Sitamaquine
Sitamaquine (WR 6026) is an orally active Antileishmanial agent and Succinate dehydrogenase inhibitor. Sitamaquine accumulates in the acidocalcisomes of Leishmania, induces organelle alkalization, and crosses the plasma membrane of Leishmania via temperature- and energy-independent diffusion. Sitamaquine disrupts oxidative phosphorylation in Leishmania, induces mitochondrial depolarization, oxidative stress, elevated intracellular calcium, plasma membrane depolarization, and Apoptosis-like cell death. Sitamaquine can be used in the research of leishmaniasis.
For research use only. We do not sell to patients.
- CAS No.: 57695-04-2
- Formula: C21H33N3O
- Molecular Weight:343.52
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
Biological Activity
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| THP-1 | IC50 |
1 μM
Compound: A
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Antileishmanial activity against intracellular amastigote stage of Leishmania donovani MHOM/IN/00/DEVI infected in human THP1 cells assessed as decrease infected macrophages after 120 hrs by microscopy
Antileishmanial activity against intracellular amastigote stage of Leishmania donovani MHOM/IN/00/DEVI infected in human THP1 cells assessed as decrease infected macrophages after 120 hrs by microscopy
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[PMID: 25846065] |
Sitamaquine (1-30 μM; 15 min) displaces the acidotropic probe Lysotracker Green from acidic organelles of Leishmania donovani L82, Leishmania donovani DD8, Leishmania tropica LCR-L39, and Leishmania tropica SAF-K27 promastigotes, confirming it accumulates in these organelles[1].
Sitamaquine (5-200 μM; 0-20 min) causes a fast, irreversible reduction in intracellular ATP levels in Leishmania donovani 3-Luc promastigotes, with a 50% reduction observed at concentrations above 30 μM 10 minutes post-treatment[2].
Sitamaquine (50-100 μM; 15 min) induces mitochondrial membrane depolarization in Leishmania donovani promastigotes, causing a 3.1-fold decrease in Rhodamine 123 accumulation with 100 μM treatment for 15 minutes, and a 3.4-fold decrease in 47% of parasites with 50 μM treatment for 15 minutes[2].
Sitamaquine (10-200 μM; 1 h) inhibits succinate dehydrogenase activity in a mitochondrion-enriched fraction from Leishmania donovani promastigotes in a dose-dependent manner[2].
Sitamaquine (50-100 μM; 1 h) induces phosphatidylserine externalization, a marker of apoptosis-like death, in Leishmania donovani promastigotes at 100 μM for 1 hour, causing a 1.9-fold increase in apoptotic cells relative to controls[2].
Sitamaquine (50-100 μM; 24 h) increases the sub-G1 DNA population, a marker of chromatin fragmentation, in Leishmania donovani promastigotes[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Leishmania donovani promastigotes
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Concentration:50, 100 μM
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Incubation Time:1 h
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Result:Caused a significant 1.9-fold increase in the percentage of apoptotic (annexin V-positive, propidium iodide-negative) promastigotes (n=3; P<0.02) relative to untreated controls at 100 μM.
Showed no significant difference from controls at 50 μM.
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Cell Line:Leishmania donovani promastigotes
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Concentration:50, 100 μM
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Incubation Time:24 h
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Result:Increased the sub-G1 DNA population, with 17.8% of parasites treated with 50 μM and 38.3% of parasites treated with 100 μM showing sub-G1 DNA content, compared to 10.7% of untreated controls (n=3; P<0.02).
Chemical Information
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CAS No. 57695-04-2
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Molecular Weight 343.52
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Formula C21H33N3O
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SMILES
N=1C=CC(=C2C=C(OC)C=C(NCCCCCCN(CC)CC)C12)C
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Synonyms
WR 6026
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. López-Martín C, et al. Sitamaquine sensitivity in Leishmania species is not mediated by drug accumulation in acidocalcisomes. Antimicrob Agents Chemother. 2008;52(11):4030-4036. [Content Brief]
[2]. Carvalho L, et al. The 8-aminoquinoline analogue sitamaquine causes oxidative stress in Leishmania donovani promastigotes by targeting succinate dehydrogenase. Antimicrob Agents Chemother. 2011;55(9):4204-4210. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
- Sitamaquine
- 57695-04-2
- WR 6026
- WR6026
- WR-6026
- Parasite
- Succinate Dehydrogenase
- Apoptosis
- Calcium Channel
- Mitochondrial Metabolism
- acidocalcisomes
- Leishmania braziliensis
- leishmaniasis
- Leishmania mexicana
- Leishmania donovani
- Leishmania major
- succinate dehydrogenase
- Leishmania infantum
- visceral leishmaniasis
- Leishmania tropica
- Inhibitor
- inhibitor
- inhibit