Research

Bio-inspired functional chemicals

The world around us is a rich source of solutions for the maintenance of life, whose mechanisms are often not fully understood. Natural phenomena are, however, the macroscopic result of a multitude of chemical and physical transformations. The advancement of methodology for chemical synthesis, modern steady-state and time-resolved spectroscopic measurements and the application of theoretical models allow us to understand how the electronic and structural characteristics of a particular chemical species determine its function(s) in Nature.

Our research group at the Institute of Chemistry of the University of São Paulo in Brazil is dedicated to the multidisciplinary investigation of natural phenomena related to the absorption and emission of light. We are particularly interested in fluorescent flowers that are pigmented by betalains.  Our studies are leading to a deeper understanding of the molecular interactions that modulate the electronic properties of betalains in condensed phases and of the relationship between the occurrence of betalains in plants and their biological roles, as well as the rationale for the mutual exclusion of betalains and anthocyanins in plants. Our ultimate goal is to create novel bio-inspired chemical systems that have the potential for advanced technological applications such as fluorescent probes for live cell imaging, new classes of antioxidants, biocompatible and biodegradable surfactants and intelligent materials.

Publications

Articles in scientific journals

Due to copyright restrictions, we are unable to provide the manuscript online. Please refer to the journal website using the DOI or email us for an electronic reprint.

2014

37. Silva AF, Bastos EL, Torres MDT, Costa-da-Silva AL, Ioshino RS et al. (2014) Antiplasmodial activity study of angiotensin II via Ala scan analogs. J Pept Sci 20: 640-648. ““

2013

36. Reddy KRKK, Rosa IML, Doriguetto AC, Bastos EL, Silva LF (2013) Iodine-catalyzed Prins cyclization of homoallylic alcohols and aldehydes. Molecules 18: 11100-11130. ““

35. Mendes LF, Zambotti-Villela L, Yokoya NS, Bastos EL, Stevani CV et al. (2013) Prediction of mono-, bi-, and trivalent metal cation relative toxicity to the seaweed Gracilaria domingensis (Gracilariales, Rhodophyta) in synthetic seawater. Environ Toxicol Chem 32: 2571-2575. ““

34. Lima FS, Cuccovia IM, Horinek D, Amaral LQ, Riske KA et al. (2013) Effect of counterions on the shape, hydration, and degree of order at the interface of cationic micelles: the triflate case. Langmuir 29: 4193-4203. ““

33. Goncalves LCP, Tonelli RR, Bagnaresi P, Mortara RA, Ferreira AG et al. (2013) A nature-inspired betalainic probe for live-cell imaging of Plasmodium-infected erythrocytes. Plos One 8: e53874. ““

32. Goncalves LCP, Di Genova BM, Dorr FA, Pinto E, Bastos EL (2013) Effect of dielectric microwave heating on the color and antiradical capacity of betanin. J Food Eng 118: 49-55. ““

31. Goncalves LCP, Da Silva SM, DeRose PC, Ando RA, Bastos EL (2013) Beetroot-pigment-derived colorimetric sensor for detection of calcium dipicolinate in bacterial spores. Plos One 8: e73701. ““

30. Chamlian M, Bastos EL, Maciel C, Capurro ML, Miranda A et al. (2013) A study of the anti-plasmodium activity of angiotensin II analogs. J Pept Sci 19: 575-580. ““

29. Bastos EL, da Silva SM, Baader WJ (2013) Solvent cage effects: basis of a general mechanism for efficient chemiluminescence. J Org Chem 78: 4432-4439. ““

28. Bartoloni FH, Goncalves LCP, Rodrigues ACB, Dorr FA, Pinto E et al. (2013) Photophysics and hydrolytic stability of betalains in aqueous trifluoroethanol. Monatsh Chem 144: 567-571. ““

2012

27. Goncalves LCP, Trassi MAD, Lopes NB, Dorr FA, dos Santos MT et al. (2012) A comparative study of the purification of betanin. Food Chem 131: 231-238. ““

