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P0667

Sigma-Aldrich

Parthenolide

≥98% (HPLC)

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About This Item

Formule empirique (notation de Hill):
C15H20O3
Numéro CAS:
20554-84-1
Poids moléculaire :
248.32
Numéro MDL:
MFCD00134592
Code UNSPSC :
12352200
ID de substance PubChem :
24278621
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Pf

115-116 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

KTEXNACQROZXEV-ZRPLFPEYSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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.

Autres remarques

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H317

Conseils de prudence

P280 - P302 + P352

Classification des risques

Skin Sens. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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.
P A Spagnuolo et al.
Leukemia, 27(6), 1236-1244 (2013-01-16)
Parthenolide is selectively toxic to leukemia cells; however, it also activates cell protective responses that may limit its clinical application. Therefore, we sought to identify agents that synergistically enhance parthenolide's cytotoxicity. Using a high-throughput combination drug screen, we identified the
Eri Takai et al.
Fertility and sterility, 100(4), 1170-1178 (2013-07-24)
To evaluate the effects of parthenolide on human endometriotic cells and murine endometriotic lesions. Experimental study. University hospital and laboratory of animal science. Twenty women with ovarian endometrioma and 30 mice. Ectopic endometrial tissue from the endometrioma was collected. Human
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
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