Investigation of reactive intermediates in complex chemical and biochemical processes

• Grant number: 21/06726-0
• Support Opportunities: Research Grants - Young Investigators Grants - Phase 2
• Start date: May 01, 2022
• End date: April 30, 2027
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Physical-Chemistry
• Principal Investigator: Thiago Carita Correra
• Grantee: Thiago Carita Correra
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Associated researchers: Thiago Regis Longo Cesar da Paixão
• Associated research grant: 14/15962-5 - Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy, AP.JP
• Associated research grant(s): 22/00498-8 - Multi-user equipment approved in grant 21/06726-0: ion mobility mass spectrometry system (IMS-MS), AP.EMU
• Associated scholarship(s): 25/06785-7 - Evaluation of polymerization reactions by differential ion mobility and infrared ion spectroscopy, BP.DD; 25/04959-8 - Development of Analytical methods for Mass Spectrometric Analysis of Complex Matrices, BP.TT; 24/09983-1 - Identification of Phase II Isomeric Metabolites of Paracetamol by Ion Mobility, BP.IC; + associated scholarships 23/16303-4 - Development of a differential ion mobility device coupled to mass spectrometry for the evaluation of complex reactive systems, BP.PD; 23/01180-4 - Developments of advanced methods for the evaluation of isomers by mass spectrometry of chemical and biological systems., BP.TT; 23/01070-4 - Development of methods for sample analysis in complex matrices by mass spectrometry., BP.TT; 22/14233-6 - Development of a differential ion mobility device coupled to mass spectrometry for the evaluation of complex reactive systems, BP.PD; 22/10797-2 - Development of Advanced Methods for the evaluation of chemical and biochemicals system's isomers using mass spectrometry, BP.TT - associated scholarships

Abstract

This proposal aims to expand the scope of the reactive systems evaluated by our research group (organo- and metal-based chiral catalysis) to including more complex reactive systems as polymerization reactions and the formation of drug metabolites and degradation products. To achieve these goals, the infrared ion spectroscopy (IRMPD spectroscopy) technique developed in the framework of the JP1 (2014/15962-5) and the advanced sample methods developed during the FAPESP research project (2019/25634-9) will be applied and enhanced by their synergic use with Ion Mobility Spectrometry (IMS), constituting the state-of-the-art IMS-IRMPD-MS platform for the study of convoluted reaction systems in complex matrices. These techniques would allow the differentiation of isomers in, virtually, any chemical system, enhancing the quality and scope of our research and allowing the access of external users to these state-of-the-art techniques by developing a multiuser instrument as successfully implemented during the JP1 project. This instrumentation will be used to study: I) the first steps of polybenzoxazine formation; II) the polymerization motifs of polyaniline; III) the oxidation products of the drug metoprolol and IV) the degradation products of chemotherapy agents cyclophosphamide and ifosfamide. Besides evaluating these relevant chemical species, this project will allow the production of qualified professionals for the mass spectrometry community and the development of a state-of-the-art technique that will be made available for research institutions and the private sectors. (AU)

Scientific publications

(10)

(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)

OBEID, GUILHERME; MORAES, GUSTAVO O.; PENNA, TATIANA C.; SCHENBERG, LEONARDO A.; DUCATI, LUCAS C.; CORRERA, THIAGO C.. Solvation effects on glyphosate protonation and deprotonation states evaluated by mass spectrometry and explicit solvation simulations. Journal of Chemical Physics, v. 158, n. 5, p. 12-pg., 2023-02-07. (20/10246-0, 19/12808-9, 17/20262-0, 17/17750-3, 15/08539-1, 19/18727-0, 19/25634-9, 20/08894-4, 21/06726-0, 14/15962-5)

RIBEIRO, FRANCISCO W. M.; OMARI, ISAAC; THOMAS, GILIAN T.; PAUL, MATHIAS; WILLIAMS, PETER J. H.; MCINDOE, J. SCOTT; CORRERA, THIAGO C.. Microstructural Analysis of Benzoxazine Cationic Ring-Opening Polymerization Pathways. MACROMOLECULAR RAPID COMMUNICATIONS, v. N/A, p. 7-pg., 2023-10-09. (21/06726-0, 17/18485-1, 23/01180-4, 22/00498-8, 19/25634-9, 19/16026-5, 15/08539-1, 14/15962-5)

