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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)

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Scientific publications (32)
(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)
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, . (14/15307-7, 14/18330-0)
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; et al. Design of Antibacterial Agents: Alkyl Dihydroxybenzoates against Xanthomonas citri subsp citri. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, v. 19, n. 10, . (13/50367-8, 14/18330-0, 15/50162-2, 17/50216-0)
DOS SANTOS, VANESSA RODRIGUES; CAIAFFA, KARINA SAMPAIO; DE OLIVEIRA, WARLLEY CAMPOS; PEREIRA, JESSE AUGUSTO; ABUNA, GABRIEL FLORES; POLAQUINI, CARLOS ROBERTO; REGASINI, LUIS OCTAVIO; GUIOTTI, AIMEE MARIA; DUQUE, CRISTIANE. Cytotoxicity and effects of curcumin and cinnamaldehyde hybrids on biofilms of oral pathogens. BIOFOULING, . (18/15083-2, 14/18330-0, 17/05892-8)
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; et al. Curcumin Analog CH-5 Suppresses the Proliferation, Migration, and Invasion of the Human Gastric Cancer Cell Line HGC-27. Molecules, v. 23, n. 2, . (17/03237-2, 14/18330-0, 14/15307-7)
DOS SANTOS, VANESSA RODRIGUES; CAIAFFA, KARINA SAMPAIO; DE OLIVEIRA, WARLLEY CAMPOS; PEREIRA, JESSE AUGUSTO; ABUNA, GABRIEL FLORES; POLAQUINI, CARLOS ROBERTO; REGASINI, LUIS OCTAVIO; GUIOTTI, AIMEE MARIA; DUQUE, CRISTIANE. Cytotoxicity and effects of curcumin and cinnamaldehyde hybrids on biofilms of oral pathogens. BIOFOULING, v. 37, n. 6, p. 591-605, . (17/05892-8, 18/15083-2, 14/18330-0)
ANSELMO, DAIANE B.; POLAQUINI, CARLOS R.; MARQUES, BEATRIZ C.; AYUSSO, GABRIELA M.; ASSIS, LETICIA R.; TORREZAN, GUILHERME S.; RAHAL, PAULA; FACHIN, ANA L.; CALMON, MARILIA F.; MARINS, MOZART A.; et al. Curcumin-cinnamaldehyde hybrids as antiproliferative agents against women's cancer cells. MEDICINAL CHEMISTRY RESEARCH, v. 30, n. 11, . (18/15083-2, 14/50880-0, 14/18330-0, 09/53989-4, 14/50926-0)
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, . (14/18330-0, 17/09245-7, 14/18577-5, 09/53989-4, 18/15083-2, 16/08084-7, 14/50926-0)
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, . (13/50367-8, 14/18330-0)
DOS SANTOS, MARIANA BASTOS; MARQUES, BEATRIZ CARVALHO; AYUSSO, GABRIELA MIRANDA; ROCHA GARCIA, MAYARA APARECIDA; PARACATU, LUANA CHIQUETTO; PAULI, IVANI; BOLZANI, VANDERLAN SILVA; ANDRICOPULO, ADRIANO DEFINI; XIMENES, VALDECIR FARIAS; ZERAIK, MARIA LUIZA; et al. Chalcones and their B-aryl analogues as myeloperoxidase inhibitors: In silico, in vitro and ex vivo investigations. BIOORGANIC CHEMISTRY, v. 110, . (16/00580-5, 14/18330-0, 09/53989-4, 18/15083-2, 14/50926-0)
LIMA, CAROLINE SPRENGEL; MOTTIN, MELINA; DE ASSIS, LETICIA RIBEIRO; DE MORAES ROSO MESQUITA, NATHALYA CRISTINA; DE PAULA SOUSA, BRUNA KATIELE; COIMBRA, LAIS DURCO; BISPO-DOS-SANTOS, KARINA; ZORN, KIMBERLEY M.; GUIDO, RAFAEL V. C.; EKINS, SEAN; et al. Flavonoids from Pterogyne nitens as Zika virus NS2B-NS3 protease inhibitors. BIOORGANIC CHEMISTRY, v. 109, . (16/00194-8, 18/03917-6, 13/07600-3, 14/18330-0, 18/15083-2)
