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| 5mg |
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| Targets |
Ferroquine exerts its parasiticidal effect on Plasmodium by inducing oxidative stress and subsequent destruction of the parasite's membrane. It is also thought to inhibit the formation of hemozoin, a disposal product of heme produced by malaria parasites, which would otherwise be toxic to the Plasmodium cells. This dual mechanism of action—oxidative stress and hemozoin inhibition—makes it effective against chloroquine-resistant strains.
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| ln Vitro |
The IC50 values of ferroquine against non-cancerous MRC-5 and HeLa cancer cells are 24.4 µM and 16.8 µM, respectively, indicating its cytotoxicity[1]. When exposed to 33.3 µM diferroquin after a 24-hour incubation period, all newly transformed Schistosoma worms (NTS) showed a substantial reduction in vitality [1].
Ferroquine shows cytotoxicity against non-cancerous MRC-5 and HeLa cancer cells with IC50 values of 24.4 μM and 16.8 μM, respectively. At a concentration of 33.3 μM, it strongly reduces the viability of newly transformed schistosomula (NTS). Its activity against Plasmodium is attributed to the induction of oxidative stress and membrane destruction, which are key to its parasiticidal effects. |
| ln Vivo |
Ferroquine dosages of 200 and 800 mg/kg decreased the overall worm burden in mice by 19.4% and 35.6%, respectively. Within 24 hours of receiving 800 mg/kg of ferroquine, one of the mice was dead. When mice were given 200 mg/kg RQ, no action was seen. Finally, following FQ-OH treatment, a drop of 17.3% in the overall worm burden was noted. Consequently, adding ferrocenyl or ruthenenyl fragments to chloroquine (CQ) does not make it more effective against schistosomiasis. By contrast, a greater reduction in parasite burden of 72.3% was obtained in S with 200 mg/kg mefloquine (MQ). mice afflicted with Mansoni. greater effects on adult female S. mansoni were also seen in mice given MQ, indicating that these medications interfere with the target in a way that is particular to a given sex. Furthermore, liver metastasis—the migration of worms to the liver—was seen in one FQ-OH-treated animal, along with a large number of dead worms. As a result, in vivo antischistosomiasis activity is weak for ferroquine and FQ-OH [1].
In mouse models of Schistosoma mansoni infection, treatment with Ferroquine at 200 and 800 mg/kg showed low total worm burden reductions of 19.4% and 35.6%, respectively. One mouse treated with 800 mg/kg died within 24 hours post-treatment. At 200 mg/kg, no activity was observed. These results indicate that modification of chloroquine by a ferrocenyl fragment does not significantly increase antischistosomal properties in vivo. |
| Enzyme Assay |
In vitro enzyme assays for Ferroquine are not standard, as its mechanism involves oxidative stress and hemozoin inhibition rather than direct enzyme inhibition. However, its effects on parasite metabolism can be studied by measuring hemozoin formation in cell-free systems. The compound's ability to generate reactive oxygen species (ROS) can be quantified using fluorescent probes in biochemical assays.
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| Cell Assay |
In vitro cellular assays for Ferroquine use Plasmodium falciparum cultures to determine its antimalarial activity and to assess its potency against chloroquine-resistant strains. Cytotoxicity is evaluated in mammalian cell lines (e.g., MRC-5, HeLa) using MTT or similar assays. The compound's ability to induce oxidative stress can be measured by ROS detection using fluorescent dyes in treated cells.
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| Animal Protocol |
In vivo animal models for Ferroquine include Plasmodium-infected mice for antimalarial efficacy studies and Schistosoma mansoni-infected mice for antischistosomal activity assessment. In these models, the compound is administered orally or via injection, and parasite burden is quantified after treatment. These studies help determine the in vivo efficacy and toxicity profile of the compound.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for Ferroquine are limited. As a ferrocenyl analogue of chloroquine, it is expected to have similar absorption, distribution, metabolism, and excretion properties to chloroquine. It is likely to be well-absorbed orally and extensively distributed in tissues. The compound is metabolized in the liver, and its metabolites are excreted in urine. Its half-life and bioavailability are subjects of ongoing research.
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| Toxicity/Toxicokinetics |
Ferroquine is classified as an irritant to the eyes and skin, and may cause respiratory irritation. In mouse studies, a dose of 800 mg/kg was lethal to one treated animal. Its toxicity profile is similar to that of other antimalarial agents, with potential for gastrointestinal and neurological side effects. Further toxicological studies are needed to fully characterize its safety.
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| References |
[1]. Keiser J, et al. In vitro and in vivo antischistosomal activity of ferroquine derivatives. Parasit Vectors. 2014 Sep 4;7:424
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| Additional Infomation |
Ferroquine is a ferrocenyl analogue of chloroquine with antimalarial activity against chloroquine-resistant Plasmodium falciparum. Its mechanism involves inducing oxidative stress and inhibiting hemozoin formation. It has been studied in preclinical models for both antimalarial and antischistosomal activity. The compound is a research tool for studying drug resistance mechanisms in malaria and for developing new antimalarial therapies.
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| Molecular Formula |
C23H24CLFEN3
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| Molecular Weight |
433.76
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| Exact Mass |
433.1
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| CAS # |
185055-67-8
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| PubChem CID |
140118553
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| Appearance |
Light yellow to orange solid powder
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| LogP |
4.729
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
28
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| Complexity |
419
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1=CC=C2C(NC[C-]34[Fe+2]56789%10%11([CH-]%12[CH]8=[CH]9[CH]%10=[CH]%11%12)C3(CN(C)C)=[CH]5[CH]6=[CH]47)=CC=NC2=C1
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| InChi Key |
DDENDDKMBDTHAX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H19ClN3.C5H5.Fe/c1-22(2)12-14-5-3-4-13(14)11-21-17-8-9-20-18-10-15(19)6-7-16(17)18;1-2-4-5-3-1;/h3-10H,11-12H2,1-2H3,(H,20,21);1-5H;/q2*-1;+2
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| Chemical Name |
7-chloro-N-[[2-[(dimethylamino)methyl]cyclopenta-2,4-dien-1-yl]methyl]quinolin-4-amine;cyclopenta-1,3-diene;iron(2+)
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| Synonyms |
SR97193; SSR-97193; SR-97193
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~4.35 mg/mL (~10.03 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.83 mg/mL (1.91 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 8.3 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3054 mL | 11.5271 mL | 23.0542 mL | |
| 5 mM | 0.4611 mL | 2.3054 mL | 4.6108 mL | |
| 10 mM | 0.2305 mL | 1.1527 mL | 2.3054 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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