How does aggregation of doxorubicin molecules affect its solvation and membrane penetration?
Literature Information
Sadaf Shirazi-Fard, Amin Reza Zolghadr
Intermolecular interactions of drug molecules can lead to aggregation, which has a significant impact on their application. This problem might escape the attention when studying their solubility as small aggregates might behave almost as single molecules. We studied the aggregation behaviour of doxorubicin (DOX) molecules through density functional (DFT) methods and molecular dynamics (MD) simulations in water, dimethylformamide (DMF), ethanol (EtOH), and dimethyl sulfoxide (DMSO). We described the degree of aggregation by MD-calculated radial distribution function, combined radial/angular distribution functions, autocorrelation functions, and the number of hydrogen bonds of individual DOX and solvent atoms. MD-calculated diffusion coefficients for DOX decrease along the series water > DMF > EtOH > DMSO (0.101 × 10−9, 0.047 × 10−9, 0.025 × 10−9, and 0.007 × 10−9 m2 s−1, respectively) consistent with increasing aggregation found in the MD simulations. These aggregates have different characters, depending on the DOX⋯solvent interactions, and include hydrogen bonding and π-stacking. Even though the solvation energy of a single DOX molecule in DMSO (−24.8 kcal mol−1) is higher than in other solvents, the formation of larger aggregates in this solvent prevents proper solvation. Further, the orientation of doxorubicin molecules at octanol/water and dipalmitoylphosphatidylcholine (DPPC)/water interfaces was studied with two different orientations from the bivariate maps. In the case of the DPPC/water interface, the anthracycline part points toward the aqueous phase, while this part is oriented almost parallel to the octanol/water interface in DMSO.
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NJC (New Journal of Chemistry) is a broad-based primary journal encompassing all branches of chemistry and its sub-disciplines. It contains full research articles, communications, perspectives and focus articles. This well-established journal, owned by the Centre National de la Recherche Scientifique (CNRS) of France, has been co-published with the Royal Society of Chemistry since January 1998. NJC is the forum for the publication of high-quality, original and significant work that opens new directions in chemistry or other scientific disciplines. In addition to having a significant chemical component, work published in NJC must demonstrate that it will have an impact on areas of research other than that of the reported work.














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