Sanguinarine chloride

Inhibitor of PP2C and MKP-1 CAS# 5578-73-4

Sanguinarine chloride

Catalog No. BCC6481----Order now to get a substantial discount!

Product Name & Size Price Stock
Sanguinarine chloride: 5mg $81 In Stock
Sanguinarine chloride: 10mg Please Inquire In Stock
Sanguinarine chloride: 20mg Please Inquire Please Inquire
Sanguinarine chloride: 50mg Please Inquire Please Inquire
Sanguinarine chloride: 100mg Please Inquire Please Inquire
Sanguinarine chloride: 200mg Please Inquire Please Inquire
Sanguinarine chloride: 500mg Please Inquire Please Inquire
Sanguinarine chloride: 1000mg Please Inquire Please Inquire
Related Products

Quality Control of Sanguinarine chloride

Number of papers citing our products

Chemical structure

Sanguinarine chloride

3D structure

Chemical Properties of Sanguinarine chloride

Cas No. 5578-73-4 SDF Download SDF
PubChem ID 68635 Appearance Orange powder
Formula C20H14ClNO4 M.Wt 367.78
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Pseudochelerythrine chloride; Sanguinarium chloride
Solubility H2O : < 0.1 mg/mL (insoluble)
DMSO : 5 mg/mL (13.60 mM; Need ultrasonic)
SMILES C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6.[Cl-]
Standard InChIKey GIZKAXHWLRYMLE-UHFFFAOYSA-M
Standard InChI InChI=1S/C20H14NO4.ClH/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;1H/q+1;/p-1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Sanguinarine chloride

1 Corydalis sp. 2 Eschscholzia sp. 3 Sanguinaria sp.

Biological Activity of Sanguinarine chloride

DescriptionSanguinarine chloride is a novel class of anti-Salmonella compounds, it could decrease the production of the SPI-1 type III secretion system main virulence proteins SipA and SipB and prevent the invasion of HeLa cells by Salmonella enterica serovar Typhimurium without affecting the growth of Salmonella. Sanguinarine chloride also shows cytotoxicity to cultured human cells from oral tissue.
TargetsAntifection
In vitro

Natural compound sanguinarine chloride targets the type III secretion system of Salmonella enterica Serovar Typhimurium[Reference: WebLink]

Biochemistry & Biophysics Reports, 2018, 14:149–154.

The type III secretion system (T3SS) is a key virulence mechanism of many Gram-negative bacterial pathogens. Upon contact between bacteria and host cells, T3SS transfers a series of effectors from the bacterial cytosol to host cells. It is widely known that a mutation in T3SS does not impair bacterial growth, thereby avoiding any subsequent development of resistance. Thus, T3SS is expected to be a candidate therapeutic target.
METHODS AND RESULTS:
While developing the T3SS screening method, we discovered that Sanguinarine chloride, a natural compound, could decrease the production of the SPI-1 type III secretion system main virulence proteins SipA and SipB and prevent the invasion of HeLa cells by Salmonella enterica serovar Typhimurium without affecting the growth of Salmonella. Furthermore, Sanguinarine chloride downregulated the transcription of HilA and consequently regulated the expression of the SPI-1 apparatus and effector genes.
CONCLUSIONS:
In summary, our study directly demonstrated that this putative SPI-1 inhibitor belongs to a novel class of anti-Salmonella compounds.

Cytotoxicity of sanguinarine chloride to cultured human cells from oral tissue.[Pubmed: 8829200]

Pharmacol Toxicol. 1996 Jun;78(6):397-403.


