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Fabrication of chitosan-bis (4-formyl-2 methoxy phenyl carbonate) Schiff base nanoparticles and evaluation of their antioxidant and anticancer properties

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Abstract

The present study details on the mechanism of synthesis of bis (4-formyl-2 methoxy phenyl carbonate), using two green reagents dimethyl carbonate and vanillin for application as therapeutic agent. The synthesized FMPC was identified from the 13C nuclear magnetic resonance spectra. The novel modified Schiff base nanoparticles resulted from the crosslinking of FMPC with chitosan were confirmed by cross-polarization magic angle spinning carbon-13 nuclear magnetic resonance spectroscopy. The incorporation of the FMPC was identified from the amorphous X-ray diffraction patterns of C-FMPC-Nps. The thermal stability of the formed nanoparticles was predicted using thermogravimetric analysis. The morphology of the nanoparticles as observed from HRTEM was found to be smooth and spherical in nature. Both FMPC and C-FMPC-Nps showed significant radical scavenging potential and anticancer property. The carbonate ester backbone and the moiety present in chitosan-FMPC-nanoparticles, underwent hydrolysis at the targeted cancer causing microenvironment to release vanillin and chitosan and enhance the anticancer activity. Both FMPC and C-FMPC-Nps exhibits a dose dependent cytotoxicity towards the different cell lines and it was tested with a commercial drug for application studies.

Graphical abstract

Effective synthesis of FMPC, successful incorporation onto chitosan nanoparticles for the formation of C-FMPC-Nps. The formed Schiff base compound proves to have enhanced antioxidant and anticancer efficacy.

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Abbreviations

FMPC:

Bis (4-formyl-2 methoxy phenyl carbonate)

DMC:

Dimethyl carbonate

13C-NMR:

13C nuclear magnetic resonance

Nps:

Nanoparticles

C:

Chitosan

CP/MAS:

13C-NMR cross-polarization magic angle spinning carbon-13 nuclear magnetic resonance

XRD:

X-ray diffraction

TGA:

Thermogravimetric analysis

HRTEM:

High resolution transmission electron microscopy

TPP:

Sodium tripolyphosphate

ATR:

Attenuated total reflectance

D2O:

Deuterium oxide

EI-MS:

Electron ionization mass spectrometry

ZrO:

Zirconium oxide

KHZ:

Kilohertz

TMS:

Tetramethyl silane

TEA:

Triethyl amine

MTT:

[3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide]

DPPH:

(1,1-Diphenyl-2-picryl hydrazyl)

MEM:

Minimal essential medium

FBS:

Fetal bovine serum

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  1. Bioproducts Laboratory, Department of Chemical Engineering, A.C. Tech, Anna University, Chennai, Tamil Nadu, 600025, India

    P. Thyriyalakshmi & K. V. Radha

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  1. P. Thyriyalakshmi
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  2. K. V. Radha
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Correspondence to K. V. Radha.

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Thyriyalakshmi, P., Radha, K.V. Fabrication of chitosan-bis (4-formyl-2 methoxy phenyl carbonate) Schiff base nanoparticles and evaluation of their antioxidant and anticancer properties. Mol Biol Rep 46, 4333–4347 (2019). https://doi.org/10.1007/s11033-019-04887-4

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