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Synthesis and biological evaluation of curcumin-cinnamaldehyde hybrids as bacterial cell division inhibitors

Abstract

Antibacterial agents are crucial drugs for life expectancy. Several reasons justify the need by new antibacterials, including high bacterial resistance and mortality caused by infectious diseases. Thus, efforts are need to develop innovative antibacterial drugs. Recently, curcumin and cinnmaldehyde exhibited potent antibacterial activity against a broad panel of fungi. The central interest by these natural products is related to their bacterial cell division inhibitory effect, and their interaction with FtsZ protein (filamentous temperature-sensitive protein Z), a vital macromolecule for all bacteria. The current project purposes the preparation of three series of curcumin-cinnamaldehyde hybrids. Series I and II/III composed by diphenylpentanoids and chalcones, respectively. These compounds will be prepared by conventional method, which employs aldol condensation reaction, under basic or acidic catalysis, using ethanol as solvent. Compounds will be tested against Gram-positive, Gram-negative bacteria and Mycobacterium species, using sensitive and resistant strains. The toxicity of selected antibacterial compounds will be evaluated on macrophages. The selective index (SI) of compounds will be calculated from IC50 and MBC values, IS = IC50/MBC. IC50 is a half maximal inhibitory concentration to kill macrophages and MBC is a minimum bactericidal concentration. Compounds displayed IS e 10 will be submitted to inhibitory bacterial cell division assays, using FtsZ sedimentation and GTP hydrolysis methods. In addition, potent bacterial cell division inhibitors will be synthesized by environmental-friendly methods, including solvent-free reactions mechanically activated by grinding, and green solvents and-or green catalysts. (AU)

