Ethoxysanguinarine is a benzophenanthridine alkaloid naturally occurring compound found mainly in Macleaya cordata. Ethoxysanguinarine is a protein phosphatase 2A (CIP2A) inhibitor that can cause apoptosis and inhibit the viability of colorectal cancer/tumor cells.

Physicochemical Properties

Molecular Formula	C22H19NO5
Molecular Weight	377.3900
Exact Mass	377.126
CAS #	28342-31-6
Related CAS #	28342-31-6
PubChem CID	5317235
Appearance	White to yellow solid
Density	1.5±0.1 g/cm3
Boiling Point	563.7±50.0 °C at 760 mmHg
Melting Point	210-212℃(ethanol)
Flash Point	169.0±27.3 °C
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.724
LogP	4.45
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Heavy Atom Count	28
Complexity	589
Defined Atom Stereocenter Count	0
SMILES	O(C([H])([H])C([H])([H])[H])C1([H])C2C3=C(C([H])=C([H])C=2C2C([H])=C([H])C4=C([H])C5=C(C([H])=C4C=2N1C([H])([H])[H])OC([H])([H])O5)OC([H])([H])O3
InChi Key	FCEXWTOTHXCQCQ-UHFFFAOYSA-N
InChi Code	InChI=1S/C22H19NO5/c1-3-24-22-19-13(6-7-16-21(19)28-11-25-16)14-5-4-12-8-17-18(27-10-26-17)9-15(12)20(14)23(22)2/h4-9,22H,3,10-11H2,1-2H3
Chemical Name	23-ethoxy-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
Synonyms	Ethoxysanguinarine
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	CIP2A; Apoptosis
ln Vitro	Ethoxysanguinarine has an IC50 of 9.37 μM (for SW480 cells), 7.19 μM (for HCT116 cells), 6.55 M (for HT69 cells), and 3.57 μM (for SW620 cells)[1]. Ethoxysanguinarine (3 μM or 5 μM, 24 h) down-regulates phospho-Akt and reduces CIP2A/PP2A/Akt pathway expression in the SW620 and HT29 cells[1]. Ethoxysanguinarine (3 μM or 5 μM, 24 h) increases PP2A activity and prevents phosphorylation of the protein kinase B downstream of CIP2A. [1]. Ethoxysanguinarine (1-3 μM or 4.5-5 μM, 24 h) decreases CIP2A transcription (protein level) and induces CIP2A proteolysis in the SW620 and HT29 cells[1].
ln Vivo	Ethoxysanguinarine (0.5 mg/kg; s.c.; 5 times per week; 4 weeks) inhibits the development of colorectal cancer (CRC) xenograft tumors in mice[1].
References	[1]. Ethoxysanguinarine inhibits viability and induces apoptosis of colorectal cancer cells by inhibiting CIP2A. Int J Oncol. 2018 Mar 16.

Solubility Data

Solubility (In Vitro)

DMSO: ~60 mg/mL (159.0 mM) H2O: < 0.1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (5.51 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.08 mg/mL (5.51 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (5.51 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6498 mL	13.2489 mL	26.4978 mL
	5 mM	0.5300 mL	2.6498 mL	5.2996 mL
	10 mM	0.2650 mL	1.3249 mL	2.6498 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.