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Safety Information

S3319

Sigma-Aldrich

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:
393569-31-8
Molecular Weight:
487.63
MDL number:
MFCD06411576
UNSPSC Code:
41106300
PubChem Substance ID:
24724605

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

SMILES string

OC(=O)CC[C@@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)CCCCCCc3ccccc3

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

InChI key

KWLUIYFCMHKLKY-NDEPHWFRSA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000054308
031M4604V
098K46071
098K4607
044K4610

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Cancer stem cell phenotype is supported by secretory phospholipase A2 in human lung cancer cells
Bennett DT, et al.
The Annals of Thoracic Surgery, 98(2), 439-446 (2014)
Yanxiao Xiang et al.
PloS one, 8(10), e77909-e77909 (2013-10-17)
Neuroinflammation is involved in various central nervous system (CNS) disorders, including brain infections, ischemia, trauma, stroke, and degenerative CNS diseases. In the CNS inflammation, secretory phospholipase A₂-IIA (sPLA₂-IIA) acts as a mediator, resulting in the generation of the precursors of
Alison L Halpern et al.
Digestive diseases and sciences, 66(3), 784-795 (2020-04-12)
Receptor tyrosine kinases of the epidermal growth factor receptor (EGFR) family such as human epidermal receptor-2 (HER2) are involved in the development and progression of esophageal adenocarcinoma (EAC). Prior studies have demonstrated that group IIa secretory phospholipase A2 (sPLA2 IIa)
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
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
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