Anionic cyclodextrins as versatile hosts for pharmaceutical nanotechnology: Synthesis, drug delivery, enantioselectivity, contrast agents for MRI

Mavridis, Irene M.; Yannakopoulou, Konstantina

doi:10.1016/j.ijpharm.2015.06.004

Cited by 32 publications

(12 citation statements)

References 130 publications

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“…Actually, fundamental research is also focusing on cyclodextrin-based nanoparticles/nanomaterials for pharmaceutical and biomedical applications and nanomedicine, e.g., molecular diagnosis, medical imaging, antifungal treatment, antimicrobial therapy, gene therapy or tissue engineering, and on self-association of cyclodextrins for applications not only for formulation and drug delivery, and medicine, but also for materials science, supramolecular chemistry and asymmetric catalysis (Hirakawa and Tomita 2013;Morohoshi et al 2013;Zhang and Ma 2013;Chilajwar et al 2014;Melotti et al 2014;Simoes et al 2014;Dong et al 2015;Macaev and Boldescu 2015;Mavridis and Yannakopoulou 2015;Miller et al 2015;Perez-Anes et al 2015;Wu et al 2015;Brackman et al 2016;Junthip et al 2016;Okano et al 2016;Oliveri and Vecchio 2016;Ryzhakov et al 2016;Sharma and Baldi 2016;Silva et al 2016;Yuan and Zhang 2016;Saokham and Loftsson 2017;Egele et al 2019;Fenyvesi et al 2019;Hammoud et al 2019;Kumar and Rao 2019;Neva et al 2019;Pawar and Shende 2019;Topuz and Uyar 2019;Zhang et al 2019a).…”

Section: Cyclodextrins: Trends and Outlookmentioning

confidence: 99%

130 years of cyclodextrin discovery for health, food, agriculture, and the industry: a review

et al. 2021

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Cyclodextrins are a group of cyclic oligosaccharides obtained by enzymatic degradation of starch. They are remarkable macrocyclic molecules that have led major theoretical and practical advances in chemistry, biology, biochemistry, health science, and agriculture. Their molecular structure is composed of a hydrophobic cavity that can encapsulate other compounds to form inclusion complexes through host-guest interactions. This unique feature is at the origin of many applications. Cyclodextrins and their derivatives have a wide variety of practical applications in almost all sectors of the industry, including pharmacy, medicine, foods, cosmetics, chromatography, catalysis, biotechnology, and the textile industry. Villiers published the first reference to cyclodextrins in 1891, and since then, these molecules have continued to fascinate academia and industry. Currently, more than 2000 publications on cyclodextrins are published each year. On the occasion of the 130th anniversary of their discovery, in this review, we present an historical overview of the development and applications of cyclodextrins. First, we present the discovery and first chemical studies on cyclodextrins. Then, the main results obtained during the 1911-1970 exploration period are discussed. A third part presents the historical landmarks in the development of cyclodextrins from 1970 to the present day.

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Section: Cyclodextrins: Trends and Outlookmentioning

confidence: 99%

130 years of cyclodextrin discovery for health, food, agriculture, and the industry: a review

et al. 2021

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“…When added to plain buffers, CyDs are able to resolve enantiomeric guests due to formation of diastereomeric inclusion complexes, which present different electrophoretic mobilities. When the background electrolyte (BGE) contains pseudostationary phases as micelles or microemulsions, it has been recently suggested that more complex phenomena may take place [15,16]. In the latter case also the monomers of surfactant can interact with the CyD, possibly involving the formation of ternary complexes 1:1:1 of CyD:enantiomer:surfactant, or giving rise to the displacement of CyD bound enantiomeric guests with surfactant tails due to competitive binding.…”

Section: Introductionmentioning

confidence: 99%

Chiral capillary zone electrophoresis in enantioseparation and analysis of cinacalcet impurities: Use of Quality by Design principles in method development

Pasquini

Orlandini

Villar-Navarro

et al. 2018

Journal of Chromatography A

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“…Compared to low‐molecular weight gadofosveset, which displays prolonged blood residence due to binding to plasma proteins, macromolecules and supramolecular structures have much higher molecular weights, which prolongs their blood circulation time. These include proteins, water‐soluble fullerenes, carbohydrates, cyclodextrins, nanoparticles, polymers, dendrimers, liposomes, and most recently micelles . The major advantage of macromolecular Gd‐chelates is increased relaxivity as a consequence of slower rotational motion of the macromolecules…”

Section: Introductionmentioning

confidence: 99%

Self‐Assembled Nanomicelles as MRI Blood‐Pool Contrast Agent

Babič

Vorobiev

Xayaphoummine

et al. 2017

Chemistry A European J

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Gadolinium-loaded nanomicelles show promise as future magnetic resonance imaging (MRI) contrast agents (CAs). Their increased size and high gadolinium (Gd) loading gives them an edge in proton relaxivity over smaller molecular Gd-complexes. Their size and stealth properties are fundamental for their long blood residence time, opening the possibility for use as blood-pool contrast agents. Using l-tyrosine as a three-functional scaffold we synthesized a nanostructure building block 8. The double C18 aliphatic chain on one side, Gd-1,4,7,10-tetraazacyclododecane-1-4-7-triacetic acid (Gd-DO3A) with access to bulk water in the center and 2 kDa PEG on the hydrophilic side gave the amphiphilic properties required for the core-shell nanomicellar architecture. The self-assembly into Gd-loaded monodispersed 10-20 nm nanomicelles occurred spontaneously in water. These nanomicelles (Tyr-MRI) display very high relaxivity at 29 mm s at low field strength and low cytotoxicity. Good contrast enhancement of the blood vessels and the heart together with prolonged circulation time in vivo, makes Tyr-MRI an excellent candidate for a new supramolecular blood-pool MRI CA.

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Anionic cyclodextrins as versatile hosts for pharmaceutical nanotechnology: Synthesis, drug delivery, enantioselectivity, contrast agents for MRI

Cited by 32 publications

References 130 publications

130 years of cyclodextrin discovery for health, food, agriculture, and the industry: a review

130 years of cyclodextrin discovery for health, food, agriculture, and the industry: a review

Chiral capillary zone electrophoresis in enantioseparation and analysis of cinacalcet impurities: Use of Quality by Design principles in method development

Self‐Assembled Nanomicelles as MRI Blood‐Pool Contrast Agent

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