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Sanguinarine

Sanguinarine

Product ID S0253
Cas No. 2447-54-3
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $54.70 In stock
5 mg $118.40 In stock
25 mg $375.60 In stock
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  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
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Description

Sanguinarine is a benzophenanthridine alkaloid that exhibits a wide variety of beneficial properties, including anticancer, anti-inflammatory, and antibacterial activities. In breast cancer cells, sanguinarine increases levels of tissue inhibitor of metalloproteinase 1 and 2 (TIMP1 and TIMP2) and heme-oxygenase 1 (HO-1), decreases expression of matrix metalloproteinases (MMPs), prostaglandin E2 (PGE2), and COX-2, and inhibits the phosphorylation of Akt and ERK as well as the activation of NF-κB. Sanguinarine also inhibits VEGF release and increases levels of ROS, inducing apoptosis and inhibiting growth of mammary adenocarcinoma cells. In animal models of colitis, this compound decreases expression of IL-6, NF-κB, and TNF-α, resulting in decreases in weight loss, disease activity, and mortality. Sanguinarine increases oxidative stress and induces DNA damage in species of Microcystis, a cyanobacterium, inhibiting cell division. In species of Bacillus, this compound decreases bacterial membrane potential. Sanguinarine may also inhibit tubulin polymerization, allosterically activate AMPK, and inhibit amino acid carboxylase.

Product Info

Cas No.

2447-54-3

Purity

≥98%

Formula

C20H14NO4

Formula Wt.

332.33

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

Synonym

Pseudochelerythrine

Solubility

Soluble in methanol, water (slightly), DMSO (10 mM), and ethanol (5 mM).

Appearance

White to off white powder

Shipping and Storage

Store Temp

4°C

Ship Temp

Ambient

Downloads

MSDS

S0253 MSDS PDF

Info Sheet

S0253 Info Sheet PDF

References

Park SY, Jin ML, Kim YH, et al. Sanguinarine inhibits invasiveness and the MMP 9 and COX 2 expression in TPA-induced breast cancer cells by inducing HO-1 expression. Oncol Rep. 2014 Jan;31(1):497-504. PMID: 24220687.

Shao J, Liu D, Gong D, et al. Inhibitory effects of sanguinarine against the cyanobacterium Microcystis aeruginosa NIES-843 and possible mechanisms of action. Aquat Toxicol. 2013 Oct 15;142-143:257-63. PMID: 24060579.

Dong XZ, Zhang M, Wang K, et al. Sanguinarine inhibits vascular endothelial growth factor release by generation of reactive oxygen species in MCF-7 human mammary adenocarcinoma cells. Biomed Res Int. 2013;2013:517698. PMID: 23762849.

Niu X, Fan T, Li W, et al. Protective effect of sanguinarine against acetic acid-induced ulcerative colitis in mice. Toxicol Appl Pharmacol. 2013 Mar 15;267(3):256-65. PMID: 23352506.

Foss MH, Eun YJ, Grove CI, et al. Inhibitors of bacterial tubulin target bacterial membranes in vivo. Medchemcomm. 2013 Jan 1;4(1):112-119. PMID: 23539337.

Choi J, He N, Sung MK, et al. Sanguinarine is an allosteric activator of AMP-activated protein kinase. Biochem Biophys Res Commun. 2011 Sep 23;413(2):259-63. PMID: 21884681.

Drsata J, Ulrichová J, Walterová D. Sanguinarine and chelerythrine as inhibitors of aromatic amino acid decarboxylase. J Enzyme Inhib. 1996;10(4):231-237. PMID: 8872743.

Wolff J, Knipling L. Antimicrotubule properties of benzophenanthridine alkaloids. Biochemistry. 1993 Dec 7;32(48):13334-9. PMID: 7902132.

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