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P0667

Sigma-Aldrich

Parthenolide

≥98% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C15H20O3
Número de CAS:
20554-84-1
Peso molecular:
248.32
MDL number:
MFCD00134592
UNSPSC Code:
12352200
PubChem Substance ID:
24278621
NACRES:
NA.77

Quality Level

100

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)

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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

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.
Anti-inflammatory agent that inhibits NF-κB activation.

Other Notes

Sesquiterpene lactone found in feverfew (Tanacetum parthenium) and other plants.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
Veera Reddy Konda et al.
Journal of inflammation (London, England), 6, 26-26 (2009-08-29)
Rho iso-alpha acids (RIAA) from hops have been shown to have anti-inflammatory properties. To understand the mechanisms, we evaluated the effect of RIAA in cell signaling pathways and inflammatory markers using various in vitro models. We also investigated their therapeutic
Shanshan Pei et al.
The Journal of biological chemistry, 288(47), 33542-33558 (2013-10-04)
The development of strategies to eradicate primary human acute myelogenous leukemia (AML) cells is a major challenge to the leukemia research field. In particular, primitive leukemia cells, often termed leukemia stem cells, are typically refractory to many forms of therapy.
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