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A series of chiral hydrogels was prepared from a homogeneous mixture of chitosan and betulinic aldehyde in different molar ratios, under the effect of ultrasound. The hydrogelation mechanism has been investigated by FTIR and CD spectroscopy, wide angle X-ray diffraction and polarized light microscopy. The morphology of hydrogels was examined by SEM. The swelling ability has been tested in three media of different pH. It was concluded that hydrogelation occurred by different pathways, closely related to the peculiarities of the chitosan-betulin systems. Circular dichroism measurements revealed chiroptical properties of the hydrogels, correlated to their content and crosslinking pathway. [ABSTRACT FROM AUTHOR]

A series of hydrogels based on chitosan polyamine and nitrosalicylaldehyde were prepared via dynamic covalent chemistry (DCC), by imination and transimination reactions towards ordered clusters which play the role of crosslinking nodes of the chitosan network. The hydrogelation mechanism has been proved through NMR and FTIR spectroscopy, X-ray diffraction and polarized light microscopy. The successful preparation of the hydrogels and their mechanical properties were further investigated using rheological measurements. By electron scanning microscopy, the hydrogels exhibited a channels microstructure morphology which critically influenced their fast swelling by capillarity. The hydrogels cytotoxicity was explored in vitro on HeLa cancer cells and their biocompatibility was monitored in vivo by subcutaneous implantation on rats. The novel hydrogels proved good in vitro cytotoxicity on the HeLa cells and also in vivo biocompatibility in rats. Thus, these novel biomaterials promise to be suitable for local cancer therapy. [ABSTRACT FROM AUTHOR]

The paper focusses on the synthesis of novel hydrogels by joining natural biodegradable compounds with the aim to achieve biocompatible materials for bio related applications. The hydrogels were prepared from chitosan and citral by constitutional dynamic chemistry, incorporating both molecular and supramolecular dynamic features. The hydrophobic flexible citral has been reversible immobilized onto the hydrophilic chitosan backbone via imine bonds to form amphiphilic glycodynamers, which further self-ordered through supramolecular interactions into a 3D-network of biodynameric hydrogel. The synthetic pathway has been demonstrated by NMR and FTIR spectroscopy, X-ray diffraction and polarized light microscopy. Studies of the hydrogel morphology revealed a 3D porous microstructure, whose pores size correlated with the crosslinking degree. Rheological investigations evidenced high elasticity, thermo-responsiveness and thixotropic behavior. As a proof of the concept, the hydrogels proved in vivo biocompatibility on laboratory mice. The paper successfully implements the constitutional dynamic chemistry in generation of chitosan high performance hydrogels. [ABSTRACT FROM AUTHOR]

Chitosan based hydrogels are a class of cross-linked materials intensely studied for their biomedical, industrial and environmental application, but their biomedical use is limited because of the toxicity of different organic crosslinkers. To overcome this disadvantage, a new strategy to produce supramolecular chitosan hydrogels using low molecular weight compounds able to form covalent linkages and H-bonds to give a dual crosslinking is proposed. For this purpose we used 2-formylphenylboronic acid, which brings the advantage of imine stabilization via iminoboronate formation and potential antifungal activity due to the presence of boric acid residue. FTIR and NMR spectroscopy indicated that the gelling process took place by chemo-physical crosslinking forming a dual iminoboronate-chitosan network. Further, X-ray diffraction demonstrated a three-dimensional nanostructuring of the iminoboronate network with consequences on the micrometer-scale morphology and on the improvement of mechanical properties, as demonstrated by SEM and rheological investigation. The hydrogels proved strong antifungal activity against Candida planktonic yeasts and biofilms, promising to be a friendly treatment of the recurrent vulvovaginitis infections. [ABSTRACT FROM AUTHOR]

The present paper focuses on the synthesis and characterization of new hydrogels and drug delivery systems, designed for local therapy. The hydrogels were obtained by reacting PEG-ylated chitosan derivatives with citral in different molar ratios of their functionalities. The drug delivery systems were obtained by the in situ hydrogelation of PEG-ylated chitosan derivatives with citral, in the presence of a hydrophilic anti-inflammatory drug, diclofenac sodium salt. The hydrogels and the drug delivery systems were characterized from the structural, supramolecular and morphological points of view by FTIR spectroscopy, wide angle X-ray diffraction, polarized optical microscopy and scanning electron microscopy. The in vitro release kinetics of the drug has been monitored in physiological conditions, while the in vivo release was evaluated by the somatic pain model on rats. The in vitro enzymatic degradability of the hydrogels was evaluated in the presence of lysozyme, leading to a significant mass loss of 47% in 21 days. All the findings, recommend the investigated materials as promising candidates for local drug delivery applications. Unlabelled Image [ABSTRACT FROM AUTHOR]

