One-pot synthesis of dibenzaldehyde-terminated poly(ethylene glycol) for preparation of dynamic chitosan-based amphiphilic hydrogels

Rahmani, Sohrab; Barzegar, Mostafa

doi:10.1007/s00289-020-03244-x

Cited by 12 publications

(5 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To confirm the in situ cross-linking of GC and DP derivatives in the hydrogels, FTIR spectroscopy was used. As shown in Figure D, GC exhibited the characteristic peaks of an amino polysaccharide: CO stretching of acetylamino groups at 1680 cm –1 and N–H bending of amino groups exhibited at 1620 cm –1 , while the absorption peaks at 2887 and 1080 cm –1 are assigned to −CH and −CO groups, respectively. , Meanwhile, it can be observed in the FTIR spectra of the hydrogel groups (GC/DP2, GC/DP4, GC/DP6) that the −NH 2 peak of GC and −CHO peak of DP at ∼1725 cm –1 disappeared, whereas a new peak consequently appeared at 1638 cm –1 corresponding to the occurrence of a reversible Schiff base bond (−CN). ,, …”

Section: Resultsmentioning

confidence: 94%

“…This behavior can be attributed to the higher number of free hydrophilic groups (i.e., −OH, −NH 2 ) present in the polymer chains of both GC and DP, allowing them to hold a significant amount of water molecules within their structure. The swelling degree of the hydrogels was enhanced by the increased molecular weight of DP, having longer chains and a higher number of hydrophilic −OH groups, 29 and lower cross-linking density. 32 Furthermore, as emphasized earlier, the swelling and absorption behavior of hydrogels greatly depends on their porosity which is negatively correlated with cross-linking density.…”

Section: Chemical Structurementioning

confidence: 99%

See 1 more Smart Citation

Healing Wounds Efficiently with Biomimetic Soft Matter: Injectable Self-Healing Neutral Glycol Chitosan/Dibenzaldehyde-Terminated Poly(ethylene glycol) Hydrogel with Inherent Antibacterial Properties

Balitaan

Luo

et al. 2023

ACS Appl. Bio Mater.

View full text Add to dashboard Cite

The high prevalence of acquiring skin wounds, along with the emergence of antibiotic-resistant strains that lead to infections, impose a threat to the physical, mental, and socioeconomic health of society. Among the wide array of wound dressings developed, hydrogels are regarded as a biomimetic soft matter of choice owing to their ability to provide a moist environment ideal for healing. Herein, neutral glycol chitosan (GC) was cross-linked via imine bonds with varying concentrations of dibenzaldehyde-terminated polyethylene glycol (DP) to give glycol chitosan/dibenzaldehyde-terminated polyethylene glycol hydrogels (GC/DP). These dynamic Schiff base linkages (absorption peak at 1638 cm–1) within the hydrogel structure endowed their ability to recover from damage as characterized by high-low strain exposure in continuous step strain rheology. Along with their good injectability and biodegradability, the hydrogels exhibited remarkable inhibition against E. coli, P. aeruginosa, and S. aureus. GC/DP hydrogels demonstrated high LC50 values in vivo using zebrafish embryos as a model system due to their relative biocompatibility and a remarkable 93.4 ± 0.88% wound contraction at 30-dpw against 49.1 ± 3.40% of the control. To the best of our knowledge, this is the first study that developed injectable glycol chitosan/dibenzaldehyde-terminated polyethylene glycol self-healing hydrogels for application in wound healing with intrinsic bacteriostatic properties against the three bacteria.

show abstract

Section: Resultsmentioning

confidence: 94%

Section: Chemical Structurementioning

confidence: 99%

Healing Wounds Efficiently with Biomimetic Soft Matter: Injectable Self-Healing Neutral Glycol Chitosan/Dibenzaldehyde-Terminated Poly(ethylene glycol) Hydrogel with Inherent Antibacterial Properties

Balitaan

Luo

et al. 2023

ACS Appl. Bio Mater.

View full text Add to dashboard Cite

show abstract

“…Compared with O-CMC, a broader endothermic peak with a much lower Δ H m value was present in the thermograms of O-CMC–PEG films, indicating a reduced crystallinity. When the PEG linker was introduced into O-CMC, the formed crosslinked structure restricted the chain motion and hindered the formation of crystalline domains 46 . Although the system was deemed partially miscible with immiscibility occurring in the amorphous phase 47 , it was noteworthy that the O-CMC–PEG −6% film exhibited the lowest Δ H m among the four samples, demonstrating superior component compatibility between O-CMC and PEG.…”

Section: Resultsmentioning

confidence: 99%

PEG-crosslinked O-carboxymethyl chitosan films with degradability and antibacterial activity for food packaging

