Plumbagin

Names

[ CAS No. ]:
481-42-5

[ Name ]:
Plumbagin

[Synonym ]:
2-Methyljuglone
5-hydroxy-2-methyl-[1,4]naphthoquinone
2-methyl-5-hydroxy-1,4-naphthalenedione
Plumbagine
EINECS 207-569-6
Plumbagin from Plumbago indica
2-Methyl-5-hydroxy-1,4-naphthoquinone
Plumbagin
5-hydroxy-2-methyl-1,4-NQ
Plumbagone
Plumbaein
5-hydroxy-2-methylnaphthalene-1,4-dione
MFCD00001682
5-hydroxy-2-methyl-1,4-naphthalenedione
5-Hydroxy-2-methyl-1,4-naphthoquinone

Biological Activity

[Description]:

Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica L, exhibits anticancer and antiproliferative activities[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

Plumbagin (0, 5, 10, and 15 μM) induces apoptosis of prostate cancer cell lines, such as DU145, CWR22rv1 and LNCaP, in a dose-dependent manner[1]. Plumbagin (5, 20 μM) obviously inhibits the invasion of PC3, DU145, and CWR22rv1 cells[1]. Apoptosis Analysis[1] Cell Line: DU145, CWR22rv1, LNCaP and RWPE-1 cells Concentration: 0, 5, 10, and 15 μM Incubation Time: 24 hours Result: Dose-dependently induced apoptosis of DU145, CWR22rv1 and LNCaP, but showed no effect on RWPE-1 cells at up to 20 μM.

[In Vivo]

Plumbagin (2 mg/kg, i.p., five days a week for 11 weeks) inhibits the growth of tumor in male athymic nude mice[1]. Plumbagin (2 mg/kg, i.p., five days a week for 11 weeks) inhibits expression of PKCε, suppresses JAK-2 and Stat3 phosphorylation, and activates Stat3, PCNA, VEGF and MMP-9 in mice[1]. Animal Model: Male athymic nude mice bearing DU145 cells[1] Dosage: 2 mg/kg Administration: I.P. after 3 days post cell implantation, five days a week. Result: Delayed tumor growth by 3 weeks, and reduced tumor weight and volume in mice.

[References]

[1]. Aziz MH, et al. Plumbagin, a medicinal plant-derived naphthoquinone, is a novel inhibitor of the growth and invasion of hormone-refractory prostate cancer. Cancer Res. 2008 Nov 1;68(21):9024-32.

Chemical & Physical Properties

[ Density]:
1.354g/cm3

[ Boiling Point ]:
383.9ºC at 760 mmHg

[ Melting Point ]:
76-78ºC(lit.)

[ Molecular Formula ]:
C₁₁H₈O₃

[ Molecular Weight ]:
188.17900

[ Flash Point ]:
200.2ºC

[ Exact Mass ]:
188.04700

[ PSA ]:
54.37000

[ LogP ]:
1.71750

[ Vapour Pressure ]:
1.92E-06mmHg at 25°C

[ Index of Refraction ]:
1.63

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL8500000

CHEMICAL NAME :: 1,4-Naphthoquinone, 5-hydroxy-2-methyl-

CAS REGISTRY NUMBER :: 481-42-5

BEILSTEIN REFERENCE NO. :: 1870475

LAST UPDATED :: 199709

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C11-H8-O3

MOLECULAR WEIGHT :: 188.19

WISWESSER LINE NOTATION :: L66 BV EVJ C1 GQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 65 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 16 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 100 mg/kg

SEX/DURATION :: female 10 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 300 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 15 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 35 mg/kg

SEX/DURATION :: female 5-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 50 mg/kg

SEX/DURATION :: female 1-5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 500 umol/L

REFERENCE :: JOBAAY Journal of Bacteriology. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1916- Volume(issue)/page/year: 164,1309,1985

Safety Information

[ Symbol ]:

GHS05, GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H314

[ Precautionary Statements ]:
P280-P305 + P351 + P338-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
22-26-36/37/39-45

[ RIDADR ]:
UN 2923 8/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
QL8500000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
2914690090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914690090

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

Antitumorigenic effect of plumbagin by induction of SH2-containing protein tyrosine phosphatase 1 in human gastric cancer cells.

Int. J. Oncol. 46 , 2380-8, (2015)

A recent study reported that plumbagin downregulated the activity of Janus kinase 2 (JAK2)-signal transducer and activator of transcription 3 (STAT3) pathway to show various antitumor effects in multi...

Binding and Anticancer Properties of Plumbagin with Human Serum Albumin.

Chem. Biol. Drug Des. 86 , 362-9, (2015)

Plumbagin has received extensive attention as a promising anticancer drug. Therefore, we investigated the binding and anticancer properties of plumbagin with human serum albumin. Fluorescence results ...

Inhibition of ANO1/TMEM16A Chloride Channel by Idebenone and Its Cytotoxicity to Cancer Cell Lines.

PLoS ONE 10 , e0133656, (2015)

The expression levels of anoctamin 1 (ANO1, TMEM16A), a calcium-activated chloride channel (CaCC), are significantly increased in several tumors, and inhibition of ANO1 is known to reduce cell prolife...