The objective of this paper was to investigate the new formulations based on salicyl-imine-chitosan hydrogels as potential controlled drug release systems. They were prepared by in situ hydrogelation of chitosan with salicylaldehyde in the presence of diclofenac sodium salt ( DCF ) as model drug. FTIR, X-ray Spectroscopy, POM and SEM techniques were used to confirm the structural, supramolecular and morphological particularities of the formulations. Swelling test, in vitro enzymatic biodegradation and release profile were investigated in similar conditions mimicking the in vivo environment, and the release mechanism was assessed by fitting into five mathematical models. It was established that the formulations have the capacity to release DCF in a sustained manner for 10 days rate, the drug release rate being correlated to the crosslinking density and hydrogelation speed. The biodegradation occurred in three main stages, reaching a mass loss of 48% after 21 days. In order to be used in the biomedical field, the in vivo biocompatibility of the formulations was investigated on experimental rats. After 7 days of subcutaneous implantation, no influence on the hematologic profile, liver, kidney or immune defence capacity were observed, suggesting these formulations as valuable materials for biomedical devices. • New formulations based on chitosan, salicylaldehyde and DCF were prepared by in situ hydrogelation • They presented porous morphology and fast swelling in physiological pH • The in vivo release study showed a prolonged DCF release, reaching 70% within 10 days • The formulations were enzymatic biodegraded attaining a mass loss of 48 % after 21 days • They display in vivo biocompatibility on rats [ABSTRACT FROM AUTHOR]

Hydrogels based on chitosan and salicyladehyde were obtained by dynamic covalent chemistry. The unusual chitosan gelling in the presence of the monoaldehyde has been deciphered following and correlating data of NMR, FTIR, single crystal and wide angle XRD, POM and optical measurements. Of significant importance in understanding the crosslinking features was the synthesis of a model compound and the successfully growth as single crystal allowing the study of its supramolecular peculiarities. The hydrogels exhibited in SEM a porous or fibrous morphology, in good correlation with the crosslinking degree. They swelled very fast, similar to the superporous hydrogels of third generation and exhibited self-healing properties. Rheological investigation demonstrated good mechanical properties, thermosensitivity and thixotropy. The paper revealed a hydrogel with suitable properties for use in bio-medical applications, and moreover, revealed a new concept of obtaining chitosan hydrogels using monoaldehydes − which are widespread in nature, cheap and beneficial to the human body. [ABSTRACT FROM AUTHOR]

The paper reports new hydrogels based on quaternary ammonium salts of chitosan designed as biocidal products. The chitosan derivative was crosslinked with salicylaldehyde via reversible imine bonds and supramolecular self-assemble to give dynamic hydrogels which respond to environmental stimuli. The crosslinking mechanism was demonstrated by 1H NMR and FTIR spectroscopy, and X-ray diffraction and polarized light microscopy. The hydrogel nature, self-healing and thixotropy were proved by rheological investigation and visual observation, and their morphology was assessed by scanning electron microscopy. The relevant properties for application as biocidal products, such as swelling, dissolution, bioadhesiveness, antimicrobial activity and ex-vivo hemocompatibility and in vivo local toxicity and biocompatibility on experimental mice were measured and analyzed in relationship with the imination degree and the influence of each component. It was found that the hydrogels are superabsorbent, have good adhesivity to skin and various surfaces and antimicrobial activity against relevant gram-positive and gram-negative bacteria, while being hemocompatible and biocompatible. Besides, the hydrogels are easily biodegraded in soil. All these properties recommend the studied hydrogels as ecofriendly biocidal agents for living tissues and surfaces, but also open the perspectives of their use as platform for in vivo applications in tissue engineering, wound healing, or drug delivery systems. [Display omitted] [ABSTRACT FROM AUTHOR]

The purpose of the study was to develop new antimicrobial hydrogels from natural resources that may promote wound healing and prevent bacterial skin infection. The new hydrogels were synthesized by crosslinking chitosan with a vanillin isomer, 5-methoxysalicylaldehyde, by a friendly and easy method. To characterize these hydrogels, their structural and morphological properties were explored by FTIR, 1H NMR, SEM, POM, and TGA. In view of the targeted application, swelling behavior, biodegradability, antimicrobial activity and biocompatibility were investigated in vitro. Structural and morphological studies confirmed the formation of new hydrogels via the imination reaction concomitant with the supramolecular organization. The hydrogels were highly porous with the average pore diameter around 80 μm, and a swelling rate controlled by the crosslinking density and medium pH. The hydrogels showed a progressive weight loss in the presence of lysozyme up to 35%, during 21 days of testing. They proved non-cytotoxic effect on Normal Human Dermal Fibroblasts using MTS test and powerful antifungal activity against Candida Albicans , as determined by disk diffusion assay. All these properties indicate the new hydrogels as a promising option for the treatment of various skin lesions. [Display omitted] • New hydrogels based on chitosan and a vanillin isomer were synthetized via imine linkage. • The hydrogels were highly porous, thermally stable and biodegradable. • The reversible imine linkage prompted a self-healing behavior. • The hydrogels had no cytotoxic effect on normal human dermal fibroblasts. • They exhibited antifungal activity. [ABSTRACT FROM AUTHOR]