26. Oliveira MA, Bartoloni FH, Augusto FA, Ciscato LFML, Bastos EL et al. (2012) Revision of singlet quantum yields in the catalyzed decomposition of cyclic peroxides. J Org Chem 77: 10537-10544. ““

25. Calderon-Ortiz LK, Tauscher E, Bastos EL, Gorls H, Weiss D et al. (2012) Hydroxythiazole-based fluorescent probes for fluoride ion detection. Eur J Org Chem: 2535-2541. ““

24. Bartoloni FH, de Oliveira MA, Augusto FA, Ciscato LFML, Bastos EL et al. (2012) Synthesis of unstable cyclic peroxides for chemiluminescence studies. J Brazil Chem Soc 23: 2093-2103. ““

2011

23. Malaspina T, Fileti EE, Bastos EL (2011) Effect of solute flexibility and polarization on the solvatochromic shift of a brominated merocyanine dye in water: a sequential MD/QM study. Int J Quantum Chem 111: 1607-1615. ““

22. Ciscato LFML, Weiss D, Beckert R, Bastos EL, Bartoloni FH et al. (2011) Chemiluminescence-based uphill energy conversion. New J Chem 35: 773-775. ““

21. Bartoloni FH, Ciscato LFML, Peixoto MMD, dos Santos APF, Santos CD et al. (2011) Light: a rare reaction product. Quim Nova 34: 544-554. ““

2010

20. Mendes LF, Bastos EL, Stevani CV (2010) Prediction of metal cation toxicity to the bioluminescent fungus Gerronema viridilucens. Environ Toxicol Chem 29: 2177-2181. ““

19. Ciscato LFML, Bastos EL, Bartoloni FH, Gunther W, Weiss D et al. (2010) Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction. J Brazil Chem Soc 21: 1896-1904. ““

18. Barros TC, Toma SH, Toma HE, Bastos EL, Baptista MS (2010) Polymethine cyanine dyes in beta-cyclodextrin solution: multiple equilibria and chemical oxidation. J Phys Org Chem 23: 893-903. ““

2009

17. Ciscato LFML, Bartoloni FH, Bastos EL, Baader WJ (2009) Direct kinetic observation of the chemiexcitation step in peroxyoxalate chemiluminescence. J Org Chem 74: 8974-8979. ““

16. Alves WA, Matos IO, Takahashi PM, Bastos EL, Martinho H et al. (2009) A chloro-bridged linear chain imine-copper(II) complex and its application as an enzyme-free amperometric biosensor for hydrogen peroxide. Eur J Inorg Chem: 2219-2228. ““

2008

15. Mendes LF, Bastos EL, Desjardin DE, Stevani CV (2008) Influence of culture conditions on mycelial growth and bioluminescence of Gerronema viridilucens. Fems Microbiol Lett 282: 132-139. ““

14. Martins CT, Lima MS, Bastos EL, El Seoud OA (2008) Thermo-solvatochromism of merocyanine polarity probes – what are the consequences of increasing probe lipophilicity through annelation? Eur J Org Chem: 1165-1180. ““

13. Chien TC, Dias LG, Arantes GM, Santos LGC, Triboni ER et al. (2008) L-(2-Quinolyl)-2-naphthol: A new intra-intermolecular photoacid-photobase molecule. J Photoch Photobio A 194: 37-48. ““

2007

12. Silva PL, Bastos EL, El Seoud OA (2007) Solvation in binary mixtures of water and polar aprotic solvents: Theoretical calculations of the concentrations of solvent-water hydrogen-bonded species and application to thermosolvatochromism of polarity probes. J Phys Chem B 111: 6173-6180, correction: J Phys Chem B 112: 187-187. ““

11. El Seoud OA, Pires PAR, Abdel-Moghny T, Bastos EL (2007) Synthesis and micellar properties of surface-active ionic liquids: 1-alkyl-3-methylimidazolium chlorides. J Colloid Interf Sci 313: 296-304. ““

