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• W2032163265 abstract "Abstract Irinotecan is an antitumor drug mostly used in the treatment of colorectal cancer. Its efficacy is influenced by the chemical state of the molecule undergoing chemical equilibria, metabolic changes and photodegradation. In this work, we describe the chemical equilibria of the drug in dimethyl sulfoxide (DMSO). The energetic barrier for hindered rotation around the bond connecting the piperidino—piperidino moiety with the camptothecin-like fragment was evaluated. Furthermore, we showed how the molecule aggregates in DMSO solution forming dimeric species able to prevent its degradation. The equilibrium constant for self-aggregation was determined by NMR based on the assumption of the isodesmic model. The formation of a dimer was highlighted by NMR diffusion ordered spectroscopy (NMR-DOSY) experiments at the concentrations used. Structural features of the complex were inferred by NOE and 13 C chemical shift data. Molecular modelling of the complex driven by experimental data, lead to a structure implying the formation of two hydrogen bonds involving the lactone ring whose opening is one of the main causes of drug degradation. This species is probably responsible for the improved stability of the drug at concentrations higher than 1 mM." @default.
• W2032163265 created "2016-06-24" @default.
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• W2032163265 date "2012-04-01" @default.
• W2032163265 modified "2023-09-24" @default.
• W2032163265 title "Aggregation properties and structural studies of anticancer drug Irinotecan in DMSO solution based on NMR measurements" @default.
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• W2032163265 doi "https://doi.org/10.1016/j.molstruc.2012.01.012" @default.
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