METHODS AND RESULTS:
The in vitro cytotoxicity of Sanguinarine chloride, a dental product used in the treatment of gingivitis and plaque, was compared using cell lines and primary cells from oral human tissues. For the established cell lines, Sanguinarine chloride exhibited similar potencies to S-G gingival epithelial cells and to KB carcinoma cells, whereas HGF-1 gingival fibroblasts were more tolerant. However, a gingival primary cell culture was more sensitive to Sanguinarine chloride than were the established cell lines. Detailed studies were performed with the S-G cells. The 24-hr midpoint (NR50) cytotoxicity value towards the S-G cells was 7.6 microM, based on the neutral red cytotoxicity assay; vacuolization and multinucleation were noted. When exposed to Sanguinarine chloride for 3 days, a lag in growth kinetics was first observed at 1.7 microM. Damage to the integrity of the plasma membrane was evident, as leakage of lactic acid dehydrogenase occurred during a 3 hr exposure to Sanguinarine chloride at 0.1275 mM and greater.
CONCLUSIONS:
The cytotoxicity of Sanguinarine chloride to the S-G cells was lessened in the presence of an S9 hepatic microsomal fraction from Aroclor-induced rats or by including fetal bovine serum (15%) in the exposure medium. Progressively increasing the pH from 6.0 to 7.8 enhanced the potency of Sanguinarine chloride, presumably due to the enhanced uptake of the lipophilic alkanolamine form, as compared to that of the cationic iminium form.

Sanguinarine chloride Dilution Calculator

Concentration (start)
x
Volume (start)
=
Concentration (final)
x
Volume (final)
 
 
 
C1
V1
C2
V2

calculate

Sanguinarine chloride Molarity Calculator

Mass
=
Concentration
x
Volume
x
MW*
 
 
 
g/mol

calculate

Preparing Stock Solutions of Sanguinarine chloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.719 mL 13.5951 mL 27.1902 mL 54.3803 mL 67.9754 mL
5 mM 0.5438 mL 2.719 mL 5.438 mL 10.8761 mL 13.5951 mL
10 mM 0.2719 mL 1.3595 mL 2.719 mL 5.438 mL 6.7975 mL
50 mM 0.0544 mL 0.2719 mL 0.5438 mL 1.0876 mL 1.3595 mL
100 mM 0.0272 mL 0.136 mL 0.2719 mL 0.5438 mL 0.6798 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Organizitions Citing Our Products recently

 
 
 

Calcutta University

University of Minnesota

University of Maryland School of Medicine

University of Illinois at Chicago

The Ohio State University

University of Zurich

Harvard University

Colorado State University

Auburn University

Yale University

Worcester Polytechnic Institute

Washington State University

Stanford University

University of Leipzig

Universidade da Beira Interior

The Institute of Cancer Research

Heidelberg University

University of Amsterdam

University of Auckland
TsingHua University
TsingHua University
The University of Michigan
The University of Michigan
Miami University
Miami University
DRURY University
DRURY University
Jilin University
Jilin University
Fudan University
Fudan University
Wuhan University
Wuhan University
Sun Yat-sen University
Sun Yat-sen University
Universite de Paris
Universite de Paris
Deemed University
Deemed University
Auckland University
Auckland University
The University of Tokyo
The University of Tokyo
Korea University
Korea University

Background on Sanguinarine chloride

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].

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.

Featured Products
New Products
 

References on Sanguinarine chloride

Cytotoxicity of sanguinarine chloride to cultured human cells from oral tissue.[Pubmed:8829200]

Pharmacol Toxicol. 1996 Jun;78(6):397-403.

The in vitro cytotoxicity of Sanguinarine chloride, a dental product used in the treatment of gingivitis and plaque, was compared using cell lines and primary cells from oral human tissues. For the established cell lines, Sanguinarine chloride exhibited similar potencies to S-G gingival epithelial cells and to KB carcinoma cells, whereas HGF-1 gingival fibroblasts were more tolerant. However, a gingival primary cell culture was more sensitive to Sanguinarine chloride than were the established cell lines. Detailed studies were performed with the S-G cells. The 24-hr midpoint (NR50) cytotoxicity value towards the S-G cells was 7.6 microM, based on the neutral red cytotoxicity assay; vacuolization and multinucleation were noted. When exposed to Sanguinarine chloride for 3 days, a lag in growth kinetics was first observed at 1.7 microM. Damage to the integrity of the plasma membrane was evident, as leakage of lactic acid dehydrogenase occurred during a 3 hr exposure to Sanguinarine chloride at 0.1275 mM and greater. The cytotoxicity of Sanguinarine chloride to the S-G cells was lessened in the presence of an S9 hepatic microsomal fraction from Aroclor-induced rats or by including fetal bovine serum (15%) in the exposure medium. Progressively increasing the pH from 6.0 to 7.8 enhanced the potency of Sanguinarine chloride, presumably due to the enhanced uptake of the lipophilic alkanolamine form, as compared to that of the cationic iminium form.

