Multiply–linked cyclodextrin–aromatic hybrids: Caps, hinges and clips

Neva, Tania; Fernández, José Manuel Garcı́a; Benito, Juan M.

doi:10.1080/07328303.2019.1609020

Cited by 12 publications

(6 citation statements)

References 140 publications

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“…Tosylates IIb and IIIb can additionally be exploited to attach the Blatter radical to hydroxyl-functionalized partners through the formation of benzyl-type ether linkages. Following prior work on the synthesis and supramolecular properties of cyclodextrin-xylylene hybrids [67][68][69][70], we have conducted preliminary experiments supporting the viability of such an approach, and the results will be published in due course.…”

Section: Discussionmentioning

confidence: 99%

Tethered Blatter Radical for Molecular Grafting: Synthesis of 6-Hydroxyhexyloxy, Hydroxymethyl, and Bis(hydroxymethyl) Derivatives and Their Functionalization

et al. 2022

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Synthetic access to 7-CF3-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals containing 4-(6-hydroxyhexyloxy)phenyl, 4-hydroxymethylphenyl or 3,5-bis(hydroxymethyl)phenyl groups at the C(3) position and their conversion to tosylates and phosphates are described. The tosylates were used to obtain disulfides and an azide with good yields. The Blatter radical containing the azido group underwent a copper(I)-catalyzed azide–alkyne cycloaddition with phenylacetylene under mild conditions, giving the [1,2,3]triazole product in 84% yield. This indicates the suitability of the azido derivative for grafting Blatter radical onto other molecular objects via the CuAAC “click” reaction. The presented derivatives are promising for accessing surfaces and macromolecules spin-labeled with the Blatter radical.

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Section: Discussionmentioning

confidence: 99%

Tethered Blatter Radical for Molecular Grafting: Synthesis of 6-Hydroxyhexyloxy, Hydroxymethyl, and Bis(hydroxymethyl) Derivatives and Their Functionalization

et al. 2022

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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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“…Polycationic cyclodextrins have become the iconic representatives in this category [5,[97][98][99][100][101][102][103][104]. The efficiency in compacting nucleic acids into nanocomplexes (so-called CDplexes) capable of mediating cell entry and subsequent expression of the nucleic acid anticipated activity (transfection) was significantly enhanced for prototypes that can additionally establish cyclodextrin-cyclodextrin interactions through either hydrophobic , host-guest [79,134] or aromatic-aromatic contacts [135][136][137][138][139][140][141][142][143][144][145][146]. As a logical extension, the formulation of CDplexes exposing biorecognizable ligands for the purpose of site-specific gene delivery has been proposed [147][148][149][150][151][152][153][154][155], including the elaboration of carbohydrate decorated CDplexes (glycoCDplexes) conceived for cell receptor glycotargeting [3].…”

Section: Biomacromolecule-templated Formation Of Functional Glycocd Nmentioning

confidence: 99%

Cyclodextrin-Based Functional Glyconanomaterials

2020

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Cyclodextrins (CDs) have long occupied a prominent position in most pharmaceutical laboratories as “off-the-shelve” tools to manipulate the pharmacokinetics of a broad range of active principles, due to their unique combination of biocompatibility and inclusion abilities. The development of precision chemical methods for their selective functionalization, in combination with “click” multiconjugation procedures, have further leveraged the nanoscaffold nature of these oligosaccharides, creating a direct link between the glyco and the nano worlds. CDs have greatly contributed to understand and exploit the interactions between multivalent glycodisplays and carbohydrate-binding proteins (lectins) and to improve the drug-loading and functional properties of nanomaterials through host–guest strategies. The whole range of capabilities can be enabled through self-assembly, template-assisted assembly or covalent connection of CD/glycan building blocks. This review discusses the advancements made in this field during the last decade and the amazing variety of functional glyconanomaterials empowered by the versatility of the CD component.

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Multiply–linked cyclodextrin–aromatic hybrids: Caps, hinges and clips

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Cited by 12 publications

References 140 publications

Tethered Blatter Radical for Molecular Grafting: Synthesis of 6-Hydroxyhexyloxy, Hydroxymethyl, and Bis(hydroxymethyl) Derivatives and Their Functionalization

Tethered Blatter Radical for Molecular Grafting: Synthesis of 6-Hydroxyhexyloxy, Hydroxymethyl, and Bis(hydroxymethyl) Derivatives and Their Functionalization

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

Cyclodextrin-Based Functional Glyconanomaterials

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