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Heteroassembly Ability of Dicationic Ionic Liquids and Neutral Active Pharmaceutical Ingredients.

ABSTRACT: Extensive investigation of interactions and aggregation properties of IL + API systems is necessary to apply ionic liquids (ILs) with different hydrophobic characteristics to drug delivery or in active pharmaceutical ingredient (API) formulations. Therefore, this study aims to investigate the heteroassembly between dicationic ILs ([BisOct(MIM)₂][2X], in which X is Br or BF₄, and [BisOct(BnIM)₂][2Br]), both in the absence and the presence of neutral APIs (salicylic acid, ibuprofen, and paracetamol) with different functional groups. Isothermal titration calorimetry results demonstrate that IL-API associations occur at very low concentrations of IL. These results were reinforced by electrospray ionization mass spectrometry with variable collision-induced dissociation, in which the IL dication interactions with APIs were detected. The strength of the dication-API interaction was determined from E _cm,1/2 data. The aggregation parameters (cac, ?G _agg ^°, and K) between ILs and APIs were evaluated by conductivity. The ¹H NMR data showed that differences in chemical shifts provided relevant insights about interaction sites in both components.

SUBMITTER: Frizzo CP

PROVIDER: S-EPMC6641490 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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Heteroassembly Ability of Dicationic Ionic Liquids and Neutral Active Pharmaceutical Ingredients.

Frizzo Clarissa P CP Bender Caroline R CR Salbego Paulo R S PRS Farias Carla A A CAA Villetti Marcos A MA Martins Marcos A P MAP

ACS omega 20180226 2

Extensive investigation of interactions and aggregation properties of IL + API systems is necessary to apply ionic liquids (ILs) with different hydrophobic characteristics to drug delivery or in active pharmaceutical ingredient (API) formulations. Therefore, this study aims to investigate the heteroassembly between dicationic ILs ([BisOct(MIM)2][2X], in which X is Br or BF4, and [BisOct(BnIM)2][2Br]), both in the absence and the presence of neutral APIs (salicyli ...[more]

PMID: 31458529

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Project description:Fluoroquinolones (FQs) and Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) are two classes of Active Pharmaceutical Ingredients (APIs), widespreadly used in human healthcare and as veterinary drugs, and that have been found throughout the water cycle in the past years. These two classes of APIs are commonly present in aqueous streams in concentrations ranging from ng.L-1 to µg.L-1. Despite such low concentrations, these contaminants tend to bioaccumulate, leading to serious environmental and health issues after chronic exposure. The low concentrations of FQs and NSAIDs in aqueous media also render their difficult identification and quantification, wich may result in an unefficient evaluation of their environmental impact and persistence. Therefore, the development of alternative pre-treatment techniques for their extraction and concentration from aqueous samples is a crucial requirement. In this work, liquid-liquid systems, namely ionic-liquid-based aqueous biphasic systems (IL-based ABS), were tested as simultaneous extraction and concentration platforms of FQs and NSAIDs. ABS composed of imidazolium-, ammonium- and phosphonium-based ILs and a citrate-based salt (C6H5K3O7) were evaluated for the single-step extraction and concentration of three FQs (ciprofloxacin, enrofloxacin and norfloxacin) and three NSAIDs (diclofenac, naproxen and ketoprofen) from aqueous samples. Outstanding one-step extraction efficiencies of APIs close to 100% were obtained. Furthermore, concentration factors of both FQs and NSAIDs were optimized by an appropriate manipulation of the phase-forming components compositions to tailor the volumes of the coexisting phases. Concentration factors of 1000-fold of both FQS and NSAIDs were obtained in a single-step, without reaching the saturation of the IL-rich phase. The concentration of APIs up to the mg.L-1 allowed their easy and straightforward identification and quantification by High-Performance Liquid Chromatography (HPLC) coupled to an UV detector, as shown either with model aqueous samples or real wastewater effluent samples.

Dataset Information

Heteroassembly Ability of Dicationic Ionic Liquids and Neutral Active Pharmaceutical Ingredients.

Publications

Heteroassembly Ability of Dicationic Ionic Liquids and Neutral Active Pharmaceutical Ingredients.

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