Oleoyl-D-lysine sodium | CAS# | GlyT2a inhibitor

MedKoo Cat#: 574134 | Name: Oleoyl-D-lysine sodium

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Description:

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

Oleoyl-D-lysine sodium is an inhibitor of glycine transporter 2a (GlyT2a). Oleoyl-D-lysine sodium selectively inhibits GlyT2a over GlyT1b and reduces allodynia in a nerve ligation rat model of neuropathic pain.

Chemical Structure

Oleoyl-D-lysine sodium

CAS#NONE

Theoretical Analysis

MedKoo Cat#: 574134

Name: Oleoyl-D-lysine sodium

CAS#: NONE

Chemical Formula: C24H45N2NaO3

Exact Mass: 432.3328

Molecular Weight: 432.62

Elemental Analysis: C, 66.63; H, 10.48; N, 6.48; Na, 5.31; O, 11.09

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 410.00
5mg	USD 575.00
10mg	USD 725.00
25mg	USD 1,200.00

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Synonym

Oleoyl-D-lysine sodium; Oleoyl D-lysine sodium; Oleoyl-D lysine sodium; Oleoyl D lysine sodium;

IUPAC/Chemical Name

N2-[(9Z)-1-oxo-9-octadecen-1-yl]-D-lysine, monosodium salt

InChi Key

OWBHGNNUDAIRSI-KVVVOXFISA-N

InChi Code

InChI=1S/C24H46N2O3.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-23(27)26-22(24(28)29)19-17-18-21-25;/h9-10,22H,2-8,11-21,25H2,1H3,(H,26,27)(H,28,29);/b10-9-;

SMILES Code

O=C(N[C@H](CCCCN)C(O)=O)CCCCCCC/C=C\CCCCCCCC.[Na]

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

>3 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

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Product Data

Product Data

Instruction

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Biological target:

Oleoyl-D-lysine sodium is an inhibitor of glycine transporter 2a (GlyT2a).

In vitro activity:

For 33 (oleoyl-D-lysine), GlyT2 was potently inhibited (IC50 48.3 nM), while little inhibition of GlyT1 was seen at maximal concentrations (3 μM). This study also tested 33 at Nav, Cav channels, and α7 nicotinic acetylcholine receptors (Table 3S) which are known pain target to rule out analgesia through this mechanism, and no significant inhibition was observed. The cannabinoid receptors, CB1 and CB2, as well as the sphingosine-1-phosphate receptor are targeted by similar lipid based ligands, such as anandamide, and so these receptors were also screened for 33 activity (Table 4S), but no activity as either an agonist or antagonist was observed for all three receptors. Reference: J Med Chem. 2019 Mar 14;62(5):2466-2484. https://pubmed.ncbi.nlm.nih.gov/30714733/

In vivo activity:

Here, intraperitoneally administered oleoyl-D-lysine, a lipid-based GlyT2 inhibitor, was characterized in mouse models of acute (hot plate), inflammatory (complete Freund's adjuvant), and chronic neuropathic (chronic constriction injury) pain. Oleoyl-D-lysine produced near complete antiallodynia for chronic neuropathic pain, but no antiallodynia/analgesia in inflammatory or acute pain. Oleoyl-D-lysine (30 mg/kg) did not cause any respiratory depression, a problematic side effect of opiates. These results show the safe and effective reversal of neuropathic pain in mice by oleoyl-D-lysine and provide evidence for a distinct role of glycine in chronic pain over acute or short-term pain conditions. Reference: J Pharmacol Exp Ther. 2022 Sep;382(3):246-255. https://pubmed.ncbi.nlm.nih.gov/35779948/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	23.11
	DMSO	30.0	69.34
	Ethanol	50.0	115.57
	PBS (pH 7.2)	0.3	0.58

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 432.62 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.

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

Formulation protocol:

1. Mostyn SN, Rawling T, Mohammadi S, Shimmon S, Frangos ZJ, Sarker S, Yousuf A, Vetter I, Ryan RM, Christie MJ, Vandenberg RJ. Development of an N-Acyl Amino Acid That Selectively Inhibits the Glycine Transporter 2 To Produce Analgesia in a Rat Model of Chronic Pain. J Med Chem. 2019 Mar 14;62(5):2466-2484. doi: 10.1021/acs.jmedchem.8b01775. Epub 2019 Feb 20. PMID: 30714733; PMCID: PMC6420064. 2. Wilson BS, Peiser-Oliver J, Gillis A, Evans S, Alamein C, Mostyn SN, Shimmon S, Rawling T, Christie MJ, Vandenberg RJ, Mohammadi SA. Peripheral Administration of Selective Glycine Transporter-2 Inhibitor, Oleoyl-D-Lysine, Reverses Chronic Neuropathic Pain but Not Acute or Inflammatory Pain in Male Mice. J Pharmacol Exp Ther. 2022 Sep;382(3):246-255. doi: 10.1124/jpet.122.001265. Epub 2022 Jul 2. PMID: 35779948.

In vitro protocol:

In vivo protocol:

1. Wilson BS, Peiser-Oliver J, Gillis A, Evans S, Alamein C, Mostyn SN, Shimmon S, Rawling T, Christie MJ, Vandenberg RJ, Mohammadi SA. Peripheral Administration of Selective Glycine Transporter-2 Inhibitor, Oleoyl-D-Lysine, Reverses Chronic Neuropathic Pain but Not Acute or Inflammatory Pain in Male Mice. J Pharmacol Exp Ther. 2022 Sep;382(3):246-255. doi: 10.1124/jpet.122.001265. Epub 2022 Jul 2. PMID: 35779948.

1. Mostyn, S.N., Rawling, T., Mohammadi, S., et al. Development of an N-acyl amino acid that selectively inhibits the glycine transporter 2 to produce analgesia in a rat model of chronic pain. J. Med. Chem. 62(5), 2466-2484 (2019).

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Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

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