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R5648

Sigma-Aldrich

Rottlerin

Sinônimo(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

Fórmula empírica (Notação de Hill):
C30H28O8
Número CAS:
82-08-6
Peso molecular:
516.54
Número CE:
201-395-4
Número MDL:
MFCD00017361
Código UNSPSC:
12352200
ID de substância PubChem:
24278679
NACRES:
NA.77

fonte biológica

plant (Mallotus philippinensis)

Ensaio

≥95% (HPLC)

Formulário

powder

pf

200.0 °C

solubilidade

ethanol: 1 mg/mL

temperatura de armazenamento

2-8°C

cadeia de caracteres 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+

chave InChI

DEZFNHCVIZBHBI-ZHACJKMWSA-N

Informações sobre genes

human ... CDK2(1017)

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Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

Potent activator of the large conductance voltage and Ca2+ activated K+ channel; hERG channel activator.
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.

Características e benefícios

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

Código de classe de armazenamento

13 - Non Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
SLBS1540V
SLBN6603V
SLBL9875V
SLBK1298V
SLBD3670V

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Rottlerin exhibits anti-cancer effect through inactivation of S phase kinase-associated protein 2 in pancreatic cancer cells
Su J, et al.
American Journal of Cancer Research, 6(10), 2178-2178 (2016)
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
Brahma N Singh et al.
Biochemical pharmacology, 84(9), 1154-1163 (2012-08-21)
Multiple lines of evidence support the idea that autophagy plays an essential role in the development of drug resistance, self-renewal, differentiation, and tumorigenic potentials of cancer stem cells (CSCs). Rottlerin (ROT) is widely used as a protein kinase C-delta (PKC-δ)
Hyperammonemia alters membrane expression of GluA1 and GluA2 subunits of AMPA receptors in hippocampus by enhancing activation of the IL-1 receptor: underlying mechanisms
Taoro-Gonzalez L, et al.
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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
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