Xantocillin

Names

[ CAS No. ]:
580-74-5

[ Name ]:
Xantocillin

[Synonym ]:
XANTHOCILLINX
XANTHOCILINX
Brevicide-x
Ophthocillin
1,4-Bis-(4-hydroxy-phenyl)-2,3-diisocyan-buta-1,3-dien
Xanthocillin
Xantocillin
1,4-bis-(4-hydroxy-phenyl)-2,3-diisocyano-buta-1,3-diene
Brevicid
Brevicide
Ethylene isocyanide,bis(p-hydroxybenzylidene)
(1Z,3Z)-2,3-diisocyano-1,4-bis(4-hydroxyphenyl)buta-1,3-diene
Trianthil

Biological Activity

[Description]:

Xanthocillin is a marine agent extracted from Penicillium commune, induces autophagy through inhibition of the MEK/ERK pathway[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> MAPK/ERK Pathway >> MEK

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Signaling Pathways >> Stem Cell/Wnt >> ERK

[In Vitro]

Xantocillin (SD118-xanthocillin X (1)) (6.9-55.56 µM; 48 hours) has a significant inhibitory effect on the proliferation of HepG2 cells with an IC50 of 22.88 ± 4.76 µM[1]. Xantocillin (SD118-xanthocillin X (1)) (24.3 µM; 12-48 hours) increases the expression of the autophagy-related genes, LC3, and Beclin 1[1]. Cell Proliferation Assay[1] Cell Line: HepG2 cells Concentration: 6.9 µM, 13.89 µM, 27.78 µM, 55.56 µM Incubation Time: 48 hours Result: A concentration-dependent inhibitory effect on cellular growth in the HepG2 cells with the IC50 of 22.88 ± 4.76 µM. Western Blot Analysis[1] Cell Line: HepG2 cells Concentration: 24.3 µM Incubation Time: 12 hours, 24 hours, 48 hours Result: Increased the expression of the autophagy-related genes, LC3, and Beclin 1.

[References]

[1]. Zhao Y,et al. SD118-xanthocillin X (1), a novel marine agent extracted from Penicillium commune, induces autophagy through the inhibition of the MEK/ERK pathway. Mar Drugs. 2012 Jun;10(6):1345-59.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₈H₁₂N₂O₂

[ Molecular Weight ]:
288.30

[ Exact Mass ]:
288.09000

[ PSA ]:
40.46000

[ LogP ]:
2.77980

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KX1625000

CHEMICAL NAME :: Ethylene isocyanide, bis(p-hydroxybenzylidene)-

CAS REGISTRY NUMBER :: 580-74-5

BEILSTEIN REFERENCE NO. :: 3700094

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C18-H12-N2-O2

MOLECULAR WEIGHT :: 288.32

WISWESSER LINE NOTATION :: QR D1UYNU1&YNU1&U1R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 45 mg/kg

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 7,98,1957

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 13500 ug/kg

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

REFERENCE :: PHARAT Pharmazie. (VEB Verlag Volk und Gesundheit, Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.) V.1- 1946- Volume(issue)/page/year: 21,217,1966

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >600 mg/kg

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 7,98,1957

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9500 ug/kg

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

REFERENCE :: PHARAT Pharmazie. (VEB Verlag Volk und Gesundheit, Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.) V.1- 1946- Volume(issue)/page/year: 21,217,1966