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Article

Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line

by
Francesca Sisto
1,
Simone Carradori
2,*,
Paolo Guglielmi
3,
Mattia Spano
3,
Daniela Secci
3,
Arianna Granese
3,
Anatoly P. Sobolev
4,
Rossella Grande
2,
Cristina Campestre
2,
Maria Carmela Di Marcantonio
5 and
Gabriella Mincione
5
1
Department of Biomedical, Surgical and Dental Sciences, University of Milan, 20122 Milan, Italy
2
Department of Pharmacy, “G. d’Annunzio” University of Chieti-Pescara, Via dei Vestini 31, 66100 Chieti, Italy
3
Department of Chemistry and Technology of Drugs, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy
4
Institute for Biological Systems, “Annalaura Segre” Magnetic Resonance Laboratory, CNR, 00015 Rome, Italy
5
Department of Innovative Technologies in Medicine and Dentistry, “G. d’Annunzio” University of Chieti-Pescara, 66100 Chieti, Italy
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(7), 1829; https://doi.org/10.3390/molecules26071829
Submission received: 7 March 2021 / Revised: 22 March 2021 / Accepted: 23 March 2021 / Published: 24 March 2021
(This article belongs to the Special Issue Novel Biologically Active Molecules, Biomaterials and Nanoparticles for the Microbial Biofilm Control in Human Medicine)
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Abstract

Following a similar approach on carvacrol-based derivatives, we investigated the synthesis and the microbiological screening against eight strains of H. pylori, and the cytotoxic activity against human gastric adenocarcinoma (AGS) cells of a new series of ether compounds based on the structure of thymol. Structural analysis comprehended elemental analysis and 1H/13C/19F NMR spectra. The analysis of structure–activity relationships within this molecular library of 38 structurally-related compounds reported that some chemical modifications of the OH group of thymol led to broad-spectrum growth inhibition on all isolates. Preferred substitutions were benzyl groups compared to alkyl chains, and the specific presence of functional groups at para position of the benzyl moiety such as 4-CN and 4-Ph endowed the most anti-H. pylori activity toward all the strains with minimum inhibitory concentration (MIC) values up to 4 µg/mL. Poly-substitution on the benzyl ring was not essential. Moreover, several compounds characterized by the lowest minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values against H. pylori were also tested in order to verify a cytotoxic effect against AGS cells with respect to 5-fluorouracil and carvacrol. Three derivatives can be considered as new lead compounds alternative to current therapy to manage H. pylori infection, preventing the occurrence of severe gastric diseases. The present work confirms the possibility to use natural compounds as templates for the medicinal semi-synthesis.
Keywords: thymol; Helicobacter pylori; AGS cells; semi-synthesis; drug resistance; dual-action agents, antimicrobial activity thymol; Helicobacter pylori; AGS cells; semi-synthesis; drug resistance; dual-action agents, antimicrobial activity

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MDPI and ACS Style

Sisto, F.; Carradori, S.; Guglielmi, P.; Spano, M.; Secci, D.; Granese, A.; Sobolev, A.P.; Grande, R.; Campestre, C.; Di Marcantonio, M.C.; et al. Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line. Molecules 2021, 26, 1829. https://doi.org/10.3390/molecules26071829

AMA Style

Sisto F, Carradori S, Guglielmi P, Spano M, Secci D, Granese A, Sobolev AP, Grande R, Campestre C, Di Marcantonio MC, et al. Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line. Molecules. 2021; 26(7):1829. https://doi.org/10.3390/molecules26071829

Chicago/Turabian Style

Sisto, Francesca, Simone Carradori, Paolo Guglielmi, Mattia Spano, Daniela Secci, Arianna Granese, Anatoly P. Sobolev, Rossella Grande, Cristina Campestre, Maria Carmela Di Marcantonio, and et al. 2021. "Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line" Molecules 26, no. 7: 1829. https://doi.org/10.3390/molecules26071829

APA Style

Sisto, F., Carradori, S., Guglielmi, P., Spano, M., Secci, D., Granese, A., Sobolev, A. P., Grande, R., Campestre, C., Di Marcantonio, M. C., & Mincione, G. (2021). Synthesis and Evaluation of Thymol-Based Synthetic Derivatives as Dual-Action Inhibitors against Different Strains of H. pylori and AGS Cell Line. Molecules, 26(7), 1829. https://doi.org/10.3390/molecules26071829

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