Synthesis and characterization of physical crosslinking systems based on cyclodextrin inclusion/host‐guest complexation

Kaya, Ethem; Mathias, Lon J.

doi:10.1002/pola.23771

Cited by 17 publications

(15 citation statements)

References 55 publications

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“…45–47 β-cyclodextrin (20 g, 17.62 mmol, 1 eq) was suspended in water (125 mL) and cooled to 0°C. p-toluenesulfonyl chloride (TosCl; 4.2 g, 22 mmol, 1.25 eq) was dissolved in minimal acetonitrile (~10 mL) and added dropwise.…”

Section: Methodsmentioning

confidence: 99%

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: Methodsmentioning

confidence: 99%

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

2013

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“…6‐(6‐Aminohexyl)amino‐6‐deoxy‐β‐cyclodextrin (CD‐HDA) synthesis was performed by adaptation of previously reported similar syntheses (Fetter, Salek, Sikorski, Kumaravel, & Lin, ; Kaya & Mathias, ; Rodell, Kaminski, & Burdick, ) and shown in Figure S3. A round‐bottom flask was charged with CD (1 equiv, 20 g, 17.6 mmol) and DDW (150 ml), and cooled on ice to 0°C for 1 hr.…”

Section: Methodsmentioning

confidence: 99%

Self‐healing injectable gelatin hydrogels for localized therapeutic cell delivery

Sisso

Boit

DeForest

2020

J Biomedical Materials Res

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Self‐healing injectable hydrogel biomaterials uniquely enable precise therapeutic deposition and deployment at specific bodily locations through versatile and minimally invasive processes that can preserve cargo integrity and cell viability. Despite the distinct advantages that injectable hydrogels offer in tissue engineering and therapeutic delivery, exceptionally few have been created using components naturally present in the cellular niche. In this work, we introduce a shear‐thinning hydrogel based on guest‐host complexation of gelatin. As a biocompatible, biodegradable, and nonimmunogenic biopolymer derived from the most abundant extracellular matrix protein (collagen), gelatin offers great utility as the structural component of biomaterials. Taking advantage of reversible guest‐host interactions between β‐cyclodextrin (CD) and adamantane (AD) on modified gelatins, we report the first strategy to afford a self‐healing material based solely on a functionalized extracellular matrix protein. By varying the initial material formulation, hydrogels were synthesized with variable moduli and shear‐thinability across a broad range. Gels were demonstrated to exhibit shear‐thinning and self‐healing properties, supporting protection of clinically relevant stem‐cell‐derived cardiomyocytes during injection. These materials are expected to expand clinical opportunities in cell delivery for in vivo tissue regeneration.

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“…The product was precipitated out of solution using cold acetone (5 × 500 mL), washed with cold diethyl ether (2 × 100 mL), and dried under vacuum to afford the final product mono-6-deoxy-6-aminohexaneamino-β-CD). 5, 64 …”

Section: Methodsmentioning

confidence: 99%

Self-Healing and Thermoresponsive Dual-Cross-Linked Alginate Hydrogels Based on Supramolecular Inclusion Complexes

et al. 2015

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β-cyclodextrin (β-CD), with a lipophilic inner cavity and hydrophilic outer surface, interacts with a large variety of non-polar guest molecules to form non-covalent inclusion complexes. Conjugation of β-CD onto biomacromolecules can form physically-crosslinked hydrogel networks upon mixing with a guest molecule. Herein describes the development and characterization of self-healing, thermo-responsive hydrogels, based on host-guest inclusion complexes between alginate-graft-β-CD and Pluronic® F108 (poly(ethylene glycol)-b-poly(propylene glycol)-b-poly(ethylene glycol)). The mechanics, flow characteristics, and thermal response were contingent on the polymer concentrations, and the host-guest molar ratio. Transient and reversible physical crosslinking between host and guest polymers governed self-assembly, allowing flow under shear stress, and facilitating complete recovery of the material properties within a few seconds of unloading. The mechanical properties of the dual-crosslinked, multi-stimuli responsive hydrogels were tuned as high as 30 kPa at body temperature, and are advantageous for biomedical applications such as drug delivery and cell transplantation.

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Synthesis and characterization of physical crosslinking systems based on cyclodextrin inclusion/host‐guest complexation

Cited by 17 publications

References 55 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

Self‐healing injectable gelatin hydrogels for localized therapeutic cell delivery

Self-Healing and Thermoresponsive Dual-Cross-Linked Alginate Hydrogels Based on Supramolecular Inclusion Complexes

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