WWL70
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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

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WWL70
CAS# 947669-91-2

Theoretical Analysis

MedKoo Cat#: 510348
Name: WWL70
CAS#: 947669-91-2
Chemical Formula: C27H23N3O3
Exact Mass: 437.17394
Molecular Weight: 437.5
Elemental Analysis: C, 74.13; H, 5.30; N, 9.60; O, 10.97

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 650.0 Ready to ship
200.0mg USD 950.0 Ready to ship
500.0mg USD 1650.0 Ready to ship
1.0g USD 2850.0 Ready to ship
2.0g USD 4250.0 Ready to ship
5.0g USD 6950.0 Ready to ship
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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

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 7.57 17.3
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 437.5 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
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.

WWL70

10.0mg / USD 150.0


Additional Information