Vanillin crosslinked chitosan films: The states of water and the effect of carriers on curcumin uptake

Rafael L C G da Silva; Oigres D Bernardinelli; Emilli C G Frachini; Henning Ulrich; Edvaldo Sabadini; Denise F S Petri

doi:10.1016/j.carbpol.2022.119725

Vanillin crosslinked chitosan films: The states of water and the effect of carriers on curcumin uptake

Carbohydr Polym. 2022 Sep 15:292:119725. doi: 10.1016/j.carbpol.2022.119725. Epub 2022 Jun 11.

Authors

Rafael L C G da Silva¹, Oigres D Bernardinelli², Emilli C G Frachini¹, Henning Ulrich³, Edvaldo Sabadini⁴, Denise F S Petri⁵

Affiliations

¹ Fundamental Chemistry Department, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508-000 São Paulo, Brazil.
² Department of Physicochemistry, Institute of Chemistry, University of Campinas (UNICAMP), 13083-970, Campinas, São Paulo, Brazil; Department of Physics, Federal University of São Carlos, São Carlos 13565-905, SP, Brazil.
³ Department of Biochemistry, Institute of Chemistry, University of São Paulo, São Paulo, SP, Brazil.
⁴ Department of Physicochemistry, Institute of Chemistry, University of Campinas (UNICAMP), 13083-970, Campinas, São Paulo, Brazil.
⁵ Fundamental Chemistry Department, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508-000 São Paulo, Brazil. Electronic address: dfsp@iq.usp.br.

PMID: 35725193
DOI: 10.1016/j.carbpol.2022.119725

Abstract

In this work, chitosan chains were crosslinked with different contents of vanillin (Van), characterized and loaded with curcumin (CUR), a hydrophobic drug. Sodium dodecyl sulfate (SDS), Tween 20® (T20) and β-cyclodextrin (βCD) were used as curcumin carriers. Films prepared with Van 20 % yielded gel content of 70 %, swelling degree of ~23 g_water/g, bound water and capillary water, as revealed by Time-Domain Nuclear Magnetic Resonance measurements. Films prepared with higher Van contents showed small swelling degree (< 1.6 g_water/g) and hydrophobicity, making them inadequate for drug loading. UV-Vis and fluorescence spectroscopic studies indicated that Van 20 % combined with SDS and SDS/βCD presented the highest CUR uptake (~3.0 mg/g), favored by electrostatic interactions and hydrophobic interactions. CHI and Van 20 % films did not present any cytotoxicity in human neuroblastoma SH-SY5Y cells. At pH 1.0 the films were completely soluble, pointing to their potential application as gastric delivery systems for hydrophobic drugs. Chemical compounds studied in the manuscript: Chitosan, vanillin, curcumin, β-cyclodextrin, sodium dodecyl sulfate, polyethylene glycol sorbitan monolaurate.

Keywords: Chitosan; Curcumin; Films; SH-SY5Y cells; Sodium dodecyl sulfate; Vanillin; β-Cyclodextrin.

MeSH terms

Benzaldehydes
Chitosan* / chemistry
Curcumin* / chemistry
Curcumin* / pharmacology
Drug Carriers / chemistry
Drug Liberation
Humans
Neuroblastoma*
Sodium Dodecyl Sulfate
Water / chemistry
beta-Cyclodextrins* / chemistry

Substances

Benzaldehydes
Drug Carriers
beta-Cyclodextrins
Water
Sodium Dodecyl Sulfate
Chitosan
vanillin
Curcumin