Self-assembly induced solubilization of drug-like molecules in nanostructured ionic liquids

Jin, Wenbin; Yang, Qiwei; Zhang, Zhiguo; Bao, Zongbi; Ren, Qilong; Yang, Yiwen; Xing, Huabin

doi:10.1039/c5cc03463a

Cited by 37 publications

(32 citation statements)

References 72 publications

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“…Furthermore, the cation and/or anion amphiphilic nature can be finely balanced to trigger the self-assembling behavior of ILs [ 40 , 41 , 42 , 43 , 44 ]. In this framework, fatty acids raised remarkable interest as building blocks for ILs containing natural hydrophobic tails [ 45 , 46 , 47 , 48 , 49 , 50 ] and such materials were investigated in pharmaceutical applications [ 42 , 51 , 52 , 53 , 54 ]. An intriguing subclass of ILs is that of the so-called protic ionic liquids (PILs), which are easily prepared by reacting a Brønsted acid and a Brønsted base [ 55 , 56 ].…”

Section: Introductionmentioning

confidence: 99%

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

et al. 2020

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For topical treatment of skin cancer, the design of pH-responsive nanocarriers able to selectively release the drug in the tumor acidic microenvironment represents a reliable option for targeted delivery. In this context, a series of newly synthesized surface-active fatty acid-protic ionic liquids (FA-PILs), based on tetramethylguanidinium cation and different natural hydrophobic fatty acid carboxylates, have been investigated with the aim of developing a pH-sensitive nanostructured drug delivery system for cutaneous administration in the skin cancer therapy. The capability of FA-PILs to arrange in micelles when combined with each other and with the non-ionic surfactant d-α-Tocopherol polyethylene glycol succinate (vitamin E TPGS) as well as their ability to solubilize imiquimod, an immuno-stimulant drug used for the treatment of skin cancerous lesions, have been demonstrated. The FA-PILs-TPGS mixed micelles showed pH-sensitivity, suggesting that the acidic environment of cancer cells can trigger nanostructures’ swelling and collapse with consequent rapid release of imiquimod and drug cytotoxic potential enhancement. The in vitro permeation/penetration study showed that the micellar formulation produced effective imiquimod concentrations into the skin exposed to acid environment, representing a potential efficacious and selective drug delivery system able to trigger the drug release in the tumor tissues, at lower and less irritating drug concentrations.

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Section: Introductionmentioning

confidence: 99%

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

et al. 2020

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“…The ILs synthesized in this work were 1-benzyl-3-methylimidazolium bromide ( [OH] and then mixed with equimolar amounts of the corresponding fatty acids including acetic acid, n-hexanoic acid and lauric acid at room temperature for 24 h [34][35][36][37]. All the obtained ILs were dried by a vacuum freeze dryer for 24 h after most solvents were removed by a rotary evaporator at 333 K. The chemical structure and purity of ILs were evaluated by a 1 H nuclear magnetic resonance (NMR) spectrum (see the Supplementary information).…”

Section: Synthesis Of 1-benzyl-3-methylimidazolium-based Ilsmentioning

confidence: 99%

Construction of anion-functionalized hypercrosslinked ionic porous polymers for efficient separation of bioactive molecules

Suo

Huang

et al. 2021

Sci. China Mater.

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Porous ionic polymers have demonstrated great potential for high-performance separation by the merits of their unique molecular recognition, but the preparation of anion-functionalized ionic polymers for the separation of bioactive molecules with highly similar structures remains a challenge. Here, through the facile Friedel-Crafts alkylation between benzylimidazole ionic liquids (ILs) and crosslinkers, several anion-functionalized hypercrosslinked ionic porous polymers (HIPs) are reported, which are well decorated with strongly basic carboxylate anions as well as feature tubular morphology and excellent thermal stability. High adsorption capacity (103.6 mg g −1 for tocopherol homologues) and selectivity (S β&γ/α , 4.26; S δ/α , 3.19) for bioactive compounds with high structural similarity have been realized, superior to those of commercial adsorbents, hypercrosslinked polymer without ILs, and HIPs with common ILs. This study manifests a new synthetic strategy and rational molecular design for functionalized adsorbents, as well as offers new opportunities to enable high-performance separation.

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“…[22,24] Since 2007, Room Temperature Ionic Liquids (RTILs) containing active pharmaceutical ingredients have aroused strong interests as they limit drugs polymorphism and improve their solubility. [29][30][31][32][33] API-ILs have also been used as solvent for poorly soluble drugs [34][35][36][37][38] and as drug delivery systems in the form of microemulsions [39] and micelles. [40] Drug delivery systems have also been obtained by immobilization of API-ILs into silica either by sol-gel processing, [41] adsorption to silica [42] or into biocompatible poly(L-lactic acid).…”

Section: Introductionmentioning

confidence: 99%

Investigation of pharmaceutically active ionic liquids as electrolyte for the electrosynthesis of polypyrrole and active component in controlled drug delivery

Carquigny

Lakard

et al. 2016

Electrochimica Acta

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Self-assembly induced solubilization of drug-like molecules in nanostructured ionic liquids

Cited by 37 publications

References 72 publications

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

Construction of anion-functionalized hypercrosslinked ionic porous polymers for efficient separation of bioactive molecules

Investigation of pharmaceutically active ionic liquids as electrolyte for the electrosynthesis of polypyrrole and active component in controlled drug delivery

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