Synthesis of mucoadhesive thiolated gelatin using a two-step reaction process

Duggan, Sarah; O’Donovan, Órla; Owens, Eleanor; Cummins, Wayne; Hughes, Helen

doi:10.1016/j.ejpb.2015.01.027

Cited by 31 publications

(17 citation statements)

References 24 publications

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“…gel-MOD/gel-MA(A) [9], gel-MOD-AEMA (B) [16], gel-MA-DA (C) [36], GMA (D) [37], gel-AA (E) [38], gelatin-acrylamide (F) [39], gel-BTHE (G) [40], gel-Boc-AEMA (H) [41], methacrylated poly(ethylene glycol)-modified gelatin(MPG) (I) [42,43], gelatin-PEG (K) [44]; Thiolated gelatins suitable for disulphide chemistry of thiol-ene chemistry (purple): gel-SH (J) [44,45], gel-SH (L) [45,46], aminated gelatin (M) [5,47], aminated-thiolated-gelatin (N) [47], gelatin-Cys-2-MPD (O) [48], gelatin-Cys (P) [48], gel-PEG-Cys (Q) [49], gelatin-TBA-MNA (R) [50], gel-S (S) [51,52], gelatin-thiobutyrolacton (T) [53];…”

Section: Introductionmentioning

confidence: 99%

(Photo-)crosslinkable gelatin derivatives for biofabrication applications

et al. 2019

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Over the recent decades gelatin has proven to be very suitable as an extracellular matrix mimic for biofabrication and tissue engineering applications. However, gelatin is prone to dissolution at typical cell culture conditions and is therefore often chemically modified to introduce (photo-)crosslinkable functionalities. These modifications allow to tune the material properties of gelatin, making it suitable for a wide range of biofabrication techniques both as a bioink and as a biomaterial ink (component).The present review provides a non-exhaustive overview of the different reported gelatin modification strategies to yield crosslinkable materials that can be used to form hydrogels suitable for 2 biofabrication applications. The different crosslinking chemistries are discussed and classified according to their crosslinking mechanism including chain-growth and step-growth polymerization.The step-growth polymerization mechanisms are further classified based on the specific chemistry including different (photo-)click chemistries and reversible systems. The benefits and drawbacks of each chemistry are also briefly discussed. Furthermore, focus is placed on different biofabrication strategies applying inkjet, deposition and light-based additive manufacturing techniques, and the applications of the obtained 3D constructs.

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Section: Introductionmentioning

confidence: 99%

(Photo-)crosslinkable gelatin derivatives for biofabrication applications

et al. 2019

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“…The measured thiol content ( X SH‐Ellman ) is in good correlation with the results calculated from NMR peaks ( X SH‐NMR ) as well as the feed ratio of components ( X CEA‐feed ), and oxidation occurred only to a small extent (Table ). As a better comparison to thiolated polymers found in the literature, the thiol content is also given in units of µmol g −1 (Table ). The thiol content achieved here is considerably larger than that of several natural and synthetic polymers reported earlier.…”

Section: Resultsmentioning

confidence: 99%

“…Other synthetic pathways are also known, but used only in a few cases. Examples are the formation of amidine bonds using iminothiolane and polyallylamine or gelatine (150–600 µmol SH g −1 ), the reductive amination of aldehydes formed by the oxidation of vicinal diols in polysaccharides with cysteine or cysteamine (1300–2000 µmol SH g −1 ) and conversion of hydroxyl groups to thiols with thiourea through bromination (130 µmol SH g −1 ) . Although attachment of thiol groups has been applied to a wide variety of polymers, there is practically no record of the conversion of these reactions and the thiol content is usually not controlled.…”

Section: Introductionmentioning

confidence: 99%

The effect of thiol content on the gelation and mucoadhesion of thiolated poly(aspartic acid)

et al. 2017

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A synthetic poly(amino acid), poly(aspartic acid) modified with thioethyl side groups, was studied as an in situ gelling and mucoadhesive dosage form. The chemical structure and the controllable, large thiol content of the polymer were confirmed using 1 H NMR spectroscopy and Ellman's assay. In situ gelation of aqueous polymer solutions was induced by oxidation and monitored using oscillation rheometry. The strength of mucoadhesion towards excised mucosa was characterised by tensile tests in ex vivo experiments. Release kinetics of ophthalmic antibiotic ofloxacin was studied from an in situ crosslinked hydrogel and a liquid formulation to prove the sustained release of the former.

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“…Numerous naturally occurring polymers, such as CS [26; 27], cellulose [28], hyaluronic acid [29], gelatin [30], collagen [31], and synthetic polymers, such as poly(acrylic acid) (PAA) [32], are commonly used as thiomer precursors. Thiomers are characterized as cationic, anionic and non-ionic based on the chemical structure of these parent molecules.…”

Section: First Generationmentioning

confidence: 99%

Thiomers and their potential applications in drug delivery

Shah

Dilawar

et al. 2016

Expert Opinion on Drug Delivery

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Thiomers are the product of the immobilization of sulfhydryl-bearing ligands onto the polymer backbone of a conventional polymer, which results in a significant improvement in mucoadhesion; in situ gelation and efflux inhibition compare with unchanged polymers. Because of thiol groups, thiomers have more reactivity and enhanced protection against oxidation. Since the late 1990s, extensive work has been conducted on these promising polymeric excipients in the pharmaceutical field. Areas covered: This review covers thiomers, their classification and their different properties. Various techniques for the synthesis, purification and characterization of thiomers are described in detail. This review also encompasses their various properties such as mucoadhesion, permeation enhancement, in situ gelation and efflux inhibition, as well as different formulations based on thiomers. In addition to the use of thiomers as multifunctional excipients, this review also encompasses their use as drugs. Expert opinion: The synthesis is realized by linkage of sulfhydryl-bearing ligands but reported methods give low yields. Higher degrees of modification are not necessary and would probably lead to extreme changes in properties. Nevertheless, an accurate characterization of the final product is important. The scale-up procedure for industrial manufacturing has been adapted to produce GMP materials; Lacrimera® eye drops have already entered the European market.

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Synthesis of mucoadhesive thiolated gelatin using a two-step reaction process

Cited by 31 publications

References 24 publications

(Photo-)crosslinkable gelatin derivatives for biofabrication applications

(Photo-)crosslinkable gelatin derivatives for biofabrication applications

The effect of thiol content on the gelation and mucoadhesion of thiolated poly(aspartic acid)

Thiomers and their potential applications in drug delivery

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