PEREIRA, JESSE AUGUSTO; POLAQUINI, CARLOS ROBERTO; DOS SANTOS, VANESSARODRIGUES; CAIAFFA, KARINA SAMPAIO; RABELO, RAFAELA LARUZO; THEODORO, REINALDO DOS SANTOS; THEODORO, LETICIA HELENA; REGASINI, LUIS OCTAVIO; DUQUE, CRISTIANE. Antibiofilm and cytotoxic effect of 3,3 `-dihydroxycurcumin (DHC) as photosensitizer agent in antimicrobial photodynamic therapy for endodontic purposes. Photodiagnosis and Photodynamic Therapy, v. 36, . (18/15083-2, 14/18330-0, 18/10857-0)
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, . (18/15083-2, 09/53989-4, 14/50926-0, 14/18330-0)
TEMPONE, ANDRE GUSTAVO; DOS SANTOS THEODORO, REINALDO; ROMANELLI, MAIARA MARIA; FERREIRA, DAYANA AGNES SANTOS; AMARAL, MAIARA; DE ASSIS, LETICIA RIBEIRO; CRUZ, LUCAS MONTEIRO SANTA; COSTA, ALAN ROBERTO; ZANELLA, ROSEMEIRE COBO; CHRISTODOULIDES, MYRON; et al. A new reduced chalcone-derivative affects the membrane permeability and electric potential of multidrug-resistant Enterococcus faecalis. Chemico-Biological Interactions, v. 365, p. 8-pg., . (14/18330-0, 21/04464-8, 18/26655-7, 19/11979-4, 17/50333-7, 18/15083-2, 09/53989-4)
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; et al. Design of Antibacterial Agents: Alkyl Dihydroxybenzoates against Xanthomonas citri subsp citri. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, v. 19, n. 10, p. 15-pg., . (15/50162-2, 13/50367-8, 14/18330-0, 17/50216-0)
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, . (17/03237-2, 14/15307-7, 14/18330-0)
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; et al. Activity of 3 `-hydroxychalcone against Cryptococcus gattii and toxicity, and efficacy in alternative animal models. FUTURE MICROBIOLOGY, v. 12, n. 13, p. 1123-1134, . (14/10446-9, 14/18330-0)
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.; et al. A simplified curcumin targets the membrane of Bacillus subtilis. MICROBIOLOGYOPEN, v. 8, n. 4, . (13/50367-8, 14/50880-0, 14/18330-0)
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, . (14/18330-0)
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.; et al. Investigating the Modes of Action of the Antimicrobial Chalcones BC1 and T9A. Molecules, v. 25, n. 20, . (16/07108-0, 17/50216-0, 14/18577-5, 14/18330-0, 18/15083-2, 16/08084-7, 14/18719-4)
GARCIA, MAYARA A. R.; THEODORO, REINALDO S.; SARDI, JANAINA C. O.; SANTOS, MARIANA B.; AYUSSO, GABRIELA M.; PAVAN, FERNANDO R.; COSTA, ALAN R.; SANTA CRUZ, LUCAS M.; ROSALEN, PEDRO L.; REGASINI, LUIS O.. Design, synthesis and antibacterial activity of chalcones against MSSA and MRSA planktonic cells and biofilms. BIOORGANIC CHEMISTRY, v. 116, . (18/15083-2, 14/50926-0, 09/53989-4, 14/18330-0)
DE ASSIS, LETICIA RIBEIRO; THEODORO, REINALDO DOS SANTOS; SILVA COSTA, MARIA BEATRIZ; SILVA NASCENTES, JULYANNA ANDRADE; DA ROCHA, MIGUEL DIVINO; DE SOUZA BESSA, MELIZA ARANTES; MENEZES, RALCIANE DE PAULA; DILARRI, GUILHERME; HYPOLITO, GIOVANE BOERNER; DOS SANTOS, VANESSA RODRIGUES; et al. Antibacterial Activity of Isobavachalcone (IBC) Is Associated with Membrane Disruption. MEMBRANES, v. 12, n. 3, p. 12-pg., . (14/18330-0, 18/15083-2)
