Novel Chitosan-Based Schiff Base Compounds: Chemical Characterization and Antimicrobial Activity

Fontana, Riccardo; Marconi, Peggy; Caputo, Antonella; Gavalyan, V. B.

doi:10.3390/molecules27092740

Cited by 19 publications

(11 citation statements)

References 22 publications

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“…Similarly, a new chitosan Schiff base synthetized from an aldehyde revealed better antimicrobial properties owing to the electron-withdrawing substituents [23]. Further study proved that CSSB-1 and CSSB-2 resultant from the reaction of chitosan with 4-(2-chloroethyl) benzaldehyde (aldehyde-1) and 4-(bromoethyl) benzaldehyde (aldehyde-2), respectively had better activities against S. aureus and P. aeruginosa with doses of 0.006 and 0.012% [53]. These results were related to the present positively charged amine groups of CSSB-1 and CSSB-2, which have the capability for binding with the negatively charged surface of bacterial wall, leading to alteration of cell permeability and followed by cell death.…”

Section: Evaluation Of Antibacterial Activitymentioning

confidence: 96%

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

et al. 2023

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This study intends to develop a novel bioactive chitosan Schiff base (CTS-SB) derivative via coupling of chitosan (CTS) with 4-((5, 5-dimethyl-3-oxocyclohex-1-en-1-yl) amino) benzene-sulfonamide. The alteration in the chemical structure of CTS-SB was verified using 1H NMR and FT-IR analysis, while the thermal and morphological properties were inspected by TGA and SEM characterization tools, respectively. Ion exchange capacity of the developed CTS-SB derivative recorded a maximal value of 12.1 meq/g compared to 10.1 meq/g for pristine CTS. In addition, antibacterial activity of CTS-SB derivative was greatly boosted against Escherichia coli (E coli) and Staphylococcus aureus (S. aureus) bacteria. Minimum inhibition concentration of CTS-SB derivative was perceived at 50 µg/mL, while the highest concentration (250 µg/mL) could inhibit the growth of S. aureus up to 91%. What’s more, enhanced antidiabetic activity by CTS-SB derivative, which displayed higher inhibitory values of α-amylase (57.9%) and α-glucosidase (63.9%), compared to those of pure CTS (49.8 and 53.4%), respectively Furthermore, cytotoxicity investigation on HepG-2 cell line revealed potential anticancer activity along with good safety margin against primary human skin fibroblasts (HSF cells) and decent cytocompatibility. Collectively, the gained results hypothesized that CTS-SB derivative could be effectively applied as a promising antibacterial, anticancer and antidiabetic agent for advanced biomedical applications.

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Section: Evaluation Of Antibacterial Activitymentioning

confidence: 96%

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

et al. 2023

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“…followed by cooling to r.t. pH value has been settled to 7 through the neutralization with the sodium bi-carbonate, and after that it has been precipitated in the acetone, followed by filtering, cleaning by acetone, then drying at a temperature of 60 o C in the oven. As shown in schemes (1), (2). Synthesis of Polymers Blend (13-20) 18 Polymers blend were produced by using the solvent casting method.…”

Section: Preparation Of Compoundsmentioning

confidence: 99%

“…Chitosan has a wide-field in biological activities such as antimicrobial, antitumor and used pharmaceutically as an anticoagulant agent 1 , also can be useful in several fields such as textiles, environmental protection, water treatment, cosmetics and bio-technology due to its ability to produce bifunctional materials [2][3][4] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Grafted Chitosan Blending with Polyvinyl alcohol / Nanocomposite and Study Biological Activity

Saeed

Attiya²,

Obead³

2023

Baghdad Sci.J

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The study of biopolymers and their derivative materials had received a considerable degree of attention from researchers in the preparation of novel material. Biopolymers and their derivatives have a wide range of applications as a result of their bio-compatibility, bio-degradability and non-toxicity. In this paper, chitosan reacted with different aldehydes(2,4 –dichloro- benzaldehyde or 2-methyl benzaldehyde), different ketones (4-bromoacetophenone or 3-aminoacetophenone) to produce chitosan schiff base (1-4) . Chitosan schiff base (1-4) reacted with glutaric acid or adipic acid in acidic media in distilled water according to the steps of Fischer and Speier to produce compounds (5-12) respectively. Grafted chitosan (5-12) blended with synthetic polymer PVA to produce compounds (13-20), then these polymers were blended with nano Ag by using a hotplate stirrer for 60 min to produce nanocomposites. The synthesized polymers were identified via spectral analysis techniques, including FTIR , 1H-NMR and scanning electron microscope (SEM). Finally, studied anti-bacterial activities of some of the prepared polymers.

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“…Schiff bases offer distinctive qualities such as high synthesis flexibility and desirable biological characteristics. [22][23][24] Several studies have focused on Schiff base complexes of organotin (IV) with diverse ligands, highlighting the influence of ligand structure on the stability, reactivity, and biological activity of the resulting complexes. For instance, triorganotin (IV) complexes derived from amino acetate functionalized Schiff base ligands exhibit favorable anticancer activities against a range of human tumor cell lines, 25 similarly with novel triphenyltin (IV) 2-or 4-(arylimino) methyl)benzoates.…”

Section: Introductionmentioning

confidence: 99%

Anthracene appended organotin (IV) compounds: Synthesis, structure elucidation and their cytotoxicity against A549 and RBL cancer cell lines

Paul,

Khan,

Shaik

et al. 2023

Applied Organom Chemis

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Two new anthracene Schiff base triorganotin (IV) compounds trimethylstannyl(E)‐4‐((anthracen‐9‐ylmethylene)amino)benzoate (1) and triphenylstannyl(E)‐4‐((anthracen‐9‐ylmethylene)amino)benzoate (2) were synthesized by mixing trimethylstannyl (or triphenylstannyl) 4‐aminobenzoate and 9‐anthraldehyde in anhydrous toluene under refluxing conditions. Elemental analysis, FT‐IR, 1H‐NMR, 119Sn NMR and ESI‐MS were used to determine the composition of the compounds. X‐ray diffraction analyses revealed the structural details of the compounds. The in vitro cytotoxicity assessment of these compunds was screened against human A‐549 (lung carcinoma) and rat RBL (leukemia) cancer cell lines. Both compounds displayed a pronounced in vitro cytotoxic effect on the subjected cancer cell lines. Notably, the proliferation of A‐549 cells experienced substantial inhibition in the presence of compound 2. The mode of interaction with Hsp90 and NF‐κB p65 proteins responsible for cancer propagation was also assessed by molecular docking. Compounds 1 and 2 bind to the Hsp90 protein with binding energies of −307.65 and −373.45 kcal/mol, respectively, while to NF‐κB p65 protein the binding energies are of −329.35 and −395.35 kcal/mol, in the same order. Compound 2 exhibited a significantly high binding affinity to NF‐κB p65 and Hsp90 proteins validating our experimental findings from the in vitro experiments.

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Novel Chitosan-Based Schiff Base Compounds: Chemical Characterization and Antimicrobial Activity

Cited by 19 publications

References 22 publications

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

Synthesis and Characterization of Grafted Chitosan Blending with Polyvinyl alcohol / Nanocomposite and Study Biological Activity

Anthracene appended organotin (IV) compounds: Synthesis, structure elucidation and their cytotoxicity against A549 and RBL cancer cell lines

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