Synthesis of biologically active phenols and derivatives

• Grant number: 11/50435-8
• Support Opportunities: Regular Research Grants
• Start date: June 01, 2011
• End date: February 28, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: José Agustín Pablo Quincoces Suárez
• Grantee: José Agustín Pablo Quincoces Suárez
• Host Institution: Pró-Reitoria Acadêmica. Universidade Bandeirantes (UNIBAN). São Paulo , SP, Brazil

Abstract

This research project is based on the biological results obtained under financial support from FAPESP, project-number: 2001/03756-1 e 2004/11351-0, exhibited by polifunctional phenols and its derivatives. The compound, sodium 4-[5-(4-hydroxy-3-methoxyphenyl)-3-oxo-penta-1,4-dienyl]-2-methoxy-phenolate, DM1 exhibited marked action as a potent antitumor agent against melanoma and breast cancer. Also, this compound exhibited an excellent activity as powerful adjuvant agent for a higher antitumor activity of conventional chemotherapeutic drugs, as a potent antimethastatic and antimutagenic, protecting and stimulating bone marrow. For this reason, we planned with DM1: a) In vivo analgesic assay in rats. We planned the synthesis of new substituted acetophenone and derivatives starting from 2-hydroxy-5-(2-methylbut-2-enyl)acetophenone used as stardard antitumor reference. Therefore we planned the synthesis of 1,4-pentadien-3-ones, starting from iodated polifunctional phenols and aromatic 1-alkyne or with alkyl acrylate, respectivelly, in the presence of different Pd-catalysts. All the compounds will be purified and their structures shall be characterized by spectroscopic methods and organic elemental quantitative analysis.Finally, antitumor, antioxidant, analgesic and anti-inflammatory properties will be determined and the impact of the in vitro treatment with synthesized componds, on epigenetic regulation of immune system cells, besides looking for markers of differential metilation on DNA, after the employment of these compounds. (AU)

Scientific publications

(4)

(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)

FAIAO-FLORES, FERNANDA; QUINCOCES SUAREZ, JOSE AGUSTIN; MARIA-ENGLER, SILVYA STUCHI; SOTO-CERRATO, VANESSA; PEREZ-TOMAS, RICARDO; MARIA, DURVANEI AUGUSTO. The curcumin analog DM-1 induces apoptotic cell death in melanoma. TUMOR BIOLOGY, v. 34, n. 2, p. 1119-1129, APR 2013. (08/58817-4, 11/50435-8)

FAIAO-FLORES, FERNANDA; QUINCOCES SUAREZ, JOSE AGUSTIN; SOTO-CERRATO, VANESSA; ESPONA-FIEDLER, MARGARITA; PEREZ-TOMAS, RICARDO; MARIA, DURVANEI AUGUSTO. Bcl-2 family proteins and cytoskeleton changes involved in DM-1 cytotoxic effect on melanoma cells. TUMOR BIOLOGY, v. 34, n. 2, p. 1235-1243, APR 2013. (11/50435-8)

FAIAO-FLORES, FERNANDA; QUINCOCES SUAREZ, JOSE AGUSTIN; FRUET, ANDREA COSTA; MARIA-ENGLER, SILVYA STUCHI; PARDI, PAULO CELSO; MARIA, DURVANEI AUGUSTO. Curcumin Analog DM-1 in Monotherapy or Combinatory Treatment with Dacarbazine as a Strategy to Inhibit In Vivo Melanoma Progression. PLoS One, v. 10, n. 3, MAR 5 2015. (11/50435-8)

PAULINO, NIRALDO; PAULINO, AMARILIS SCREMIN; DINIZ, SUSANA N.; DE MENDONCA, SERGIO; GONCALVES, IVAIR D.; FLORES, FERNANDA FAIAO; SANTOS, REGINALDO PEREIRA; RODRIGUES, CARINA; PARDI, PAULO CELSO; QUINCOCES SUAREZ, JOSE AGUSTIN. Evaluation of the anti-inflammatory action of curcumin analog (DM1): Effect on iNOS and COX-2 gene expression and autophagy pathways. Bioorganic & Medicinal Chemistry, v. 24, n. 8, p. 1927-1935, APR 15 2016. (11/50435-8)