An alkaloid with anticancer and antimalarial activities
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Isomer(s)
19874Tetrandrine
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Cycleanine

Item No. 36020

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(12aR,24aR)-2,3,12a,13,14,15,24,24a-octahydro-5,6,17,18-tetramethoxy-1,13-dimethyl-8,11:20,23-dietheno-1H,12H-[1,10]dioxacyclooctadecino[2,3,4-ij:11,12,13-i'j′]diisoquinoline
CAS Number
518-94-5
Synonyms
  • O,O-Dimethylisochondrodendrine
  • O-Methylnorcycleanine
Molecular Formula
C38H42N2O6
Formula Weight
622.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetone: solubleDichloromethane: solubleDMSO: solubleEthyl Acetate: soluble
SMILES
CN1[C@@](CC2=CC=C3C=C2)([H])C4=C(CC1)C=C(OC)C(OC)=C4OC5=CC=C(C[C@](N(CC6)C)([H])C7=C6C=C(OC)C(OC)=C7O3)C=C5
InChi Code
InChI=1S/C38H42N2O6/c1-39-17-15-25-21-31(41-3)35(43-5)37-33(25)29(39)19-23-7-11-28(12-8-23)46-38-34-26(22-32(42-4)36(38)44-6)16-18-40(2)30(34)20-24-9-13-27(45-37)14-10-24/h7-14,21-22,29-30H,15-20H2,1-6H3/t29-,30-/m1/s1
InChi Key
ANOXEUSGZWSCQL-LOYHVIPDSA-N
Origin
Plant/Stephania japonica (Thunb.) Miers.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Cycleanine is an alkaloid that has been found in T. subcordata and has anticancer and antimalarial activities.1,2 It selectively inhibits the growth of OVCAR-8, A2780, IGROV-1, and OVCAR-4 ovarian cancer cells (IC50s = 10, 7.6, 14, and 7.2 µM, respectively) over non-cancerous ovarian surface epithelial cells (IC50 = 35 µM).1 It also halts the cell cycle at the subG1 phase and induces apoptosis in OVCAR-8 cells. Cycleanine (25 and 50 mg/kg) reduces parasitemia and increases survival in a mouse model of infection with a chloroquine-resistant strain of P. berghei.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Uche, F.I., Drijfhout, F.P., McCullagh, J., et al. Cytotoxicity effects and apoptosis induction by bisbenzylisoquinoline alkaloids from Triclisia subcordata. Phytother. Res. 30(9), 1533-1539 (2016).

    2. Uche, F.I., Guo, X., Okokon, J., et al. In vivo efficacy and metabolism of the antimalarial cycleanine and improved in vitro antiplasmodial activity of semisynthetic analogues. Antimicrob. Agents Chemother. 65(2), e01995-01920 (2021).