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Thiophenoporphyrins as biomimetic models of Cytochrome P450: catalysis of hydrocarbons and triazine herbicides

Grant number: 18/17352-0
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): November 01, 2018
Effective date (End): October 31, 2019
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Yassuko Iamamoto
Grantee:Kelita Angelo de Paula
Home Institution: Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (FFCLRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil


The Metaloporphyrins are heme enzymes of cytochrome P450 (P450), responsible for oxidative catalysis of exogenous compounds, such as drugs and pesticides. The prospect of reproducing the highly specific and selective reactions promoted by P450 enzymes has led to the development of synthetic metalloporphyrins (MePs). Currently one of the bigger challenges of modern chemistry today is the desing of new porphyrin systems capable of reproducing the catalytic activity of P450 enzymes, for example, in the study of metabolism of xenobiotics (eg natural products, pharmaceuticals, pesticides). In this sense, this project search to synthesize and explore the catalytic properties of meso-tetraenyl porphyrins (H2TThP), replaced with nitro (-NO2) groups, as biomimetic catalysts of P450 enzymes. Mononitrated catalysts (MnTTh (NO2) P) and tetranitrates (MnTTh (NO2) 4P) will be synthesized in order to compare the catalytic efficiency under the electron density withdrawing action from the nitro groups. The reactivity, stability and selectivity of these new catalysts will be evaluated in oxidation studies of cyclohexane hydrocarbon. Posteriorly, the catalysts will be applied to the metabolism of xenobiotics, with featured on triazine herbicides (terbuthylazine, atrazine and simazine), widely used in the control of weeds in agricultural crops, such as sugarcane, coffee, bananas and corn , which present high leaching potential, which can contaminate soil, groundwater and streams. Exposure to these herbicides can cause neurological and reproductive problems in humans; therefore, it is necessary to identify the metabolites produced during the biotransformation reactions of these herbicides in the human body. In this way, studies with in vitro biomimetic systems based on P450 enzymes may contribute to the identification of these metabolites and possible intermediates.