New Chitosan Polymer Scaffold Schiff Bases as Potential Cytotoxic Activity: Synthesis, Molecular Docking, and Physiochemical Characterization

Packialakshmi, Ponnusamy; Gobinath, Perumal; Ali, Daoud; Alarifi, Saud; Raman, Gurusamy; Idhayadhulla, Akbar; Surendrakumar, Radhakrishnan

doi:10.3389/fchem.2021.796599

Cited by 14 publications

(9 citation statements)

References 34 publications

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“…6B) were determined to be 109.6 and 76.74 μg/mL with SI values of 6.63 ± 0.10 and 6.19 after treatment for 24 and 72 h, respectively. These outcomes prove the significant safety for the prepared CTS-SB toward the normal human cells with high selectivity against hepatoma cancer cells [61,62]. On the other hand, both chitosan (CTS) and berberine (standard drug) showed moderate antitumor activity against HepG-2 cells (Table 3).…”

Section: Anticancer Effect and Cytotoxicity Evaluationmentioning

confidence: 73%

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: Anticancer Effect and Cytotoxicity Evaluationmentioning

confidence: 73%

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

et al. 2023

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“…However, a slight increase in toxicity was observed at the highest concentration of 200 mg with maximum values not exceeded than 7.5%, which was recorded by CHQ (1) Schiff base derivative compared to 5.56% for pure chitosan. Preceding studies verified that diverse chitosan Schiff base derivatives had no substantial toxicity towards human cells 60 , 69 . Since at low doses of the prepared CHQ manifested no antiproliferative impact on the normal HSF cells as CH without any modification, while it can affect the survival of normal HSF cells only if used in elevated doses.…”

Section: Resultsmentioning

confidence: 88%

Developing a new multi-featured chitosan-quinoline Schiff base with potent antibacterial, antioxidant, and antidiabetic activities: design and molecular modeling simulation

Abdel-Baky,

Omer,

El-Fakharany

et al. 2023

Sci Rep

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A new chitosan Schiff base was developed via the reaction of chitosan (CH) with 2-chloro-3-formyl-7-ethoxy quinoline (Q) derivative. The alteration in the chemical structure and morphology of CHQ derivative was confirmed by 1H NMR, FT-IR spectroscopy and SEM analysis. The antibacterial activity was considerably promoted with increasing quinoline concentration up to 1 M with maximal inhibition reached 96 and 77% against Staphylococcus haemolyticus and Escherichia coli, respectively. Additionally, CHQ derivative afforded higher ABTS·+ radical scavenging activity reached 59% compared to 13% for native chitosan, approving its acceptable antioxidant activity. Moreover, the developed CHQ derivative can stimulate the glucose uptake in HepG-2 and yeast cells, while better inhibition of α-amylase and α-glucosidase was accomplished with maximum values of 99.78 and 92.10%, respectively. Furthermore, the molecular docking simulation clarified the binding mode of CHQ derivative inside the active site of α-amylase and α-glucosidase, suggesting its potential use as diabetes mellitus drug. The DFT calculations indicated an improvement in the electronic properties of CHQ with a lower energy band gap reached 4.05eV compared to 5.94eV for CH. The cytotoxicity assay revealed the safety of CHQ towards normal HSF cells, hypothesizing its possible application as non-toxic antibacterial, antioxidant, and antidiabetic agent for biomedical applications.

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“…Researchers are trying to find a new drug, which has made them think about new agents with less systemic toxicity and better cytotoxicity . Furthermore, numerous papers described the anticancer effects of Schiff bases employing a range of human tumor cell lines …”

Section: Introductionmentioning

confidence: 99%

“… 17 Furthermore, numerous papers described the anticancer effects of Schiff bases employing a range of human tumor cell lines. 18 …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral Characterization, Thermal Investigation, Computational Studies, Molecular Docking, and In Vitro Biological Activities of a New Schiff Base Derived from 2-Chloro Benzaldehyde and 3,3′-Dimethyl-[1,1′-biphenyl]-4,4′-diamine

Thakor,

Patel,

Giri

et al. 2023

ACS Omega

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The current research involves the synthesis of a new Schiff base through the reaction between 2-chlorobenzaldehyde and 3,3′-dimethyl-[1,1′-biphenyl]-4,4′-diamine by using a natural acid catalyst and a synthesized compound physicochemically characterized by X-ray diffraction, Fourier transform infrared spectroscopy, 1H- and 13C-nuclear magnetic resonance, and liquid chromatography–mass spectrometry. Thermal studies were conducted using thermogravimetric, differential thermal analysis, and differential thermogravimetric curves. These curves were obtained in an inert nitrogen environment from ambient temperature to 1263 K using heating rates of 10, 15, and 20 K·min–1. Using thermocurve data, model-free isoconversional techniques such as Kissinger–Akahira–Sunose, Flynn–Wall–Ozawa, and Friedman are used to determine kinetic parameters. These parameters include activation energy, phonon frequency factor, activation enthalpy, activation entropy, and Gibb’s free energy change. All of the results have been thoroughly investigated. The molecule’s anti-inflammatory and antidiabetic properties were also examined. To learn more about the potential of the Schiff base and how successfully it can suppress the amylase enzyme, a molecular docking experiment was also conducted. For in silico research, the Swiss Absorption, Distribution, Metabolism, Excretion, and Toxicity algorithms were used to calculate the theoretical pharmacokinetic properties, oral bioavailability, toxic effects, and biological activities of the synthesized molecule. Moreover, the cytotoxicity tests against a human lung cancer cell line (A549) using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay demonstrated that the synthesized Schiff base exhibited significant anticancer properties.

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New Chitosan Polymer Scaffold Schiff Bases as Potential Cytotoxic Activity: Synthesis, Molecular Docking, and Physiochemical Characterization

Cited by 14 publications

References 34 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

Developing a new multi-featured chitosan-quinoline Schiff base with potent antibacterial, antioxidant, and antidiabetic activities: design and molecular modeling simulation

Synthesis, Spectral Characterization, Thermal Investigation, Computational Studies, Molecular Docking, and In Vitro Biological Activities of a New Schiff Base Derived from 2-Chloro Benzaldehyde and 3,3′-Dimethyl-[1,1′-biphenyl]-4,4′-diamine

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