Floral betalamic pigments: fluorescence and antiradical capacity

• Grant number: 11/23036-5
• Support Opportunities: Regular Research Grants
• Start date: March 01, 2012
• End date: February 28, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Erick Leite Bastos
• Grantee: Erick Leite Bastos
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

Betalains are colorful, water-soluble and nontoxic chemical substances, which replace anthocyanins in the pigmentation of a reduced number of plants and fungi. In this research plan, we propose to continue our study on photophysical and antiradical properties of betalains, focusing their structural modification and structure-activity relationships. Phenolic betalains and the corresponding tert-butyldimethylsilyl ethers will be semisynthesized to investigate the effect of structure on the antiradical capacity of betalains. A route for the obtaining of water-soluble, stable betalamic probes bearing a BODIPY moiety is presented. Furthermore, we propose the preparation of amphiphilic betalains by the N-alkylation of the 2-piperidene ring or by aldiminic coupling with fatty amines; in this subproject, the precursor compounds are renewable and the oxidation of the products lead to neobetalamic derivatives containing a 2,6-dipicolinic portion with chelating properties. Finally, we shall continue our investigation into the formation of betalamic and neobetalamic complexes with Eu(III) and its application in the determination of calcium dipicolinate (CaDPA), which is present in considerable amounts in bacterial spores, including Bacillus anthracis, the causative agent of anthrax. Photophysical properties of most compounds obtained will be characterized both experimentally and by quantum-chemical methods. (AU)

Scientific publications

(7)

(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)

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, NOV 2012. (07/00684-6, 12/02428-5, 11/23036-5)

PIRES GONCALVES, LETICIA CHRISTINA; DA SILVA, SANDRA MARIA; DEROSE, PAUL C.; ANDO, ROMULO AUGUSTO; BASTOS, ERICK LEITE. Beetroot-Pigment-Derived Colorimetric Sensor for Detection of Calcium Dipicolinate in Bacterial Spores. PLoS One, v. 8, n. 9, SEP 3 2013. (11/23036-5, 07/00684-6, 07/59407-1)

SILVA, ADRIANA FARIAS; BASTOS, ERICK LEITE; TORRES, MARCELO DER TOROSSIAN; COSTA-DA-SILVA, ANDRE LUIS; IOSHINO, RAFAELLA SAYURI; CAPURRO, MARGARETH LARA; ALVES, FLAVIO LOPES; MIRANDA, ANTONIO; FISCHER VIEIRA, RENATA DE FREITAS; OLIVEIRA, JR., VANI XAVIER. Antiplasmodial activity study of angiotensin II via Ala scan analogs. JOURNAL OF PEPTIDE SCIENCE, v. 20, n. 8, p. 640-648, AUG 2014. (11/23036-5, 11/10823-9)

BARTOLONI, FERNANDO H.; GONCALVES, LETICIA CHRISTINA P.; RODRIGUES, ANA CLARA B.; DOERR, FELIPE AUGUSTO; PINTO, ERNANI; BASTOS, ERICK L.. Photophysics and hydrolytic stability of betalains in aqueous trifluoroethanol. MONATSHEFTE FUR CHEMIE, v. 144, n. 4, p. 567-571, APR 2013. (07/00684-6, 07/59407-1, 10/15042-2, 10/16082-8, 11/23036-5)

BUZZO, G. S.; RODRIGUES, A. C. B.; DE SOUZA, R. F. B.; SILVA, J. C. M.; BASTOS, E. L.; SPINACE, E. V.; NETO, A. O.; ASSUMPCAO, M. H. M. T.. Synthesis of hydroquinone with co-generation of electricity from phenol aqueous solution in a proton exchange membrane fuel cell reactor. Catalysis Communications, v. 59, p. 113-115, JAN 10 2015. (12/22731-4, 12/03516-5, 11/23036-5, 11/18246-0, 13/01577-0)

PIRES GONCALVES, LETICIA CHRISTINA; TONELLI, RENATA ROSITO; BAGNARESI, PIERO; MORTARA, RENATO ARRUDA; FERREIRA, ANTONIO GILBERTO; BASTOS, ERICK LEITE. A Nature-Inspired Betalainic Probe for Live-Cell Imaging of Plasmodium-Infected Erythrocytes. PLoS One, v. 8, n. 1, JAN 16 2013. (11/23036-5, 07/00684-6, 07/59407-1, 10/15042-2)

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, DEC 7 2012. (07/00684-6, 12/02428-5, 11/23036-5)