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Article

Structural, Vibrational and Electrochemical Analysis and Antibacterial Potential of Isomeric Chalcones Derived from Natural Acetophenone

by
Priscila Teixeira da Silva
1,
Thiago Sampaio de Freitas
1,
Diniz Maciel Sena, Jr.
1,
Paulo Nogueira Bandeira
2,
Murilo Ségio da Silva Julião
2,
Emmanuel Silva Marinho
3,
Ana Aline Coêlho Alcanfor
4,
Emanuelle Machado Marinho
4,
Pedro de Lima-Neto
4,
Carlos Emídio Sampaio Nogueira
1,5,
Henrique Douglas Melo Coutinho
1,
Antonio Linkoln Alves Borges Leal
1,6,
Humberto Medeiros Barreto
6,
Natália Martins
7,8,*,
Alexandre Magno Rodrigues Teixeira
1 and
Hélcio Silva dos Santos
1,2,9,*
1
Departamento de Química Biológica, Universidade Regional do Cariri, Crato CE 63.105-000, Brazil
2
Centro de Ciências Exatas e Tecnologia, Curso de Química, Universidade Vale do Acaraú, Sobral CE 62.040-370, Brazil
3
Grupo de Química Teórica e eletroquímica, Faculdade de Filosofia Dom Aureliano Matos, FAFIDAM, Universidade Estadual do Ceará, Limoeiro do Norte CE 62.930-000, Brazil
4
Departamento de Química Analítica e Físico-Química, Universidade Federal do Ceará, Fortaleza CE 60.440-900, Brazil
5
Departamento de Física, Universidade Regional do Cariri, Crato CE 63.041-145, Brazil
6
Departamento de Parasitologia e Microbiologia, Universidade Federal do Piauí, Teresina PI 64.049-550, Brazil
7
Faculty of Medicine, University of Porto, Alameda Prof. Hernâni Monteiro, 4200-319 Porto, Portugal
8
Institute for Research and Innovation in Health (i3S), University of Porto, 4200-135 Porto, Portugal
9
Centro de Ciências e Tecnologia, Universidade Estadual do Ceará, Fortaleza CE 60.714.903, Brazil
*
Authors to whom correspondence should be addressed.
Appl. Sci. 2020, 10(14), 4713; https://doi.org/10.3390/app10144713
Submission received: 8 June 2020 / Revised: 2 July 2020 / Accepted: 2 July 2020 / Published: 8 July 2020
(This article belongs to the Section Applied Biosciences and Bioengineering)
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Abstract

Background: Chalcones are part of a family of small phenolic compounds that are being extensively studied for presenting a diversity of molecular structures and biological activities. In this paper, two chalcones, (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (1), (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (2), were synthesized by Claisen–Schmidt condensation. Methods: The molecular structures of these chalcones were determined by Nuclear Magnetic Resonance and characterized by infrared, Raman spectroscopy, and electrochemical analysis at room temperature. Vibrational wavenumbers were predicted using Functional Density Theory (DFT) calculations, and their normal modes were analyzed in terms of potential energy distribution (PED). Besides this, DFT calculations were performed to obtain the molecular orbitals and their quantum descriptors. The UV-Vis absorption spectrum of the synthesized chalcones was measured and compared with each other. In addition, analyses of antimicrobial activity and modulation of antibiotic resistance were carried out to assess the antibacterial potential of these chalcones. Results: The vibrational spectra of polycrystalline chalcones obtained by ATR-FTIR, FT-Raman and DFT calculations allowed a complete assignment of the vibrational modes, and revealed the quantum chemical parameters. Both chalcones did not show good responses when associated with the antibiotics Ciprofloxacin and Cephalexin against S. aureus 10 and E. coli 06 strains. However, a significant potentiating of the Gentamicin activity against S. aureus 10 and E. col 06 strains was observed for chalcone 2. On the other hand, when associated with Norfloxacin, an antagonistic effect was observed. The results found for EtBr suggest that, although the tested chalcones behave as efflux pump inhibitors, probably inhibiting other efflux pumps, they were not able to inhibit NorA. Thus, these synthetic chalcones are not recommended for use in association with Norfloxacin against strains of S. aureus 1199-B that overexpress the NorA gene. Conclusions: Spectroscopic data confirmed the structure of the chalcones, and chalcone 2 showed potential as an adjuvant in antibiotic therapy.
Keywords: chalcones; NMR; UV-VIS; FT-Raman; ATR-FTIR; electrochemical; DFT; antibacterial activity chalcones; NMR; UV-VIS; FT-Raman; ATR-FTIR; electrochemical; DFT; antibacterial activity

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MDPI and ACS Style

Silva, P.T.d.; Freitas, T.S.d.; Sena, D.M., Jr.; Bandeira, P.N.; Julião, M.S.d.S.; Marinho, E.S.; Alcanfor, A.A.C.; Marinho, E.M.; Lima-Neto, P.d.; Nogueira, C.E.S.; et al. Structural, Vibrational and Electrochemical Analysis and Antibacterial Potential of Isomeric Chalcones Derived from Natural Acetophenone. Appl. Sci. 2020, 10, 4713. https://doi.org/10.3390/app10144713

AMA Style

Silva PTd, Freitas TSd, Sena DM Jr., Bandeira PN, Julião MSdS, Marinho ES, Alcanfor AAC, Marinho EM, Lima-Neto Pd, Nogueira CES, et al. Structural, Vibrational and Electrochemical Analysis and Antibacterial Potential of Isomeric Chalcones Derived from Natural Acetophenone. Applied Sciences. 2020; 10(14):4713. https://doi.org/10.3390/app10144713

Chicago/Turabian Style

Silva, Priscila Teixeira da, Thiago Sampaio de Freitas, Diniz Maciel Sena, Jr., Paulo Nogueira Bandeira, Murilo Ségio da Silva Julião, Emmanuel Silva Marinho, Ana Aline Coêlho Alcanfor, Emanuelle Machado Marinho, Pedro de Lima-Neto, Carlos Emídio Sampaio Nogueira, and et al. 2020. "Structural, Vibrational and Electrochemical Analysis and Antibacterial Potential of Isomeric Chalcones Derived from Natural Acetophenone" Applied Sciences 10, no. 14: 4713. https://doi.org/10.3390/app10144713

APA Style

Silva, P. T. d., Freitas, T. S. d., Sena, D. M., Jr., Bandeira, P. N., Julião, M. S. d. S., Marinho, E. S., Alcanfor, A. A. C., Marinho, E. M., Lima-Neto, P. d., Nogueira, C. E. S., Coutinho, H. D. M., Leal, A. L. A. B., Barreto, H. M., Martins, N., Rodrigues Teixeira, A. M., & Santos, H. S. d. (2020). Structural, Vibrational and Electrochemical Analysis and Antibacterial Potential of Isomeric Chalcones Derived from Natural Acetophenone. Applied Sciences, 10(14), 4713. https://doi.org/10.3390/app10144713

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