Recognition of polymer side chains by cyclodextrins

Hashidzume, Akihito; Harada, Akira

doi:10.1039/c1py00162k

Cited by 61 publications

(40 citation statements)

References 79 publications

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“…As discussed in a recent review, others have reported inhibition of the CD complex formation with guest compounds having a low molecular weight or molar volume when the guest is attached to a polymer chain. 43 It is therefore essential to the molecular design that the binding of the guest and host motifs is not impeded, such as by steric hindrance of the proximal bulky HA polymer backbone.…”

Section: Resultsmentioning

confidence: 99%

“…Particularly, cyclodextrins have been investigated for their ability to complex with and control the release of small organic molecules, 24, 26 and their interaction with proteins has also been investigated for pharmaceutical applications as discussed in recent reviews. 43 While such small molecule interactions have proven efficacy, the utilization of supramolecular network structure to control biomolecule release has rarely been examined. 57 In order to perform a generalizable examination of this behavior, we utilize bovine serum albumin (BSA) as it is a moderately sized biomolecule (66.5 kDa) with globular structure.…”

Section: Resultsmentioning

confidence: 99%

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Rational Design of Network Properties in Guest–Host Assembled and Shear-Thinning Hyaluronic Acid Hydrogels

2013

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Shear-thinning hydrogels afford direct injection or catheter delivery to tissues without potential premature gel formation and delivery failure or the use of triggers such as chemical initiators or heat. However, many shear-thinning hydrogels require long reassembly times or exhibit rapid erosion. We developed a shear-thinning hyaluronic acid (HA) hydrogel based on the guest-host interactions of adamantane modified HA (guest macromer, Ad-HA) and β-cyclodextrin modified HA (host macromer, CD-HA). The ability of the guest and host molecules to interact with their counterpart following conjugation to HA was confirmed by 1H-NMR spectroscopy and was similar to that of the native complex. Mixing of Ad-HA and CD-HA resulted in rapid formation of a hydrogel composed of guest-host bonds. The hydrogel physical properties including mechanics and flow characteristics were dependent on crosslink density and network structure, which were controlled through macromer concentration, the extent of guest macromer modification, and the molar ratio of guest and host functional groups. The guest-host assembly mechanism permitted both shear-thinning behavior for ease of injection and near-instantaneous reassembly for material retention at the target sight. The hydrogel erosion and release of a model biomolecule were also dependent on design parameters and were sustained for over 60 days. These hydrogels show potential as a minimally-invasive injectable hydrogel for biomedical applications.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Rational Design of Network Properties in Guest–Host Assembled and Shear-Thinning Hyaluronic Acid Hydrogels

2013

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“…CD chemistry,i np articular, is responsive to av ariety of external fields that break and form complexes,t hereby enabling the construction of adaptive and dynamic assemblies.I na ddition, stimuli-responsive polymers can also be employed as base materials,thereby leading to an additional level of dynamics that can be finely adjusted with respect to the intended function. Several reviews are available that cover aw ide range of aspects of CD-based host-guest chemistry,f or example,b iomedical applications, [34] recognition of polymer side chains, [35] hydrogels, [18,36] and the combination of macromolecular and supramolecular chemistry.…”

Section: Introduction 8351mentioning

confidence: 99%

Dynamic Macromolecular Material Design—The Versatility of Cyclodextrin‐Based Host–Guest Chemistry

2017

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Dynamic and adaptive materials are powerful constructs in macromolecular and polymer chemistry with a wide array of applications in drug delivery, bioactive systems, and self‐healing materials. Very often, dynamic materials are based on carefully tailored cyclodextrin host–guest interactions. The precise incorporation of these host and guest moieties into macromolecular building blocks allows the formation of complex macromolecular structures with predefined functions. Thus, dynamic materials with extraordinary adaptive property profiles—responsive to thermal, chemical, and photonic fields—become accessible. This Review explores the hierarchical formation of dynamic materials and complex macromolecular structures from the molecular via the macromolecular to the colloidal and macroscopic level, with a specific emphasis on the functionality and responsiveness of the assemblies, specifically in biological contexts.

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“…So the study of conformation helps the understanding of the life forms [1][2][3][4]. To date, the control of the conformation strongly attracts the attention of synthetic polymer scientists [5][6][7][8]. Synthetic polymers can be tailor-made from a wide variety of compositions, molecular weights, dispersities, functionalities, shapes, etc.…”

Section: Introductionmentioning

confidence: 99%

Copolymerization of chiral propargylethers and N-propargylamide and conformational control of the copolymers

Dai

2012

Designed Monomers and Polymers

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The novel acetylene monomers, L-proline-derived chiral propargylether (PA, PC, PL, and PM) were synthesized. The copolymerization of L-proline-based propargylether having amide group (PR) with N-(tert-butoxycarbonyl)-L-alanine-Npropargylamide (LA) by different unit ratio and the control of conformation of poly(LA-co-PR) were discussed. The copolymerization catalyzed by (nbd)Rh + [η 6 -C 6 H 5 B À (C 6 H 5 ) 3 ] afforded copolymers with medium M n . The specific rotation of poly(LA 88 -co-PA 12 ), poly(LA 88 -co-PC 12 ), and poly(LA 88 -co-PL 12 ) was 250°, 967°, and 1117°, respectively. The specific rotation of poly(LA-co-PC) ranged from À967°to À167°. Conformation change of poly(LA 88 -co-PR 12 ) and poly(LA-co-PC) in different solvents was studied and it was found that the intramolecular hydrogen bonding in the side chain significantly contribute to the stabilization of helical conformation of the copolymers and that solvent polarity strongly affected the stability of helical conformation. The helical structure of poly(LA 88 -co-PL 12 ) was affected by temperature change.

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Recognition of polymer side chains by cyclodextrins

Cited by 61 publications

References 79 publications

Rational Design of Network Properties in Guest–Host Assembled and Shear-Thinning Hyaluronic Acid Hydrogels

Rational Design of Network Properties in Guest–Host Assembled and Shear-Thinning Hyaluronic Acid Hydrogels

Dynamic Macromolecular Material Design—The Versatility of Cyclodextrin‐Based Host–Guest Chemistry

Copolymerization of chiral propargylethers and N-propargylamide and conformational control of the copolymers

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