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R5648

Sigma-Aldrich

Rottlerin

Synonyme(s) :

1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one, Mallotoxin

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About This Item

Formule empirique (notation de Hill):
C30H28O8
Numéro CAS:
82-08-6
Poids moléculaire :
516.54
Numéro CE :
201-395-4
Numéro MDL:
MFCD00017361
Code UNSPSC :
12352200
ID de substance PubChem :
24278679
Nomenclature NACRES :
NA.77

Source biologique

plant (Mallotus philippinensis)

Pureté

≥95% (HPLC)

Forme

powder

Pf

200.0 °C

Solubilité

ethanol: 1 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

CC(=O)c1c(O)c(C)c(O)c(Cc2c(O)c3C=CC(C)(C)Oc3c(c2O)C(=O)\C=C\c4ccccc4)c1O

InChI

1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+

Clé InChI

DEZFNHCVIZBHBI-ZHACJKMWSA-N

Informations sur le gène

human ... CDK2(1017)

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Description générale

Rottlerin is extracted from Mallotus philippinensis. It is a protein kinase Cδ (PKCδ) inhibitor. Rottlerin acts as an uncoupler of mitochondrial respiration from oxidative phosphorylation. It has antitumor, autophagy, anti-proliferative, anti-metastasis and anti-invasive properties.

Application

Rottlerin has been used:
  • as a protein kinase C δ (PKCδ) inhibitor for the analysis of protein content and phosphorylation in rats
  • to examine the gene expression of early osteoblast markers
  • to attenuate pyruvate dehydrogenase (PDH) phosphorylation by succinate
  • to depolarise mitochondria
  • to investigate its antitumor activity in pancreatic cancer (PC) cells

Actions biochimiques/physiologiques

Recently, Rottlerin (mallotoxin) has been shown to be a potent activator of the large conductance voltage and Ca2 activated K+ channel and to potently leftward shift the conductance-voltage relationship of the channel. Mallatoxin tested on hERG channels increased both step and tail hERG current by leftward shifting the voltage dependence of hERG activation and slowing channel deactivation. These actions distinguish Mallatoxin as a novel naturally occurring hERG channel activator.

Caractéristiques et avantages

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

13 - Non 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)

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Consulter la Bibliothèque de documents

Rottlerin exhibits antitumor activity via down-regulation of TAZ in non-small cell lung cancer
Zhao Z, et al.
Testing, 8(5), 7827-7827 (2017)
Ruihuan Pan et al.
Cell transplantation, 29, 963689720946020-963689720946020 (2020-08-05)
Astragalus membranaceus (Ast) and ligustrazine (Lig) have a protective effect on lower hemorrhagic transformation induced by pharmaceutical thrombolysis. The cerebral ischemia rat model was induced with autologous blood clot injections. A combination of Ast and Lig, or a protein kinase
Chun-Yin Huang et al.
Arthritis and rheumatism, 64(10), 3344-3354 (2012-06-08)
Thrombin is a key factor involved in the stimulation of fibrin deposition, angiogenesis, and proinflammatory processes. Abnormalities in these processes are primary features of rheumatoid arthritis (RA). The aim of this study was to investigate the intracellular signaling pathways involved
Stephen P Soltoff
Trends in pharmacological sciences, 28(9), 453-458 (2007-08-19)
Rottlerin has been used as a protein kinase Cdelta (PKCdelta)-selective inhibitor in hundreds of studies, on the basis of initial substrate phosphorylation studies in vitro. However, in more recent studies, rottlerin did not block PKCdelta activity but did block other
The unfolded protein response plays a predominant homeostatic role in response to mitochondrial stress in pancreatic stellate cells
Su HY, et al.
Testing, 11(2), e0148999-e0148999 (2016)
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