5-Hydroxy-2-methyl-1,4-naphthochinon

Bezeichnung:5-Hydroxy-2-methyl-1,4-naphthochinon

CAS-Nr481-42-5

Englisch Name:PLUMBAGIN

CBNumberCB4144779

SummenformelC11H8O3

Molgewicht188.18

MOL-Datei481-42-5.mol

Synonyma

5-Hydroxy-2-methyl-1,4-naphthochinon

5-Hydroxy-2-methyl-1,4-naphthochinon physikalisch-chemischer Eigenschaften

Schmelzpunkt	76-78 °C(lit.)
Siedepunkt	283.17°C (rough estimate)
Dichte	1.354
Brechungsindex	1.6310 (estimate)
storage temp.	-20°C
Löslichkeit	very faint turbidity in hot Methanol
pka	6.70±0.20(Predicted)
Aggregatzustand	Crystals or Crystalline Powder
Farbe	Orange
Merck	7538
Stabilität	Hygroscopic
LogP	2.450 (est)
EPA chemische Informationen	1,4-Naphthalenedione, 5-hydroxy-2-methyl- (481-42-5)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25-34-36/37/38
S-Sätze:	22-26-36/37/39-45-37/39-28A
RIDADR	UN 2923 8/PG 2
WGK Germany	3
RTECS-Nr.	QL8500000
Hazard Note	Toxic
HazardClass	6.1(a)
PackingGroup	II
HS Code	29146990
Toxizität	LD50 i.p. in mice: ~0.015 g/kg (Debray)

Gefahreninformationscode (GHS)

PLUMBAGIN Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
Plumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.
Chemische Eigenschaften
ORANGE CRYSTALLINE POWDER OR CRYSTALS
Verwenden
Plumbagin from Plumbago indica has been used:
- as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblasts
- as an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiae
- as a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples
Verwenden
antibacterial, antifungal, tuberculostatic; antifeedant (worm)
Definition
ChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.
Allgemeine Beschreibung
Plumbagin is a bioactive naphthoquinone present majorly in Plumbago indica L. It is a quinoid and is also derived from the roots of Plumbago zeylanica?roots.
Biochem/physiol Actions
Plumbagin exhibits various pharmacological activities including antimicrobial, anticancer, anti-atherosclerotic, antidiabetic, anti-inflammatory, hypolipidemic, and neuroprotective activities. It inhibits the signal transducer and activator of transcription 3 (STAT3) signaling and halts the proliferation of esophageal squamous cell carcinoma (ESCC). Plumbagin elicits protective antioxidative functionality in 4-nitroquinoline-N-oxide (NQNO) induced stress in lymphoma. Plumbagin in a nanoemulsion formulation has antiproliferative effect towards prostate cancer.
in vitro
plumbagin exhibited effective cell growth inhibition via inducing cancer cells to undergo g2/m phase arrest and apoptosis. blockade of cell cycle was associated with increased levels of p21 and reduced amounts of cdc2, cdc25c and cyclinb1. plumbagin treatment also found to enhance the levels of inactivated phosphorylated cdc2 and cdc25c. blockade of p53 activity partially decreased plumbagin-induced apoptosis and g2/m arrest, indicating it might be operated by p53-dependent and independent pathway [1].
in vivo
to determine whether plumbagin inhibited the in vivo tumor growth, a549 cells were injected into nude mice. tumor growth inhibition was most evident in mice treated with plumbagin at 2 mg/kg/day, where around 80% reductions in tumor size were observed, in contrast with mice treated with the vehicle. no sign of toxicity was observed in plumbagin-treated mice as judged by monitoring body weight [1].
IC 50
11.69 μm for a549 cells
läuterung methode
It crystallises in yellow needles from aqueous EtOH. It is soluble in organic solvents, it is steam volatile and it sublimes on heating in a vacuum. [Fieser & Dunn J Am Chem Soc 58 572 1936, Beilstein 8 III 2576, 8 IV 2376.]
Einzelnachweise
[1] hsu yl,cho cy,kuo pl,huang yt,lin cc. plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) induces apoptosis and cell cycle arrest in a549 cells through p53 accumulation via c-jun nh2-terminal kinase-mediated phosphorylation at serine 15 in vitro and in vivo. j pharmacol exp ther.2006 aug;318(2):484-94.

PLUMBAGIN Upstream-Materialien And Downstream Produkte

5-Hydroxy-2-methyl-1,4-naphthochinon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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