Physicochemical characterization of choline based ionic liquids with chelating anions

Panić, Jovana; Tot, Aleksandar; Popsavin, Mirjana; Jocić, Ana; Gadžurić, Slobodan

doi:10.1016/j.jct.2018.10.026

Cited by 12 publications

(4 citation statements)

References 22 publications

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“…The syntheses of cholinium lactate ([Ch][Lac]), cholinium nicotinate ([Ch][Nia]), and cholinium taurate ([Ch][Tau]) were performed according to previously described protocols. Cholinium pyruvate ([Ch][Pyr]) was synthesized in this work for the first time by acid–base titration.…”

Section: Methodsmentioning

confidence: 99%

Valorization of Expired Energy Drinks by Designed and Integrated Ionic Liquid-Based Aqueous Biphasic Systems

Dimitrijević

Tavares

Almeida

et al. 2020

ACS Sustainable Chem. Eng.

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Expired energy drinks are rich in bioactive value-added compounds that can be recovered and reused in order to valorize food waste within a circular economy perspective. However, to accomplish such requirements, it is necessary to develop sustainable extraction and recovery processes, which must consist of decreasing the number of steps required or developing integrated strategies. In this work, novel aqueous biphasic systems (ABS) composed of ionic liquids (ILs) and a biocompatible polymer polypropylene glycol (400 g·mol–1, PPG 400) were studied for the simultaneous extraction and recovery of three value-added compounds, namely, caffeine, taurine, and niacin, from expired energy drinks. ILs were designed and synthesized in order to have similar anions to the target compounds, thus allowing enhanced selectivity and biological activity, while avoiding an extra step of separation of these high-value compounds from the IL-rich phase. To this end, cholinium-based ILs comprising the anions lactate, pyruvate, taurate, and nicotinate were synthesized, and their cytotoxicity and ecotoxicity credentials were evaluated. Overall, taurine and niacin are majorly enriched in the IL-rich phase, while caffeine preferentially migrates in the majority of the cases toward the PPG-rich phase. However, caffeine also partitions to the IL-rich phase in the ABS formed by cholinium pyruvate or cholinium nicotinate. The ABS formed by cholinium nicotinate and PPG 400 is the best system identified, allowing the almost complete recovery (recovery efficiencies > 82%) of all target compounds into the IL-rich phase in one step. Furthermore, cholinium nicotinate exhibits marginal cytotoxic potential and is harmless from an ecotoxicological point of view. This system is thus a promising platform to simultaneously extract, recover, and reuse value-added compounds from expired energy drinks without the need of removing the IL or recovering the target compounds from the IL-rich phase, thus contributing to a sustainable and circular food economy.

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Section: Methodsmentioning

confidence: 99%

Valorization of Expired Energy Drinks by Designed and Integrated Ionic Liquid-Based Aqueous Biphasic Systems

Dimitrijević

Tavares

Almeida

et al. 2020

ACS Sustainable Chem. Eng.

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“…By virtue of the fact that the density of ILs dependent upon directly on cation-anion interaction, it can be concluded that denser lidocaine salicylate has a better geometric t of planar aromatic systems and stronger stabilization p-p interactions existence between lidocaine and salicylate than between lidocaine and ibuprofenate. 13 Additionally, a higher thermal expansion coefficient of lidocaine ibuprofenate evidenced a faster movement of the cation from the anion, due to weaker interactions between them.…”

Section: Densitymentioning

confidence: 98%

Physicochemical and structural properties of lidocaine-based ionic liquids with anti-inflammatory anions

et al. 2020

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“…At physiological pH, CK147 contains two positive charges from the quaternary ammonium moieties, and three negative charges from the carboxylates of the Glu-Urea-Lys peptide. Although not zwitterionic due to the charge imbalance, we propose a putative mechanism where the positive quaternary ammonium charges may be masked by inter- or intramolecular electrostatic interactions which neutralize the charges and form unfavorable structural configurations capable of inhibiting both PSMA-binding and CHKA activity ( Figure 10 ) [ 55 ]. The inactivity of CK147 observed in kinase screening was hypothesized to be related to the electrostatic neutralization; likely due to ionization of three carboxylate anions and two quaternary ammonium moieties at physiological pH.…”

Section: Discussionmentioning

confidence: 99%

Novel Non-Congeneric Derivatives of the Choline Kinase Alpha Inhibitor ICL-CCIC-0019

et al. 2021

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Choline kinase alpha (CHKA) is a promising target for the development of cancer therapeutics. We have previously reported ICL-CCIC-0019, a potent CHKA inhibitor with high cellular activity but with some unfavorable pharmacological properties. In this work, we present an active analogue of ICL-CCIC-0019 bearing a piperazine handle (CK146) to facilitate further structural elaboration of the pharmacophore and thus improve the biological profile. Two different strategies were evaluated in this study: (1) a prodrug approach whereby selective CHKA inhibition could be achieved through modulating the activity of CK146, via the incorporation of an ε-(Ac) Lys motif, cleavable by elevated levels of histone deacetylase (HDAC) and cathepsin L (CTSL) in tumour cells; (2) a prostate-specific membrane antigen (PSMA) receptor targeted delivery strategy. Prodrug (CK145) and PSMA-targeted (CK147) derivatives were successfully synthesized and evaluated in vitro. While the exploitation of CK146 in those two strategies did not deliver the expected results, important and informative structure-activity relationships were observed and have been reported.

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Physicochemical characterization of choline based ionic liquids with chelating anions

Cited by 12 publications

References 22 publications

Valorization of Expired Energy Drinks by Designed and Integrated Ionic Liquid-Based Aqueous Biphasic Systems

Valorization of Expired Energy Drinks by Designed and Integrated Ionic Liquid-Based Aqueous Biphasic Systems

Physicochemical and structural properties of lidocaine-based ionic liquids with anti-inflammatory anions

Novel Non-Congeneric Derivatives of the Choline Kinase Alpha Inhibitor ICL-CCIC-0019

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