Methyl 5'-(hydroxymethyl)-7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5-carboxylate

Product NameMethyl 5'-(hydroxymethyl)-7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5-carboxylate
CAS118159-48-1
MFC19H18O9
MW390.34
EINECS
MOL File118159-48-1.mol

Chemical Properties

Boiling point	608.1±55.0 °C(Predicted)
Density	1.410±0.06 g/cm3(Predicted)
storage temp.	Inert atmosphere,2-8°C
solubility	DMSO: >10mg/mL
pka	13.85±0.10(Predicted)
form	powder
color	white to off-white
InChI	InChI=1S/C19H18O9/c1-22-11-4-9(6-20)13(17-15(11)25-7-27-17)14-10(19(21)24-3)5-12(23-2)16-18(14)28-8-26-16/h4-5,20H,6-8H2,1-3H3
InChIKey	KXMTXZACPVCDMH-UHFFFAOYSA-N
SMILES	O1C2=C(OC)C=C(C(OC)=O)C(C3=C4C(=C(OC)C=C3CO)OCO4)=C2OC1

Safety Information

Hazard Codes	N
Risk Statements	50/53
Safety Statements	60-61
RIDADR	UN 3077 9 / PGIII
RTECS	DT4312000

Usage And Synthesis

Description

Bicyclol is a hepatoprotective agent. It has antiviral activity against hepatitis B (HBV), reducing viral DNA and the secretion of the HBV antigens HBsAg and HBeAg by 59 and 35%, respectively, in infected 2.2.15 HepG2 cells. In vivo, bicyclol reduces duck HBV (DHBV) DNA in DHBV-infected ducks at doses ≥0.4 g/kg. It also reduces the expression of TNF-α and the accumulation of lymphocytes in the liver in a mouse model of liver injury induced by concanavalin A . Oral administration of bicyclol prior to injection of diethylnitrosamine (DEN) and phenobarbital (PB; Item Nos. 9001494 | 20987) prevents formation of DEN/PB-induced hepatocellular carcinomas. It also reduces liver fibrosis in a rat model of bile duct ligation-induced hepatic fibrosis.

Uses

Bicyclol is a novel hepatoprotectant shown to protect against liver injury by inducing Hsps, including Hsp27 and Hsp 70; Anti-inflammatory activity.

in vivo

Bicyclol (50, 100 and 200 mg/kg; p.o.; single dose) has a dose-dependent protective effect against liver damage induced by different drugs in mice^[1]. Bicyclol (50 and 150 mg/kg; p.o.; once a day for 3 days) has a significant protective effect against Acetaminophen (HY-66005) induced mitochondrial damage in mouse hepatocytes^[1]. Bicyclol (150 mg/kg; p.o.; once a day for 3 days) inhibits the expression of Fas/FasL mRNA and the release of TNF-α in mouse hepatocytes induced by ConA and plays an anti-apoptotic role in hepatocytes^[1]. Bicyclol (300 mg/kg; p.o.; once daily for 3 days) alleviates ConA- and Acetaminophen (HY-66005) induced liver damage in mice, reducing serum transaminases, liver necrosis, mitochondrial cytochrome C and apoptosis-inducing factor (AIF) release, and liver DNA fragmentation^[1]. Bicyclol (75 and 150 mg/kg; p.o.; 6 times per week except Sunday for 7 weeks) significantly improves liver damage and fibrosis in rats and mice induces by chronic CCl4 and Dimethylnitosamine hepatotoxicity^1]. Bicyclol (25 and 50 mg/kg; p.o.; once every other day for 4 weeks) alleviates hyperlipidemia and liver damage and inhibites inflammatory signaling pathways in HFD-induced NAFLD mice^[2]. Bicyclol (200 mg/kg; i.p.; 3 times a day for 2 days) inhibits iron-induced apoptosis in the liver of CCl4-induced ALI mice and exerts a hepatoprotective effect^[5].

Animal Model:	CCl4, D-Galactosamine, Acetaminophen-Induced Liver Injury in Mice ^[1]
Dosage:	50, 100 and 200 mg/kg
Administration:	Oral gavage (p.o.) Single dose administration
Result:	Reduced the elevated serum ALT and AST levels in a dose-dependent manner, and also ameliorated the liver lesions.

Animal Model:	Acetaminophen-Induced Liver Injury in Mice ^[1]
Dosage:	50 and 150 mg/kg
Administration:	Oral gavage (p.o.); Once a day for 3 days
Result:	Reduced mitochondrial ultrastructural damage, mitochondrial AST release, mitochondrial fluidity and mitochondrial swelling, and mitochondrial cytochrome C release.

Animal Model:	ConA and acetaminophen-Induced Liver Injury in Mice ^[1]
Dosage:	300 mg/kg
Administration:	Oral gavage (p.o.); Once a day for 3 days
Result:	Induced the expression of HSP70/27 mRNA and protein in mouse liver and activated heat shock factor-1 (HSF1) in mouse liver.

Animal Model:	HFD-induced liver inflammation in mice^[2]
Dosage:	25 and 50 mg/kg
Administration:	Oral gavage (p.o.); once every other day for the last four weeks of the 16-week HFD induction
Result:	Inhibited the expression levels of pro-inflammatory genes IL-6, TNF-α, IL-1β, COX-2, ICAM-1, VCAM-1, and MCP-1.

Animal Model:	CCl4-induced ALI mice^[6].
Dosage:	200 mg/kg
Administration:	Intraperitoneal injection (i.p.); 3 times a day for 2 days
Result:	Inhibited iron accumulation, excessive production of reactive oxygen species, enhanced lipid peroxidation, altered mitochondrial morphology, and decreased GPx4 and xCT protein levels in mouse liver.

References

[1] LIU G T. Bicyclol: a novel drug for treating chronic viral hepatitis B and C.[J]. Medicinal Chemistry, 2009, 5 1: 29-43. DOI: 10.2174/157340609787049316
[2] MIN LI Geng T L. Inhibition of Fas/FasL mRNA expression and TNF-alpha release in concanavalin A-induced liver injury in mice by bicyclol.[J]. World Journal of Gastroenterology, 2004, 10 12: 1775-1779. DOI: 10.3748/wjg.v10.i12.1775
[3] HUA SUN. A novel antihepatitis drug, bicyclol, prevents liver carcinogenesis in diethylnitrosamine-initiated and phenobarbital-promoted mice tumor model.[J]. Journal of Biomedicine and Biotechnology, 2012: 584728. DOI: 10.1155/2012/584728
[4] YONG-ZHAN ZHEN. Protective effect of bicyclol against bile duct ligation-induced hepatic fibrosis in rats.[J]. World Journal of Gastroenterology, 2015, 21 23: 7155-7164. DOI: 10.3748/wjg.v21.i23.7155

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