Injectable dynamic covalent hydrogels of boronic acid polymers cross-linked by bioactive plant-derived polyphenols

Huang, Zhuojun; Delparastan, Peyman; Burch, Patrick A.; Cheng, Jing; Cao, Yi; Messersmith, Phillip B.

doi:10.1039/c8bm00453f

Cited by 80 publications

(69 citation statements)

References 68 publications

(64 reference statements)

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“…The second endothermic peak, observed to start at temperatures as low as 65 C, is associated with collagen denaturation, where interchain hydrogen bonds rupture, causing irreversible damage to the collagen structure. 30,68 Denaturation temperatures for the NP and AF were similar to each other and to other biological tissues, such as bovine pericardium, rat-tail tendon, and human skin. 30,62,69 The small kink observed between 65 C and 70 C (Figure 2-"*") has been associated with cleavage of weak bonds between water and matrix macromolecules or conformational changes within fibrils (eg, partial fibril shrinkage), rather than breaking of stronger bonds, which occurs at a slightly higher temperature (~80 C).…”

Section: Discussionmentioning

confidence: 61%

“…Thermal properties of the bovine disc were determined to identify temperatures associated with water freezing and melting, and collagen stability. The second endothermic peak, observed to start at temperatures as low as 65°C, is associated with collagen denaturation, where interchain hydrogen bonds rupture, causing irreversible damage to the collagen structure . Denaturation temperatures for the NP and AF were similar to each other and to other biological tissues, such as bovine pericardium, rat‐tail tendon, and human skin .…”

Section: Discussionmentioning

confidence: 94%

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Radial variation in biochemical composition of the bovine caudal intervertebral disc

et al. 2019

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Bovine caudal discs have been widely used in spine research due to their increased availability, large size, and mechanical and biochemical properties that are comparable to healthy human discs. However, despite their extensive use, the radial variations in bovine disc composition have not yet been rigorously quantified with high spatial resolution. Previous studies were limited to qualitative analyses or provided limited spatial resolution in biochemical properties. Thus, the main objective of this study was to provide quantitative measurements of biochemical composition with higher spatial resolution than previous studies that employed traditional biochemical techniques. Specifically, traditional biochemical analyses were used to measure water, sulfated glycosaminoglycan, collagen, and DNA contents. Gravimetric water content was compared to data obtained through Raman spectroscopy and differential scanning calorimetry. Additionally, spatial distribution of lipids in the disc's collagen network was visualized and quantified, for the first time, using multi‐modal second harmonic generation (SHG) and Coherent anti‐Stokes Raman (CARS) microscopy. Some heterogeneity was observed in the nucleus pulposus, where the water content and water‐to‐protein ratio of the inner nucleus were greater than the outer nucleus. In contrast, the bovine annulus fibrosus exhibited a more heterogeneous distribution of biochemical properties. Comparable results between orthohydroxyproline assay and SHG imaging highlight the potential benefit of using SHG microscopy as a less destructive method for measuring collagen content, particularly when relative changes are of interest. CARS images showed that lipid deposits were distributed equally throughout the disc and appeared either as individual droplets or as clusters of small droplets. In conclusion, this study provided a more comprehensive assessment of spatial variations in biochemical composition of the bovine caudal disc.

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Section: Discussionmentioning

confidence: 61%

Section: Discussionmentioning

confidence: 94%

Radial variation in biochemical composition of the bovine caudal intervertebral disc

et al. 2019

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“…Huang et al. reported injectable dynamic covalent hydrogels formed by tetra‐armed poly(ethylene glycol) with BA termini and plant‐derived poly(phenol) derivatives containing diol or triol groups . The resultant hydrogel showed gradual release of ellagic acid over 20 days.…”

Section: Stimuli‐responsive Release Systemsmentioning

confidence: 99%

“…He et al developed pH-responsive self-healing hydrogels consisting of a 1,3-benzenediboronic acid cross-linker and tetraarmed poly(ethylene glycol) that had terminal catechol groups. [69] The mixture of a polymer and diboronic acid crosslinker formed a hydrogel at pH 9, which transformed to sol at acidic pH. The dynamic nature imparted the hydrogel with shear-thinning and self-healing properties.…”

Section: Self-healing Materialsmentioning

confidence: 99%

Cross‐Linking Building Blocks Using a “Boronate Bridge” to Build Functional Hybrid Materials

Nakahata

Sakai

2018

ChemNanoMat

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Boronic acids are not only a substrate for metal‐catalyzed cross‐coupling but also a molecular recognition tool. Especially, boronic acid‐diol or boronate‐diol interactions have been used to construct molecular‐scale self‐assemblies. This focus review summarizes recent researches using boronic acids as a bridge between similar or dissimilar (macro)molecules to build functional hybrid materials. Functional properties of boronic acid moieties such as molecular selectivity and stimuli‐responsiveness impart the materials with characteristic functions suitable for applications such as release systems, dynamic materials, and bioactive surfaces and scaffolds.

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“…Fast gel-sol-gel transitions lead to aw ide range of applications including 3D printing, drug release,e lectromagnetic shielding and supercapacitors. [6][7][8][9] Although low molecular weight (LMW) hydrogels have betterh omogeneity, reversibility and tunability than polymerich ydrogels, LMW based 3D-printable hydrogels are rare in the literature and are in the very early stages of development. [6,10,11] Suitable building blocks and self-assembling strategies are required for the development of 3D-printable hydrogels.…”

Section: Introductionmentioning

confidence: 99%

Redox‐Active Dynamic Self‐Supporting Thixotropic 3D‐Printable G‐Quadruplex Hydrogels

Biswas

Maiti

Kalaskar

et al. 2018

Chemistry An Asian Journal

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Redox-activeG -quadruplex hydrogels were prepared by dynamic boronate ester formation between ferroceneboronic acid and guanosine. Dynamic boronate esters imparted thixotropic and 3D-printabilityt ot he hydrogel. Initially,t he ferrocene moiety was oxidised to produce a weakerf errocenium-basedg reen hydrogel. However,t he less stable ferrocenium converted into more stable ferrocene to produce ah ydrophobic,w ater-stablea nd robust hydrogel.

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Injectable dynamic covalent hydrogels of boronic acid polymers cross-linked by bioactive plant-derived polyphenols

Abstract: Wisdom from nature: Plant-derived polyphenolic compounds can crosslink boronic acid functionalized polymers through formation of dynamic covalent bonds and function as both cross-linker and bioactive cargo.

Cited by 80 publications

References 68 publications

Radial variation in biochemical composition of the bovine caudal intervertebral disc

Radial variation in biochemical composition of the bovine caudal intervertebral disc

Cross‐Linking Building Blocks Using a “Boronate Bridge” to Build Functional Hybrid Materials

Redox‐Active Dynamic Self‐Supporting Thixotropic 3D‐Printable G‐Quadruplex Hydrogels

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