10. Bastos EL, Ciscato LFML, Bartoloni FH, Catalani LH, Romoff P et al. (2007) Studies on PVP hydrogel-supported luminol chemiluminescence: 2. Luminometer calibration and potential analytical applications. Luminescence 22: 126-133. ““

9. Bastos EL, Ciscato LFML, Bartoloni FH, Catalani LH, Baader WJ (2007) Studies on PVP hydrogel-supported luminol chemiluminescence: 1. Kinetic and mechanistic aspects using multivariate factorial analysis. Luminescence 22: 113-125. ““

8. Bastos EL, Baader WJ (2007) Theoretical studies on thermal stability of alkyl-substituted 1,2-dioxetanes. Arkivoc: 257-272. ““

2006

7. Oliveira CS, Bastos EL, Duarte EL, Itri R, Baptista MS (2006) Ion pairs of crystal violet in sodium bis(2-ethylhexyl) sulfosuccinate reverse micelles. Langmuir 22: 8718-8726. ““

6. Bastos EL, Silva PL, El Seoud OA (2006) Thermosolvatochromism of betaine dyes revisited: theoretical calculations of the concentrations of alcohol-water hydrogen-bonded species and application to solvation in aqueous alcohols. J Phys Chem A 110: 10287-10295, correction: J Phys Chem A 110: 13122-13122. ““

5. Bastos EL, Monteiro Leite Ciscato LF, Weiss D, Beckert R, Baader WJ (2006) Comparison of convenient alternative synthetic approaches to 4-[(3-tert-Butyldimethylsilyloxy)phenyl]-4-methoxyspiro[1,2-dioxetane-3,2 ‘-adamantane]. Synthesis-Stuttgart: 1781-1786. ““

2005

4. Rodrigues MA, Bemquerer MP, Tada DB, Bastos EL, Baptista MS et al. (2005) Synthesis and characterization of silica gel particles functionalized with bioactive materials. Adsorption 11: 595-602. ““

3. Bastos EL, Ciscato LFML, Baader WJ (2005) Microwave-assisted protection of phenols as tert-butyldimethylsilyl (TBDMS) ethers under solvent-free conditions. Synthetic Commun 35: 1501-1509. ““

2003

2. Bastos EL, Romoff P, Eckert CR, Baader WJ (2003) Evaluation of antiradical capacity by H2O2-hemin-induced luminol chemiluminescence. J Agr Food Chem 51: 7481-7488. ““

1998

1. Albertin R, Arribas MAG, Bastos EL, Ropke S, Sakai PN et al. (1998) Organic chemiluminescence: some classroom demonstration experiments. Quim Nova 21: 772-779. ““

Book Chapters

8. Bastos, E. L., Bartoloni, F. H., Gonçalves, L. C. P.. (2014) Acid Base and Solvation Properties of Metal Phenolates. In: Jacob Zabicky. (Org.). The Chemistry of Metal Phenolates. Chichester: Wiley, 1: 191-262.

7. Baader, W. J., Bastos, E. L.. (2008) Four-Membered Cyclic Peroxides (1,2-Dioxetanes, 1,2-Dioxetanones). In: Berkessel, A.. (Org.). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Stuttgart: Thieme Chemistry, 38: 323-344.

6. Baader, W. J., Bastos, E. L.. (2008) Five-Membered Cyclic Peroxides with No Further Heteroatoms in the Ring (1,2-Dioxolanes and 1,2-Dioxolan-3-ones). In: Berkessel, A.. (Org.). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Stuttgart: Thieme Chemistry, 38: 345-378.

5. Baader, W. J., Bastos, E. L.. (2008) Five-Membered Cyclic Peroxides with One Further Oxygen Atom in the Ring (1,2,4-Trioxolanes). In: Berkessel, A.. (Org.). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Stuttgart: Thieme Chemistry, 38: 379-396.

4. Baader, W. J., Bastos, E. L.. (2008) Six-Membered Cyclic Peroxides with No Further Heteroatoms in the Ring (1,2-Dioxanes and 3,6-Dihydro-1,2-dioxins). In: Berkessel, A.. (Org.). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Stuttgart: Thieme Chemistry, 38: 397-420.

