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Table II.
Comparative properties of chloroquine (CQ) and ferroquine (FQ).
| Properties | CQ | FQ |
|---|---|---|
| Intramolecular hydrogen bond | Yes | Yes |
| Weak base properties (pKa1 and pKa2 values) | 10.03 and 7.94 | 8.19 and 6.99 |
| Neutral and protonated forms at vacuolar pH | One time | Ten times |
| Lipophilicity at pH 5.2 | - 1.2 | - 0.77 |
| Lipophilicity at pH 7.4 | 0.85 | 2.95 |
| Complex with hematin and stoichiometry | Yes (1:1) | Yes (1:1) |
| Interaction with monomeric hematin (log K) | Yes (5.52) | Yes (5.52) |
| Inhibition of β-hematin formation (IRS) | Yes | Yes |
| BHIA50 | 1.9 | 0.78 |
| Production of hydroxyl radicals | No | Yes |
| Activity on CQR clones and isolates | No | Yes |
| Relation with specific molecular resistance markers | Yes | No |
IRS = infrared spectroscopy. BHIA50 = 50% inhibitory concentration for β-hematin inhibition in equivalents of compounds to hemin (Biot et al., 2005).
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