Abstract:This review summarizes the advancements in the field of biomedical sciences using choline geranate (CAGE) ionic liquid (IL)/deep eutectic solvent (DES) in view of its unique properties.
“…The combination of EmimAc and AcH is an example of a mixture formed during the esterification of biomass with acetic anhydride. The combination of a quaternary ammonium salt and organic acid as a hydrogen-bond donor generates a deep eutectic mixture, a kind of third-type deep eutectic solvent (DES), which is a promising solvent for application in biomass processing, − CO 2 capture, and pharmaceutics. − The properties of such DESs depend on their stoichiometry and solvation, implying that control of their composition and stoichiometry is important. The separation technique presented in this study is, for example, promising for applications in the separation of such complicated mixtures and the regeneration of DESs.…”
1-Ethyl-3-methylimidazolium acetate (EmimAc), an excellent
solvent
for cellulosic biomass, is expected to be utilized in chemical conversion,
such as in biomass acetylation with acetic anhydride. The corresponding
carboxylic acid, acetic acid (AcH), is quantitatively generated as
a byproduct and should be separated from EmimAc for recycling. However,
the strong interaction between EmimAc and AcH makes their separation
difficult under moderate conditions. This study examined the efficacy
of protic solvents in distillation and extraction to weaken this interaction
through solvation or hydrogen-bonding interactions. The separation
efficiency of AcH from EmimAc via distillation increased as the boiling
point of the protic solvent increased. Water addition was more effective
than the addition of alcohols with boiling points similar to those
of water such as 1-propanol and 2-butanol. Furthermore, the favorable
effect of water addition on the extraction of AcH was confirmed using
common organic solvents, such as diisopropyl ether, diethyl ether,
and ethyl acetate. The partition coefficient (α) of AcH between
the aqueous and organic phases increased with an increasing dielectric
constant of the organic solvent, whereas the α value of EmimAc
decreased. Repeated treatments in both distillation and extraction
facilitated the complete separation of AcH from EmimAc.
“…The combination of EmimAc and AcH is an example of a mixture formed during the esterification of biomass with acetic anhydride. The combination of a quaternary ammonium salt and organic acid as a hydrogen-bond donor generates a deep eutectic mixture, a kind of third-type deep eutectic solvent (DES), which is a promising solvent for application in biomass processing, − CO 2 capture, and pharmaceutics. − The properties of such DESs depend on their stoichiometry and solvation, implying that control of their composition and stoichiometry is important. The separation technique presented in this study is, for example, promising for applications in the separation of such complicated mixtures and the regeneration of DESs.…”
1-Ethyl-3-methylimidazolium acetate (EmimAc), an excellent
solvent
for cellulosic biomass, is expected to be utilized in chemical conversion,
such as in biomass acetylation with acetic anhydride. The corresponding
carboxylic acid, acetic acid (AcH), is quantitatively generated as
a byproduct and should be separated from EmimAc for recycling. However,
the strong interaction between EmimAc and AcH makes their separation
difficult under moderate conditions. This study examined the efficacy
of protic solvents in distillation and extraction to weaken this interaction
through solvation or hydrogen-bonding interactions. The separation
efficiency of AcH from EmimAc via distillation increased as the boiling
point of the protic solvent increased. Water addition was more effective
than the addition of alcohols with boiling points similar to those
of water such as 1-propanol and 2-butanol. Furthermore, the favorable
effect of water addition on the extraction of AcH was confirmed using
common organic solvents, such as diisopropyl ether, diethyl ether,
and ethyl acetate. The partition coefficient (α) of AcH between
the aqueous and organic phases increased with an increasing dielectric
constant of the organic solvent, whereas the α value of EmimAc
decreased. Repeated treatments in both distillation and extraction
facilitated the complete separation of AcH from EmimAc.
