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Novel fluoro-quinazoline derivatives bearing a bioreductive group for tumoral hypoxia diagnosis

Grant number: 17/04599-5
Support type:Scholarships abroad - Research Internship - Doctorate
Effective date (Start): May 12, 2017
Effective date (End): November 11, 2017
Field of knowledge:Health Sciences - Pharmacy
Principal researcher:Ivone Carvalho
Grantee:Paulo Sérgio Gonçalves Nunes
Supervisor abroad: Kuo-Shyan Lin
Home Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
Research place: University of British Columbia, Vancouver (UBC), Canada  
Associated to the scholarship:13/27186-7 - Biorreductive Quinazolines: synthesis and biological evaluation for PET diagnostic and treatment of hypoxic tumors, BP.DR


Tumor hypoxia diagnosis is extremely important for the accurate cancer treatment, since some type of somatic lesions have negative prognosis. Amongst the hypoxia diagnostic tools, molecular PET is the most sensitive method and non-invasive once it uses radiotracers bearing specific reactive groups that exploits differences between the reducing potential of a tumor microenvironment in normoxia and hypoxia. The present work aims to identify new molecular probes for hypoxia tumors diagnosis from a quinazoline core, which is a privileged structure in cancer treatment. The target quinazoline-based compounds (series A and B) comprise two different functional motifs, the bioreductive (2-nitroimidazole) and the radiotracer (radionuclide 18F), switching at C-4 and C-6 positions of the quinazoline ring. Regarding the radiotracer motif, classical fluor-ethylene and trifluoroborate groups along with Copper(I)-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) reactions (Click Chemistry strategy) will enable the synthesis of a small set of potential probes. Moreover, we also have proposed the synthesis a derivative without the quinazoline scaffold in order to evaluate its biological impact/influence in the absence of the quinazoline core when compared to the quinazoline derivatives. The synthesized compounds will be then evaluated toward their stability in mouse plasma, PET/CT imaging and biodistribution, partition coefficients and in vitro cell uptake.

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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)
GONCALVES NUNES, PAULO SERGIO; ZHANG, ZHENGXING; KUO, HSIOU-TING; ZHANG, CHENGCHENG; ROUSSEAU, JULIE; ROUSSEAU, ETIENNE; LAU, JOSEPH; KWON, DANIEL; CARVALHO, IVONE; BENARD, FRANCOIS; et al. Synthesis and evaluation of an F-18-labeled trifluoroborate derivative of 2-nitroimidazole for imaging tumor hypoxia with positron emission tomography. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, v. 61, n. 4, p. 370-379, . (17/04599-5)

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