CURY SATOKATA, ALESSANDRA AKEMI; SOUZA, JONATHAN HENRIQUE; OLIVEIRA SILVA, LUANA LUIZA; SANTIAGO, MARIANA BRENTINI; RAMOS, SALVADOR BOCCALETTI; DE ASSIS, LETICIA RIBEIRO; THEODORO, REINALDO DOS SANTOS; RODRIGUES E OLIVEIRA, LIGIA; REGASINI, LUIS OCTAVIO; GOMES MARTINS, CARLOS HENRIQUE. Chalcones with potential antibacterial and antibiofilm activities against periodontopathogenic bacteria. Anaerobe, v. 76, p. 9-pg., . (14/50926-0, 14/18330-0, 14/50880-0, 09/53989-4, 18/15083-2)
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; et al. Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones. Molecules, v. 22, n. 10, . (16/06401-5, 14/18330-0)
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, . (14/18330-0)
LIMA, CAROLINE SPRENGEL; PEREIRA, MATHEUS HENRIQUE; GAINZA, YOUSMEL ALEMAN; HOSTE, HERVE; REGASINI, LUIS OCTAVIO; DE SOUZA CHAGAS, ANA CAROLINA. Anthelmintic effect of Pterogyne nitens (Fabaceae) on eggs and larvae of Haemonchus contortus: Analyses of structure-activity relationships based on phenolic compounds. INDUSTRIAL CROPS AND PRODUCTS, v. 164, . (18/15083-2, 14/18330-0)
POLAQUINI, CARLOS R.; MARQUES, BEATRIZ C.; AYUSSO, GABRIELA M.; MORAO, LUANA G.; SARDI, JANAINA C. O.; CAMPOS, DEBORA L.; SILVA, ISABEL C.; CAVALCA, LUCIA B.; SCHEFFERS, DIRK-JAN; ROSALEN, PEDRO L.; et al. Antibacterial activity of a new monocarbonyl analog of curcumin MAC 4 is associated with divisome disruption. BIOORGANIC CHEMISTRY, v. 109, . (18/00163-0, 14/50880-0, 14/18330-0, 17/50216-0, 15/50162-2, 09/53989-4, 18/15083-2, 14/50926-0, 13/50367-8)
RAMOS, PAULO RICARDO PIMENTA DA SILVA; MOTTIN, MELINA; LIMA, CAROLINE SPRENGEL; ASSIS, LETICIA R.; DE OLIVEIRA, KETLLYN ZAGATO; MESQUITA, NATHALYA CRISTINA DE MORAES ROSO; CASSANI, NATASHA MARQUES; SANTOS, IGOR ANDRADE; BORBA, JOYCE VILLA VERDE BASTOS; FIAIA COSTA, VINICIUS ALEXANDRE; et al. Natural Compounds as Non-Nucleoside Inhibitors of Zika Virus Polymerase through Integration of In Silico and In Vitro Approaches. PHARMACEUTICALS, v. 15, n. 12, p. 17-pg., . (14/18330-0, 19/01762-8, 13/07600-3, 18/15083-2, 20/12904-5)
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; et al. 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, . (18/15083-2, 14/18330-0)
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, p. 14-pg., . (14/15307-7, 17/03237-2, 14/18330-0)
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. 6-pg., . (14/15307-7, 14/18330-0)
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; et al. Activity of 3 '-hydroxychalcone against Cryptococcus gattii and toxicity, and efficacy in alternative animal models. FUTURE MICROBIOLOGY, v. 12, n. 13, p. 12-pg., . (14/10446-9, 14/18330-0)
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, . (14/18330-0)

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