An antileishmanial agent
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Sitamaquine (tosylate)

Item No. 33590

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N1,N1-diethyl-N6-(6-methoxy-4-methyl-8-quinolinyl)-1,6-hexanediamine, 4-monomethylbenzenesulfonate
CAS Number
1019640-33-5
Synonyms
  • WR-6026
Molecular Formula
C21H33N3O • C7H8O3S
Formula Weight
515.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 30 mg/ml
SMILES
O=S(O)(C1=CC=C(C)C=C1)=O.COC2=CC3=C(C)C=CN=C3C(NCCCCCCN(CC)CC)=C2
InChi Code
InChI=1S/C21H33N3O.C7H8O3S/c1-5-24(6-2)14-10-8-7-9-12-22-20-16-18(25-4)15-19-17(3)11-13-23-21(19)20;1-6-2-4-7(5-3-6)11(8,9)10/h11,13,15-16,22H,5-10,12,14H2,1-4H3;2-5H,1H3,(H,8,9,10)
InChi Key
LOBPWLFCZDGYKW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Sitamaquine is an antileishmanial agent.1 It is active against L. donovani, L. infantum, L. mexicana, L. braziliensis, and L. tropica (EC50s = 9.5-19.8 µM). It inhibits mitochondrial complex II, also known as succinate dehydrogenase (SDH), in a cell-free assay when used at concentrations ranging from 10 to 200 µM.2 Sitamaquine (100 µM) increases intracellular levels of reactive oxygen species (ROS) and decreases intracellular ATP levels, as well as induces phosphatidylserine externalization, chromatin fragmentation, and depolarization of the mitochondrial membrane potential, markers of apoptosis, in L. donovani promastigotes.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. López-Martín, C., Pérez-Victoria, J.M., Carvalho, L., et al. Sitamaquine sensitivity in Leishmania species is not mediated by drug accumulation in acidocalcisomes. Antimicrob. Agents Chemother. 52(11), 4030-4036 (2008).

    2. Carvalho, L.J.M., Luque-Ortega, J.R., López-Martín, C., et al. The 8-aminoquinoline analogue sitamaquine causes oxidative stress in Leishmania donovani promastigotes by targeting succinate dehydrogenase. Antimicrob. Agents Chemother. 55(9), 4204-4210 (2011).