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Chemical modification of BODIPY fluorophores aiming at structural and photophysical diversity for the development of novel fluorescent probes

Grant number: 13/24408-9
Support Opportunities:Scholarships abroad - Research Internship - Doctorate
Effective date (Start): June 01, 2014
Effective date (End): March 31, 2015
Field of knowledge:Health Sciences - Pharmacy
Principal Investigator:Flavio da Silva Emery
Grantee:Lucas Cunha Dias de Rezende
Supervisor: Wim Dehaen
Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
Research place: University of Leuven, Leuven (KU Leuven), Belgium  
Associated to the scholarship:11/23342-9 - Synthesis, characterization and applications of BODIPY fluorophores., BP.DR


The emergence and spread of spectroscopic and imaging techniques based on fluorescence emission has stimulated research on different classes of fluorescent compounds, among which our research group has been working in the preparation, characterization and application of BODIPYs. So far our group has successfully synthesized and characterized a series of BODIPYs that have been applied by several collaborators. In order to extend the scope of the compounds synthesized by our group, we plan to establish modern synthetic methods for the chemical modification and photophysical tuning of BODIPYs. In this context, this project aims to establish collaboration with the research group of prof. Wim Dehaen from KU Leuven in Belgium, who has published a series of papers describing methods of chemical modification of BODPYs. We propose to apply modern synthetic methods seeking to obtain novel fluorophores with structural and photophysical diversity. The proposed chemical modification methods involve direct arylation via palladium catalyzed C-H activation, condensation of vinyl aromatic derivatives and preparation of dihydronaphthalenic derivatives. In addition to the synthesis we will realize the photophysical characterization of each compound by studying their absorption spectroscopy, fluorescence spectroscopy and time-resolved fluorescence spectroscopy. Finally we will perform functionalizations of some compounds with functional groups classically used in bioconjugation, aiming their application in this field. (AU)

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Scientific publications (4)
(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)
DIAS DE REZENDE, LUCAS CUNHA; GIL DE MELO, SHAIANI MARIA; BOODTS, STIJN; VERBELEN, BRAM; DEHAEN, WIM; EMERY, FLAVIO DA SILVA. Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 13, n. 21, p. 6031-6038, . (13/24408-9, 11/23342-9, 12/20990-2)
AMORIM, VANESSA G.; MELO, SHAIANI M. G.; LEITE, RUAN F.; COUTINHO, PAULO ARTHUR; DA SILVA, SARAH M. P.; DA SILVA, ANDRE R.; AMORIM, FERNANDA G.; PIRES, RITA G. W.; COITINHO, JULIANA B.; EMERY, FLAVIO S.; et al. Synthesis and characterization of two novel red-shifted isothiocyanate BODIPYs and their application in protein conjugation. DYES AND PIGMENTS, v. 182, . (14/18973-8, 13/24408-9, 11/23342-9)
REZENDE, LUCAS C. D.; EMERY, FLAVIO S.. Fluorescence Quenching of Two meso-Substituted Tetramethyl BODIPY Dyes by Fe(III) Cation. Journal of the Brazilian Chemical Society, v. 26, n. 5, p. 1048-1053, . (13/24408-9, 11/23342-9)
VERBELEN, BRAM; DIAS REZENDE, LUCAS CUNHA; BOODTS, STIJN; JACOBS, JEROEN; VAN MEERVELT, LUC; HOFKENS, JOHAN; DEHAEN, WIM. Radical CH Alkylation of BODIPY Dyes Using Potassium Trifluoroborates or Boronic Acids. CHEMISTRY-A EUROPEAN JOURNAL, v. 21, n. 36, p. 12667-12675, . (13/24408-9)

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