Yang,

Liu,

Gao

et al. 2024

Sci Rep

View full text Add to dashboard Cite

This study developed a kind of PEG-crosslinked O-carboxymethyl chitosan (O-CMC–PEG) with various PEG content for food packaging. The crosslinking agent of isocyanate-terminated PEG was firstly synthesized by a simple condensation reaction between PEG and excess diisocyanate, then the crosslink between O-carboxymethyl chitosan (O-CMC) and crosslinking agent occurred under mild conditions to produce O-CMC–PEG with a crosslinked structure linked by urea bonds. FT-IR and 1H NMR techniques were utilized to confirm the chemical structures of the crosslinking agent and O-CMC–PEGs. Extensive research was conducted to investigate the impact of the PEG content (or crosslinking degree) on the physicochemical characteristics of the casted O-CMC–PEG films. The results illuminated that crosslinking and components compatibility could improve their tensile features and water vapor barrier performance, while high PEG content played the inverse effects due to the microphase separation between PEG and O-CMC segments. The in vitro degradation rate and water sensitivity primarily depended on the crosslinking degree in comparison with the PEG content. Furthermore, caused by the remaining –NH2 groups of O-CMC, the films demonstrated antibacterial activity against Escherichia coli and Staphylococcus aureus. When the PEG content was 6% (medium crosslinking degree), the prepared O-CMC–PEG−6% film possessed optimal tensile features, high water resistance, appropriate degradation rate, low water vapor transmission rate and fine broad-spectrum antibacterial capacity, manifesting a great potential for application in food packaging to extend the shelf life.

show abstract

“…A new peak appeared at 1640 cm –1 , attributed to the imine bond (−CN) formed by the Schiff base reaction (Figure S1). − In addition to the covalent cross-linking of gelatin chains and MD copolymers, the engineered Gel-MD hydrogel may also exhibit noncovalent interactions, including π–π stacking, π–cation, hydrogen bonding (H-bonding), and electrostatic interactions (Figure d). Combinations of these physical and chemical interactions have been previously demonstrated to play a significant role in enhancing the stability and mechanical properties of the resulting gelatin-based hydrogels. , …”

Section: Resultsmentioning

confidence: 99%

Designing a Naturally Inspired Conductive Copolymer to Engineer Wearable Bioadhesives for Sensing Applications

Oz,

Roy,

Jain

et al. 2024

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

The design of adhesive and conductive soft hydrogels using biopolymers with tunable mechanical properties has received significant interest in the field of wearable sensors for detecting human motions. These hydrogels are primarily fabricated through the modification of biopolymers to introduce cross-linking sites, the conjugation of adhesive components, and the incorporation of conductive materials into the hydrogel network. The development of a multifunctional copolymer that integrates adhesive and conductive properties within a single polymer chain with suitable cross-linking sites eliminates the need for biopolymer modification and the addition of extra conductive and adhesive components. In this study, we synthesized a copolymer based on poly([2-(methacryloyloxy)ethyl] trimethylammonium chloride-co-dopamine methacrylamide) (p(METAC-DMA)) using a controlled radical polymerization, allowing for the efficient conjugation of both adhesive and conductive units within a single polymer chain. Subsequently, our multifunctional hydrogel named Gel-MD was fabricated by mixing the p(METAC-DMA) copolymer with non-modified gelatin in which cross-linking took place in an oxidative environment. We confirmed the biocompatibility of the Gel-MD hydrogel through in vitro studies using NIH 3T3 cells as well as in vivo subcutaneous implantation in rats. Furthermore, the Gel-MD hydrogel was effective and sensitive in detecting various human motions, making it a promising wearable sensor for health monitoring and diagnosis.

show abstract

One-pot synthesis of dibenzaldehyde-terminated poly(ethylene glycol) for preparation of dynamic chitosan-based amphiphilic hydrogels

Cited by 12 publications

References 30 publications

Healing Wounds Efficiently with Biomimetic Soft Matter: Injectable Self-Healing Neutral Glycol Chitosan/Dibenzaldehyde-Terminated Poly(ethylene glycol) Hydrogel with Inherent Antibacterial Properties

Healing Wounds Efficiently with Biomimetic Soft Matter: Injectable Self-Healing Neutral Glycol Chitosan/Dibenzaldehyde-Terminated Poly(ethylene glycol) Hydrogel with Inherent Antibacterial Properties

PEG-crosslinked O-carboxymethyl chitosan films with degradability and antibacterial activity for food packaging

Designing a Naturally Inspired Conductive Copolymer to Engineer Wearable Bioadhesives for Sensing Applications

Contact Info

Product

Resources

About