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Cyclic organic peroxides: synthesis and mechanism of reduction

Grant number:12/02428-5
Support Opportunities:Regular Research Grants
Start date: June 01, 2012
End date: November 30, 2014
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Luiz Francisco Monteiro Leite Ciscato
Grantee:Luiz Francisco Monteiro Leite Ciscato
Host Institution: Centro de Ciências Naturais e Humanas (CCNH). Universidade Federal do ABC (UFABC). Santo André , SP, Brazil
City of the host institution:Santo André

Abstract

The fenton-like reductive cleavage of organic peroxides by FeII species is a chemical reaction whose mechanistic pathway has not been yet fully understood. However, it is known that there is production of radical species centered at both the oxygen and carbon. The mechanism should therefore involve a ²-scission after the formation of the initial oxyradicals through a still unknown way. This research project suggests the synthesis of cyclic peroxides of the classes 1,2-dioxetane and 1,2,4-trioxolane, and the mechanistic study of the reductive cleavage of those peroxides by FeII, from thermodynamic and kinetic studies backed by reaction products determination by direct and indirect methods. The evaluation of the generating capacity of radicalar species from the reductive cleavage reaction will be done according to the structure of those formed species and their yields, and the peroxides will be tested against Plasmodium microorganisms. The mechanism of action of those peroxidic drugs involve the reductive cleavage of the peroxide by a free heme group inside the Plasmodium parasite, which results in the formation of carbon-centered radicals, that can attack and alkylate biomolecules that are vital to the survival of the parasite, which is destroyed or inactivated. The determination of the operating mechanism and the energetics of cyclic peroxides made in this project will be correlated to the antimalarial activity of those peroxides. (AU)

