The role of crown ethers in drug delivery

Chehardoli, Gholamabbas; Bahmani, Asrin

doi:10.1080/10610278.2019.1568432

Cited by 49 publications

(36 citation statements)

References 102 publications

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“…These properties, together with their ionophoric qualities, make them ideal compounds for use in ocular drug delivery, where the formulation has to interact with both aqueous and lipophilic phases. At the time of writing of this review, there was only one published study investigating the use of crown ethers for enhanced ocular drug delivery [99]; Morrison et al [100] investigated 12C4, 15C5, and 18C6 for use in ocular drug delivery, and they were able to show enhanced aqueous solubility of riboflavin up to 46%, potentially improving bioavailability (Table 1). Furthermore, all crown ether variants studied were capable of significantly enhancing Ca 2+ extraction from bovine corneas in vitro compared with phosphate-buffered saline.…”

Section: Penetration Enhancersmentioning

confidence: 99%

Penetration Enhancers in Ocular Drug Delivery

Moiseev

Morrison

Steele³

et al. 2019

Pharmaceutics

163

124

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There are more than 100 recognized disorders of the eye. This makes the development of advanced ocular formulations an important topic in pharmaceutical science. One of the ways to improve drug delivery to the eye is the use of penetration enhancers. These are defined as compounds capable of enhancing drug permeability across ocular membranes. This review paper provides an overview of anatomical and physiological features of the eye and discusses some common ophthalmological conditions and permeability of ocular membranes. The review also presents the analysis of literature on the use of penetration-enhancing compounds (cyclodextrins, chelating agents, crown ethers, bile acids and bile salts, cell-penetrating peptides, and other amphiphilic compounds) in ocular drug delivery, describing their properties and modes of action.

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Section: Penetration Enhancersmentioning

confidence: 99%

Penetration Enhancers in Ocular Drug Delivery

Moiseev

Morrison

Steele³

et al. 2019

Pharmaceutics

163

124

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“…Another family of heterocycles prepared under flow conditions were crown ethers, which are very relevant molecules for supramolecular recognition and highly studied as drug delivery systems . A KOH‐catalyzed cyclization of 2,6‐ bis (iodomethyl)pyridines and tetraethylene glycol allowed the preparation of a small library of pyridino‐18‐crown‐6‐ether derivatives in moderate to good yields.…”

Section: Heterocyclic Synthesismentioning

confidence: 99%

Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis

2019

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Flow Chemistry is a revolutionary field in Organic Chemistry. By changing the conventional methods and apparatus applied in the chemical synthesis, flow chemistry emerges as a game changer for organic synthesis laboratories, in both academia and industries. Considered as a sustainable practice, flow processes play an important role in the development of fine chemical products and in drug discovery development pro- [a] The main advantages of flow chemistry are that it allows the reaction to be carried out safely with high selectivity, high reproducibility and reduced energy consumption/carbon footprint. These features make this emerging technology for organic synthesis desirable for green and sustainable chemical synthesis, giving the chemist time for work planning and design, instead of using it in repetitive tasks, [5b,12] as expressed by the CHEM21 project by awarding a green flag for continuousflow reactions, in opposition to an amber flag for those performed under batch conditions. [13] Pedro Brandão received his MSc in Pharmaceutical Sciences from the Faculty of Pharmacy -University of Porto, in 2011. Pursuing his passion on studies in the field of Drug Discovery and Development, he is currently undergoing his PhD studies in Chemistry, in the field of Catalysis and Sustainability. His main focus of work is the discovery of new drug candidates through sustainable techniques. Marta Pineiro received her Ph.D. in Organic Chemistry in 2003 in the University of Coimbra, Portugal, and since 2002 has been enrolled at the University of Coimbra, being at present Auxiliary Professor. Her research interests are in the area of sustainable organic synthesis, microwave-assisted organic synthesis and synthesis and biological applications of tetrapyrrolic macrocycles. Teresa M. V. D. Pinho e Melo studied Chemistry at the University of Coimbra, where she graduated in 1985, got her M. 7191CPBA) as the oxidizing agent, avoiding the handling of this expensive and explosive reagent. [25] Recently, Morodo et al. explored the synthesis of two very important oxiranes (epichlorohydrin and glycidol) from biobased glycerol, under flow conditions. As depicted in Scheme 1, and using pimelic acid as the catalyst (10 mol-%), a sequential hydrochlorination/dichlorination process allows high conversion of glycerol (> 99 %) into 1,3-dichloro-2-propanol, followed by the quantitative conversion into a separable mixture of glycidol and epichlorohydrin (2:3). The separation of these two products is performed by an in-line membrane separation system, which allows the first product to be collected in the aqueous phase, while the second is collected in MTBE. This heterocycle can be further used as a synthetic precursor to relevant APIs bearing -amino alcohol moieties (e.g., propranolol, alprenolol and naftopidil). [26] Scheme 1. Sequential flow setup for the preparation of glycidol and epichlorohydrin, important APIs synthetic intermediates.Scheme 3. Synthesis and inline purification of a bicyclic aziridine (SGMR = silicon-glass microfluidic react...

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“…The supramolecular chemistry showed a broad interest during the last few decades in different aspects of applications such as electrochemical sensors, catalysis, drug delivery systems, biotherapy, and self-healing [ 1 , 2 , 3 , 4 ]. New macrocycles were synthesized such as crown ethers [ 5 ], calix[ n ]arenes [ 6 ], etc., which have the ability to host different types of molecules for numerous applications [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

et al. 2021

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The interaction between meloxicam and sulfonatocalix[4]naphthalene was investigated to improve the meloxicam solubility and its dissolution performance. Solubility behavior was investigated in distilled water (DW) and at different pH conditions. Besides, solid systems were prepared in a 1:1 molar ratio using coevaporate, kneading, and simple physical mixture techniques. Further, they were characterized by PXRD, FT-IR, DCS, and TGA. In vitro dissolution rate for coevaporate, kneaded, and physical mixture powders were also investigated. Solubility study revealed that meloxicam solubility significantly increased about 23.99 folds at phosphate buffer of pH 7.4 in the presence of sulfonatocalix[4]naphthalene. The solubility phase diagram was classified as AL type, indicating the formation of 1:1 stoichiometric inclusion complex. PXRD, FT-IR, DCS, and TGA pointed out the formation of an inclusion complex between meloxicam and sulfonatocalix[4]naphthalene solid powders prepared using coevaporate technique. In addition, in vitro meloxicam dissolution studies revealed an improvement of the drug dissolution rate. Furthermore, a significantly higher drug release (p ≤ 0.05) and a complete dissolution was achieved during the first 10 min compared with the other solid powders and commercial meloxicam product. The coevaporate product has the highest increasing dissolution fold and RDR10 in the investigated media, with average values ranging from 5.4–65.28 folds and 7.3–90.7, respectively. In conclusion, sulfonatocalix[4]naphthalene is a promising host carrier for enhancing the solubility and dissolution performance of meloxicam with an anticipated enhanced bioavailability and fast action for acute and chronic pain disorders.

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The role of crown ethers in drug delivery

Cited by 49 publications

References 102 publications

Penetration Enhancers in Ocular Drug Delivery

Penetration Enhancers in Ocular Drug Delivery

Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis

Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam towards Enhancing Its Solubility and Dissolution Performance

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