Hydrogels represent 3D polymeric networks specially designed for various medical applications. Due to their porous structure, they are able to swollen and to entrap large amounts of therapeutic agents and other molecules. In addition, their biocompatibility and biodegradability properties, together with a controlled release profile, make hydrogels a potential drug delivery system. In vivo studies have demonstrated their effectiveness as curing platforms for various diseases and affections. In addition, the results of the clinical trials are very encouraging and promising for the use of hydrogels as future target therapy strategies.

https://www.mdpi.com/1999-4923/11/9/432/pdf

Hydrogels Based Drug Delivery Synthesis, Characterization and Administration

Labile crosslinked hyaluronic acid via urethane formation using bis(β- isocyanatoethyl) disulphide with tuneable physicochemical and immunomodulatory properties

Hyaluronic acid (HA) is widely distributed in human connective tissue, and its unique biological and physicochemical properties and ability to facilitate biological structure repair make it a promising candidate for three-dimensional (3D) bioprinting in the field of tissue regeneration and biomedical engineering. Moreover, HA is an ideal raw material for bioinks in tissue engineering because of its histocompatibility, non-immunogenicity, biodegradability, anti-inflammatory properties, anti-angiogenic properties, and modifiability. Tissue engineering is a multidisciplinary field focusing on in vitro reconstructions of mammalian tissues, such as cartilage tissue engineering, neural tissue engineering, skin tissue engineering, and other areas that require further clinical applications. In this review, we first describe the modification methods, cross-linking methods, and bioprinting strategies for HA and its derivatives as bioinks and then critically discuss the strengths, shortcomings, and feasibility of each method. Subsequently, we reviewed the practical clinical applications and outcomes of HA bioink in 3D bioprinting. Finally, we describe the challenges and opportunities in the development of HA bioink to provide further research references and insights. 

3D printed scaffolds based on hyaluronic acid bioinks for tissue engineering: a review

Polyelectrolyte hydrogels play an important role in tissue engineering and can be produced from natural polymers, such as the glycosaminoglycan hyaluronan. In order to control charge density and mechanical properties of hyaluronan-based hydrogels, we developed cross-linkers with a neutral or positively charged triazole core with different lengths of spacer arms and two terminal maleimide groups. These cross-linkers react with thiolated hyaluronan in a fast, stoichiometric thio-Michael addition. Introducing a positive charge on the core of the cross-linker enabled us to compare hydrogels with the same interconnectivity, but a different charge density. Positively charged cross-linkers form stiffer hydrogels relatively independent of the size of the cross-linker, whereas neutral cross-linkers only form stable hydrogels at small spacer lengths. These novel cross-linkers provide a platform to tune the hydrogel network charge and thus the mechanical properties of the network. In addition, they might offer a wide range of applications especially in bioprinting for precise design of hydrogels.

https://www.mdpi.com/1996-1944/9/10/810/pdf

Charged Triazole Cross-Linkers for Hyaluronan-Based Hybrid Hydrogels

https://www.tandfonline.com/doi/pdf/10.1080/14686996.2020.1783967

Structural reorganization and crack-healing properties of hydrogels based on dynamic diselenide linkages.

A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.

Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels

The extracellular matrix (ECM) represents a highly charged and hydrated network in which different cells in vertebrate tissues are embedded. Hydrogels as minimal ECM mimetics with a controlled chemistry offer the opportunity to vary material properties by varying the negative network charge. In this paper, a synthetic biology model of the ECM based on natural and highly negatively charged polyelectrolyte hyaluronic acid (HA) is characterized with specific emphasis on its charge-related bioactivity. Therefore, the thiol-Michael addition click reaction is used to produce HA hydrogels with defined network structure and charge density. The presented hydrogels show enzymatic degradability and cell attachment. These properties depend on both covalent and electrostatic interactions within the hydrogel network. Furthermore, no unspecific or specific attachment of proteins to the presented hydrogels is observed. In addition, these fundamental insights into charge-related ECM behavior and the influence of electrostatic properties could also lead to innovations in existing biomedical products.

https://www.mdpi.com/1420-3049/23/4/769/pdf

Charge-Controlled Synthetic Hyaluronan-Based Cell Matrices

Hyaluronic acid (HA) is a vital, functional component of the extracellular matrix (ECM). Following a synthetic biology approach, we designed polyelectrolyte hydrogels composed of HA as a polymeric backbone interconnected by short covalent crosslinkers. Utilizing a thiol-Michael addition, defined network structures are created, which can be modulated by the aromatic core and charge of the crosslinkers. With increasing negative network charge, varied both through the charge of the crosslinker and the degree of functionalization of the HA chain, the Young's modulus of the hydrogels decreases linearly as swelling ratios increase. Interestingly, secondary interactions with aromatic crosslinkers are stronger for elastin inspired crosslinkers with a pyridinium core compared to analogous triazolium crosslinkers. Based on the defined covalent interconnectivity of these HA-hydrogels, we were able to demonstrate the specific electrostatic and aromatic interactions induced by different short crosslinkers.

https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/slct.201701908

Charge Matters: Modulating Secondary Interactions in Hyaluronan Hydrogels

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Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels

Charge-Controlled Synthetic Hyaluronan-Based Cell Matrices

Charge Matters: Modulating Secondary Interactions in Hyaluronan Hydrogels