Photocrosslinked hydrogels from coumarin derivatives of hyaluronic acid for tissue engineering applications

Beninatto, Riccardo; Barbera, Carlo; Lucchi, Ottorino De; Borsato, Giuseppe; Serena, Elena; Guarise, Cristian; Pavan, M.; Luni, Camilla; Martewicz, Sebastian; Galesso, Devis; Elvassore, Nicola

doi:10.1016/j.msec.2018.11.052

Cited by 43 publications

(48 citation statements)

References 30 publications

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“…Other light-induced covalent crosslinking strategies have been explored that do not involve free radical polymerization, thus avoiding the need for initiator molecules. A GAG system based on the incorporation of coumarin groups in HA backbone was shown to promote covalent crosslinking by coumarin cyclodimerization, without the need for a radical initiator [45]. In this study, a coumarin group was linked to HA backbone through a triethylene glycol (TEG) side arm, and covalent crosslinking occurred between two coumarin groups, upon exposure to near-UV light (λ = 365 nm) ( Figure 4A) [45].…”

Section: Light and Temperature Induced Crosslinkingmentioning

confidence: 77%

“…Molecules 2020, 25, 978 5 of 38 coumarin cyclodimerization, without the need for a radical initiator [45]. In this study, a coumarin group was linked to HA backbone through a triethylene glycol (TEG) side arm, and covalent crosslinking occurred between two coumarin groups, upon exposure to near-UV light (λ = 365 nm) ( Figure 4A) [45].…”

Section: Light and Temperature Induced Crosslinkingmentioning

confidence: 86%

“…A GAG system based on the incorporation of coumarin groups in HA backbone was shown to promote covalent crosslinking by coumarin cyclodimerization, without the need for a radical initiator [45]. In this study, a coumarin group was linked to HA backbone through a triethylene glycol (TEG) side arm, and covalent crosslinking occurred between two coumarin groups, upon exposure to near-UV light (λ = 365 nm) ( Figure 4A) [45]. Interestingly, while coumarin works as the covalent linker in the HA hydrogel, this compound and its derivatives are also reported to have, per se, relevant biological roles as anti-inflammatory [46,47], antioxidant [48] and anti-cancer [49] agents.…”

Section: Light and Temperature Induced Crosslinkingmentioning

confidence: 99%

“…They should also provide enough mechanical and structural stability to endure such procedures without compromising their performance on host tissues. Representation of coumarin derivatized HA undergoing crosslinking when exposed to near-UV light stimulus (λ = 365 nm) via photocycloaddition reaction between coumarin moieties and without any catalysts or radical initiators [45]. (B) Synthesis of HA derivatives incorporating transglutaminase (TG) peptides; thiol groups were incorporated in HA backbone via carbodiimide reaction (HA-SH); thiol groups were then substituted with vinyl sulfones (HA-VS) and subsequently with TG/glutamine (HA-TG/Gln) and TG/lysine (HA-TG-Lys) peptides via Michael addition; MMP cleavage site marked by an arrow, cysteines (C) that provide thiols for conjugation onto HA-VS are in bold and the Lys (K) and Gln (Q) covalently coupled to each other on their side chains by FXIIIa are underlined [39].…”

Section: Crosslinking With Protein Binding Domainsmentioning

confidence: 99%

“…Central sequence in TriCatchers may incorporate RGDSP-containing or MMP-cleavable linkers [56]. (E) (i) Representation of the HA/CS/PEGDA hydrogel and gelation process that leads to a polymeric network covalently crosslinked via thiol-ene Michael addition click reactions; (ii) chemical crosslinking of GAG thiol derivative mixtures, HA-SH (blue) and CS-SH (red), with PEGDA (green) by conjugate addition [58] (Reproduced with permission from [39,45,53,56,58]).…”

Section: Crosslinking With Protein Binding Domainsmentioning

confidence: 99%

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Glycosaminoglycan-Inspired Biomaterials for the Development of Bioactive Hydrogel Networks

et al. 2020

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Glycosaminoglycans (GAG) are long, linear polysaccharides that display a wide range of relevant biological roles. Particularly, in the extracellular matrix (ECM) GAG specifically interact with other biological molecules, such as growth factors, protecting them from proteolysis or inhibiting factors. Additionally, ECM GAG are partially responsible for the mechanical stability of tissues due to their capacity to retain high amounts of water, enabling hydration of the ECM and rendering it resistant to compressive forces. In this review, the use of GAG for developing hydrogel networks with improved biological activity and/or mechanical properties is discussed. Greater focus is given to strategies involving the production of hydrogels that are composed of GAG alone or in combination with other materials. Additionally, approaches used to introduce GAG-inspired features in biomaterials of different sources will also be presented.