CUGNASCA, BEATRIZ S.; JUNIOR, THARCISIO C. T.; PENNA, TATIANA C.; ZULUAGA, NORMA L. B.; BUSTOS, SILVINA O.; CHAMMAS, ROGER; CUCCOVIA, IOLANDA M.; CORRERA, THIAGO C.; DOS SANTOS, ALCINDO A.. Seleno-BODIPY as a fluorescent sensor for differential and highly selective detection of Cysteine and Glutathione for bioimaging in HeLa cells. DYES AND PIGMENTS, v. 236, p. 12-pg., 2025-01-21. (14/50983-3, 21/06726-0, 17/20262-0, 23/01092-8, 15/08539-1, 22/10797-2, 19/07634-1, 22/00498-8, 18/24434-3)

RIBEIRO, FRANCISCO W. M.; SILVA-OLIVEIRA, DANILO; CERVI, GUSTAVO; KOYANAGUI, EDUARDO D.; CORRERA, THIAGO C.. Isomeric Speciation of Bisbenzoxazine Intermediates by Ion Spectroscopy and Ion Mobility Mass Spectrometry. ACS OMEGA, v. 9, n. 39, p. 9-pg., 2024-09-18. (17/18485-1, 21/06726-0, 22/00498-8, 23/01180-4, 23/01070-4, 15/08539-1, 19/16026-5)

ESTEVES, LARISSA CERRATO; MACHADO, CAROLINE OLIVEIRA; PIRES GONCALVES, LETICIA CHRISTINA; CAVALCANTE, VICTOR FERNANDES; OBEID, GUILHERME; CORRERA, THIAGO CARITA; BASTOS, ERICK LEITE. Structural Effects on the Antioxidant Properties of Amino Acid Betaxanthins. ANTIOXIDANTS, v. 11, n. 11, p. 19-pg., 2022-11-01. (21/06726-0, 20/08894-4, 19/25634-9, 15/24760-0, 19/15412-9)

RIBEIRO, FRANCISCO WANDERSON MOREIRA; MATSUSHIMA, JULLYANE EMI; OBEID, GUILHERME; VINHATO, ELISANGELA; RODRIGUES, ALESSANDRO; CORRERA, THIAGO CARITA. Mechanistic Investigation of an Organocatalytic Bromocyclization of O-Allyl Carbamates. CHEMCATCHEM, v. 17, n. 8, p. 10-pg., 2025-03-16. (19/25634-9, 21/06726-0, 17/18485-1, 14/15962-5, 15/08539-1, 23/01180-4, 20/08894-4, 22/00498-8, 16/21676-0)

FERNANDES, ANDRE S.; OBEID, GUILHERME; LAURENO, TIAGO J. N.; CORRERA, THIAGO C.. Protonated and Sodiated Cyclophosphamide Fragmentation Pathways Evaluation by Infrared Multiple Photon Dissociation Spectroscopy. Journal of Physical Chemistry A, v. N/A, p. 10-pg., 2023-06-07. (15/08539-1, 19/25634-9, 20/08894-4, 21/06726-0, 14/15962-5)

RIBEIRO, FRANCISCO W. M.; OMARI, ISAAC; MCINDOE, J. SCOTT; CORRERA, THIAGO C.. Protonation Effects on the Benzoxazine Formation Pathways and Products Distribution. ChemPhysChem, v. 25, n. 19, p. 214-pg., 2024-07-30. (19/25634-9, 17/18485-1, 21/06726-0, 14/15962-5, 22/00498-8, 23/01180-4, 15/08539-1, 19/16026-5)

HENNEMANN, ARTUR L.; NOGUEIRA, HELTON P.; RAMOS, MIGUEL D.; CORRERA, THIAGO C.; HENNEMANN, BRUNO L.; ARAKI, KOITI. Amorphous Titanium Dioxide Nanoparticles and Their Unexpected Fragmentation in MALDI-TOF/MS. ACS OMEGA, v. N/A, p. 11-pg., 2024-11-18. (18/21489-1, 21/06726-0)

DANTAS, CESARA. G.; GARCIA, PEDRO H. M.; CORRERA, THIAGO C.. Characterization of Pharmaceutical Transformation Products by High-Field Asymmetric Waveform Ion Mobility and Infrared Ion Spectroscopy Coupled to Mass Spectrometry. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, v. 36, n. 6, p. 9-pg., 2025-05-12. (21/06726-0, 22/00498-8, 15/08539-1, 23/16303-4)