3. Baader, W. J., Bastos, E. L.. (2008) Six-Membered Cyclic Peroxides with One Further Oxygen Atom in the Ring (1,2,4-Trioxanes). In: Berkessel, A.. (Org.). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Stuttgart: Thieme Chemistry, 38: 421-448.

2. Baader, W. J., Bastos, E. L.. (2008) Six-Membered Cyclic Peroxides with Two Further Oxygen Atoms in the Ring (1,2,4,5-Tetroxanes). In: Berkessel, A.. (Org.). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Stuttgart: Thieme Chemistry, 38: 449-468.

1. Baader, W. J., Stevani, C. V., Bastos, E. L.. (2006) Chemiluminescence of Organic Peroxides. In: Zvi Rappoport. (Org.). The Chemistry of Peroxides. Chichester: Wiley, 1211-1278.

Books

1. Marson, G. A., Bastos, E. L., Stevani, C. V., Bazito, R. C., Freire, R. S., Teruya, L. C., Moulatlet, A. C. B.. (2011) Onde está a química?. São Paulo: Evoluir Cultural, ISBN: 9788587420985. ““

  • All
  • qn2
    QN 21: 772 (1998)
  • ejoc_2
    EJOC 1165 (2008)
  • njc_2
    NJC 35: 773 (2011)
  • joc_2009_2
    JOC 74: 8974 (2009)
  • joc_2011_2
    JOC 77: 10537 (2012)

The Lab

Steady-state spectroscopy

Varian Cary 50 Spectrophotometer ““

+ Water-thermostatized 18-cell holder, remote DRA (diffuse reflectance accessory) with video bundle, quartz dip probe fiber optic (o.p.: 10 mm), torlon dip probe fiber optic (o.p.: 2, 5, and 10 mm), Color software.

 

Varian Eclipse Spectrofluorometer ““

+ Peltier thermostatized 4-cell holder, microplate reader accessory.

 

Spex Fluorolog II Spectrofluorometer ““

+ Peltier thermostatized cell holder.

 

Hitachi F4500 Spectrofluorometer ““

+ Water-thermostatized cell holder, quartz dewar for low temperature measurements (77K).

 

Time-resolved spectroscopy

Edinburgh Instruments FLS980 Fluorescence Spectrometer ““

+ Polarizing filter set, nF920 ultrafast nanosecond flashlamp (100 ps – 50 ms).

 

Electrochemistry

MicroAutolab III Potentiostat/Galvanostat ““

+ spectroelectrochemistry accessory (200 – 1100 nm, 2048 px CCD detection), 10 mA to 10 nA limit, interface for screen-printed electrodes.

 

Microwave-assisted synthesis

CEM Discover monomode laboratory microwave reactor ““

 

High Performance Computing Cluster

Rubinho, 4x AMD Opteron 6376 16-core 2.3GHz, 16x 8GB DDR3 1600 MHz, 6x HD 1TB SATA 6 Gb/s.

Remote access to the following clusters: Bachianas (UFABC, Altix 4700, 136 Itanium 2 cores), Cromo (UFABC, 52 Xeon cores), Cobalto (UFABC, 176 Xeon cores), Puma (LCCA-USP, 472 Xeon cores), Jaguar (LCCA-USP, 56 Itanium 2 cores).

Software: Gamess, Gaussian09, Molcas, Gromacs.

 

Other equipments

Metrohm 907 Titrando Titrator ““

+ pH, conductance and photometric sensor, water-thermostated electrochemical cell (5 – 70 mL).

Labconco FreeZone Triad Cascade Benchtop Freeze Dry System ““

 

Thermo Scientific-Sorvall refrigerated benchtop centrifuge ST16R ““

+ F15-6×100 rotor, Microliter 30 x 2 mL sealed rotor, swinging bucket rotor TX200.

Group

ERICK L. BASTOS

PRINCIPAL INVESTIGATOR

Erick Bastos is a chemist interested in fluorescent plants and other extraordinary natural phenomena.

