Production of galactan phthalates derivatives extracted from Gracilaria birdie: Characterization, cytotoxic and antioxidant profile

Int J Biol Macromol. 2023 Jul 15:243:125254. doi: 10.1016/j.ijbiomac.2023.125254. Epub 2023 Jun 7.

Abstract

The present work explores the esterification reaction in the polysaccharide extracted from the seaweed Gracilaria birdiae and investigates its antioxidant potential. The reaction process was conducted with phthalic anhydride at different reaction times (10, 20 and 30 min), using a molar ratio of 1:2 (polymer: phthalic anhydride). Derivatives were characterized by FTIR, TGA, DSC and XRD. The biological properties of derivatives were investigated by assays of cytotoxicity and antioxidant activity (2,2-diphenyl-1-picrylhydroxyl - DPPH and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt - ABTS). The results obtained by FT-IR confirmed the chemical modification, there was a reduction related to the presence of carbonyl and hydroxyl groups when compared to the in nature polysaccharide spectrum. TGA analysis showed a change in the thermal behavior of the modified materials. X-ray diffraction, it was shown that the in nature polysaccharide appeared as an amorphous material, while the material obtained after the chemical modification process had increased crystallinity, due to the introduction of phthalate groups. For the biological assays, it was observed that the phthalate derivative was more selective than the unmodified material for the murine metastatic melanoma tumor cell line (B16F10), revealing a good antioxidant profile for DPPH and ABTS radicals.

Keywords: Agar; Biological activity; Chemical modification; Phthalate biomaterial.

MeSH terms

  • Animals
  • Antineoplastic Agents* / chemistry
  • Antioxidants / chemistry
  • Galactans
  • Gracilaria*
  • Mice
  • Phthalic Anhydrides
  • Polysaccharides / chemistry
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Antioxidants
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • phthalic acid
  • Phthalic Anhydrides
  • Galactans
  • Antineoplastic Agents
  • Polysaccharides