A Water-Based Chitosan-Maleimide Precursor for Bioconjugation: An Example of a Rapid Pathway for an In Situ Injectable Adhesive Gel

Abstract

Chitosan conjugated with maleimide (CS-Mal) as a potential precursor for bioconjugation and the example of the application in in situ injectable adhesive gel is proposed. The homogeneous reaction in water/dimethyl sulfoxide (DMSO) (1:1) followed by dialysis in HCl (10 × 10 m) is a good condition to obtain CS-Mal. When SH-PEG-SH is applied as the crosslinker, the gel can be obtained in a few seconds without any by-products at room temperature. The gel formation and properties are controllable by simply varying the concentration and the molecular weight of CS, the Mal substitution degree, and the temperature. The gel is injectable and shows adhesive property for soft tissue. Moreover, the gel shows not only biocompatibility to SAOS2 cells but also antimicrobial activity against both gram-negative and gram-positive bacteria. CS-Mal is useful not only for bioconjugation of CS but also for development of biomaterials.

Hydrolytic and lysozymic degradability of chitosan systems with heparin-mimicking pendant groups

“…Network formation was accomplished via a nucleophilic addition/elimination mechanism of CT primary amino groups with NHS-activated diacids (Scheme S1, SI). An averaged degree of crosslinking was measured via TNBS calorimetric assay in the range of 8 -26 mol.-%; samples CT-4Ph and CT-PEG displayed the highest and lowest crosslink densities, respectively (Table 1), in agreement with previous studies [1,10,14]. TNBS values of PhS-crosslinked CT were used to determine the molar content of sulfonic acid moieties, considering a 1:2 molar ratio between the former and PhS-crosslinked amino groups.…”

Diels-Alder-Chitosan based dissociative covalent adaptable networks

“…Hannaa, * , 2005) , (Kaya et al, 2018) Crosslinked chitosan films are generally obtained by reaction with glutaraldehyde, diepoxides, dianhydride, genipin and tripolyphosphate (Divya Nataraj, Seema Sakkara, 2018) , (Jin et al, 2004) , (Singh, Kuldeep Rajat Suri & Rana, 2012) , (Tiwary & Rana, 2010) , (Kavianinia et al, 2014) and few literature is provided on Diels-Alder based hydrogels for chitosan but not in view of film forming. (Matsumoto et al, 2016) , (Montiel-Herrera et al, 2015) , , (Elschner et al, 2018) In 2015, Montiel-Herrera et al (Montiel-Herrera et al, 2015) synthesized Diels-Alder chitosan microparticles. They functionalized chitosan with furan chitosan by a two-step reductive amidation (Erreur !…”

Enzyme Degradable Polymersomes from Chitosan‐g‐[poly‐l‐lysine‐block‐ε‐caprolactone] Copolymer

“…In the first step, maleimide groups were introduced as side chains at the chitosan backbone with different degrees of substitution (DS) via a reaction between carboxylic acid of N-maleoyl-βalanine and the amine function of chitosan ( Figure 2, Step 1). [17] www.advancedsciencenews.com www.mbs-journal.de…”

“…CS-Mal was synthesized according to Matsumoto et al (Figure 2, Step 1). [ 17 ] Briefly, CS (100 mg) and HOBt (91 mg, 0.5 mmol) were dissolved in 3 mL of ultrapure water and stirred overnight. To the CS solution, 33 mL of dimethyl sulfoxide (DMSO) and a variable amount of 3-maleimidopropionic acid were added.…”