A benzophenanthridine alkaloid with diverse biological activities
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6-Methoxydihydrosanguinarine

Item No. 43281

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(-)-13,14-dihydro-14-methoxy-13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine
CAS Number
72401-54-8
Synonyms
  • (-)-Sanguinarine pseudomethanolate
Molecular Formula
C21H17NO5
Formula Weight
363.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/mlDMSO: Slightly soluble: 0.1-1 mg/ml
SMILES
COC1C2=C(OCO3)C3=CC=C2C4=CC=C(C=C5C(OCO5)=C6)C6=C4N1C
InChi Code
InChI=1S/C21H17NO5/c1-22-19-13(4-3-11-7-16-17(8-14(11)19)26-9-25-16)12-5-6-15-20(27-10-24-15)18(12)21(22)23-2/h3-8,21H,9-10H2,1-2H3
InChi Key
MHPDDMNAUJQRSW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $83

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    5 mg

    $330

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    10 mg

    $495

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    25 mg

    $1,032

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    Product Description

    6-Methoxydihydrosanguinarine is a benzophenanthridine alkaloid that has been found in H. hylomeconoides and has diverse biological activities.1,2,3,4 It is active against methicillin-resistant S. aureus (MRSA; MIC = 3.9 µg/ml).1 6-Methoxydihydrosanguinarine (8 µM) induces apoptosis and increases the levels of reactive oxygen species (ROS) in HepG2 hepatocellular carcinoma cells.2 It induces DNA fragmentation in HT-29 colon cancer cells when used at a concentration of 5 µM.3 6-Methoxydihydrosanguinarine (0.75, 1.5, and 3 µM) reduces basal and maximal respiration and ATP production in SKOV3 ovarian cancer cells.4 In vivo, 6-methoxydihydrosanguinarine (5 mg/kg) decreases tumor volume and weight in a Caov-3 ovarian cancer mouse xenograft model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Choi, J.-G., Kang, O.-H., Chae, H.-S., et al. Antibacterial activity of Hylomecon hylomeconoides against methicillin-resistant Staphylococcus aureus. Appl. Biochem. Biotechnol. 160(8), 2467-2474 (2010).

    2. Yin, H.-Q., Kim, Y.-H., Moon, C.-K., et al. Reactive oxygen species-mediated induction of apoptosis by a plant alkaloid 6-methoxydihydrosanguinarine in HepG2 cells. Biochem. Pharmacol. 70(2), 242-248 (2005).

    3. Lee, Y.-J., Yin, H.-Q., Kim, Y.-H., et al. Apoptosis inducing effects of 6-methoxydihydrosanguinarine in HT29 colon carcinoma cells. Arch. Pharm. Res. 27(12), 1253-1257 (2004).

    4. Zhang, H., Shangguan, F., Zhang, L., et al. A novel mechanism of 6-methoxydihydroavicine in suppressing ovarian carcinoma by disrupting mitochondrial homeostasis and triggering ROS/ MAPK mediated apoptosis. Front. Pharmacol. 14, 1093650 (2023).