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Evaluation of the antimicrobial and antiparasitic activities of Artepillin C and its derivatives and study of their gas-phase fragmentation reactions using tandem mass spectrometry

Grant number: 19/11700-0
Support Opportunities:Scholarships in Brazil - Doctorate
Effective date (Start): September 01, 2019
Effective date (End): July 31, 2023
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Antônio Eduardo Miller Crotti
Grantee:Tatiana Manzini Vieira
Host Institution: Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (FFCLRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
Associated research grant:17/04138-8 - Attainment of chemical, analytical, biological, pharmacological and technological studies to fill the gaps on the development of Brazilian propolis sector, AP.TEM


Schistosomiasis, Leishmaniasis, and Trypanosomiasis (or Chagas' Disease) are Neglected Tropical Diseases (NTDs) typical of places without minimal hygiene conditions or potable water, such as the poorest areas in Brazil North and Northeast regions. These diseases are caused by parasites of the genus Schistosoma, Leishmania, and Trypanosoma cruzi, respectively. Although effective, the drugs currently used to control these diseases have been showing several limitations, mainly regarding low solubility, long-term toxicity, and side effects, as well as the emergence of resistant strains. Likewise schistosomiasis, leishmaniasis and trypanosomiasis, caries is also one of the major public health problems in Brazil and worldwide. Caries is triggered by the accumulation of dental biofilm, which can be controlled by maintaining adequate oral hygiene through mechanical methods (brushing and dental flossing). Chlorhexidine, which is the most commonly incorporated antimicrobial agent in mouth rinses, presents some inconvenient, such as a variety of undesirable effects and the emergence of resistant bacterial strains has been reported. In this project, we will synthesize and evaluated the antimicrobial, schistosomicidal, leishmanicidal, trypanocidal and cytotoxic activity of Artepillin C and a series of semisynthetic derivatives. Artepillin C was chosen due to previous reports on its antimicrobial and antiparasitic activities. Also, we will investigate the gas-phase fragmentation reactions of these compounds using electrospray ionization tandem mass spectrometry (ESI-MS/MS) in combination with data from deuterium exchange experiments, thermochemical data, accurate mass data and multi-stage mass spectrometry (MSn). Data from this study will contribute to the future identification of in vivo or in vitro metabolism products of Artepillin C and/or its derivatives using high-performance liquid chromatography combined with ESI-MS/MS (LC-ESI -MS/MS) without the need for isolation or availability of authentic standards. (AU)

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Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
VIEIRA, Tatiana Manzini. Evaluation of the antibacterial and antiparasitic activities of artepillin C and its prenylated analogs and study of their gas-phase fragmentation reactions using tandem mass spectrometry. 2023. Doctoral Thesis - Universidade de São Paulo (USP). Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (PCARP/BC) Ribeirão Preto.

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