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Cytotoxic Activity of Salicylic Acid-Containing Drug Models with Ionic and Covalent Binding

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N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russia
Institute of Gene Biology, Russian Academy of Sciences, Vavilova str. 34/5, Moscow 119334, Russia
§ D. Rogachev Federal Scientific Clinical Centre of Pediatric Hematology, Oncology and Immunology, Ministry of Health of Russian Federation, Samory Mashela str., Moscow 117198, Russia
Peoples’ Friendship University of Russia, 6 Miklukho-Maklay Street, Moscow 117198, Russian Federation
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, Moscow 119991, Russian Federation
# Saint Petersburg State University, Universitetsky Prospekt 26, Stary Petergof 198504, Russia
Cite this: ACS Med. Chem. Lett. 2015, 6, 11, 1099–1104
Publication Date (Web):September 28, 2015
Copyright © 2015 American Chemical Society

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    Three different types of drug delivery platforms based on imidazolium ionic liquids (ILs) were synthesized in high preparative yields, namely, the models involving (i) ionic binding of drug and IL; (ii) covalent binding of drug and IL; and (iii) dual binding using both ionic and covalent approaches. Seven ionic liquids containing salicylic acid (SA-ILs) in the cation or/and in the anion were prepared, and their cytotoxicity toward the human cell lines CaCo-2 (colorectal adenocarcinoma) and 3215 LS (normal fibroblasts) was evaluated. Cytotoxicity of SA-ILs was significantly higher than that of conventional imidazolium-based ILs and was comparable to the pure salicylic acid. It is important to note that the obtained SA-ILs dissolved in water more readily than salicylic acid, suggesting benefits of possible usage of traditional nonsoluble active pharmaceutical ingredients in an ionic liquid form.

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    • Structural data for [PrMIM-OSal][Cl] (CIF)

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