Monosubstituted Cyclodextrins as Precursors for Further Use

Řezanka, Michal

doi:10.1002/ejoc.201600693

Cited by 36 publications

(15 citation statements)

References 180 publications

(268 reference statements)

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“…That is why complexes of CDs with various molecules have found multitude applications in many branches of science and industry, for example: in supramolecular polymers [ 226 – 228 ], hydrogels [ 229 ], bioactive materials [ 230 ], drug delivery [ 231 – 234 ], dynamic materials [ 235 ], catalysis [ 236 ] and separation methods [ 237 – 239 ]. Substituted cyclodextrins give the possibility of the more specific modification of different type of substrates, molecules and surfaces [ 240 ], changing their physical and chemical properties, which opens the way to the new applications of such hopeful systems [ 241 ]. Among them, derivatives bearing azobenzene moiety at various locations of the cyclodextrin(s)’ containing architectures, are intensively studied due to their chromogenic character and unique photo-responsive properties induced by the photochemical trans – cis isomerization.…”

Section: Cyclodextrins With Anchored Azo Moietymentioning

confidence: 99%

Azo group(s) in selected macrocyclic compounds

Wagner‐Wysiecka

Łukasik

Biernat

et al. 2018

J Incl Phenom Macrocycl Chem

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Azobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for their interesting binding properties. In this article selected macrocyclic compounds bearing azo group(s) are comprehensively described. Here, the relationship between compounds’ structure and their properties (as e.g. ability to guest complexation, supramolecular structure formation, switching and motion) is reviewed.

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Section: Cyclodextrins With Anchored Azo Moietymentioning

confidence: 99%

Azo group(s) in selected macrocyclic compounds

Wagner‐Wysiecka

Łukasik

Biernat

et al. 2018

J Incl Phenom Macrocycl Chem

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“…Monosubstituted derivatives of CDs [ 10 ] include three regioisomers, namely 2 I - O -, 3 I - O -, and 6 I - O -substituted ones. To separate pure regioisomers from their mixture is tricky.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

Blahová

Filippov

Kováčik

et al. 2017

Beilstein J. Org. Chem.

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Monosubstituted derivatives of γ-cyclodextrin (γ-CD) are suitable building blocks for supramolecular polymers, and can also serve as precursors for the synthesis of other regioselectively monosubstituted γ-CD derivatives. We prepared a set of monosubstituted 2I-O-, 3I-O-, and 6I-O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of γ-CD using two different methods. A key step of the first synthetic procedure is a cross-metathesis between previously described regioisomers of mono-O-allyl derivatives of γ-CD and 2-vinylnaphthalene which gives yields of about 16–25% (2–5% starting from γ-CD). To increase the overall yields, we have developed another method, based on a direct alkylation of γ-CD with 3-(naphthalen-2-yl)allyl chloride as the alkylating reagent. Highly regioselective reaction conditions, which differ for each regioisomer in a used base, gave the monosubstituted isomers in yields between 12–19%. Supramolecular properties of these derivatives were studied by DLS, ITC, NMR, and Cryo-TEM.

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“…To prepare the final PCL-PPyHA-CD scaffold, commonly used 6 A -deoxy-6 A -amino-β-cyclodextrin [28,29] was conjugated onto a PCL-PPyHA scaffold with the aid of carbodiimide chemistry. First, carboxylic groups on the surface were activated with EDC/NHS in an MES buffer (pH 6).…”

Section: Resultsmentioning

confidence: 99%

Cyclodextrin-Polypyrrole Coatings of Scaffolds for Tissue Engineering

et al. 2019

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Polypyrrole is one of the most investigated conductive polymers used for tissue engineering applications because of its advantageous properties and the ability to promote different cell types’ adhesion and proliferation. Together with β-cyclodextrin, which is capable of accommodating helpful biomolecules in its cavity, it would make a perfect couple for use as a scaffold for tissue engineering. Such scaffolds were prepared by the polymerisation of 6-(pyrrol-3-yl)hexanoic acid on polycaprolactone microfibres with subsequent attachment of β-cyclodextrin on the polypyrrole layer. The materials were deeply characterised by several physical and spectroscopic techniques. Testing of the cyclodextrin enriched composite scaffold revealed its better performance in in vitro experiments compared with pristine polycaprolactone or polypyrrole covered polycaprolactone scaffolds.

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Monosubstituted Cyclodextrins as Precursors for Further Use

Cited by 36 publications

References 180 publications

Azo group(s) in selected macrocyclic compounds

Azo group(s) in selected macrocyclic compounds

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

Cyclodextrin-Polypyrrole Coatings of Scaffolds for Tissue Engineering

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