Interactions of Glycopolymers with Assemblies of Peptide Amphiphiles via Dynamic Covalent Bonding

Wang, Jue; Gao, Zhenfei; Qi, Wenjing; Zhao, Yu; Zhang, Pan; Lin, Ming‐Chang; Li, Zhiming; Chen, Guosong; Jiang, Ming

doi:10.1021/acsbiomaterials.7b00642

Cited by 5 publications

(5 citation statements)

References 25 publications

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“…In a recent study, a peptide amphiphile with a benzoboroxole (BOB) group attached at the hydrophilic end was assembled into fibers, leading to aligned BOB/saccharide pairs with low molecular mobility, high density and multivalent effect. 141 Thus, enhanced nuclear Overhauser effects could be observed by NMR (NOESY), confirming the binding between BOB and mannopyranoside on the site of diols at 2,3-position instead of 4,6-position.…”

Section: Recognition Of Biologically Active Compoundsmentioning

confidence: 66%

Dynamic covalent polymers for biomedical applications

Zhang

Ulrich

et al. 2020

Mater. Chem. Front.

121

103

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Section: Recognition Of Biologically Active Compoundsmentioning

confidence: 66%

Dynamic covalent polymers for biomedical applications

Zhang

Ulrich

et al. 2020

Mater. Chem. Front.

121

103

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“…Benzoxaborole has been shown by Hall and co-workers to have a strong binding affinity to cis -1,2/1,3-diols of saccharides under physiological conditions. , Therefore, complexation between galactose groups of PLDL and benzoxaborole groups of PAB can lead to cross-linking and subsequent hydrogel formation. To prepare the hydrogels, PLDL and PAB polymers were separately dissolved in PBS, followed by mixing with pipetting.…”

Section: Resultsmentioning

confidence: 99%

Injectable, Self-Healing, and Multi-Responsive Hydrogels via Dynamic Covalent Bond Formation between Benzoxaborole and Hydroxyl Groups

et al. 2018

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Hydrogels that are injectable, self-healing, and multiresponsive are becoming increasingly relevant for a wide range of applications. In this work, we have successfully developed a novel approach in the fabrication of smart hydrogels with all the above properties. A symmetrical ABA triblock copolymer was first synthesized via atom transfer radical polymerization with a temperature responsive middle block and two permanently hydrophilic glycopolymer chains on both ends. Hydrogels were subsequently constructed by mixing the triblock copolymer with another linear hydrophilic copolymer bearing benzoxaborole groups. The interactions of the benzoxaborole groups with the sugar hydroxyl groups allowed the formation of dynamic covalent bonds. The resulting hydrogels exhibited temperature, pH, and sugar responsiveness. Rheological studies confirmed that the mechanical property can be tuned by changing the pH as well as the galactose/ benzoxaborole molar ratio. Furthermore, the hydrogels showed excellent self-healing ability and shear-thinning performance due to the inherent well-known dynamic covalent bonds of boronic esters. Therefore, these types of hydrogels can have excellent biomedical applications.

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“…150 endows these viruses with rich liquid crystal phases. − Recent works have also demonstrated that such rodlike viruses are valuable candidates as the backbone for multiple responsive hydrogels. , In the current work, a phenylboronic acid (PBA) derivative ( 1 in Scheme ) with a p K a that is close to the physiological pH was tailor-synthesized and coupled to the nanofibrous M13 virus, leading to fibrous bioconjugates of the PBA-M13 virus that can form dynamic covalent bonds with 1,2 or 1,3 diol-containing agents at physiological pH . Dynamic hydrogels are instantly formed upon mixing poly(vinyl alcohol) (PVA) and PBA-M13 at the physiological pH, due to binding of the multiple diols of the linear PVA chain with several viruses that cross-link the virus backbone into a three-dimensional network. ,− The mechanical strength can be tuned by the amount of each component. Excellent injectability and self-healing properties were demonstrated with the current gels.…”

Section: Introductionmentioning

confidence: 98%

Nanofilamentous Virus-Based Dynamic Hydrogels with Tunable Internal Structures, Injectability, Self-Healing, and Sugar Responsiveness at Physiological pH

et al. 2018

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With expanding applications of hydrogels in diverse fields ranging from biomaterials to sensors, actuators, and soft robotics, there is an urgent need to endow one single gel with multiple physicochemical properties, such as stimuli-responsiveness, injectability, self-healing, and tunable internal structures. However, it is challenging to simultaneously incorporate these highly sought-after properties into one single gel. Herein, a conceptual hydrogel system with all of these properties is presented via combining bioconjugate chemistry, filamentous viruses, and dynamic covalent bonds. Nanofilamentous bioconjugates with diol affinity were prepared by coupling a tailor-synthesized low-pK a phenylboronic acid (PBA) derivative to a well-defined green nanofiber the M13 virus with a high aspect ratio (PBA-M13). Dynamic hydrogels with tunable mechanical strength were prepared by using multiple diol-containing agents such as poly(vinyl alcohol) to cross-link such PBA-M13 via the classic boronic–diol dynamic bonds. The as-prepared hydrogels exhibit excellent injectability and self-healing behaviors as well as easy chemical accessibility of the PBA moieties on the virus backbone inside the gel matrix. Ordered internal structures were imparted into virus-based hydrogels by simple shear-induced alignment of the virus nanofibers. Furthermore, unique hydrogels with chiral internal structures were fabricated through in situ gelation induced by diffusion of diol-containing molecules to fix the chiral liquid crystal phase of the PBA-M13 virus. Sugar responsiveness of this gel leads to a glucose-regulated release behavior of payloads such as insulin. All of these properties have been implemented at physiological pH, which will facilitate future applications of these hydrogels as biomaterials.

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Interactions of Glycopolymers with Assemblies of Peptide Amphiphiles via Dynamic Covalent Bonding

Cited by 5 publications

References 25 publications

Dynamic covalent polymers for biomedical applications

Dynamic covalent polymers for biomedical applications

Injectable, Self-Healing, and Multi-Responsive Hydrogels via Dynamic Covalent Bond Formation between Benzoxaborole and Hydroxyl Groups

Nanofilamentous Virus-Based Dynamic Hydrogels with Tunable Internal Structures, Injectability, Self-Healing, and Sugar Responsiveness at Physiological pH

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