WWL70 | CAS#947669-91-2 | ABHD6 Inhibitor

WWL70
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 510348

CAS#: 947669-91-2

Description: WWL70 is a potent inhibitor of α/β-hydrolase domain 6 (ABHD6) (IC50 = 70 nM), an enzyme which catalyzes the hydrolysis of 2-arachidonylglycerol.

Chemical Structure

WWL70

CAS# 947669-91-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 510348
Name: WWL70
CAS#: 947669-91-2
Chemical Formula: C27H23N3O3
Exact Mass: 437.17
Molecular Weight: 437.500
Elemental Analysis: C, 74.13; H, 5.30; N, 9.60; O, 10.97

Price and Availability

Size	Price	Availability
10mg	USD 150	Ready to ship
25mg	USD 250	Ready to ship
50mg	USD 450	Ready to ship
100mg	USD 650	Ready to ship
200mg	USD 950	Ready to ship
500mg	USD 1650	Ready to ship
1g	USD 2850	Ready to ship
2g	USD 4250	Ready to ship
5g	USD 6950	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: WWL 70; WWL70; WWL-70.

IUPAC/Chemical Name: 4'-carbamoyl-[1,1'-biphenyl]-4-yl methyl(3-(pyridin-4-yl)benzyl)carbamate

InChi Key: QTWNORFUQILKJL-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H23N3O3/c1-30(18-19-3-2-4-24(17-19)22-13-15-29-16-14-22)27(32)33-25-11-9-21(10-12-25)20-5-7-23(8-6-20)26(28)31/h2-17H,18H2,1H3,(H2,28,31)

SMILES Code: CN(C(OC1=CC=C(C2=CC=C(C(N)=O)C=C2)C=C1)=O)CC3=CC=CC(C4=CC=NC=C4)=C3

Appearance: White to off-white 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, not in water

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:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#S7S11C27
View CoA: current batch, Lot#S9S04C23

QC Data:

View QC data: current batch, Lot#S7S11C27
View QC data: current batch, Lot#S9S04C23

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	WWL70 is a selective alpha/beta hydrolase domain 6 (ABHD6) inhibitor with an IC50 of 70 nM.
In vitro activity:	In this study, WWL70 treatment inhibited 2-AG hydrolysis and increased the intracellular levels of 2-AG. WWL70 also significantly reduced the production of PGE2 in LPS-activated BV2 and primary microglia cells. However, the increased PGE2 production was not affected by another newly developed ABHD6 inhibitor KT182, and the inhibitory effect of WWL70 was also observed in BV2 cells with ABHD6 knockdown. These results suggest that the inhibitory effect of WWL70 on PGE2 production in LPS-activated microglia is not dependent on its inhibition of ABHD6 activity. Treatment with WWL70 reduced the expression of both COX2 and mPGES, the metabolic enzymes crucial for PGE2 production from AA. Furthermore, WWL70 directly inhibited the enzymatic activity of microsomal PGE2 biosynthesis. Reference: J Neuroinflammation. 2017; 14: 7. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5234251/
In vivo activity:	The increased activation of microglia and astrocytes in the DRG, sciatic nerve, and dorsal horn of the lumbar spinal cord of the CCI (chronic constriction injury) vehicle group indicates the importance of glial activation in CCI-induced neuropathic pain. Considering the inhibitory effect of WWL70 on microglial activation in previous studies, the possibility of WWL70 in the treatment of neuropathic pain was explored. As anticipated, systemic administration of WWL70 to mice with CCI dramatically reduced microglia and astrocyte activation in the spinal cord dorsal horn and macrophage infiltration in the sciatic nerve and DRG. Moreover, the reduced activation of glial cells by WWL70 treatment after CCI further alleviated the release of pro-nociceptive mediators to facilitate pain relief. These results are consistent with several recent studies indicating spinal microgliosis and macrophage accumulation in DRG and sciatic nerve contribute to pain hypersensitivity after peripheral nerve injury. Reference: J Neuroinflammation. 2018; 15: 9. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5759843/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	7.6	17.30
	DMF	2.0	4.57
	DMF:PBS (pH 7.2) (1:3)	0.2	0.46

