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. 2023 Feb 27;28(5):2209.
doi: 10.3390/molecules28052209.

Photoantibacterial Poly(vinyl)chloride Films Applying Curcumin Derivatives as Bio-Based Plasticizers and Photosensitizers

Fábio M S Rodrigues  1 , Iúri Tavares  1 , Rafael T Aroso  1 , Lucas D Dias  1   2 , Carolina V Domingos  1 , Clara M G de Faria  2 , Giusi Piccirillo  1 , Teresa M R Maria  1 , Rui M B Carrilho  1 , Vanderlei S Bagnato  2   3 , Mário J F Calvete  1 , Mariette M Pereira  1
Affiliations

Photoantibacterial Poly(vinyl)chloride Films Applying Curcumin Derivatives as Bio-Based Plasticizers and Photosensitizers

Fábio M S Rodrigues et al. Molecules. .

Abstract

Herein we describe the design of natural curcumin ester and ether derivatives and their application as potential bioplasticizers, to prepare photosensitive phthalate-free PVC-based materials. The preparation of PVC-based films incorporating several loadings of newly synthesized curcumin derivatives along with their standard solid-state characterization is also described. Remarkably, the plasticizing effect of the curcumin derivatives in the PVC material was found to be similar to that observed in previous PVC-phthalate materials. Finally, studies applying these new materials in the photoinactivation of S. aureus planktonic cultures revealed a strong structure/activity correlation, with the photosensitive materials reaching up to 6 log CFU reduction at low irradiation intensities.

Keywords: PVC films; antimicrobial photodynamic inactivation (aPDT); bioplasticizer; curcumin; photodecontamination; photosensitive material; photosensitizer.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
(a) Synthesis of curcumin ester and ether derivatives. (b) Synthesis of saturated fatty acids from waste cooking oil.
Figure 1
Figure 1
Normalized UV-Vis absorption spectra of curcumin (1) and its derivatives 2–5, recorded in THF.
Figure 2
Figure 2
Photodegradation profile of curcumin 1 (black), curcumin derivative 3 (red) and curcumin derivative 4 (blue) under different light doses (0, 9.4 and 23.5 J/cm2 using a 450 nm Biotable® light source device) using DMSO/H2O as solvent. Three experiments were carried out (n = 3), and the results are shown as means (± SD deviation).
Figure 3
Figure 3
Examples of prepared films with 15% w/w curcumin derivative loads on PVC: (A) pure PVC, (B) PVC (1)-curc, (C) PVC(4)-etherC10, (D) PVC(3)-esterC10.
Figure 4
Figure 4
Normalized solid-state UV-Vis absorption spectra of the PVC–curcumin-based films (0.1% w/w curcumin derivative/PVC).
Figure 5
Figure 5
TGA curves of PVC and PVC–curcumin-based materials (30% w/w curcumin derivative/PVC); β = 10 °C/min.
Figure 6
Figure 6
Examples of stress–strain curves for: (a) PVC; (b) PVC(4)-etherC10.
Figure 7
Figure 7
(a) Comparative study of different PVC loads with 1 on the photodynamic inactivation of S. aureus planktonic cultures. (b) Comparative study of PVC(1)–(4) (30% w/w curcumin derivative/PVC) on the photodynamic inactivation of S. aureus planktonic cultures. The label *** (p < 0.001) represents statistical difference.
Figure 8
Figure 8
Cytotoxicity of curcumin-based plasticizer 4 against human fibroblast cell line (HDFn). Each condition was carried out at all times and three independent experiments were conducted (n = 3). p < 0.05 was considered to be statistically significant. Ctrl (black bar): control without exposure to formulation; Ctrl 2.5, Ctrl 5 and Ctrl 10 (gray bars): formulation control (2.5 µg/mL, 5 µg/mL and 10 µg/mL); Curcumin derivative 4 (blue bar): incubation with 4 at 2.5 µg/mL, 5 µg/mL and 10 µg/mL.
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