“…[158] The CAGE eutectic system was selected due to the ease of preparation, excellent stability under stressed storage conditions, inherent antimicrobial properties, low toxicity, and the ability to improve drug delivery through the skin. [159,133] After 12 weeks of treatment, the resulting formulation demonstrated a significant reduction in the lesion (~70 %) with mild to moderate side effects. These results prove the significant potential of CAGE gel for the treatment of rosacea.…”
Section: Des As An Active Ingredient For Pharmaceutical Applicationsmentioning
confidence: 99%
“…described the different phases for translational studies including, scale‐up, characterization, stability test, mechanism of action, dose selection, toxicity study, and human clinical study [158] . The CAGE eutectic system was selected due to the ease of preparation, excellent stability under stressed storage conditions, inherent antimicrobial properties, low toxicity, and the ability to improve drug delivery through the skin [159,133] . After 12 weeks of treatment, the resulting formulation demonstrated a significant reduction in the lesion (~70 %) with mild to moderate side effects.…”
Section: Role Of Deep Eutectic Solvents In Drug Engineeringmentioning
In the spirit of circular economy and sustainable chemistry, the use of environmentally friendly chemical products in pharmacy has become a hot topic. In recent years, organic solvents have been the subject of a great range of restriction policies due to their harmful effects on the environment and toxicity to human health. In parallel, deep eutectic solvents (DESs) have emerged as suitable greener solvents with beneficial environmental impacts and a rich palette of physico‐chemical advantages related to their low cost and biocompatibility. Additionally, DESs can be accompanied by a remarkable solubilizing effect for several active pharmaceutical ingredients (APIs), thus forming therapeutic DESs (TheDESs). In this work, special attention is paid to DESs, presenting a precise definition, classification, methods of preparation, and characterization. A description of natural DESs (NaDESs), i.e., eutectic solvents present in natural sources, is also reported. Moreover, the present review article is the first one to detail the different approaches for judiciously selecting the constituents of DESs in order to minimize the number of experiments. The role of DESs in the biomedical and pharmaceutical sectors and their impact on the development of successful therapies are also discussed.
“…This IL is nontoxic (shown in vitro using human bronchial epithelial (NHBE) cells 90 ) and is suitable for delivery of multiple drugs. 375 Compounds delivered with CAGE include nobiletin, 376 mannitol, 90 cefadoxil, 90,377,378 insulin, 379 acarbose, 380 ruxolitinib, 380 sorafenib, 381 imiquimod, 382 triamcinolone acetonide, 382 curcumin. 383 Permeation of dextrans with different molecular weights was also reported, 384 opening the door to delivery of proteins, peptides, and even antibodies.…”
Section: Using Ils To Enhance Transdermal Deliverymentioning
confidence: 99%
“…Perhaps, the most well-known IL system studied for drug delivery is cholinium geranate ([Cho][H(Ger) 2 ]), known as CAGE. This IL is nontoxic (shown in vitro using human bronchial epithelial (NHBE) cells) and is suitable for delivery of multiple drugs . Compounds delivered with CAGE include nobiletin, mannitol, cefadoxil, ,, insulin, acarbose, ruxolitinib, sorafenib, imiquimod, triamcinolone acetonide, curcumin .…”
This Review aims to summarize advances over the last
15 years in
the development of active pharmaceutical ingredient ionic liquids
(API-ILs), which make up a prospective game-changing strategy to overcome
multiple problems with conventional solid-state drugs, for example,
polymorphism. A critical part of the present Review is the collection
of API-ILs and deep eutectic solvents (DESs) prepared to date. The
Review covers rules for rational design of API-ILs and tools for API-IL
formation, syntheses, and characterization. Nomenclature and ionic
speciation, and the confusion that these may cause, are highlighted,
particularly for speciation in both ILs and DESs of intermediate ionicity.
We also highlight in vivo and in vitro pharmaceutical activity studies, with differences in pharmacokinetic/pharmacodynamic
depending on ionicity of API-ILs. A brief overview is provided for
the ILs used to deliver drugs, and the Review concludes with key prospects
and roadblocks in translating API-ILs into pharmaceutical manufacturing.
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