Vitamin B6 is an essential micronutrient in the mammalian diet, with role of coenzyme and synergistic effect with some antibiotics and antitumor drugs. Based on these, we hypothesized that its use for the preparation of hydrogels can yield multifunctional biomaterials suitable for in vivo applications. To this aim, chitosan was reacted with the active form of vitamin B6, pyridoxal 5-phosphate, via acid condensation, when clear hydrogels were obtained. Their investigation by structural characterization methods proved that the hydrogelation was a consequence of both covalent imine formation and physical interactions. The novel hydrogels had microporous morphology and showed shrinking effect in phosphate buffer, indicating good shape preservation and slow dissolution in in vivo environment. Their enzymatic biodegradation could be controlled by the imination degree, varying from 40 to 61% in 21 days. They demonstrated very good in vitro cytocompatibility on normal human dermal fibroblasts cells and no harmful effect on experimental mice, confirming their safely use for in vivo application. [Display omitted] [ABSTRACT FROM AUTHOR]

Microbial infections are a serious healthcare related problem, causing several complications and even death. That is why, the development of new drug delivery systems with prolonged effect represents an interesting research topic. This study presents the synthesis and characterization of new hydrogels based on chitosan and three halogenated monoaldehydes. Further, the hydrogels were used as excipients for the development of drug delivery systems (DDS) by the incorporation of fluconazole, an antifungal drug. The systems were structurally characterized by Fourier Transformed Infrared Spectroscopy and Nuclear Magnetic Resonance, both methods revealing the formation of the imine linkages between chitosan and the aldehydes. The samples presented a high degree of ordering at supramolecular level, as demonstrated by WXRD and POM and a good water-uptake, reaching a maximum of 1.6 g/g. The obtained systems were biodegradable, loosing between 38 and 49 % from their initial mass in the presence of lysozyme in 21 days. The ability to release the antifungal drug in a sustained manner for seven days, along with the high values of the inhibition zone diameter, reaching a maximum of 64 mm against Candida parapsilosis for the chlorine containing sample, recommend these systems as promising materials for bioapplications. [ABSTRACT FROM AUTHOR]

The paper reports hydrogels prepared from chitooligosaccharides with different polymerization degrees (14 to 51), by crosslinking with 2-formylphenylboronicacid in three molar ratios of their functionalities. The structural, morphological and supramolecular characterization confirmed a hydrogelation mechanism based on self-assembling of newly formed imine units and porous morphology. Rheological measurements confirmed the formation of thixotropic hydrogels, and swelling tests indicated mass equilibrium swelling values up to 25 in water and 9 in phosphate buffer saline. The monitoring of enzymatic degradability demonstrated the enhancing of biodegradation rate as long as the polymerization degrees of the oligomers decreased, the mass loss increasing from 16% to 43%. In vivo and ex-vivo biocompatibility investigation on experimental mice showed no cytotoxic effect, and in vitro antimicrobial tests revealed remarkable antimicrobial properties on nine strains, with a maximum inhibition diameter of 49 mm on Aspergilius brasiliensis and very good results on Cladosporium cladosporioides , Penicillium crysogenum and different Candida species. [Display omitted] [ABSTRACT FROM AUTHOR]

• Urea controlled release systems based on chitosan and salicyladehyde were prepared. • They showed porous structure, good water absorbency and hydrolytic stability. • Urea has been anchored into the hydrogel walls as micrometric crystals by H-bonds. • The in vivo release study revealed a prolonged urea delivery during 35 days. • The new formulations are promising candidates as multifunctional soil conditioners. The paper reports new soil conditioner systems obtained by in situ hydrogelation of chitosan with salicylaldehyde in the presence of urea fertilizer, designed to address both fertilization and water retention of the soil. The new systems were structural, supramolecular and morphological characterized by FTIR spectroscopy, XRD diffraction, POM and SEM microscopy. The rate of urea release has been investigated by NMR analysis and the release mechanism has been assessed by fitting five mathematical models. The formulations showed high water absorbency of 68 g/g, and they induced water holding capacity in soil up to 154% and an increment of the nitrogen content in soil to almost double, leading to a growth of plants with almost 70% higher compared to the reference soil. All these data revealed the new systems as new multifunctional soil conditioner ecoproducts capable to address both fertilizing and water retention issues, with high potential of application for sustainable agriculture. [ABSTRACT FROM AUTHOR]