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Evaluation of the antimicrobial activity of curcuminoids and study of their fragmentation reactions in the gas-phase by tandem mass spectrometry

Grant number: 16/19272-9
Support type:Scholarships in Brazil - Master
Effective date (Start): February 01, 2017
Effective date (End): January 31, 2019
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Cooperation agreement: Coordination of Improvement of Higher Education Personnel (CAPES)
Principal Investigator:Antônio Eduardo Miller Crotti
Grantee:Tatiana Manzini Vieira
Home Institution: Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (FFCLRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil

Abstract

Caries is one of the main health problems worldwide. According to the literature, caries affects 75% of the world population. Dental biofilms are considered the major cause of caries and gingivitis. Biofilm control requires maintenance of the buccal hygiene, which can be efficiently achieved by mechanical methods (brushing). Chemotherapy agents have been used as co-adjuvants for the mechanical removal of the dental biofilm. Curcumin, or diferuloylmethane, is a hydrophobic curcuminoid that is present in Curcuma longa L, Zingiberaceae (turmeric) rhizomes. This compound displays an ±,²-unsaturated bis-²diketone. The antimicrobial activity of curcumin against cariogenic bacteria has been extensively investigated, and very promising results have been obtained. However, the very low absorption and fast metabolism of this compound have prevented its approval as therapeutic agent despite its efficacy and safety. Some curcuminoids also display activity against cariogenic bacteria, with the advantage that they are more stable than curcumin. There are no literature data on the antimicrobial activity of monoketone curcuminoids against cariogenic bacteria. Moreover, there are no systematic studies on the fragmentation pathways of these compounds in the gas-phase by electrospray ionization tandem mass spectrometry (ESI-MS/MS), which could help to identify these compounds in complex mixtures. This project aims to synthesize a series of monoketone curcuminoids and evaluate their antimicrobial activity against a panel of representative cariogenic bacteria. We will also investigate the fragmentation pathways of these compounds by ESI-MS/MS. The curcuminoids will be synthesized by condensation reactions in the presence of acetone and different aromatic aldehydes. Tandem and sequential mass spectrometry (MS/MS and MSn, respectively) as well as thermochemical data estimated by Computacional Chemistry will be used to elucidate the fragmentation pathways of the synthesized curcuminoids, aiming to obtain structure-fragmentation relationships that could enable identification/dereplication of these compounds and their metabolites by IES-EM/EM or liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). (AU)

Scientific publications
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
VIEIRA, TATIANA M.; ORENHA, RENATO P.; CREVELIN, EDUARDO J.; FURTADO, SAULO S. P.; VESSECCHI, RICARDO; PARREIRA, RENATO L. T.; CROTTI, ANTONIO E. M. Electrospray ionization tandem mass spectrometry of monoketone curcuminoids. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, FEB 2020. Web of Science Citations: 0.
VIEIRA, TATIANA M.; DOS SANTOS, ISABELLA A.; SILVA, THAYNA S.; MARTINS, CARLOS H. G.; CROTTI, ANTONIO E. M. Antimicrobial Activity of Monoketone Curcuminoids Against Cariogenic Bacteria. CHEMISTRY & BIODIVERSITY, v. 15, n. 8 AUG 2018. Web of Science Citations: 0.
SOARES, MARINA H.; DIAS, HERBERT J.; VIEIRA, TATIANA M.; DE SOUZA, MARIA G. M.; CRUZ, ANA F. F.; BADOCO, FERNANDA R.; NICOLELLA, HELOIZA D.; CUNHA, WILSON R.; GROPPO, MILTON; MARTINS, CARLOS H. G.; TAVARES, DENISE C.; MAGALHAES, LIZANDRA G.; CROTTI, ANTONIO E. M. Chemical Composition, Antibacterial, Schistosomicidal, and Cytotoxic Activities of the Essential Oil of Dysphania ambrosioides (L.) Mosyakin & Clemants (Chenopodiaceae). CHEMISTRY & BIODIVERSITY, v. 14, n. 8 AUG 2017. Web of Science Citations: 7.
Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
VIEIRA, Tatiana Manzini. Evaluation of the antimicrobial activity of curcuminoids and study of their gas phase fragmentation reactions by sequential mass spectrometry. 2019. Master's Dissertation - Universidade de São Paulo (USP). Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto Ribeirão Preto.

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