Design and Selection of Ionic Liquids Via COSMO for Pharmaceuticals and Medicine

Khan, Huma Warsi; Elgharbawy, 
                Amal A. M.; Bustam, Azmi; Moniruzzaman, Muhammad

doi:10.1007/978-981-16-4365-1_8

Huma Warsi Khan³,
Amal A. M. Elgharbawy⁴,
Azmi Bustam^3,5 &
…
Muhammad Moniruzzaman^3,5

767 Accesses
5 Citations

Abstract

Ionic liquids (ILs) have been used significantly in pharmaceutics and medicine because of their exceptional “green” properties and tailor-made physicochemical and biological properties. ILs can dissolve many important drug molecules at ambient conditions, which are sparingly soluble in water and other conventional organic solvents. However, the selection of potential ILs from thousands of anion–cation combinations is quite challenging. To address this limitation, various computation methods have been used to screen appropriate ILs for solubility and applications of a specific drug molecule. Among those methods, the conductor-like screening model (COSMO)—a continuum solvation model based on quantum chemistry—is found remarkably effective in screening suitable ILs for pharmaceutical applications due to its excellent capability in predicting physical and chemical properties. The advantage of these optimizing tools is that only the molecular structure is enough for prior predictions. Solubility, activity coefficient, selectivity, free energies, partition coefficient, and octanol–water coefficient are few properties that can be easily predicted. This chapter presents a detailed discussion on the COSMO screening of cations and anions of ILs for various applications and highlighting the advantages of this predictive tool.

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Abbreviations

AAD:: Average absolute deviation
AC^id:: Activity coefficient at infinite dilution
ACV:: Acyclovir
AMT:: Amitriptyline
API:: Active pharmaceutical ingredients
BP:: Becke and Perdew
COSMO-RS:: Conductor-like screening model for real solvents
COSMO-SAC:: Conductor-like screening model-segment activity coefficient
CYANEX:: Trialkylphosphine
CYPHOS 105:: Tetradecyltrihexylphosphonium dicynamide
CYPHOS 109:: Tetradecyltrihexylphosphonium bistriflamide
DCP:: Dichlorophenol
DDT:: Dichlorodiphenyl trichloraethane
DES:: Deep eutectic solvents
DFT:: Density functional theory
DHA:: Docosanohexaenoic acid
DLLME:: Dispersive liquid–liquid microextraction
DMSO:: Dimethyl sulfoxide
DTZ:: Diltiazem
EPA:: Eicosapentaenoic acid
ETO:: Etodolac
GMV:: Gamavuton-0
GSEq:: General solubility equations (GSEq)
HBA:: Hydrogen bonding ability
HBC:: Hydrogen bonding capacity
HSP:: Hansen solubility parameter
ILs:: Ionic liquids
LA:: Lactic acid
LLE:: Liquid–liquid equilibrium
MSD:: Mean square deviation
NRTL:: Non-random two-liquid model
RMSD:: Root mean square deviation
RMSE:: Root mean square error
SLE:: Solid–liquid equilibrium
TCP:: Trichlorophenol
UNIFAC:: Universal Quasi-Chemical Functional Group Model
UNIQUAC:: Universal Quasi-Chemical Model
VLE:: Vapor–liquid equilibrium
[BDMAAm]:: Benzyldimethylalkylammonium
[BGu]:: Benzyl-1-butylguanidinium
[BMIm]:: 1-Butyl-3-methyl imidazolium
[BMPip]:: 1-Butyl 3-methylpiperidinium
[BMPy]:: 1-Butyl-3-methylpyridinium
[DMIm]:: 1-Decyl-3-methylimidazolium
[DMPh]:: Dimethylphosphate
[EMIm]:: 1-Ethyl-3-methylimidazolium
[EMPy]:: 1-Ethyl-3-methylpyridinium
[HMIm]:: 1-Hexyl-3 methyl imidazolium
[HTDPh]:: Hexyltridecylphosphonium
[MAm]:: Methylammonium
[OMIm]:: 1-Octyl-3-methylimidazolium
[TBPh]:: Tetrabutylphosphonium
[TOAm]:: Trioctylammonium
[AlC_l4]:: Aluminium tetrachloride
[Br]:: Bromide
[Cin]:: Cinnamate
[Cl]:: Chloride
[ClO₄]:: Perchlorate
[Ffm]:: Flufenamicate
[Lac]:: Lactate
[Ntf₂]:: Bis(trifluoromethylsulfonyl)imide
[Oct]:: Octanoate
[Otf]:: Trifluoromethanesulfonate
[PF₆]:: Hexafluorophosphate
[Sa]:: Salicylate
[TBP]:: Tributylphosphate
[TOA]:: Trioctylamine
[Tos]:: Tosylate

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Department of Chemical Engineering, Universiti Teknologi PETRONAS, 32610, Perak, Malaysia
Huma Warsi Khan, Azmi Bustam & Muhammad Moniruzzaman
International Institute for Halal Research and Training (INHART), International Islamic University, Kuala Lampur, Malaysia
Amal A. M. Elgharbawy
Centre of Research in Ionic Liquids, Universiti Teknologi PETRONAS, Seri Iskandar, Perak, Malaysia
Azmi Bustam & Muhammad Moniruzzaman

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Huma Warsi Khan
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Amal A. M. Elgharbawy
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Department of Applied Chemistry, Kyushu University, Fukuoka, Japan
Masahiro Goto
Department of Chemical Engineering, Universiti Teknologi PETRONAS, Perak, Malaysia
Muhammad Moniruzzaman

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Khan, H.W., Elgharbawy, ., Bustam, A., Moniruzzaman, M. (2021). Design and Selection of Ionic Liquids Via COSMO for Pharmaceuticals and Medicine. In: Goto, M., Moniruzzaman, M. (eds) Application of Ionic Liquids in Drug Delivery. Springer, Singapore. https://doi.org/10.1007/978-981-16-4365-1_8

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DOI: https://doi.org/10.1007/978-981-16-4365-1_8
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