Interaction of quinoline antimalarial drugs with ferriprotoporphyrin IX, a solid state spectroscopy study

Asghari-Khiavi, Mehdi; Vongsvivut, Jitraporn; Perepichka, Inna; Mechler, Ádám; Wood, Bayden Robert; McNaughton, Don; Bohle, D. Scott

doi:10.1016/j.jinorgbio.2011.08.005

Cited by 23 publications

(25 citation statements)

References 51 publications

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“…Most of the currently available antimalarial drugs act against the formation of hemozoin. [146] An elegant method to study hemozoin formation within single erythrocytes has been developed by the group of Wood and McNaughton. [144] Several hypotheses about the mechanism of the hemozoin formation, which might involve lipid mediation or nucleation by histidine-rich protein HRP2, were investigated by resonance Raman spectroscopy (for at horough review of this early work, please see an article by Wood and co-workers).…”

Section: Cytochromes and Hemoglobinmentioning

confidence: 99%

“…Theresults of the study,w hich were supported by density functional calculations,s howed the formation of as alt bridge between the tertiary amino group of the quinoline and apropionate group of the heme,and different mechanisms of action for different quinoline derivatives. [146] An elegant method to study hemozoin formation within single erythrocytes has been developed by the group of Wood and McNaughton. Cells can be brought into the focus of the exciting laser beam by acoustic levitation.…”

Section: Cytochromes and Hemoglobinmentioning

confidence: 99%

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Label‐Free Molecular Imaging of Biological Cells and Tissues by Linear and Nonlinear Raman Spectroscopic Approaches

et al. 2017

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Raman spectroscopy is an emerging technique in bioanalysis and imaging of biomaterials owing to its unique capability of generating spectroscopic fingerprints. Imaging cells and tissues by Raman microspectroscopy represents a nondestructive and label-free approach. All components of cells or tissues contribute to the Raman signals, giving rise to complex spectral signatures. Resonance Raman scattering and surface-enhanced Raman scattering can be used to enhance the signals and reduce the spectral complexity. Raman-active labels can be introduced to increase specificity and multimodality. In addition, nonlinear coherent Raman scattering methods offer higher sensitivities, which enable the rapid imaging of larger sampling areas. Finally, fiber-based imaging techniques pave the way towards in vivo applications of Raman spectroscopy. This Review summarizes the basic principles behind medical Raman imaging and its progress since 2012.

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Section: Cytochromes and Hemoglobinmentioning

confidence: 99%

Section: Cytochromes and Hemoglobinmentioning

confidence: 99%

Label‐Free Molecular Imaging of Biological Cells and Tissues by Linear and Nonlinear Raman Spectroscopic Approaches

et al. 2017

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“…79 The side chain tertiary amino group of CQ forms a salt bridge with the heme carboxylate in solution ( cf. Scheme ) 78. In line with the lipophilic nature of heme itself,27, 80 the complexes are likely to be lipid‐soluble.…”

Section: Discussionmentioning

confidence: 99%

“…The association of CQ with monomeric heme–Fe III occurs through a π–π interaction 77. Whether the quinoline or side chain nitrogen atoms of CQ also coordinate with iron is a matter of contention, but if there is such a coordination, this must be weak 78. 79 The side chain tertiary amino group of CQ forms a salt bridge with the heme carboxylate in solution ( cf.…”

Section: Discussionmentioning

confidence: 99%

Interactions between Artemisinins and other Antimalarial Drugs in Relation to the Cofactor Model—A Unifying Proposal for Drug Action

