Description
Sanguinarine caused cell death in a dose dependent manner in all neuroblastoma cell lines except SK-N-BE(2) with rates of 18% in SH-SY5Y and 21% in Kelly human neuroblastoma cells. Treatment with sanguinarine, but not berberine, inhibited the proliferation of Rac1b cells, which was accompanied by significantly increased the level of PARP-89, and decreased both the level of cyclin-D1 and the percentage of BrdU positive cells. Sanguinarine treatment resulted in a reduction of cell migration, in a dose-dependent inhibition of cell viability and in the induction of cell death by apoptosis in both human (MDA-MB-231 cells) and mouse (A17 cells) in vitro models of BLBC.
SG pretreatment significantly increased the survival rate of mice from 25% to 58%, 75% and 91% respectively. The production of PGE2 in BALF, the lung MPO activity and the (W/D) weight ratios were also markedly reduced. In addition, immunohistochemical analysis showed that the expression of COX-2 was significantly suppressed in vivo. oral administration of sanguinarine reduced the development and growth of A17 transplantable tumors in FVB syngeneic mice.
Synonyms
Pseudochelerythrine; Sanguinarin
IUPAC Name
24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
Molecular Formula
C20H14NO4+
Canonical SMILES
C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
InChI
InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
InChIKey
INVGWHRKADIJHF-UHFFFAOYSA-N
Boiling Point
483.53°C (rough estimate)
Density
1.3463 g/cm3(rough estimate)
Solubility
Chloroform (Slightly), DMSO (Slightly)
Storage
Keep in dark place,Sealed in dry,Room Temperature
Definition
Sanguinarine is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadendid. Limited available evidence indicates that it may be used to prevent and treat UV-induced
skin damage. Specifically, topical application of sanguinarine on the skin of SKH-1 hairless mice before or after UVB irradiation resulted in significantly lower UVB-mediated skin edema, skin hyperplasia and
infiltration of leukocytes, and markers of oxidative stress (e.g., H2O2).
Refractive Index
1.5180 (estimate)
Toxicity
LD50 oral in rat: 1660mg/kg
Uses
Sanguinarium induces HO-1 expression thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.