Raman and infrared characterization of the vibrational properties of the antimalarial drug artemisinin

Abstract

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 d-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.

Recent advances in linear and non‐linear Raman spectroscopy. Part III

“…Eight alternating polar/nonpolar peptides derived from β-sheet EAK-16 were studied by Tinti et al [104] for their possible use as biomimetic materials due to their self-assembling properties. Moroni et al [105] performed a Raman and infrared spectroscopic characterisation of the vibrational properties of artemisinin, one of the most powerful new generation antimalarial drugs. The vibrational data of artemisinin and its derivative artemether and δ-valerolactone have been analysed by comparison with ab initio calculations.…”

Raman spectroscopy and related techniques: state of the art and future directions in Italy

“…During the GNSR meeting many papers were presented on biomimetic materials that 'mimic' natural biological systems and tissues, 20,21 drugs' characterizations and metallomics that is the study of free metal ions in cellular compartments. 22,23 Last, but not least, many presentations were made on the application of Raman spectroscopy in cultural heritages. Of course, this is a particular heartfelt topic in Italy for the conservation, restoration and classification of numerous artworks.…”

FT-IR and FT-Raman Spectral Investigation and DFT Computations of Pharmaceutical Important Molecule: Ethyl 2-(4-Benzoyl-2,5- Dimethylphenoxy) Acetate

“…In recent years, there has been an increasing interest in the application of DFT calculations to pharmaceutical drugs as calculations provide additional interpretation of the vibrational spectroscopic data collected [14][15][16][17]. During the past decade, DFT [18] has been accepted by the ab initio quantum chemistry community as a popular approach for the computation of molecular structure, vibrational frequencies and energies of chemical reactions.…”