMID: 29397723. 3: Fisher NM, Gogliotti RG, Vermudez SAD, Stansley BJ, Conn PJ, Niswender CM. Genetic Reduction or Negative Modulation of mGlu7 Does Not Impact Anxiety and Fear Learning Phenotypes in a Mouse Model of MECP2 Duplication Syndrome. ACS Chem Neurosci. 2018 Sep 19;9(9):2210-2217. doi: 10.1021/acschemneuro.7b00414. Epub 2017 Dec 14. PMID: 29227625; PMCID: PMC6002927. 4: Rovira X, Trapero A, Pittolo S, Zussy C, Faucherre A, Jopling C, Giraldo J, Pin JP, Gorostiza P, Goudet C, Llebaria A. OptoGluNAM4.1, a Photoswitchable Allosteric Antagonist for Real-Time Control of mGlu4 Receptor Activity. Cell Chem Biol. 2016 Aug 18;23(8):929-34. doi: 10.1016/j.chembiol.2016.06.013. Epub 2016 Jul 28. PMID: 27478159. 5: Woźniak M, Gołembiowska K, Noworyta-Sokołowska K, Acher F, Cieślik P, Kusek M, Tokarski K, Pilc A, Wierońska JM. Neurochemical and behavioral studies on the 5-HT1A-dependent antipsychotic action of the mGlu4 receptor agonist LSP4-2022. Neuropharmacology. 2017 Mar 15;115:149-165. doi: 10.1016/j.neuropharm.2016.06.025. Epub 2016 Jul 25. PMID: 27465045. 6: Woźniak M, Acher F, Marciniak M, Lasoń-Tyburkiewicz M, Gruca P, Papp M, Pilc A, Wierońska JM. Involvement of GABAB Receptor Signaling in Antipsychotic-like Action of the Novel Orthosteric Agonist of the mGlu4 Receptor, LSP4-2022. Curr Neuropharmacol. 2016;14(5):413-26. doi: 10.2174/1570159x13666150516000630. PMID: 26769224; PMCID: PMC4983756. 7: Podkowa K, Rzeźniczek S, Marciniak M, Acher F, Pilc A, Pałucha-Poniewiera A. A novel mGlu4 selective agonist LSP4-2022 increases behavioral despair in mouse models of antidepressant action. Neuropharmacology. 2015 Oct;97:338-45. doi: 10.1016/j.neuropharm.2015.05.039. Epub 2015 Jun 12. PMID: 26074092. 8: Klar R, Walker AG, Ghose D, Grueter BA, Engers DW, Hopkins CR, Lindsley CW, Xiang Z, Conn PJ, Niswender CM. Activation of Metabotropic Glutamate Receptor 7 Is Required for Induction of Long-Term Potentiation at SC-CA1 Synapses in the Hippocampus. J Neurosci. 2015 May 13;35(19):7600-15. doi: 10.1523/JNEUROSCI.4543-14.2015. PMID: 25972184; PMCID: PMC4429158. 9: Vilar B, Busserolles J, Ling B, Laffray S, Ulmann L, Malhaire F, Chapuy E, Aissouni Y, Etienne M, Bourinet E, Acher F, Pin JP, Eschalier A, Goudet C. Alleviating pain hypersensitivity through activation of type 4 metabotropic glutamate receptor. J Neurosci. 2013 Nov 27;33(48):18951-65. doi: 10.1523/JNEUROSCI.1221-13.2013. PMID: 24285900; PMCID: PMC6618701. 10: Goudet C, Vilar B, Courtiol T, Deltheil T, Bessiron T, Brabet I, Oueslati N, Rigault D, Bertrand HO, McLean H, Daniel H, Amalric M, Acher F, Pin JP. A novel selective metabotropic glutamate receptor 4 agonist reveals new possibilities for developing subtype selective ligands with therapeutic potential. FASEB J. 2012 Apr;26(4):1682-93. doi: 10.1096/fj.11-195941. Epub 2012 Jan 5. PMID: 22223752.