Preparing Stock Solutions

The following data is based on the product molecular weight 437.50 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. Tanaka M, Moran S, Wen J, Affram K, Chen T, Symes AJ, Zhang Y. WWL70 attenuates PGE2 production derived from 2-arachidonoylglycerol in microglia by ABHD6-independent mechanism. J Neuroinflammation. 2017 Jan 10;14(1):7. doi: 10.1186/s12974-016-0783-4. PMID: 28086912; PMCID: PMC5234251. 2. Wen J, Jones M, Tanaka M, Selvaraj P, Symes AJ, Cox B, Zhang Y. WWL70 protects against chronic constriction injury-induced neuropathic pain in mice by cannabinoid receptor-independent mechanisms. J Neuroinflammation. 2018 Jan 8;15(1):9. doi: 10.1186/s12974-017-1045-9. PMID: 29310667; PMCID: PMC5759843. 3. Tchantchou F, Zhang Y. Selective inhibition of alpha/beta-hydrolase domain 6 attenuates neurodegeneration, alleviates blood brain barrier breakdown, and improves functional recovery in a mouse model of traumatic brain injury. J Neurotrauma. 2013 Apr 1;30(7):565-79. doi: 10.1089/neu.2012.2647. Epub 2013 Apr 5. PMID: 23151067; PMCID: PMC3636589.
In vitro protocol:	1. Tanaka M, Moran S, Wen J, Affram K, Chen T, Symes AJ, Zhang Y. WWL70 attenuates PGE2 production derived from 2-arachidonoylglycerol in microglia by ABHD6-independent mechanism. J Neuroinflammation. 2017 Jan 10;14(1):7. doi: 10.1186/s12974-016-0783-4. PMID: 28086912; PMCID: PMC5234251.
In vivo protocol:	1. Wen J, Jones M, Tanaka M, Selvaraj P, Symes AJ, Cox B, Zhang Y. WWL70 protects against chronic constriction injury-induced neuropathic pain in mice by cannabinoid receptor-independent mechanisms. J Neuroinflammation. 2018 Jan 8;15(1):9. doi: 10.1186/s12974-017-1045-9. PMID: 29310667; PMCID: PMC5759843. 2. Tchantchou F, Zhang Y. Selective inhibition of alpha/beta-hydrolase domain 6 attenuates neurodegeneration, alleviates blood brain barrier breakdown, and improves functional recovery in a mouse model of traumatic brain injury. J Neurotrauma. 2013 Apr 1;30(7):565-79. doi: 10.1089/neu.2012.2647. Epub 2013 Apr 5. PMID: 23151067; PMCID: PMC3636589.

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1: Alhouayek M, Masquelier J, Cani PD, Lambert DM, Muccioli GG. Implication of the anti-inflammatory bioactive lipid prostaglandin D2-glycerol ester in the control of macrophage activation and inflammation by ABHD6. Proc Natl Acad Sci U S A. 2013 Oct 22;110(43):17558-63. doi: 10.1073/pnas.1314017110. Epub 2013 Oct 7. PubMed PMID: 24101490; PubMed Central PMCID: PMC3808642.

2: Tchantchou F, Zhang Y. Selective inhibition of alpha/beta-hydrolase domain 6 attenuates neurodegeneration, alleviates blood brain barrier breakdown, and improves functional recovery in a mouse model of traumatic brain injury. J Neurotrauma. 2013 Apr 1;30(7):565-79. doi: 10.1089/neu.2012.2647. Epub 2013 Apr 5. PubMed PMID: 23151067; PubMed Central PMCID: PMC3636589.

3: Straiker A, Hu SS, Long JZ, Arnold A, Wager-Miller J, Cravatt BF, Mackie K. Monoacylglycerol lipase limits the duration of endocannabinoid-mediated depolarization-induced suppression of excitation in autaptic hippocampal neurons. Mol Pharmacol. 2009 Dec;76(6):1220-7. doi: 10.1124/mol.109.059030. Epub 2009 Sep 18. PubMed PMID: 19767452; PubMed Central PMCID: PMC2784730.

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