127
Hough WL, Smiglak M, Rodríguez H, Swatloski RP, Spear SK, Daly DT, Pernak J, Grisel JE,
Carliss RD, Soutullo MD, Davis JH, Rogers RD (2007) The third evolution of ionic liquids:
active pharmaceutical ingredients. New J Chem 31:1429–1436. https://doi.org/10.1039/
b706677p
Kudlak B, Owczarek K, Namiesnik J (2015) Selected issues related to the toxicity of ionic liquids
and deep eutectic solvents — a review. Environ Sci Pollut Res 22:11975–11992. https://doi.
org/10.1007/s11356-015-4794-y
Kümmerer K (2007) Sustainable from the very beginning: rational design of molecules by life
cycle engineering as an important approach for green pharmacy and green chemistry. Green
Chem 9:899–907. https://doi.org/10.1039/b618298b
Kümmerer K (2010) Pharmaceuticals in the environment. Annu Rev Environ Resour 35:57–75.
https://doi.org/10.1146/annurev-environ-052809-161223
Li Z, Lee PI (2016) Investigation on drug solubility enhancement using deep eutectic solvents
and their derivatives. Int J Pharm 505:283–288. https://doi.org/10.1016/j.ijpharm.2016.04.018
Liu Y, Friesen JB, McAlpine JB, Lankin DC, Chen SN, Pauli GF (2018a) Natural deep eutectic solvents: properties, applications, and perspectives. J Nat Prod 81:679–690. https://doi.
org/10.1021/acs.jnatprod.7b00945
Liu Y, Zhang Y, Chen SN, Friesen JB, Nikolić D, Choules MP, McAlpine JB, Lankin DC,
Gemeinhart RA, Pauli GF (2018b) The influence of natural deep eutectic solvents on bioactive
natural products: studying interactions between a hydrogel model and Schisandra chinensis
metabolites. Fitoterapia 127:212–219. https://doi.org/10.1016/j.fitote.2018.02.024
Lowrie A, Jones MJ, Eastley RJ (1989) Effect of a eutectic mixture of local anaesthetic (EMLA) on
tourniquet pain in volunteers. Br J Anaesth 63:751–753. https://doi.org/10.1093/bja/63.6.751
Mann SK, Pham TN, Mcqueen LL, Lewandowski JR, Brown SP (2019) Revealing intermolecular
hydrogen bonding structure and dynamics in a deep eutectic pharmaceutical by magic-angle
spinning NMR spectroscopy. Mol Pharm. https://doi.org/10.1021/acs.molpharmaceut.9b01075
Mano F, Martins M, Sá-Nogueira I, Barreiros S, Borges JP, Reis RL, Duarte ARC, Paiva A (2016)
Production of electrospun fast-dissolving drug delivery systems with therapeutic eutectic systems encapsulated in gelatin. AAPS Pharm Sci Tech 18:2579–2585. https://doi.org/10.1208/
s12249-016-0703-z
Martins MAR, Pinho SP, Coutinho JAP (2018) Insights into the nature of eutectic and deep eutectic mixtures. J Solut Chem. https://doi.org/10.1007/s10953-018-0793-1
Mbous YP, Hayyan M, Hayyan A, Wong WF, Hashim MA, Looi CY (2017a) Applications of deep
eutectic solvents in biotechnology and bioengineering - promises and challenges. Biotechnol
Adv 35:105–134. https://doi.org/10.1016/j.biotechadv.2016.11.006
Mbous YP, Hayyan M, Wong WF, Looi CY, Hashim MA (2017b) Unraveling the cytotoxicity and
metabolic pathways of binary natural deep eutectic solvent systems. Sci Rep 7:41257–41271.
https://doi.org/10.1038/srep41257
Meneses L, Santos F, Gameiro AR, Paiva A, Duarte ARC (2019) Preparation of binary and ternary
deep eutectic systems. JoVE 152:1–5. https://doi.org/10.3791/60326
Morrison HG, Sun CC, Neervannan S (2009) Characterization of thermal behavior of deep eutectic
solvents and their potential as drug solubilization vehicles. Int J Pharm 378:136–139. https://
doi.org/10.1016/j.ijpharm.2009.05.039
Owczarek K, Szczepanska N, Plotka-Wasylka J, Rutkowska M, Shyshchak O, Bratychak M,
Namiesnik J (2016) Natural deep eutectic solvents in extraction process. Ch&ChT 10:601–606.
https://doi.org/10.23939/chcht10.04si.601
Paiva A, Craveiro R, Aroso I, Martins M, Reis RL, Duarte ARC (2014) Natural deep eutectic
solvents–solvents for the 21
st century. ACS Sustain Chem Eng 2:1063–1071. https://doi.
