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

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Abstract

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.

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Abbreviations

BSA:

Bovine serum albumin

CrI:

Crystallinity index

DMEM:

Dulbecco’s Modified Eagle’s medium

DMSO:

Dimethyl sulfoxide

DPPH:

2,2-diphenyl-2-picrylhydrazyl

DRPs:

Drug resistance profiles

EC50 :

Effective concentration 50

FT-IR:

Fourier transform infrared

H2O2 :

Hydrogen peroxide

IZD:

Inhibition zone diameter

MA*CS*pNBA:

Aminated chitosan bearing p-nitrobenzaldehyde

MCF-10A:

Normal breast epithelial cell line

MCF-7:

Cancerous breast epithelial cell line

MDR:

Multi-drug resistance

MDR-EC:

MDR Escherichia coli

MDR-KP:

MDR Klebsiella pneumonia

MDR-PA:

MDR Pseudomonas aeruginosa

MDR-SA:

MDR Staphylococcus aureus

MHA:

Mueller-Hinton agar

MHB:

Mueller-Hinton broth

MIC:

Minimum inhibitory concentration

MTT:

3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

NIH-3 T3:

Mouse embryonic fibroblast cell line

PBS:

Phosphate buffered saline

RBCs:

Red blood cells

RCV:

Relative cell viability

TCA:

Trichloroacetic acid

TEM:

Transmission electron microscope

TGA:

Thermogravimetric analysis

TSB:

Tryptic Soy Broth

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Author information

Authors and Affiliations

  1. Biofuels Institute, School of the Environment and Safety Engineering, Jiangsu University, Zhenjiang, 212013, China

    Sameh S. Ali, Jianzhong Sun & Liu Huizi

  2. Botany Department, Faculty of Science, Tanta University, Tanta, 31527, Egypt

    Sameh S. Ali & Nessma A. El-Zawawy

  3. Polymer Research Group, Department of Chemistry, Faculty of Science, Tanta University, Tanta, 31527, Egypt

    El-Refaie Kenawy & Marwa Al-Etewy

  4. Department of Microbiology, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt

    Fatma I. Sonbol

  5. Ministry of Health and Population, Chest Directorate, Abbassia Chest Hospital, Cairo, Egypt

    Asmaa Ali

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  1. Sameh S. Ali
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  2. El-Refaie Kenawy
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  3. Fatma I. Sonbol
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Correspondence to Sameh S. Ali or Jianzhong Sun.

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Ali, S.S., Kenawy, ER., Sonbol, F.I. et al. Pharmaceutical Potential of a Novel Chitosan Derivative Schiff Base with Special Reference to Antibacterial, Anti-Biofilm, Antioxidant, Anti-Inflammatory, Hemocompatibility and Cytotoxic Activities. Pharm Res 36, 5 (2019). https://doi.org/10.1007/s11095-018-2535-x

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