Antibacterial and Cytotoxic Activities of Copper-Functionalized Silsesquioxane 3-<i>n</i>-Propylpyridinium Chloride

Pedroso, Flávia de Brito; Aguiar, Deize Basílio dos Santos de; Brito, Priscilla Salles de; Pessôa, Christiana Andrade; Fujiwara, Sérgio Toshio; Kanunfre, Carla Cristine; Estrada, Ruben Auccaise; Baglie, Sinvaldo; Nadal, Jessica Mendes; Novatski, Andressa; Farago, Paulo Vitor; Loguércio, Alessandro Dourado

doi:10.1590/1678-4324-2022220228

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Article - Human and Animal Health • Braz. arch. biol. technol. 65 • 2022 • https://doi.org/10.1590/1678-4324-2022220228 copy

Antibacterial and Cytotoxic Activities of Copper-Functionalized Silsesquioxane 3-n-Propylpyridinium Chloride

Authorship SCIMAGO INSTITUTIONS RANKINGS

HIGHLIGHTS

Silsesquioxane 3-n-propylpyridinium chloride (SiPy⁺Cl^-) was synthesized.
Copper functionalization of SiPy⁺Cl^- was performed to obtain Cu-SiPy⁺Cl^-.
Antimicrobial and cytotoxic effects of SiPy⁺Cl^- and Cu-SiPy⁺Cl^- were demonstrated.
Cu-SiPy⁺Cl^- shows a promising use in oral care products.

Abstract

Silsesquioxane 3-n-propylpyridinium chloride (SiPy⁺Cl^-) is a water-soluble polymer that can be used as a promising material with remarkable biological effects. SiPy⁺Cl^- can form thin films on substrate surfaces and shows suitable adhesiveness. Besides, it has high affinity for metal ions. Considering this effect as exchanger polymer and the well-known antimicrobial and cytotoxic features of copper, the aim of this study was to perform the copper functionalization of silsesquioxane 3-n-propylpyridinium chloride Cu-SiPy⁺Cl^-. The SiPy⁺Cl^- was obtained by the sol-gel processing method and the incorporation of copper (II) chloride was carried out by immobilization. Its characterization was performed by spectroscopic methods of Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR). The FTIR spectrum of SiPy⁺Cl^- showed symmetric and asymmetric stretching of Si-O-Si group and also exhibited vibrational bands of pyridinium ring. The FTIR spectrum of Cu-SiPy⁺Cl^- assigned typical bands displacements of the metal coordination to nitrogen atoms. Spectroscopic data recorded by ¹³C and ²⁹S NMR confirmed the chemical structures of SiPy⁺Cl^- and Cu-SiPy⁺Cl^-. Concerning to the in vitro susceptibility assay, the antimicrobial activity against Staphylococcus aureus, Escherichia coli and Streptococus mutans was achieved by the agar-well diffusion method. Cu-SiPy⁺Cl^- showed similar cytotoxicity than SiPy⁺Cl^- against Calu-3 and 3T3 cell lines by the MTT colorimetric assay. Further studies are required to investigate the use of Cu-SiPy⁺Cl^- as a novel dental material.

Keywords:
antimicrobial activity; cell viability; copper functionalization; novel dental materials.

Chemical environment	Chemical shift (ppm)
	SiPy⁺Cl^-	Cu-SiPy⁺Cl^-	Reference [21]^* * The carbon labeling was related to the cartoon molecule at the top of Figure 3. The chemical shifts were supported by previous reports discussing similar (not the same) chemistry developments.	Reference [1]^* * The carbon labeling was related to the cartoon molecule at the top of Figure 3. The chemical shifts were supported by previous reports discussing similar (not the same) chemistry developments.
1	10.26	18.02	9.4	10
2	26.72	31.40	25.4	26
‘3	48.26	--		49
3	63.94	68.20	63.9	65
Α	129.10	142.90	129.2	129
β, γ	145.10	149.30	145.1	145

	Chemical Shift (ppm)
Chemical Environment	SiPy⁺Cl^-	Cu-SiPy⁺Cl^-	*Reference [13]^ * The silicon labeling and chemical shifts were supported by previous reports discussing similar (not the same) chemistry developments.**	*Reference [1]^ * The silicon labeling and chemical shifts were supported by previous reports discussing similar (not the same) chemistry developments.**	*Reference [21]^ * The silicon labeling and chemical shifts were supported by previous reports discussing similar (not the same) chemistry developments.**
T₂	-49.87	-48.20		-49		-50
T₃	-58.56	-57.10	-57	-58		-59
T₄	-67.85	-66.35	-65	-68		-68
Q₂	-91.75	-90.80		-86^* * The silicon labeling and chemical shifts were supported by previous reports discussing similar (not the same) chemistry developments.		-91
Q₃	-101.30	-101.30	-101	-101		-101
Q₄	-110.80	-111.00	-110	-110		-111

	SiPy⁺Cl^- (%)
	0.5	1.0	2.0	Positive Control
Staphylococcus aureus	8.66 ± 1.15^b	12.33 ± 0.58^a	13.67 ± 1.15^a	19.66 ± 0.58
Escherichia coli	12.67 ± 1.52^a	18.00 ± 1.00^b	22.33 ± 0.60^c	20.00 ± 0.00
Streptococcus mutans	11.56 ± 0.57^a	15.67 ± 0.58^b	18.00 ± 1.00^c	19.66 ± 0.58

	Cu-SiPy⁺Cl^- (%)
	0.5	1.0	2.0	Positive Control
Staphylococus aureus	10.67 ± 0.58^a	11.33 ± 1.15^a	13.0 ± 1.64^a	19.66 ± 0.58
Escherichia coli	12.0 ± 0.60^a	19.33 ± 0.57^b	23.0 ± 1.00^c	20.00 ± 0.00
Streptococcus mutans	12.33 ± 1.15^a	16.00 ± 1.00^b	19.67 ± 0.57^c	19.66 ± 0.58

Instituto de Tecnologia do Paraná - Tecpar Rua Prof. Algacyr Munhoz Mader, 3775 - CIC, 81350-010 Curitiba PR Brazil, Tel.: +55 41 3316-3052/3054, Fax: +55 41 3346-2872 - Curitiba - PR - Brazil
E-mail: babt@tecpar.br

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[1] Editor-in-Chief: Yasmine Mendes Pupo