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ANA CLARA RODRIGUES

DOCTORAL STUDENT

Ana Clara is a doctoral student working on the interaction between betalains and biomembranes.

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ANA PAULA PAGANO

DOCTORAL STUDENT

Ana Paula is a doctoral student working on the photophysical characterization of encapsulated betalains.

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BARBARA FREITAS

DOCTORAL STUDENT

Barbara is a doctoral student working on the synthesis and photophysical characterization of betalains.

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NATHANA LOPES

DOCTORAL STUDENT

Nathana is a doctorate student working on the semisynthesis of fluorescent probes.

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KARINA NAKASHIMA

MASTER STUDENT

Karina is a master student working on the antiradical properties of betalains and derivatives.

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LARISSA ESTEVES

MASTER STUDENT

Larissa is a master student working on the interactions between betalains and ions.

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AMANDA PINHEIRO

UNDERGRADUATE STUDENT

Amanda is a fourth year chemistry student awarded a FAPESP undergraduate research fellowship.

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CAROLINA WATTS

UNDERGRADUATE STUDENT

Carolina is a second year pharmacy/biochemistry student at the University of Sao Paulo.

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CAROLINE MACHADO

UNDERGRADUATE STUDENT

Caroline is a fourth year chemistry student awarded a CNPq-PIBIC undergraduate research fellowship.

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LUIZA ISSA

UNDERGRADUATE STUDENT

Luiza is a second year chemical engineering student at the University of São Paulo.

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LUIZ CARLOS MONIZ

LABORATORY TECHNICIAN

Luiz Carlos Moniz is a chemist who provides technical assistance to the Bastos group.

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Alumni

Dr. LETÍCIA CHRISTINA GONÇALVES

2007 – 2012 (Ph.D.),  2013 (Post-doc)

Postdoctoral fellow, Prof. M. Mihovilovic.
Vienna University of Technology, Austria.

Dr. FRANCES STÖCKNER

2010 – 2011 (Post-doc)

Senior Researcher.
Germany.

Dr. THACIANA MALASPINA

2012 – 2013 (Post-doc)

Adjunct Professor.
UNIFESP-SJC, LINK.

Dr. FERNANDO BARTOLONI

2012 – 2013 (Post-doc)

Adjunct Professor.
UFABC, LINK.

M.Sc. MARCO AURÉLIO TRASSI

2010 – 2012 (M.Sc.)

Specialist
DOW Chemical

M.Sc. MONICA  SANTOS

2007 – 2009 (M.Sc.)

Specialist.
Colgate-Palmolive.

Opportunities

We have positions open at all levels, including visiting professors, post-docs, graduate students and undergraduate students. Independent, creative and motivated people (who really enjoy scientific discovery) are welcome to apply.

Students looking for graduate or undergraduate research projects are encouraged to contact us to arrange an interview. Candidates for both the M.Sc or Ph.D programs must be admitted as graduate students of either the Institute of Chemistry of the University of São Paulo (IQ-USP) or the Center for Natural and Human Sciences of the Federal University of ABC (CCNH-UFABC). Entrance exams at both institutions are administered every six months (February and July) and can be replaced by the GRE Chemistry test. In our group, the M.Sc takes about 24 months to complete, whereas around 48 months are required to finish a Ph.D. M.Sc students may transfer to Ph.D depending on the project development. Postdocs are welcome to contact us any time of the year. Excellent candidates are encouraged to seek fellowship support and apply.

São Paulo is one of the most important economic centers of Brazil and one of the largest cities in the world. Students and researchers from other countries are welcome to apply and will certainly have a rich cultural and scientific experience here.

Contact

MAIL ADDRESS

Institute of Chemistry, University of Sao Paulo, Brazil
Av. Prof. Lineu Prestes, 748, Bl. 4S, office 460 and lab 477
05508-000 São Paulo, SP, Brasil

CONTACT

Phone: +55(11) 3091.9133 (Office) | +55(11) 3091.9165 (Lab)
E-mail: contact@bastoslab.com
Skype: bastos.erick