P0667
Parthenolide
≥98% (HPLC), NF-κB activation inhibitor, powder
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Fórmula empírica (notación de Hill):
C15H20O3
Número CAS:
Peso molecular:
248.32
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Servicio técnico
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Permítanos ayudarleNombre del producto
Parthenolide, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
mp
115-116 °C (lit.)
storage temp.
2-8°C
SMILES string
C/C(CC[C@]12[H])=C/CC[C@]3(C)[C@H](O3)[C@]1(OC(C2=C)=O)[H]
InChI
1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-/t11-,12-,13+,15+/m0/s1
InChI key
KTEXNACQROZXEV-ZRPLFPEYSA-N
Gene Information
human ... ELA2(1991), IKBKG(8517), NFKB1(4790), NKAP(79576), NKRF(55922)
Application
Parthenolide has been used:
- in the crystallization with vasohibin 1 (VASH1) to study tubulin detyrosination inhibition
- as an inhibitor of nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) and signal transduction and activation of transcription (STAT) inhibitor to study its effects on the cytoadhesion of CD36-binding Plasmodium falciparum-infected erythrocytes (IECD36)
- as a lipophilic agent to study its effects on the production of interleukin?13 and interferon?γ by peripheral blood-derived CD8+ T cells
Biochem/physiol Actions
Anti-inflammatory agent that inhibits NF-κB activation.
Parthenolide is a sesquiterpene lactone present abundantly in the leaves and flowers of Tanacetum parthenium. It exhibits anti-cancer properties for the treatment of invasive cancers. Parthenolide exhibits therapeutic effects against inflammation and migraine. It plays a role in signal transduction and activation of transcription (STAT)-inhibition-mediated transcriptional repression of pro-apoptotic genes.
Other Notes
Sesquiterpene lactone found in feverfew (Tanacetum parthenium) and other plants.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Skin Sens. 1
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Wieslaw Kozak et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 290(4), R871-R880 (2005-11-19)
Bacterial DNA containing unmethylated cytosine-phosphate-guanosine motif (CpG-DNA) has been identified as a pathogen-associated molecular pattern, which is recognized by Toll-like receptors and activates immune cells to produce cytokines. The aim of the study was to characterize the ability of CpG-DNA
Maria Regina Orofino Kreuger et al.
Anti-cancer drugs, 23(9), 883-896 (2012-07-17)
Sesquiterpene lactones (SLs) constitute a large and diverse group of biologically active plant compounds that possess anti-inflammatory and antitumor activity. The subclass germacranolides is one of the major groups of SLs. It includes parthenolide, a highly cytotoxic SL that is
Akram Ghantous et al.
Drug discovery today, 18(17-18), 894-905 (2013-05-22)
Parthenolide (PTL), a sesquiterpene lactone (SL) originally purified from the shoots of feverfew (Tanacetum parthenium), has shown potent anticancer and anti-inflammatory activities. It is currently being tested in cancer clinical trials. Structure-activity relationship (SAR) studies of parthenolide revealed key chemical