Superior remedy colon cancer HCT-116 cells via new chitosan Schiff base nanocomposites: Synthesis and characterization.

Cancer is a serious worldwide health problem and colon cancer is the major cancer public prevailing form. The innovative pharmaceuticals with great cancer efficacy are metal nanoparticles. Therefore, the present study relies on developing chitosan Schiff base nanocomposites and investigating their antitumor ability against human colon carcinoma (HCT-116 cell line) using the MTT method. Thus, chitosan (CS) is modified with 9-ethyl-3-carbazolecarboxaldehyde (ECCA) in the absence or presence of the biomedical crosslinker poly(ethylene glycol) diglycidyl ether (PEGDGE) under microwave irradiation to afford CS-Schiff bases CS-SB-I and CS-SB-II, respectively. The assembly method is applied to formulate CS-Schiff base (Ag, Au and ZnO) nanocomposites. These new CS-Schiff bases and their nanocomposites are characterized by utilizing elemental analysis, FTIR, TGA, XRD, SEM, TEM and EDX. Cytotoxicity test showed that CS-SB-I (IC50 112.10 ± 4.23 µg/mL) and CS-SB-II (IC50 98.54 ± 4.09 µg/mL) inhibit the growth of HCT-116 more effectively than chitosan (IC50 181.38 ± 6.54 µg/mL). Additionally, CS-Schiff base nanocomposites revealed superior anticancer efficiency which displayed the lowest IC50 values CS-SB-I-Ag (IC50 10.99 ± 0.37 µg/mL), CS-SB-II-Ag (IC50 12.79 ± 0.49 µg/mL), CS-SB-I-Au (IC50 14.96 ± 0.51 µg/mL), CS-SB-II-Au (IC50 26.72 ± 1.57 µg/mL), CS-SB-I-ZnO (IC50 22.79 ± 1.28 µg/mL) and CS-SB-II-ZnO (IC50 22.24 ± 1.34 µg/mL). The findings demonstrated that CS-Schiff base nanocomposites are promising agents for the HCT-116 cell therapeutic.

Synthesis of new quaternized chitosan Schiff bases and their N-alkyl derivatives as antimicrobial and anti-biofilm retardants in membrane technology.

New quaternized salicylidene chitosan Schiff bases (QSCSBs) and their N-octyl derivatives (OQCs) have been synthesized and characterized, aiming to develop innovative antimicrobial and anti-biofilm agents. This research holds immense potential, as these compounds could be utilized as anti-biofouling additives in membrane technology in the future. The synthesis involved the modification of low molecular-weight-chitosan (LMC) through simultaneous Schiff base formation and quaternization processes to create QSCSBs. Subsequently, QSCSBs were catalytically reduced to form quaternized N-benzyl chitosan (QBCs) intermediates, which then underwent nucleophilic substitution reactions affording N-octyl quaternized chitosans (OQCs). Characterization techniques such as elemental, spectral, and microscopic analyses were used to confirm the successful synthesis of these materials. As membrane technology relies on surface charge, QSCSBs and OQCs with large zeta potentials could be used as positively charged additives. Moreover, SEM image revealed the regular distribution of pores and voids across the additives' surfaces raises intriguing questions about their implications for membrane performance. Meanwhile, the superior antibacterial and antibiofilm potential of these materials, particularly QSCSB2 and OQC2, indicate that the utilization of these compounds as anti-biofouling additives in membrane technology could significantly improve the performance and longevity of membranes used in various applications such as water treatment and desalination.

Facile fabrication of chitosan Schiff bases from giant tiger prawn shells (Penaeus monodon) via solvent-free mechanochemical grafting.

Fabrication of chitosan Schiff bases (ChSB) from giant tiger prawn shells (Penaeus monodon) using an environmentally friendly method has been conducted successfully. Transformation of Prawn Shells (PS) as raw material into chitin then chitosan was executed under ambient temperature. Later, three Ch Schiff bases (ChSB-A, ChSB-S, and ChSB-V) were successfully synthesized for the first time via solvent-free mechanochemical grafting with 2-hydroxy benzaldehyde, 4-methoxy benzaldehyde, and 3-methoxy-4-hydroxy benzaldehyde, respectively. Synthesis was carried out with Shaker Mill-Ultimate Gravity equipped with a Teflon jar with zirconia balls; then the product was characterized. FTIR analysis proved the conversion of free amine to imine groups. The degree of substitution (DS) and crystallinity index (CrI) were determined by elemental analysis and X-ray diffraction. The DS values obtained were about 0.343, 0.795, and 0.055 for ChSB-A, ChSB-S, and ChSB-V, respectively. The CrI of ChSB-A, ChSB-S, and ChSB-V was 53.3, 51.7, and 46.9 %, respectively. The thermal gravimetric analysis showed that the mechanochemical grafting of Ch improves the thermal stability of ChSB. This developed method provides a novel potential technique to convert PS into ChSB products by solvent-free mechanochemical grafting.

