ArticleJournal of the American Chemical Society2013
The single crystal X-ray structure of β-hematin DMSO solvate grown in the presence of chloroquine, a β-hematin growth-rate inhibitor.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 64 citations in OpenAlex.
- Cryo-tomography and 3D Electron Diffraction Reveal the Polar Habit and Chiral Structure of the Malaria Pigment Crystal Hemozoin.ACS central science · 2024Article
- Integrating Pharmacokinetic-Pharmacodynamic Modeling and Physiologically Based Pharmacokinetic Modeling to Optimize Human Dose Predictions for Plasmodium falciparum Malaria: a Chloroquine Case Study.Antimicrobial agents and chemotherapy · 2023Article
- Adsorption to the Surface of Hemozoin Crystals: Structure-Based Design and Synthesis of Amino-Phenoxazine β-Hematin Inhibitors.ChemMedChem · 2022Article
- Heme Detoxification in the Malaria Parasite: A Target for Antimalarial Drug Development.Accounts of chemical research · 2021Review
- Malaria Pigment Crystals: The Achilles' Heel of the Malaria Parasite.ChemMedChem · 2021Review
- Mode of action of quinoline antimalarial drugs in red blood cells infected byProceedings of the National Academy of Sciences of the United States of America · 2019Article
- [(7-chloroquinolin-4-yl)amino]acetophenones and their copper(II) derivatives: Synthesis, characterization, computational studies and antimalarial activity.EXCLI journal · 2019Article
- Chloroquine analogs as antimalarial candidates with potent in vitro and in vivo activity.International journal for parasitology. Drugs and drug resistance · 2018Article
- The Effects of Quinoline and Non-Quinoline Inhibitors on the Kinetics of Lipid-Mediated β-Hematin Crystallization.Langmuir : the ACS journal of surfaces and colloids · 2017Article
- Antimalarials inhibit hematin crystallization by unique drug-surface site interactions.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Characterization and optimization of the haemozoin-like crystal (HLC) assay to determine Hz inhibiting effects of anti-malarial compounds.Malaria journal · 2015Article
- Malarial hemozoin: from target to tool.Biochimica et biophysica acta · 2014Review
- Growth of Large Hematin Crystals in Biomimetic Solutions.Crystal growth & design · 2014Article
- Malarial pigment hemozoin and the innate inflammatory response.Frontiers in immunology · 2014Review
- Article
- Selective binding of antimicrobial porphyrins to the heme-receptor IsdH-NEAT3 of Staphylococcus aureus.Protein science : a publication of the Protein Society · 2013Article
- Dual-functioning antimalarials that inhibit the chloroquine-resistance transporter.Future microbiology · 2013Review
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4 authors at 2 institutions in 1 country.
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Abstract
Single crystals of solvated β-hematin were grown from a DMSO solution containing the antimalarial drug chloroquine, a known inhibitor of β-hematin formation. In addition, a kinetics study employing biomimetic lipid-water emulsion conditions was undertaken to further investigate the effect of chloroquine and quinidine on the formation of β-hematin. Scanning electron microscopy shows that the external morphology of the β-hematin DMSO solvate crystals is almost indistinguishable from that of malaria pigment (hemozoin), and single crystal X-ray diffraction confirms the presence of μ-propionato coordination dimers of iron(III) protoporphyrin IX. The free propionic acid functional groups of adjacent dimers hydrogen bond to included DMSO molecules, rather than forming carboxylic acid dimers. The observed exponential kinetics were modeled using the Avrami equation, with an Avrami constant equal to 1. The decreased rate of β-hematin formation observed at low concentrations of both drugs could be accounted for by assuming a mechanism of drug adsorption to sites on the fastest growing face of β-hematin. This behavior was modeled using the Langmuir isotherm. Higher concentrations of drug resulted in decreased final yields of β-hematin, and an irreversible drug-induced precipitation of iron(III) protoporphyrin IX was postulated to account for this. The model permits determination of the equilibrium adsorption constant (K(ads)). The values for chloroquine (log K(ads) = 5.55 ± 0.03) and quinidine (log K(ads) = 4.92 ± 0.01) suggest that the approach may be useful as a relative probe of the mechanism of action of novel antimalarial compounds.
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