2019-Sustainable Industrial Processing Summit
SIPS2019 Volume 1: Angell Intl. Symp. / Molten Salt, Ionic & Glass-forming Liquids: Processing and Sustainability
| Editors: | F. Kongoli, M. Gaune-Escard, J. Dupont, R. Fehrmann, A. Loidl, D. MacFarlane, R. Richert, M. Watanabe, L. Wondraczek, M. Yoshizawa-Fujita, Y. Yue |
| Publisher: | Flogen Star OUTREACH |
| Publication Year: | 2019 |
| Pages: | 177 pages |
| ISBN: | 978-1-989820-00-1 |
| ISSN: | 2291-1227 (Metals and Materials Processing in a Clean Environment Series) |
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Thermophysical Properties and Citotoxicity of New Biologically Friendly Agmatine-based Ionic Liquids and Salts
Jovana Panic1; Aleksandar Tot2; Slobodan Gadzuric1; Milan Vraneš3;1FACULTY OF SCIENCES, UNIVERSITY OF NOVI SAD, Novi Sad, Serbia and Montenegro (formerly Yugoslavia); 2FACULTY OF SCIENCES, UNIVERSITY OF NOVI SAD, DEPARTMENT OF CHEMISTRY, BIOCHEMISTRY AND ENVIRONMENTAL PROTECTION, Novi Sad, Serbia and Montenegro (formerly Yugoslavia); 3FACULTY OF SCIENCES, UNIVERSITY OF NOVI SAD, Novi Sad, Serbia and Montenegro;
Type of Paper: Regular
Id Paper: 45
Topic: 13
Abstract:
Recently, studies on ions and ionic interactions in solution have raised as a leading research direction of culminating importance.[1] In medicine, pharmacy and drug development, including sports supplementation, ionizable molecules are required for better bioavailability in the organism.[2] The main problem in medicine and the food industry is the implementation of substances which have a tendency to create polymorphs since each form shows different solubility and biological activity.[3] The most promising strategy to avoid this issue, can be observed in the field of ionic liquids (ILs), compounds which are usually composed of large asymmetric cations and organic/inorganic anions, and exist as a liquid at temperatures below 100°C. ILs have numerous advantages that may be applied in medicine and food industry such as good solubility in water, which leads to improved bioavailability, designed lipophilicity which allows easier transport of the desired compounds through the cell membrane and possibility of ILs synthesis with synergistic cation and anion performances.[4] Unique dynamic micro- and nanoheterogeneous structuring of these substances has been shown to have a significant effect on physicochemical and biological properties of ILs. Until now, a large number of ILs with different pharmacologically and biological active anions (amino acids, Krebs cycle molecules, etc.) were synthesized, but the selection of cation is mostly dedicated to choline as a widespread biological nutrient.[5] The extensive search in the field of ionic liquids started for new, biologically active cation besides choline. One of the possible solution can be agmatine, endogenous polycationic amine derived from L-arginine through enzymatic decarboxylation.
Six new agmatine bioinspired salts, agmatine citrate, agmatine ascorbate, agmatine glutamate, agmatine m-hydroxybenzoate, agmatine nitrate, and agmatine chloride, and three ionic liquids, agmatine ibuprofenate, agmatine salicylate, and agmatine nicotinate were synthesized. For all newly synthesized compounds the glass transition temperature, melting and decomposition temperature were determined using thermogravimetric and DSC analysis. The cytotoxicity on MRC-5 and HT-29 cell lines was tested also, where results indicate lower toxicity of examined compounds compared to ascorbic acid on the human non-tumor cell lines. Densimetric and viscosimetric measurements of their aqueous solutions were performed, supported by molecular dynamics simulation. From obtained results, it can be concluded that all investigated compounds have a structrure-making properties. The effect of the anion nature on the conformation of agmatine cation is negligible in the investigated concentration range.
Keywords:
Density; Solvation; Thermophysical; Viscosity;References:
(1) K.S. Egorova, V.P. Ananikov, J. Mol. Liq. 272 (2018) 271-300.(2) J.L. Shamshina, S.P. Kelley, G. Gurau, R.D. Rogers, Nature 528 (2015) 188-189.
(3) I.M. Marrucho, L.C. Branco, L.P. Rebelo, Annu. Rev. Chem. Biomol. Eng. 5 (2014) 527-546.
(4) M. Petkovic, J.L. Ferguson, H.Q.N. Gunaratne, R. Ferreira, M.C. Leitão, K.R. Seddon, L.P.N. Rebelo, C.S. Pereira, Green. Chem. 12 (2010) 643-649.
(5) X.D. Hou, Q.P. Liu, T.J. Smith, N. Li, M.H. Zong, PLoS ONE. 8 (2013), e59145.