Scientific publications (15)
(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)
MORAO, LUANA G.; LORENZONI, ANDRE S. G.; CHAKRABORTY, PARICHITA; AYUSSO, GABRIELA M.; CAVALCA, LUCIA B.; SANTOS, MARIANA B.; MARQUES, BEATRIZ C.; DILARRI, GUILHERME; ZAMUNER, CAIO; REGASINI, LUIS O.; FERREIRA, HENRIQUE; SCHEFFERS, DIRK-JAN. Investigating the Modes of Action of the Antimicrobial Chalcones BC1 and T9A. Molecules, v. 25, n. 20 OCT 2020. Web of Science Citations: 0.
TORREZAN, GUILHERME SILVA; POLAQUINI, CARLOS ROBERTO; LIMA, MARCELO FREITAS; REGASINI, LUIS OCTAVIO. Use of glycerol, waste glycerol from biodiesel production and other protic solvents in bioactive alpha, beta-unsaturated ketones synthesis. SUSTAINABLE CHEMISTRY AND PHARMACY, v. 16, JUN 2020. Web of Science Citations: 0.
MARQUES, BEATRIZ C.; SANTOS, MARIANA B.; ANSELMO, DAIANE B.; MONTEIRO, DIEGO A.; GOMES, ELENI; SAIKI, MARILIA F. C.; RAHAL, PAULA; ROSALEN, PEDRO L.; SARDI, JANAINA C. O.; REGASINI, LUIS O. Methoxychalcones: Effect of Methoxyl Group on the Antifungal Antibacterial and Antiproliferative Activities. Medicinal Chemistry, v. 16, n. 7, p. 881-891, 2020. Web of Science Citations: 0.
CAMPOS, MONICA S.; SILVA, JOAO P. A.; LIMA, DANILO S.; REGASINI, LUIS O.; MARQUES, MARA RUBIA; BIANCARDI, MANOEL F.; TABOGA, SEBASTIAO R.; SANTOS, FERNANDA C. A. Short-term exposure to chrysin promotes proliferative responses in the ventral male prostate and female prostate of adult gerbils. International Journal of Experimental Pathology, v. 100, n. 3, p. 192-201, JUN 2019. Web of Science Citations: 0.
KOPACZ, MALGORZATA M.; LORENZONI, ANDRE S. G.; POLAQUINI, CARLOS R.; REGASINI, LUIS O.; SCHEFFERS, DIRK-JAN. Purification and characterization of FtsZ from the citrus canker pathogen Xanthomonas citri subsp. citri. MICROBIOLOGYOPEN, v. 8, n. 5 MAY 2019. Web of Science Citations: 1.
MORAO, LUANA G.; POLAQUINI, CARLOS R.; KOPACZ, MALGORZATA; TORREZAN, GUILHERME S.; AYUSSO, GABRIELA M.; DILARRI, GUILHERME; CAVALCA, LUCIA B.; ZIELINSKA, ALEKSANDRA; SCHEFFERS, DIRK-JAN; REGASINI, LUIS O.; FERREIRA, HENRIQUE. A simplified curcumin targets the membrane of Bacillus subtilis. MICROBIOLOGYOPEN, v. 8, n. 4 APR 2019. Web of Science Citations: 2.
DOS SANTOS, MARIANA BASTOS; ANSELMO, DAIANE BERTHOLIN; DE OLIVEIRA, JESSICA GISLEINE; JARDIM-PERASSI, BRUNA V.; MONTEIRO, DIEGO ALVES; SILVA, GABRIEL; GOMES, ELENI; FACHIN, ANA LUCIA; MARINS, MOZART; PIRES DE CAMPOS ZUCCARI, DEBORA APARECIDA; REGASINI, LUIS OCTAVIO. Antiproliferative activity and p53 upregulation effects of chalcones on human breast cancer cells. Journal of Enzyme Inhibition and Medicinal Chemistry, v. 34, n. 1, p. 1093-1099, JAN 1 2019. Web of Science Citations: 1.
NAZARE, ANA CAROLINA; POLAQUINI, CARLOS ROBERTO; CAVALCA, LUCIA BONCI; ANSELMO, DAIANE BERTHOLIN; CALMON SAIKI, MARILIA DE FREITAS; MONTEIRO, DIEGO ALVES; ZIELINSKA, ALEKSANDRA; RAHAL, PAULA; GOMES, ELENI; SCHEFFERS, DIRK-JAN; FERREIRA, HENRIQUE; REGASINI, LUIS OCTAVIO. Design of Antibacterial Agents: Alkyl Dihydroxybenzoates against Xanthomonas citri subsp citri. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, v. 19, n. 10 OCT 2018. Web of Science Citations: 1.
CAMPOS, MONICA S.; RIBEIRO, NAIARA C. S.; DE LIMA, RODRIGO F.; SANTOS, MARIANA B.; VILAMAIOR, PATRICIA S. L.; REGASINI, LUIS O.; BIANCARDI, MANOEL F.; TABOGA, SEBASTIAO R.; SANTOS, FERNANDA C. A. Anabolic effects of chrysin on the ventral male prostate and female prostate of adult gerbils (Meriones unguiculatus). REPRODUCTION FERTILITY AND DEVELOPMENT, v. 30, n. 9, p. 1180-1191, AUG 2018. Web of Science Citations: 0.
LIMA, FELIPE TEIXEIRA; SEBA, VIVIANE; SILVA, GABRIEL; TORREZAN, GUILHERME SILVA; POLAQUINI, CARLOS ROBERTO; PINHANELLI, VITOR CARESSATO; BAEK, SEUNG J.; FACHIN, ANA LUCIA; REGASINI, LUIS OCTAVIO; MARINS, MOZART. The Curcumin Analog CH-5 Exerts Anticancer Effects in Human Osteosarcoma Cells via Modulation of Transcription Factors p53/Sp1. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, v. 19, n. 7 JUL 2018. Web of Science Citations: 1.
SILVA, GABRIEL; LIMA, FELIPE TEIXEIRA; SEBA, VIVIANE; MENDES LOURENCO, ANA LAURA; LUCAS, THAISE GRAMINHA; DE ANDRADE, BIANCA VIEIRA; TORREZAN, GUILHERME SILVA; POLAQUINI, CARLOS ROBERTO; GARCIA, MARCELO ENGRACIA; COUTO, LUCELIO BERNARDES; BESTETTI, REINALDO BULGARELLI; FRANCA, SUZELEI DE CASTRO; FACHIN, ANA LUCIA; REGASINI, LUIS OCTAVIO; MARINS, MOZART. Curcumin Analog CH-5 Suppresses the Proliferation, Migration, and Invasion of the Human Gastric Cancer Cell Line HGC-27. Molecules, v. 23, n. 2 FEB 2018. Web of Science Citations: 6.
RIBEIRO, NAIARA C. S.; CAMPOS, MONICA S.; SANTOS, MARIANA B.; AYUSSO, GABRIELA M.; VILAMAIOR, PATRICIA S. L.; REGASINI, LUIS O.; TABOGA, SEBASTIAO R.; BIANCARDI, MANOEL F.; PEREZ, ANA P. S.; SANTOS, FERNANDA C. A. Prepubertal chrysin exposure upregulates either AR in male ventral prostate or AR and ER alpha in Skene's paraurethral gland of pubertal and adult gerbils. Fitoterapia, v. 124, p. 137-144, JAN 2018. Web of Science Citations: 3.
PALANCO, ANA CERREJN; SINGULANI, JUNYA DE LACORTE; COSTA-ORLANDI, CAROLINE BARCELOS; GULLO, FERNANDA PATRICIA; STROHMAYER LOURENCETTI, NATALIA MANUELA; GOMES, PAULO CESAR; AYUSSO, GABRIELA MIRANDA; DUTRA, LUIZ ANTONIO; BOLZANI, VANDERLAN DA SILVA; REGASINI, LUIS OCTAVIO; SOARES MENDES-GIANNINI, MARIA JOSE; FUSCO-ALMEIDA, ANA MARISA. Activity of 3 `-hydroxychalcone against Cryptococcus gattii and toxicity, and efficacy in alternative animal models. FUTURE MICROBIOLOGY, v. 12, n. 13, p. 1123-1134, OCT 2017. Web of Science Citations: 9.
POLAQUINI, CARLOS R.; TORREZAN, GUILHERME S.; SANTOS, VANESSA R.; NAZARE, ANA C.; CAMPOS, DEBORA L.; ALMEIDA, LAIZA A.; SILVA, ISABEL C.; FERREIRA, HENRIQUE; PAVAN, FERNANDO R.; DUQUE, CRISTIANE; REGASINI, LUIS O. Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones. Molecules, v. 22, n. 10 OCT 2017. Web of Science Citations: 7.
SANTOS, MARIANA B.; PINHANELLI, VITOR C.; GARCIA, MAYARA A. R.; SILVA, GABRIEL; BAEK, SEUNG J.; FRANCA, SUZELEI C.; FACHIN, ANA L.; MARINS, MOZART; REGASINI, LUIS O. Antiproliferative and pro-apoptotic activities of 2 `- and 4 `-aminochalcones against tumor canine cells. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v. 138, p. 884-889, SEP 29 2017. Web of Science Citations: 9.

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