Chitosan Schiff bases-based polyelectrolyte complexes with graphene quantum dots and their prospective biomedical applications.

Chitosan (Cs) bis-aldehyde Schiff base derivatives were synthesized by condensation of Cs with three bis-aldehydes namely; butane-1,4-diyl bis(4-formylbenzoate), N,N'-(butane-1,4-diyl)bis(2-(4-formylphenoxy)acetamide) and 4,4'-(butane-1,4-diylbis(oxy))dibenzaldehyde. The prepared Cs derivatives were blended with carboxymethyl chitosan(CMC) and graphene quantum dots (GQDs) to produce semi-IPNs polyelectrolyte complexes (PECs). and characterized with respect to their molecular structure and physio-chemical properties. The antibacterial activity against H. pylori (and in vitro Inosine 5'-monophosphate dehydrogenase IMPDH inhibitory assay) was evaluated. Additionally, a preliminary in vitro assessment for wound healing was performed against PECs in which wound closure percentages, and rates were investigated indicating an accelerated wound healing compared with untreated cells. The PEC based on Schiff base PEC containing amide linkage showed the highest wound healing ability. A minimal inhibitory concentration (MIC) was obtained for the PEC sample containing Cs Schiff base derived from 4,4'-(butane-1, 4-diylbis(oxy))dibenzaldehyde at a dose of 0.98 µg/ml inhibiting H. pylori growth by 100%. Additionally, the selected above-mentioned compound was selected to test its inhibitory activity against the HpIMPDH enzyme in addition to its selectivity towards the hIMPDH2 enzyme and was found to have promising activity against the HpIMPDH enzyme with IC50 value of 0.65 µM, and to be safer and less active against the hIMPDH2 enzyme with IC50 > 10 µM, reflecting its selectivity.

Ionic chitosan Schiff bases supported Pd(II) and Ru(II) complexes; production, characterization, and catalytic performance in Suzuki cross-coupling reactions.

Taking the advantage of multifunctional characteristics of chitosan (CS), we have developed new scaffolds (imidazolium-vanillyl-chitosan Schiff bases (IVCSSBs)) for supporting Pd(II) and Ru(II) ions in catalyzing Suzuki coupling reactions. The structures of new materials were described based on their elemental, spectral, thermal, and microscopic analysis. The strong interactions between the binding sites of IVCSSB ligand (OH, H-C=N, and OCH3 groups) and Pd(II) ions resulted in the formation of an excellent heterogeneous catalyst (Pd(II)IVCSSB1) with amazing catalytic activity (up to 99%) and highly stable in the reaction medium. The reusability experiments for Pd(II)IVCSSB1 revealed that there is no appreciable decrease in its catalytic activity even after five consecutive operation runs. Furthermore, this heterogeneous catalyst showed an excellent selectivity toward the cross-coupling reaction where no homo-coupling byproducts were observed in the 1H NMR spectra of the obtained products. Consequently, the present ionic catalytic system may open a new window for a novel generation of ionic bio-based catalysts for organic transformations.

Dual ionic liquid-based crosslinked chitosan for fine-tuning of antifouling, water throughput, and denitrification performance of polysulfone membrane.

This study aimed to design a facile and efficient protocol for upgrading the performance indices of polysulfone (PS) membrane (porosity, hydrophilicity, pure water flux (PWF), surface charge, and fouling-resistance) by blending with newly synthesized poly(ionic) crosslinked chitosan Schiff bases (PICCSBs). The PS-PICCSBs mixed-matrix membranes (MMMs) have successfully fabricated and characterized based on spectral and microscopic analyses, porosity, zeta potential, water contact angle, and water uptake (wettability) measurements. The PWF, fouling-resistance against bovine serum albumin (BSA), as well as ion exchange capacity (IEC) against nitrate anion were studied. The wettability, hydrophilicity and overall porosity of new MMMs have greatly increased, in comparison to a pristine PS membrane (M0). In addition, blending of PS with PICCSBs resulted in switching its surface from negatively- to positively-charged. The PWF of MMMs has increased to reach a maximum value of 238.6 L/m2 h for MMM1 (9.3-fold higher than M0). Meanwhile, BSA rejection has declined from 96.62% for M0 to 41.9% for MMM1. The fouling parameters results of MMMs indicated their low fouling propensity. The IEC of nitrate anions revealed that the nitrate uptake by MMM1 is higher than that for M0 and MMM2 by 34% and 14%, respectively.

Pharmaceutical Potential of a Novel Chitosan Derivative Schiff Base with Special Reference to Antibacterial, Anti-Biofilm, Antioxidant, Anti-Inflammatory, Hemocompatibility and Cytotoxic Activities.

