Special Section on Selected Topics in Biophotonics: Photodynamic Therapy and Optical Micromanipulation for Biophotonics

Structural analysis of the antimalarial drug halofantrine by means of Raman spectroscopy and density functional theory calculations

[+] Author Affiliations
Torsten Frosch, Jürgen Popp

Friedrich-Schiller-Universität Jena, Institut für Physikalische Chemie, Helmholtzweg 4, Jena, D-07743 Germany and Institut für Photonische Technologien, Albert-Einstein-Straße 9, Jena, D-07745 Germany

J. Biomed. Opt. 15(4), 041516 (July 07, 2010). doi:10.1117/1.3432656
History: Received October 01, 2009; Revised October 29, 2009; Accepted November 05, 2009; Published July 07, 2010; Online July 07, 2010
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The structure of the antimalarial drug halofantrine is analyzed by means of density functional theory (DFT) calculations, IR, and Raman spectroscopy. Strong, selective enhancements of the Raman bands of halofantrine at 1621 and 1590cm1 are discovered by means of UV resonance Raman spectroscopy with excitation wavelength λexc=244nm. These signal enhancements can be exploited for a localization of small concentrations of halofantrine in a biological environment. The Raman spectrum of halofantrine is calculated by means of DFT calculations [B3LYP6-311+G(d,p)]. The calculation is very useful for a thorough mode assignment of the Raman bands of halofantrine. The strong bands at 1621 and 1590cm1 in the UV Raman spectrum are assigned to combined CC stretching vibrations in the phenanthrene ring of halofantrine. These bands are considered as putative marker bands for ππ interactions with the biological target molecules. The calculation of the electron density demonstrates a strong distribution across the phenanthrene ring of halofantrine, besides the electron withdrawing effect of the Cl and CF3 substituents. This strong and even electron density distribution supports the hypothesis of ππ stacking as a possible mode of action of halofantrine. Complementary IR spectroscopy is performed for an investigation of vibrations of polar functional groups of the halofantrine molecule.

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© 2010 Society of Photo-Optical Instrumentation Engineers

Citation

Torsten Frosch and Jürgen Popp
"Structural analysis of the antimalarial drug halofantrine by means of Raman spectroscopy and density functional theory calculations", J. Biomed. Opt. 15(4), 041516 (July 07, 2010). ; http://dx.doi.org/10.1117/1.3432656


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