S3319
sPLA2 inhibitor
Synonym(s):
5-(4-Benzyloxyphenyl)-4S-(7-phenylheptanoylamino)pentanoic acid, KH064
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About This Item
Empirical Formula (Hill Notation):
C31H37NO4
CAS Number:
Molecular Weight:
487.63
UNSPSC Code:
41106300
PubChem Substance ID:
MDL number:
InChI
1S/C31H37NO4/c33-30(16-10-2-1-5-11-25-12-6-3-7-13-25)32-28(19-22-31(34)35)23-26-17-20-29(21-18-26)36-24-27-14-8-4-9-15-27/h3-4,6-9,12-15,17-18,20-21,28H,1-2,5,10-11,16,19,22-24H2,(H,32,33)(H,34,35)/t28-/m0/s1
SMILES string
OC(=O)CC[C@@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)CCCCCCc3ccccc3
InChI key
KWLUIYFCMHKLKY-NDEPHWFRSA-N
assay
≥97.5% (HPLC)
form
powder
storage condition
under inert gas
color
white
mp
133-135 °C
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
Application
sPLA2 inhibitor has been used in:
- human lung adenocarcinoma cells in matrigel invasion assay
- pre-treatment of cultured oligodendrocytes
- the inhibition of secretory phospholipase A2 in lung adenocarcinoma.
sPLA2 inhibitor was used to study the effects on cell proliferation and apoptosis of lung cancer cells and oligodendrocytes.
Biochem/physiol Actions
Orally active, potent secretory Phospholipase A2 (sPLA2; Group IIa) inhibitor.
Secretory phospholipase A2 inhibitor blocks the activation of NF-κB, Akt, p38 MAPK and ERK pathways. It reduces proliferation and induces apoptosis of lung cancer cells and is a potent anti-inflammatory agent. sPLA2 inhibitor prevents deposition of collagen and has anti-fibrotic effects in hypertensive rats.
sPLA2 inhibitor is lipophilic and corresponds to a molecular weight of 487.63 Da. It regulates inflammatory responses and lipoprotein function and may be useful in treating atherosclerosis.
sPLA2 inhibitor (pla2g2a) is an orally active, potent secretory Phospholipase A2 (sPLA2; Group IIa) inhibitor. Secretory phospholipase A2 inhibitor blocks the activation of NF-KB, Akt, p38 MAPK and ERK pathways. sPLA2 inhibitor reduces proliferation and induces apoptosis of lung cancer cells and is a potent anti-inflammatory agent. sPLA2 inhibitor prevents deposition of collagen and has anti-fibrotic effects in hypertensive rats.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Jessica A Yu et al.
Anticancer research, 32(9), 3601-3607 (2012-09-21)
Group IIa secretory phospholipase A2 (sPLA2 IIa) has been implicated in the regulation of metastasis of non-small cell lung cancer (NSCLC) and the present study investigates its contribution to lung cancer growth and progression. PLA2s initiate signaling in several pathways
Discovery of AZD2716: a novel secreted phospholipase A2 (sPLA2) inhibitor for the treatment of coronary artery disease
Giordanetto F, et al.
ACS Medicinal Chemistry Letters, 7(10), 884-889 (2016)
Maung-Maung Thwin et al.
Arthritis research & therapy, 11(5), R138-R138 (2009-09-22)
Secretory phospholipase A2 (sPLA2) and matrix metalloproteinase (MMP) inhibitors are potent modulators of inflammation with therapeutic potential, but have limited efficacy in rheumatoid arthritis (RA). The objective of this study was to understand the inhibitory mechanism of phospholipase inhibitor from
Robert C Reid
Current medicinal chemistry, 12(25), 3011-3026 (2005-12-28)
Phospholipases A2 cleave membrane phospholipids to release arachidonic acid, the precursor to a large family of pro-inflammatory eicosanoids including prostaglandins and leukotrienes that have been proven to exacerbate numerous diseases that have an inflammatory component. Current therapies include NSAIDs' that
Scott Levick et al.
Journal of immunology (Baltimore, Md. : 1950), 176(11), 7000-7007 (2006-05-20)
The development of fibrosis in the chronically hypertensive heart is associated with infiltration of inflammatory cells and cardiac hypertrophy. In this study, an inhibitor of the proinflammatory enzyme, group IIA human secretory phospholipase A2 (sPLA2-IIA), has been found to prevent
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