Collagen functionalized with unsaturated cyclic anhydrides—interactions in solution and solid state

Potorac, S.; Popa, Marcel; Picton, Luc; Dulong, Virginie; Vereştiuc, Liliana; Cerf, Didier Le

doi:10.1002/bip.22319

Cited by 11 publications

(10 citation statements)

References 29 publications

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“…Collagen, as the most abundant fibrous protein in connective tissues of land-based mammals (e.g. calf skin) which are common raw materials in leather industry, has been widely applied in food, pharmaceutical, biochemistry and cosmetic products, because of its unusual combination of good biocompatibility, low antigenicity and controlled biodegradability [9][10][11][12]. These great biological properties of collagen are ascribed mostly to its unique triple helix conformation, which is stabilized by hydrogen bonds [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Investigation of the solubility and dispersion degree of calf skin collagen in ionic liquids

2019

J Leather Sci Eng

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The dissolution of collagen in ionic liquids (ILs) was highly dependent on the polarity of ILs, which was influenced by their sorts and concentrations. Herein, the solubility and dispersion degree of collagen in two sorts of ILs, namely 1-ethyl-methylimidazolium tetrafluoroborate ([EMIM][BF 4 ]) with low polarity and 1-ethyl-3methylimidazolium acetate ([EMIM][Ac]) with high polarity in a concentration range from 10% to 70% at 10°C were investigated. When 150 mg of collagen was added to 30 mg of ILs, the minimum soluble collagen concentration was 0.02 mg/mL in 70% [EMIM][BF 4 ] with lowest polarity and the maximum was 3.57 mg/mL in 70% [EMIM][Ac] with highest polarity, which indicates that soluble collagen and insoluble collagen fibers were both present. For insoluble collagens, differential scanning calorimetry showed that the thermal-stability was weakened when increasing the ILs concentration and polarity, and the fiber arrangement was looser with a more uniform lyophilized structure, observed by atomic force microscopy and scanning electron microscopy. For soluble collagens, electrophoresis patterns and Fourier transform infrared spectroscopy showed that no polypeptide chain degradation occurred during dissolution, but the thermal denaturation temperature decreased by 0.26°C~7.63°C with the increase of ILs concentrations, measured by ultra-sensitive differential scanning calorimetry. Moreover, the aggregation of collagen molecules was reduced when ILs polarity was increased as determined by fluorescence measurements and dynamic light scattering, which resulted in an increased loose fiber arrangement observed by atomic force microscopy. If the structural integrity of collagen needs to be retained, then the ILs sorts and concentrations should be considered.

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Section: Introductionmentioning

confidence: 99%

Investigation of the solubility and dispersion degree of calf skin collagen in ionic liquids

2019

J Leather Sci Eng

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“…Strategies for collagen functionalization. (A) Methacrylic anhydride (Gaudet and Shreiber, 2012; Pupkaite et al, 2017); (B) 4-vinylbenzylchloride and (C) glycidyl methacrylate (Tronci et al, 2013); (D) thiol-functionalization (Holmes et al, 2017) and (E,F) unsaturated cyclic anhydrides (Potorac et al, 2014). …”

Section: Collagenmentioning

confidence: 99%

Collagen-Based Tissue Engineering Strategies for Vascular Medicine

Copes

Pien

Vlierberghe

et al. 2019

Front. Bioeng. Biotechnol.

157

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Cardiovascular diseases (CVDs) account for the 31% of total death per year, making them the first cause of death in the world. Atherosclerosis is at the root of the most life-threatening CVDs. Vascular bypass/replacement surgery is the primary therapy for patients with atherosclerosis. The use of polymeric grafts for this application is still burdened by high-rate failure, mostly caused by thrombosis and neointima hyperplasia at the implantation site. As a solution for these problems, the fast re-establishment of a functional endothelial cell (EC) layer has been proposed, representing a strategy of crucial importance to reduce these adverse outcomes. Implant modifications using molecules and growth factors with the aim of speeding up the re-endothelialization process has been proposed over the last years. Collagen, by virtue of several favorable properties, has been widely studied for its application in vascular graft enrichment, mainly as a coating for vascular graft luminal surface and as a drug delivery system for the release of pro-endothelialization factors. Collagen coatings provide receptor–ligand binding sites for ECs on the graft surface and, at the same time, act as biological sealants, effectively reducing graft porosity. The development of collagen-based drug delivery systems, in which small-molecule and protein-based drugs are immobilized within a collagen scaffold in order to control their release for biomedical applications, has been widely explored. These systems help in protecting the biological activity of the loaded molecules while slowing their diffusion from collagen scaffolds, providing optimal effects on the targeted vascular cells. Moreover, collagen-based vascular tissue engineering substitutes, despite not showing yet optimal mechanical properties for their use in the therapy, have shown a high potential as physiologically relevant models for the study of cardiovascular therapeutic drugs and diseases. In this review, the current state of the art about the use of collagen-based strategies, mainly as a coating material for the functionalization of vascular graft luminal surface, as a drug delivery system for the release of pro-endothelialization factors, and as physiologically relevant in vitro vascular models, and the future trend in this field of research will be presented and discussed.

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“…However, DMA and CTA can be at least as promising as the itaconic anhydride and maleic anhydride recently mentioned by Potorac at al. 16 which had registered a substitution degree of 10.3 and 5.1 respectively.…”

Section: Industrial and Engineering Chemistry Researchmentioning

confidence: 99%

Preparation and Characterization of Methyl Substituted Maleic Anhydride: Modified Collagens Destined for Medical Applications

Pamfil

Nistor

Zemljič

et al. 2014

Ind. Eng. Chem. Res.

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Porous modified collagens with vinyl groups were synthesized by reaction with 2,3-dimethylmaleic anhydride or citraconic anhydride. The structure of modified collagen was assessed by analytical determination of the amino groups in collagen and spectroscopic methods (Fourier transform infrared (FT-IR) and proton nuclear magnetic resonance (1H NMR)). The amount of protonated amino groups and carboxylic acid moieties of the samples have been determined by potentiometric titration. The dependence of the viscosity of diluted collagen solutions on the concentration and temperature was followed to determine their denaturation transitions. The increased average molecular weight, particle size, and second virial coefficient of modified collagen solutions with respect to the unmodified one proved that modification took place. Coupled thermal analyses (TG/DTG/DTA/FT-IR/MS) also indicated the collagen modification by increased thermal stability and new volatile compounds formed during decomposition. The adhesion tests revealed their potential application in wound dressing and tissue engineering.

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Collagen functionalized with unsaturated cyclic anhydrides—interactions in solution and solid state

Cited by 11 publications

References 29 publications

Investigation of the solubility and dispersion degree of calf skin collagen in ionic liquids

Investigation of the solubility and dispersion degree of calf skin collagen in ionic liquids

Collagen-Based Tissue Engineering Strategies for Vascular Medicine

Preparation and Characterization of Methyl Substituted Maleic Anhydride: Modified Collagens Destined for Medical Applications

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