Sanguinarine as a potent and specific inhibitor of protein phosphatase 2C in vitro and induces apoptosis via phosphorylation of p38 in HL60 cells.[Pubmed:20208361]

Biosci Biotechnol Biochem. 2010;74(3):548-52.

Sanguinarine, a plant alkaloid, was identified as a potent and specific protein phosphatase (PP) 2C inhibitor. It inhibited PP2C competitively with respect to alpha-casein (Ki=0.68 microM) and showed selectivity for PP2C as compared with PP1, PP2A, and PP2B in vitro. In vivo, sanguinarine showed cytotoxicity toward human promyelocytic leukemia cell line HL60, with an IC(50) value of 0.37 microM, and induced apoptosis through a caspase-3/7-dependent mechanism involving the phosphorylation of p38, a PP2Calpha substrate. The apoptosis activity induced by sanguinarine was partially inhibited by a p38 inhibitor, SB203580, and was involved in the phospho-p38 protein in HL60 cells.

The benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-1.[Pubmed:15753082]

J Biol Chem. 2005 May 13;280(19):19078-86.

Mitogen-activated protein kinase phosphatase-1 (MKP-1) is a dual specificity phosphatase that is overexpressed in many human tumors and can protect cells from apoptosis caused by DNA-damaging agents or cellular stress. Small molecule inhibitors of MKP-1 have not been reported, in part because of the lack of structural guidance for inhibitor design and definitive assays for MKP-1 inhibition in intact cells. Herein we have exploited a high content chemical complementation assay to analyze a diverse collection of pure natural products for cellular MKP-1 inhibition. Using two-dimensional Kolmogorov-Smirnov statistics, we identified sanguinarine, a plant alkaloid with known antibiotic and antitumor activity but no primary cellular target, as a potent and selective inhibitor of MKP-1. Sanguinarine inhibited cellular MKP-1 with an IC50 of 10 microM and showed selectivity for MKP-1 over MKP-3. Sanguinarine also inhibited MKP-1 and the MKP-1 like phosphatase, MKP-L, in vitro with IC50 values of 17.3 and 12.5 microM, respectively, and showed 5-10-fold selectivity for MKP-3 and MKP-1 over VH-1-related phosphatase, Cdc25B2, or protein-tyrosine phosphatase 1B. In a human tumor cell line with high MKP-1 levels, sanguinarine caused enhanced ERK and JNK/SAPK phosphorylation. A close congener of sanguinarine, chelerythrine, also inhibited MKP-1 in vitro and in whole cells, and activated ERK and JNK/SAPK. In contrast, sanguinarine analogs lacking the benzophenanthridine scaffold did not inhibit MKP-1 in vitro or in cells nor did they cause ERK or JNK/SAPK phosphorylation. These data illustrate the utility of a chemical complementation assay linked with multiparameter high content cellular screening.

Description

Sanguinarine chloride, a benzophenanthridine alkaloid derived from the root of Sanguinaria Canadensis, can stimulate apoptosis via activating the production of reactive oxygen species (ROS). Sanguinarine-induced apoptosis is associated with the activation of JNK and NF-κB.

Keywords:

Sanguinarine chloride,5578-73-4,Pseudochelerythrine chloride; Sanguinarium chloride,Natural Products,Protein Ser/Thr Phosphatases, buy Sanguinarine chloride , Sanguinarine chloride supplier , purchase Sanguinarine chloride , Sanguinarine chloride cost , Sanguinarine chloride manufacturer , order Sanguinarine chloride , high purity Sanguinarine chloride

Online Inquiry for:

      Fill out the information below

      • Size:Qty: - +

      * Required Fields

                                      Result: