Synthesis of chitin-glucan-aldehyde-quercetin conjugate and evaluation of anticancer and antioxidant activities

Carbohydr Polym. 2018 Aug 1:193:99-107. doi: 10.1016/j.carbpol.2018.03.092. Epub 2018 Mar 27.

Abstract

In the present study, we have synthesized chitin-glucan-aldehyde-quercetin (chi-glu-ald-que) conjugate via condensation reaction. Synthesis of chitin-glucan-aldehyde (chi-glu-ald) complex was facilitated by the oxidation of chitin-glucan (chi-glu) complex. Formation of conjugate was confirmed by Proton nuclear magnetic resonance spectroscopy (1H NMR) and Fourier-transform infrared spectroscopy (FT-IR). Morphological studies showed that after grafting of quercetin, several changes on surface were depicted and a more crystalline nature was observed. The chi-glu-ald-que conjugate displayed strong antioxidant activity. It showed 69% of 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical, DPPH* scavenging activity at 1 mg/mL and 72% of 2, 2-azinobis-(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical cation, ABTS*+ scavenging activity at 1 mg/mL concentration, which are much higher than that of chi-glu complex. The anticancer activity of chi-glu-ald-que conjugate was performed in Macrophage cancer cell lines (J774) and biocompatibility was performed in Peripheral blood mononuclear cells (PBMCs). The chi-glu-ald-que conjugate showed excellent cytotoxicity against J774 cell lines but no cytotoxicity towards PBMCs.

Keywords: Anticancer properties; Antioxidant properties; Chitin-glucan complex; Chitin-glucan-aldehyde-quercetin conjugate; Quercetin.

MeSH terms

  • Aldehydes / chemistry
  • Aldehydes / pharmacology*
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Chitin / chemistry
  • Chitin / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Glucans / chemistry
  • Glucans / pharmacology*
  • Mice
  • Molecular Structure
  • Particle Size
  • Quercetin / chemistry
  • Quercetin / pharmacology*
  • Structure-Activity Relationship
  • Surface Properties
  • Tumor Cells, Cultured

Substances

  • Aldehydes
  • Antineoplastic Agents
  • Antioxidants
  • Glucans
  • Chitin
  • Quercetin