org/10.1021/sc500096j
3 Therapeutic Deep Eutectic Systems for the Enhancement of Drug Bioavailability
Hough WL, Smiglak M, Rodríguez H, Swatloski RP, Spear SK, Daly DT, Pernak J, Grisel JE,
Carliss RD, Soutullo MD, Davis JH, Rogers RD (2007) The third evolution of ionic liquids:
active pharmaceutical ingredients. New J Chem 31:1429–1436. https://doi.org/10.1039/
b706677p
Kudlak B, Owczarek K, Namiesnik J (2015) Selected issues related to the toxicity of ionic liquids
and deep eutectic solvents — a review. Environ Sci Pollut Res 22:11975–11992. https://doi.
org/10.1007/s11356-015-4794-y
Kümmerer K (2007) Sustainable from the very beginning: rational design of molecules by life
cycle engineering as an important approach for green pharmacy and green chemistry. Green
Chem 9:899–907. https://doi.org/10.1039/b618298b
Kümmerer K (2010) Pharmaceuticals in the environment. Annu Rev Environ Resour 35:57–75.
https://doi.org/10.1146/annurev-environ-052809-161223
Li Z, Lee PI (2016) Investigation on drug solubility enhancement using deep eutectic solvents
and their derivatives. Int J Pharm 505:283–288. https://doi.org/10.1016/j.ijpharm.2016.04.018
Liu Y, Friesen JB, McAlpine JB, Lankin DC, Chen SN, Pauli GF (2018a) Natural deep eutectic solvents: properties, applications, and perspectives. J Nat Prod 81:679–690. https://doi.
org/10.1021/acs.jnatprod.7b00945
Liu Y, Zhang Y, Chen SN, Friesen JB, Nikolić D, Choules MP, McAlpine JB, Lankin DC,
Gemeinhart RA, Pauli GF (2018b) The influence of natural deep eutectic solvents on bioactive
natural products: studying interactions between a hydrogel model and Schisandra chinensis
metabolites. Fitoterapia 127:212–219. https://doi.org/10.1016/j.fitote.2018.02.024
Lowrie A, Jones MJ, Eastley RJ (1989) Effect of a eutectic mixture of local anaesthetic (EMLA) on
tourniquet pain in volunteers. Br J Anaesth 63:751–753. https://doi.org/10.1093/bja/63.6.751
Mann SK, Pham TN, Mcqueen LL, Lewandowski JR, Brown SP (2019) Revealing intermolecular
hydrogen bonding structure and dynamics in a deep eutectic pharmaceutical by magic-angle
spinning NMR spectroscopy. Mol Pharm. https://doi.org/10.1021/acs.molpharmaceut.9b01075
Mano F, Martins M, Sá-Nogueira I, Barreiros S, Borges JP, Reis RL, Duarte ARC, Paiva A (2016)
Production of electrospun fast-dissolving drug delivery systems with therapeutic eutectic systems encapsulated in gelatin. AAPS Pharm Sci Tech 18:2579–2585. https://doi.org/10.1208/
s12249-016-0703-z
Martins MAR, Pinho SP, Coutinho JAP (2018) Insights into the nature of eutectic and deep eutectic mixtures. J Solut Chem. https://doi.org/10.1007/s10953-018-0793-1
Mbous YP, Hayyan M, Hayyan A, Wong WF, Hashim MA, Looi CY (2017a) Applications of deep
eutectic solvents in biotechnology and bioengineering - promises and challenges. Biotechnol
Adv 35:105–134. https://doi.org/10.1016/j.biotechadv.2016.11.006
Mbous YP, Hayyan M, Wong WF, Looi CY, Hashim MA (2017b) Unraveling the cytotoxicity and
metabolic pathways of binary natural deep eutectic solvent systems. Sci Rep 7:41257–41271.
https://doi.org/10.1038/srep41257
Meneses L, Santos F, Gameiro AR, Paiva A, Duarte ARC (2019) Preparation of binary and ternary
deep eutectic systems. JoVE 152:1–5. https://doi.org/10.3791/60326
Morrison HG, Sun CC, Neervannan S (2009) Characterization of thermal behavior of deep eutectic
solvents and their potential as drug solubilization vehicles. Int J Pharm 378:136–139. https://
doi.org/10.1016/j.ijpharm.2009.05.039
Owczarek K, Szczepanska N, Plotka-Wasylka J, Rutkowska M, Shyshchak O, Bratychak M,
Namiesnik J (2016) Natural deep eutectic solvents in extraction process. Ch&ChT 10:601–606.
https://doi.org/10.23939/chcht10.04si.601
Paiva A, Craveiro R, Aroso I, Martins M, Reis RL, Duarte ARC (2014) Natural deep eutectic
solvents–solvents for the 21
st century. ACS Sustain Chem Eng 2:1063–1071. https://doi.
org/10.1021/sc500096j
3 Therapeutic Deep Eutectic Systems for the Enhancement of Drug Bioavailability