SANGUINARINE CHLORIDE Chemical Properties

Melting point:

281-285°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

methanol: 20 mg/mL, clear, orange

form 

Orange solid.

color 

Orange to Dark Orange

Stability:

Hygroscopic, Light Sensitive

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36-26

WGK Germany 

3

RTECS 

VP5220000

F 

10

HS Code 

29399990

MSDS

• Language:English Provider:SigmaAldrich

SANGUINARINE CHLORIDE Usage And Synthesis

Uses

Sanguinarium Chloride is a natural product with antimicrobial, anti-inflammatory, and anti-oxidant properties. Sanguinarium Chloride has antiproliferative, pro-apoptosis effects in some cancer cell lines.

Uses

antineoplastic, antiplaque agent

Uses

Sanguinarine chloride hydrate was tested for anti-schistosomal activities against Schistosoma mansoni.⁹ It was tested for anti-lipase activity against Candida rugosa lipase.¹⁰

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biological Activity

sanguinarine chloride is a potent and specific inhibitor of pp2c with ki value of 0.68 μm, and is also a selective and cell-active inhibitor of mkp-1 with ic50 value of 10 μm. sanguinarine is also an allosteric activator of ampk [1][2][3].protein phosphatase 2c (pp2c) is a serine/threonine-specific phosphatase, the activity of which is dependent on mg2+ or mn2+. pp2c dephosphorylates a number of substrates such as cyclin-dependent kinase, mitogen-activated kinase (mapk) and bad. mitogen-activated protein kinase phosphatase-1 (mkp-1) is a dual specificity phosphatase. amp-activated protein kinase (ampk) plays an important role in the regulation of cellular metabolism [1][2][3].sanguinarine chloride is an inhibitor of pp2c and mkp-1, and also an allosteric activator of ampk with antibiotic and antitumor activity. sanguinarine competed with α-casein to inhibit pp2c and exhibited selectivity for pp2c as compared with pp1, pp2a and pp2b. in human promyelocytic leukemia cell line hl60, sanguinarine exhibited cytotoxicity with ic50 value of 0.37 μm and induced apoptosis via a caspase-3/7-dependent mechanism involving the phosphorylation of p38, a pp2c substrate [1]. sanguinarine inhibited mkp-1 and mkp-l with ic50 values of 17.3 and 12.5 μm. in panc-1 human pancreatic cancer cells, sanguinarine increased erk and jnk/sapk phosphorylation [2]. in the mda mb-231 cell line, sanguinarine caused ampk and the downstream acetyl-coa carboxylase (acc) phosphorylation [3]. in lncap and du145 cells, sanguinarine inhibited cell growth, induced g0/g1 phase arrest and apoptosis [4].

Biochem/physiol Actions

Sanguinarine is a benzophenanthridine alkaloid isolated from plants belonging to the family Papaveracea. It exhibits anti-bacterial, anti-fungal, anti-inflammatory and anti-cancer properties. It induces cell cycle arrest and sensitizes cancer cells to apoptosis by activating TNF-related apoptosis inducing ligand.6,7 It inhibits STAT3, MMP-2, MMP-9, interacts with glutathione, induces generation of ROS, disrupts the microtubule assembly and causes DNA damage resulting the death of the cancer cells.6,7,8

storage

Store at +4°C

References

[1]. aburai n, yoshida m, ohnishi m, et al. sanguinarine as a potent and specific inhibitor of protein phosphatase 2c in vitro and induces apoptosis via phosphorylation of p38 in hl60 cells. biosci biotechnol biochem, 2010, 74(3): 548-552.
[2]. vogt a, tamewitz a, skoko j, et al. the benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-1. j biol chem, 2005, 280(19): 19078-19086.
[3]. choi j, he n, sung mk, et al. sanguinarine is an allosteric activator of amp-activated protein kinase. biochem biophys res commun, 2011, 413(2): 259-263.
[4]. adhami vm, aziz mh, reagan-shaw sr, et al. sanguinarine causes cell cycle blockade and apoptosis of human prostate carcinoma cells via modulation of cyclin kinase inhibitor-cyclin-cyclin-dependent kinase machinery. mol cancer ther, 2004, 3(8): 933-940.

SANGUINARINE CHLORIDE(5578-73-4)Related Product Information

• SANGUINARINE CHLORIDE(RG)
• DIHYDROSANGUINARINE(P)
• SANGUINARINE CHLORIDE ISOLATED FROM MACL EAY
• SANGUINARINE NITRATE
• 1-Methylpyridinium chloride
• 7-Hydroxyisoquinoline
• 2-Methoxynaphthalene
• quinoline,hydrochloride
• 2,3-Dihydroxynaphthalene
• 8-Isoquinolinol
• SANGUINARINE CHLORIDE
• 7-METHOXY-ISOQUINOLINE
• 8-Methoxyisoquinoline
• 7,8-BENZOQUINOLINE
• Isoquinoline
• Phenanthridine
• Sanguinarine citrate
• Ethoxysanguinarine