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Section: Light and Temperature Induced Crosslinkingmentioning

confidence: 77%

Section: Light and Temperature Induced Crosslinkingmentioning

confidence: 86%

Section: Light and Temperature Induced Crosslinkingmentioning

confidence: 99%

Section: Crosslinking With Protein Binding Domainsmentioning

confidence: 99%

Section: Crosslinking With Protein Binding Domainsmentioning

confidence: 99%

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Glycosaminoglycan-Inspired Biomaterials for the Development of Bioactive Hydrogel Networks

et al. 2020

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Photoresponsive Drug Delivery Systems: Challenges and Progress

Yang,

Long,

Chu

et al. 2024

Adv Funct Materials

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Photoresponsive drug delivery systems (PDDSs) have emerged as a promising toolbox for drug delivery, offering precise control over the site, duration, and dosage of light‐triggered medication. It allows controlled drug release, photo‐triggered targeting, diagnosis, and treatment, improving the precision and efficacy of therapies for various diseases. Despite progress in designing different PDDSs, clinical translation has been limited due to various obstacles. Herein, this review article focuses on three critical challenges of PDDSs: 1) accumulation at diseased lesions, 2) precision of light irradiation, and 3) penetration of light in tissues. Also, this article summarizes and discusses current advancements and strategies to address these challenges. Overall, it emphasizes the need to clarify the current challenges from bench to bedside and develop strategies to enhance therapeutic outcomes, increase compatibility and patient compliance, and unlock the possibilities in different clinical therapies.

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A Photopolymerizable Biocompatible Hyaluronic Acid Hydrogel Promotes Early Articular Cartilage Repair in a Minipig Model In Vivo

Gao,

Beninatto,

Oláh

et al. 2023

Adv Healthcare Materials

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Articular cartilage defects represent an unsolved clinical challenge. Photopolymerizable hydrogels are attractive candidates supporting repair. This study investigates the short‐term safety and efficacy of two novel hyaluronic acid (HA)‐triethylene glycol (TEG)‐coumarin hydrogels photocrosslinked in situ in a clinically relevant large animal model. We hypothesize that HA‐hydrogel‐augmented microfracture (MFX) is superior to MFX in enhancing early cartilage repair, and that the molar degree of substitution and concentration of HA affects repair. We treat chondral full‐thickness defects in the knees of adult minipigs with either (1) debridement (No MFX), (2) debridement and MFX, (3) debridement, MFX and HA hydrogel (30% molar derivatization, 30 mg/ml HA; F3) (MFX+F3), and (4) debridement, MFX and HA hydrogel (40% molar derivatization, 20 mg/ml HA; F4) (MFX+F4). After 8 weeks postoperatively, MFX+F3 significantly improves total macroscopic and histological scores compared with all other groups without negative effects, besides significantly enhancing the individual repair parameters “defect architecture”, “repair tissue surface” (compared with No MFX, MFX), and “subchondral bone” (compared with MFX). These data indicate that photopolymerizable HA hydrogels enable a favorable metastable microenvironment promoting early chondrogenesis in vivo. This work also uncovers a mechanism for effective HA‐augmented cartilage repair by combining lower molar derivatization with higher concentrations.This article is protected by copyright. All rights reserved

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Photocrosslinked hydrogels from coumarin derivatives of hyaluronic acid for tissue engineering applications

Cited by 43 publications

References 30 publications

Glycosaminoglycan-Inspired Biomaterials for the Development of Bioactive Hydrogel Networks

Glycosaminoglycan-Inspired Biomaterials for the Development of Bioactive Hydrogel Networks

Photoresponsive Drug Delivery Systems: Challenges and Progress

A Photopolymerizable Biocompatible Hyaluronic Acid Hydrogel Promotes Early Articular Cartilage Repair in a Minipig Model In Vivo

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