et al. 2012

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Artemisinins are proposed to act in the malaria parasite cytosol by oxidizing dihydroflavin cofactors of redox-active flavoenzymes, and under aerobic conditions by inducing their autoxidation. Perturbation of redox homeostasis coupled with the generation of reactive oxygen species (ROS) ensues. Ascorbic acid-methylene blue (MB), N-benzyl-1,4-dihydronicotinamide (BNAH)-MB, BNAH-lumiflavine, BNAH-riboflavin (RF), and NADPH-FAD-E. coli flavin reductase (Fre) systems at pH 7.4 generate leucomethylene blue (LMB) and reduced flavins that are rapidly oxidized in situ by artemisinins. These oxidations are inhibited by the 4-aminoquinolines piperaquine (PPQ), chloroquine (CQ), and others. In contrast, the arylmethanols lumefantrine, mefloquine (MFQ), and quinine (QN) have little or no effect. Inhibition correlates with the antagonism exerted by 4-aminoquinolines on the antimalarial activities of MB, RF, and artemisinins. Lack of inhibition correlates with the additivity/synergism between the arylmethanols and artemisinins. We propose association via π complex formation between the 4-aminoquinolines and LMB or the dihydroflavins; this hinders hydride transfer from the reduced conjugates to the artemisinins. The arylmethanols have a decreased tendency to form π complexes, and so exert no effect. The parallel between chemical reactivity and antagonism or additivity/synergism draws attention to the mechanism of action of all drugs described herein. CQ and QN inhibit the formation of hemozoin in the parasite digestive vacuole (DV). The buildup of heme-Fe(III) results in an enhanced efflux from the DV into the cytosol. In addition, the lipophilic heme-Fe(III) complexes of CQ and QN that form in the DV are proposed to diffuse across the DV membrane. At the higher pH of the cytosol, the complexes decompose to liberate heme-Fe(III) . The quinoline or arylmethanol reenters the DV, and so transfers more heme-Fe(III) out of the DV. In this way, the 4-aminoquinolines and arylmethanols exert antimalarial activities by enhancing heme-Fe(III) and thence free Fe(III) concentrations in the cytosol. The iron species enter into redox cycles through reduction of Fe(III) to Fe(II) largely mediated by reduced flavin cofactors and likely also by NAD(P)H-Fre. Generation of ROS through oxidation of Fe(II) by oxygen will also result. The cytotoxicities of artemisinins are thereby reinforced by the iron. Other aspects of drug action are emphasized. In the cytosol or DV, association by π complex formation between pairs of lipophilic drugs must adversely influence the pharmacokinetics of each drug. This explains the antagonism between PPQ and MFQ, for example. The basis for the antimalarial activity of RF mirrors that of MB, wherein it participates in redox cycling that involves flavoenzymes or Fre, resulting in attrition of NAD(P)H. The generation of ROS by artemisinins and ensuing Fenton chemistry accommodate the ability of artemisinins to induce membrane damage and to affect the parasite SERCA PfATP6 Ca(2+) transporter. Thus, the effect exerted by ...

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“…Die Stärke und Geometrie der Bindung zwischen dem Wirkstoff und dem Porphyrin sind für den Wirkungsgrad wichtig. Die Ergebnisse der Studie, die durch Dichtefunktionalrechnungen gestützt wurden, zeigten die Bildung einer Salzbrücke zwischen der tertiären Aminogruppe der Chinoline und einer Propionatgruppe des Häms sowie verschiedene Wirkmechanismen für verschiedene Chinolinderivate . Eine elegante Methode, die Hämozoin‐Bildung innerhalb einzelner Erythrozyten zu untersuchen, wurde in der Gruppe von Wood und McNaughton entwickelt.…”

Section: Raman‐signalverstärkungunclassified

Markerfreie molekulare Bildgebung biologischer Zellen und Gewebe durch lineare und nichtlineare Raman‐spektroskopische Ansätze

et al. 2017

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Raman‐Spektroskopie ist eine aufstrebende Technik in der Analyse und Bildgebung von Biomaterialien, da sie in der Lage ist, einen einzigartigen spektroskopischen Fingerabdruck zu erzeugen. Die Darstellung von Zellen und Geweben durch Raman‐Mikrospektroskopie stellt einen zerstörungsfreien und markerfreien Ansatz dar. Dabei tragen alle Komponenten zu den Raman‐Signalen bei, die komplexe spektrale Signaturen liefern. Verfahren wie Resonanz‐Raman‐Streuung und oberflächenverstärkte Raman‐Streuung verstärken die Signale und ergeben einfachere Spektren. Raman‐aktive Markierungen können eingeführt werden, um die Spezifität und die Multimodalität zu erhöhen. Nichtlineare kohärente Raman‐Streuung bietet höhere Empfindlichkeiten, die eine schnelle Abbildung größerer Probenflächen ermöglichen. Schließlich eröffnen faserbasierte Bildgebungsverfahren den Weg zu In‐vivo‐Anwendungen der Raman‐Spektroskopie. Dieser Aufsatz fasst die Grundlagen der medizinischen Raman‐Bildgebung und ihre Fortschritte seit 2012 zusammen.

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Interaction of quinoline antimalarial drugs with ferriprotoporphyrin IX, a solid state spectroscopy study

Cited by 23 publications

References 51 publications

Label‐Free Molecular Imaging of Biological Cells and Tissues by Linear and Nonlinear Raman Spectroscopic Approaches

Label‐Free Molecular Imaging of Biological Cells and Tissues by Linear and Nonlinear Raman Spectroscopic Approaches

Interactions between Artemisinins and other Antimalarial Drugs in Relation to the Cofactor Model—A Unifying Proposal for Drug Action

Markerfreie molekulare Bildgebung biologischer Zellen und Gewebe durch lineare und nichtlineare Raman‐spektroskopische Ansätze

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