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Dihydrosanguinarine

Dihydrosanguinarine

Product ID D3430
Cas No. 3606-45-9
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $63.60 In stock
5 mg $155.00 In stock
25 mg $583.50 In stock
Bulk Quote

Quicklinks

  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

Dihydrosanguinarine (DHS) is a benzophenanthridine alkaloid that is a metabolite of sanguinarine. This compound exhibits a wide variety of antimicrobial activities (anti-parasitic, antifungal, and antibacterial) as well as anticancer and anti-inflammatory properties. DHS is active against Leishmania, Botrytis, Erysiphe, Candida, and various gram positive and gram negative bacteria including MRSA. In leukemia cells, DHS induces dissipation of the mitochondrial membrane potential, resulting in apoptosis and necrosis. DHS also binds DNA sequences containing alternating G and C base pairs. In vitro, DHS also inhibits LPS-induced production of NO and IL-6 and inhibits phosphorylation of ERK1/2 and p38.

Product Info

Cas No.

3606-45-9

Purity

≥98%

Formula

C20H15NO4

Formula Wt.

333.34

IUPAC Name

24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene

Synonym

Dihydro sanguinarine

Solubility

10mM in DMSO

Appearance

White to off white powder

Shipping and Storage

Store Temp

4°C

Ship Temp

Ambient

Downloads

MSDS

D3430 MSDS PDF

Info Sheet

D3430 Info Sheet PDF

References

Chae HS, Kang OH, Keum JH, et al. Anti-inflammatory effects of Hylomecon hylomeconoides in RAW 264.7 cells. Eur Rev Med Pharmacol Sci. 2012 Jul;16 Suppl 3:121-5. PMID: 22957426.

Yao JY, Zhou ZM, Li XL, et al. Antiparasitic efficacy of dihydrosanguinarine and dihydrochelerythrine from Macleaya microcarpa against Ichthyophthirius multifiliis in richadsin (Squaliobarbus curriculus). Vet Parasitol. 2011 Dec 29;183(1-2):8-13. PMID: 21813242.

Feng G, Zhang J, Liu YQ. Inhibitory activity of dihydrosanguinarine and dihydrochelerythrine against phytopathogenic fungi. Nat Prod Res. 2011 Jul;25(11):1082-9. PMID: 21500094.

Choi JG, Kang OH, Chae HS, et al. Antibacterial activity of Hylomecon hylomeconoides against methicillin-resistant Staphylococcus aureus. Appl Biochem Biotechnol. 2010 Apr;160(8):2467-74. PMID: 19578993.

Vrba J, Dolezel P, Vicar J, et al. Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells. Toxicol In Vitro. 2009 Jun;23(4):580-8. PMID: 19346183.

Bai LP, Zhao ZZ, Cai Z, et al. DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine. Bioorg Med Chem. 2006 Aug 15;14(16):5439-45. PMID: 16730995.

Navarro V, Delgado G. Two antimicrobial alkaloids from Bocconia arborea. J Ethnopharmacol. 1999 Aug;66(2):223-6. PMID: 10433482.

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