Abstract
By examining natural-abundance 13C and 15N solid-state nuclear magnetic resonance (NMR) spectra of acid-precipitated chloroquine−ferriprotoporphyrin IX (CQ−FPIX) aggregates, the first direct evidence is provided for CQ−FPIX complexes in the solid state, formed in a physiologic aqueous solution that mimics the environment inside the digestive vacuole of the malaria parasite. The 13C spectra demonstrate a loss of signal from aromatic sites, whereas 15N experiments indicate the disappearance of the signal from the N atom of the quinoline ring. These signal losses are due to the paramagnetic Fe(III) center of FPIX. In addition, contact shifts are also observed for both 13C and 15N spectra, suggesting the formation of a covalent complex between CQ and FPIX in the solid state.
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