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Raman and infrared characterization of the vibrational properties of the antimalarial drug artemisinin
Author(s) -
Moroni Laura,
Gellini Cristina,
Miranda Maurizio Muniz,
Salvi Pier Remigio,
Foresti Maria Luisa,
Innocenti Massimo,
Loglio Francesca,
Salvietti Emanuele
Publication year - 2008
Publication title -
journal of raman spectroscopy
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.748
H-Index - 110
eISSN - 1097-4555
pISSN - 0377-0486
DOI - 10.1002/jrs.1880
Subject(s) - artemisinin , chemistry , trioxane , combinatorial chemistry , molecule , plasmodium falciparum , artemether , raman spectroscopy , heme , peroxide , ring (chemistry) , drug discovery , infrared , computational chemistry , stereochemistry , malaria , organic chemistry , biochemistry , physics , optics , copolymer , immunology , biology , enzyme , polymer
Artemisinin is one of the most powerful new generation antimalarial drugs. The active center is the peroxide group of the caged trioxane heterocycle, which either blocks the free heme released by the Plasmodium falciparum parasite or acts on key proteins causing the parasite death. Both processes involve the activation of the 1,2,4‐trioxanic ring through interaction with the Fe(II)–heme complex. Since considerable effort was made to synthesize antimalarial drugs containing the endoperoxide group, it becomes fundamental to know the structural and dynamical properties of artemisinin. For this reason, Raman and Fourier transform (FT) infrared studies have been undertaken here on the vibrational properties of artemisinin, its derivative artemether and δ‐valerolactone, the latter being the molecule mimicking the lactonic ring of artemisinin. The vibrational data of the three molecules have been analyzed through the comparison with ab initio calculations based on DFT/B3‐LYP/cc‐pVDZ procedures. Modes of artemisinin have been correlated with those of component units. Copyright © 2008 John Wiley & Sons, Ltd.