PURPOSE: Chitosan and its derivatives possess several unique properties relevant in the field of pharmaceutics and medicinal chemistry. This study aimed to evaluate the pharmaceutical performance of an innovative chitosan derivative, methyl acrylate chitosan bearing p-nitrobenzaldehyde (MA*CS*pNBA) Schiff base. METHODS: The antibacterial activity of MA*CS*pNBA was tested against multi-drug resistant (MDR) Gram-negative and Gram-positive bacteria using agar-well diffusion method. Anti-biofilm formation was analyzed using a microtitre plate. Antioxidant assays were performed to assess the scavenging activity of MA*CS*pNBA using DPPH, hydrogen peroxide, superoxide together with its reducing power activity. Anti-inflammatory activity was evaluated by albumin denaturation, membrane stabilization, and proteinase inhibition methods. MA*CS*pNBA was tested for its hemolytic efficiency on human erythrocytes. Cytotoxicity of MA*CS*pNBA was evaluated by MTT assay. RESULTS: MA*CS*pNBA showed a significant performance as an antibacterial candidate against MDR bacteria, anti-biofilm, antioxidant and anti-inflammatory biomaterial, evidencing hemocompatibility and no cytotoxicity. It exhibited a significant negative correlation with biofilm formation by the MDR-PA-09 strain. Biological activities were found to be significantly concentration-dependent. CONCLUSIONS: the newly chitosan derivative MA*CS*pNBA showed to be promising for pharmaceutical applications, expanding the treatment ways toward skin burn infections since it allied excellent antibacterial, anti-biofilm, antioxidant, anti-inflammatory, hemocompatibility and absence of cytotoxic activities.

Pharmacological performance of novel poly-(ionic liquid)-grafted chitosan-N-salicylidene Schiff bases and their complexes.

In our endeavor to develop a new class of pharmacological candidates with antimicrobial and anticancer efficacy, a series of biopolymeric chitosan Schiff bases bearing salicylidene ionic liquid (IL-Sal) brushes (ILCSB1-3, poly-(GlcNHAc-GlcNH2-(GlcN-Sal-IL)) was successfully synthesized by adopting efficient synthetic routes. Unfortunately, metalation trials of these biopolymeric Schiff bases afford the corresponding Ag(I)/M(II) complexes (where M=Co, Pd). These designed architectures were structurally characterized and pharmacologically evaluated for their in vitro antimicrobial, against common bacterial and fungal pathogens, and anticancer activities against human colon carcinoma (HCT-116) cell line. In conclusion functionalization of chitosan with IL-Sal brushes coupled with metalation of formed ILCSBs were synergistically enhanced its antimicrobial and antitumor properties to a great extent. Noteworthy, Ag-ILCSB2 (IC50=9.13µg/mL) was ca. 5-fold more cytotoxic against HCT-116 cell line than ILCSB2 (IC50=43.30µg/mL).

Synthesis, characterization and biological activity of Schiff bases based on chitosan and arylpyrazole moiety.

The Schiff bases of chitosan were synthesized by the reaction of chitosan with 3-(4-substituted-phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde. The structure of the prepared chitosan derivatives was characterized by FT-IR spectroscopy, elemental analysis, and X-ray diffraction studies and thermogravimetric analysis (TG). The results show that the specific properties of Schiff bases of chitosan can be altered by modifying the molecular structures with proper substituent groups.TG results reveal that the thermal stability of the prepared chitosan Schiff bases was lower than chitosan. The activation energy of decomposition was calculated using Coats-Redfern model. The antimicrobial activity of chitosan and Schiff bases of chitosan were investigated against Streptococcus pneumonia, Bacillis subtilis, Escherichia coli (as examples of bacteria) and Aspergillus fumigatus, Geotricum candidum and Syncephalastrum recemosum (as examples of fungi). The results indicated that the antimicrobial activity of the Schiff bases was stronger than that of chitosan and was dependent on the substituent group. The activity of un-substituted arylpyrazole chitosan derivative toward the investigated bacteria and fungi species was better than the other derivatives.

Fluorescent imino and secondary amino chitosans as potential sensing biomaterials.

A variety of fluorescent imino and secondary amino chitosans were synthesized under very mild conditions by reaction of the biopolymer amino functions with aromatic aldehydes in an acidified methanolic suspension. Simultaneous reactions of several aldehydes with chitosan were successfully carried out, and kinetic studies showed that 1-pyrenecarboxaldehyde reacts the fastest among them. An unprecedented study on the evaluation of the degree of N-substitution (DS, ranging from 31.7% to 12.0%) for the chitosan Schiff bases by using solid state CPMAS (13)C NMR is performed. A linear correlation between the DS obtained for the secondary amino chitosans by (1)H NMR (55.3-10.2%) and those obtained by CPMAS (13)C NMR (34.4-13.8%) has allowed us to calculate an empirical correlation factor that could be applied on chitosan-based aromatic systems. The new chiral-labelled chitosan derivatives exhibit a stable fluorescent behaviour, which was used to explore solvent sensoring applications.