Interaction between artemisinin and heme. A Density Functional Theory study of structures and interaction energies

Density Functional Theory calculations were employed to calculate interaction energies between the heme group and artemisinin. The results suggest a thermodynamically favorable interaction. Malaria is an infectious disease caused by the unicellular parasite Plasmodium sp. Currently, the malaria para...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-05, Vol.16 (9), p.5021-5029
Main Authors: Araújo, Jocley Queiroz, Carneiro, José Walkimar de Mesquita, Araujo, Martha Teixeira de, Leite, Franco Henrique Andrade, Taranto, Alex Gutterres
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiparasitic agents
Artemisinin
Artemisinins - chemistry
Biological and medical sciences
Computer Simulation
DFT
Electron Transport
Heme
Heme - chemistry
Humans
Intermolecular interaction
Malaria
Medical sciences
Models, Chemical
Molecular Conformation
Pharmacology. Drug treatments
Plasmodium
Quantum Theory
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Summary:Density Functional Theory calculations were employed to calculate interaction energies between the heme group and artemisinin. The results suggest a thermodynamically favorable interaction. Malaria is an infectious disease caused by the unicellular parasite Plasmodium sp. Currently, the malaria parasite is becoming resistant to the traditional pharmacological alternatives, which are ineffective. Artemisinin is the most recent advance in the chemotherapy of malaria. Since it has been proven that artemisinin may act on intracellular heme, we have undertaken a systematic study of several interactions and arrangements between artemisinin and heme. Density Functional Theory calculations were employed to calculate interaction energies, electronic states, and geometrical arrangements for the complex between the heme group and artemisinin. The results show that the interaction between the heme group and artemisinin at long distances occurs through a complex where the iron atom of the heme group retains its electronic features, leading to a quintet state as the most stable one. However, for interaction at short distances, due to artemisinin reduction by the heme group, the most stable complex has a septet spin state. These results suggest that a thermodynamically favorable interaction between artemisinin and heme may happen.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2008.03.033