Antibacterial performance of fully biobased chitosan-grafted-polybenzoxazine films: Elaboration and properties of released material

Nisha Yadav; Monisha Monisha; Rashmi Niranjan; Amrita Dubey; Sachin Patil; Richa Priyadarshini; Bimlesh Lochab

doi:10.1016/j.carbpol.2020.117296

Antibacterial performance of fully biobased chitosan-grafted-polybenzoxazine films: Elaboration and properties of released material

Carbohydr Polym. 2021 Feb 15:254:117296. doi: 10.1016/j.carbpol.2020.117296. Epub 2020 Oct 24.

Authors

Nisha Yadav¹, Monisha Monisha², Rashmi Niranjan³, Amrita Dubey⁴, Sachin Patil⁵, Richa Priyadarshini⁶, Bimlesh Lochab⁷

Affiliations

¹ Materials Chemistry Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh, 201314, India; Department of Fibre and Polymer Technology, KTH Royal Institute of Technology, Teknikringen 58, 100 44 Stockholm, Sweden. Electronic address: ny345@snu.edu.in.
² Materials Chemistry Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh, 201314, India. Electronic address: mo447@snu.edu.in.
³ Department of Life Sciences, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh, 201314, India. Electronic address: rn161@snu.edu.in.
⁴ Department of Life Sciences, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh, 201314, India. Electronic address: ad358@snu.edu.in.
⁵ Materials Chemistry Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh, 201314, India. Electronic address: sp658@snu.edu.in.
⁶ Department of Life Sciences, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh, 201314, India. Electronic address: richa.priyadarshini@snu.edu.in.
⁷ Materials Chemistry Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh, 201314, India. Electronic address: bimlesh.lochab@snu.edu.in.

PMID: 33357864
DOI: 10.1016/j.carbpol.2020.117296

Abstract

A fully biobased benzoxazine monomer, V-fa (using vanillin and furfurylamine) was grafted onto chitosan (CS) at different weight ratios (C_XV_Y) using "grafting to" benign Schiff base chemistry. Incorporation of V-fa onto CS increased the tensile strength and improved chemical resistance of the CS-graft-V-fa films. Reversible labile linkages, expansion of CS galleries and leaching out of phenolic species from biobased polymer films led to an improved antibacterial activity against Staphylococcus aureus, which is ∼125 times higher than the bare CS film, V-fa and oligomeric V-fa. The leached out species from films were analyzed extensively by NMR, FTIR, GPC, ABTS and HRMS analysis. Oxidative-stress seems to be responsible for antibacterial activity. Current work illustrates an attractive synthetic approach and the improved antibacterial performance of biobased CS-graft-poly(V-fa) films which may hold as a potential alternative for wound-healing and implant applications in future.

Keywords: Antibacterial; Benzoxazine; Biobased films; Chitosan; Grafting; Sustainable; Vanillin; Wound healing.

MeSH terms

Anti-Bacterial Agents / chemistry*
Antioxidants / chemistry*
Benzaldehydes / chemistry
Benzoxazines / chemistry*
Chitosan / chemistry*
Drug Liberation*
Furans / chemistry
Hydrophobic and Hydrophilic Interactions
Microbial Viability / drug effects
Oxidative Stress / drug effects
Reactive Oxygen Species / metabolism
Signal Transduction / drug effects
Solvents / chemistry
Staphylococcus aureus / drug effects*
Staphylococcus aureus / metabolism
Tensile Strength
Transplantation / methods
Water / chemistry
Wound Healing / drug effects

Substances

Anti-Bacterial Agents
Antioxidants
Benzaldehydes
Benzoxazines
Furans
Reactive Oxygen Species
Solvents
Water
furfurylamine
Chitosan
vanillin