| Identification | Back Directory | [Name]
Methyl 5'-(hydroxymethyl)-7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5-carboxylate | [CAS]
118159-48-1 | [Synonyms]
SY801
CS-1347
Bicyclol
Bicyclol, SY 801
Bicyclol USP/EP/BP
Methyl 5'-(hydroxymethyl)-7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5-carboxylate
4, 4′-dimethoxy-2, 3, 2′, 3′-bis(methylenedioxy)-6-hydroxymethyl-6′-methoxy-carbonyl biphenyl
[4,4'-Bi-1,3-benzodioxole]-5-carboxylic acid, 5'-(hydroxymethyl)-7,7'-dimethoxy-, methyl ester
methyl 4-[5-(hydroxymethyl)-7-methoxy-1,3-benzodioxol-4-yl]-7-methoxy-1,3-benzodioxole-5-carboxylate | [Molecular Formula]
C19H18O9 | [MDL Number]
MFCD00889471 | [MOL File]
118159-48-1.mol | [Molecular Weight]
390.34 |
| Chemical Properties | Back Directory | [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 | [form ]
powder | [pka]
13.85±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [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 hepatotoxicity1].
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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