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Scientific publications (14)
(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)
DE OLIVEIRA, MARCELO ALMEIDA; BARTOLONI, FERNANDO HEERING; AUGUSTO, FELIPE ALBERTO; MONTEIRO LEITE CISCATO, LUIZ FRANCISCO; BASTOS, ERICK LEITE; BAADER, WILHELM JOSEF. Revision of Singlet Quantum Yields in the Catalyzed Decomposition of Cyclic Peroxides. Journal of Organic Chemistry, v. 77, n. 23, p. 10537-10544, . (07/00684-6, 12/02428-5, 11/23036-5)
BARTOLONI, FERNANDO HEERING; DE OLIVEIRA, MARCELO ALMEIDA; MONTEIRO LEITE CISCATO, LUIZ FRANCISCO; AUGUSTO, FELIPE ALBERTO; BASTOS, ERICK LEITE; BAADER, WILHELM JOSEF. Chemiluminescence Efficiency of Catalyzed 1,2-Dioxetanone Decomposition Determined by Steric Effects. Journal of Organic Chemistry, v. 80, n. 8, p. 3745-3751, . (14/14866-2, 14/22136-4, 12/13807-7, 12/02428-5)
KHALID, MUHAMMAD; SOUZA, JR., SERGIO P.; CISCATO, LUIZ F. M. L.; BARTOLONI, FERNANDO H.; BAADER, WILHELM J.. Solvent viscosity influence on the chemiexcitation efficiency of inter and intramolecular chemiluminescence systems. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, v. 14, n. 7, p. 1296-1305, . (12/02428-5)
LOPES, NICOLAS S.; YOSHITAKE, ARIANE M.; SILVA, ADRIANA F.; OLIVEIRA, JR., VANI X.; SILVA, LEANDRO S.; PINHEIRO, ANA A. S.; CISCATO, LUIZ FRANCISCO M. L.. Antimalarial Effect of 3-Methoxy-1,2-Dioxetanes on the Erythrocytic Cycle of Plasmodium falciparum. CHEMICAL BIOLOGY & DRUG DESIGN, v. 86, n. 6, p. 1373-1377, . (12/02428-5, 11/10823-9)
LOPES, NICOLAS S.; CISCATO, LUIZ FRANCISCO M. L.. Kinetic parameters for the reaction of 1,2,4-trioxolanes and artemisinin with iron(II): New evidence for the source of antimalarial activity. CHEMICAL BIOLOGY & DRUG DESIGN, v. 91, n. 1, p. 328-331, . (12/02428-5)
KHALID, MUHAMMAD; OLIVEIRA, MARCELO A.; SOUZA, JR., SERGIO P.; CISCATO, LUIZ F. M. L.; BARTOLONI, FERNANDO H.; BAADER, WILHELM J.. Efficiency of intermolecular chemiluminescence systems lacks significant solvent cavity effect in binary toluene/diphenylmethane mixtures. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v. 312, p. 81-87, . (12/02428-5, 14/22136-4)
ALVES, J.; BOARO, A.; DA SILVA, J. S.; FERREIRA, T. L.; KESLAREK, V. B.; CABRAL, C. A.; ORFAO, JR., R. B.; CISCATO, L. F. M. L.; BARTOLONI, F. H.. Lophine derivatives as activators in peroxyoxalate chemiluminescence. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, v. 14, n. 2, p. 320-328, . (13/17332-6, 12/02428-5, 11/17587-9, 12/13807-7)
SILVA, ADRIANA F.; OLIVEIRA, JR., VANI X.; SILVA, LEANDRO S.; PINHEIRO, ANA A. S.; CISCATO, LUIZ F. M. L.. Antiplasmodial activity of alkyl-substituted 1,2-dioxetanes against Plasmodium falciparum. Bioorganic & Medicinal Chemistry Letters, v. 26, n. 20, p. 5007-5008, . (12/02428-5, 11/10823-9)
SCHRAMM, STEFAN; MONTEIRO LEITE CISCATO, LUIZ FRANCISCO; OESAU, PASCAL; KRIEG, REIMAR; RICHTER, JAN FRANK; NAVIZET, ISABELLE; ROCA-SANJUAN, DANIEL; WEISS, DIETER; BECKERT, RAINER. Investigations on the synthesis and chemiluminescence of novel 2-coumaranones - II. ARKIVOC, n. 5, p. 44-59, . (12/02428-5)
CISCATO, LUIZ FRANCISCO M. L.; BARTOLONI, FERNANDO H.; COLAVITE, ALINE S.; WEISS, DIETER; BECKERT, RAINER; SCHRAMM, STEFAN. Evidence supporting a 1,2-dioxetanone as an intermediate in the benzofuran-2(3H)-one chemiluminescence. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, v. 13, n. 1, p. 32-37, . (12/02428-5, 12/13807-7)
WUERFEL, HENDRYK; CISCATO, LUIZ FRANCISCO MONTEIRO LEITE; WEISS, DIETER; GOERLS, HELMAR; BECKERT, RAINER. Synthesis of Extended Chromophores Derived From 5,5-Dimethyloxyluciferin by Barton-Kellogg Methodology. SYNTHESIS-STUTTGART, v. 46, n. 8, p. 1114-1120, . (12/02428-5)
BARTOLONI, FERNANDO H.; DE OLIVEIRA, MARCELO A.; AUGUSTO, FELIPE A.; CISCATO, LUIZ FRANCISCO M. L.; BASTOS, ERICK L.; BAADER, WILHELM J.. Synthesis of Unstable Cyclic Peroxides for Chemiluminescence Studies. Journal of the Brazilian Chemical Society, v. 23, n. 11, p. 2093-2103, . (07/00684-6, 12/02428-5, 11/23036-5)
SCHRAMM, STEFAN; MONTEIRO LEITE CISCATO, LUIZ FRANCISCO; OESAU, PASCAL; KRIEG, REIMAR; RICHTER, JAN FRANK; NAVIZET, ISABELLE; ROCA-SANJUAN, DANIEL; WEISS, DIETER; BECKERT, RAINER. Investigations on the synthesis and chemiluminescence of novel 2-coumaranones - II. ARKIVOC, v. N/A, p. 16-pg., . (12/02428-5)
SALATINO, CARLA T.; MELO, DIEGO U.; YOSHITAKE, ARIANE M.; SGARBI, LUCAS S.; HOMEM-DE-MELLO, PAULA; BARTOLONI, FERNANDO H.; CISCATO, LUIZ F. M. L.. Mechanistic model for the firefly luciferin regeneration in biomimetic conditions: a model for the in vivo process?. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 15, n. 16, p. 3479-3484, . (12/02428-5, 12/13807-7)