Institute Quimica e Biotecnologia

Maceió, Brazil

Institute Quimica e Biotecnologia

Maceió, Brazil
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Araujo A.J.,Federal University of Ceará | de Souza A.A.,Federal University of Alagoas | da Silva Junior E.N.,Federal University of Minas Gerais | da Silva Junior E.N.,Federal University of Rio de Janeiro | And 15 more authors.
Toxicology in Vitro | Year: 2012

In this study, the cytotoxicity, genotoxicity and early ROS generation of 2,2-dimethyl-(3H)-3-(N-3'-nitrophenylamino)naphtho[1,2-b]furan-4,5-dione (QPhNO 2) were investigated and compared with those of its precursor, nor-beta-lapachone (nor-beta), with the main goal of proposing a mechanism of antitumor action. The results were correlated with those obtained from electrochemical experiments held in protic (acetate buffer pH 4.5) and aprotic (DMF/TBABF 4) media in the presence and absence of oxygen and with those from dsDNA biosensors and ssDNA in solution, which provided evidence of a positive interaction with DNA in the case of QPhNO 2. QPhNO 2 caused DNA fragmentation and mitochondrial depolarization and induced apoptosis/necrosis in HL-60 cells. Pre-treatment with N-acetyl-l-cysteine partially abolished the observed effects related to the QPhNO 2 treatment, including those involving apoptosis induction, indicating a partially redox-dependent mechanism. These findings point to the potential use of the combination of pharmacology and electrochemistry in medicinal chemistry. © 2012 Elsevier Ltd.


Da Cruz E.H.G.,Federal University of Minas Gerais | Hussene C.M.B.,Federal University of Minas Gerais | Dias G.G.,Federal University of Minas Gerais | Diogo E.B.T.,Federal University of Minas Gerais | And 11 more authors.
Bioorganic and Medicinal Chemistry | Year: 2014

1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, IC50 values below 2 μM. The cytotoxic potential of the tested naphthoquinones was also assayed on non-tumor cells such as human peripheral blood mononucluear cells (PBMC) and two murine fibroblast lines (L929 and V79 cells). α-Lapachone- and nor-α-lapachone-based 1,2,3-triazoles and arylamino-substituted naphthoquinones showed potent cytotoxicity against different cancer cell lines. The compounds may represent promising new lead derivatives for anticancer drug development. The electrochemical properties of selected compounds were evaluated in an attempt to correlate them with antitumor activity. © 2014 Elsevier Ltd. All rights reserved.


PubMed | Institute Quimica e Biotecnologia, Federal Rural University of Pernambuco, Federal University of Minas Gerais, Federal University of Pernambuco and Federal University of Ceará
Type: Journal Article | Journal: Bioorganic & medicinal chemistry | Year: 2014

1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, IC50 values below 2 M. The cytotoxic potential of the tested naphthoquinones was also assayed on non-tumor cells such as human peripheral blood mononucluear cells (PBMC) and two murine fibroblast lines (L929 and V79 cells). -Lapachone- and nor--lapachone-based 1,2,3-triazoles and arylamino-substituted naphthoquinones showed potent cytotoxicity against different cancer cell lines. The compounds may represent promising new lead derivatives for anticancer drug development. The electrochemical properties of selected compounds were evaluated in an attempt to correlate them with antitumor activity.


De Paiva Y.G.,Institute Quimica e Biotecnologia | Da Rocha Ferreira F.,Institute Quimica e Biotecnologia | Silva T.L.,Institute Quimica e Biotecnologia | Labbe E.,CNRS PASTEUR Laboratory | And 3 more authors.
Current Topics in Medicinal Chemistry | Year: 2015

This review discusses the state of the art, challenges and perspectives in recent applications of electrochemistry in the life sciences. It deals mainly with the elucidation of molecular mechanisms of drug action, drug design and development, involving electron transfer, pharmaco-electrochemistry (the combination of electrochemical and pharmacological assays), and electrochemical studies of membrane models and drug delivery. It aims to shed light on the question: does electrochemistry really contribute to this area? It includes a general introduction for the use of electrochemistry in the life sciences, with a focus on how electrochemistry can uniquely provide both kinetic and thermodynamic information. A number of studies are reported in the literature and from the authors’ laboratories, including the investigation of biooxidative/bioreductive activation of pro-drugs, DNA alkylation, electrochemically-based release of reactive oxygen and nitrogen species, with a particular emphasis on quinones, ferrocifens and compounds with mixed-functionality. Within the context of drug delivery and bioavailability, the electrochemical investigation of supramolecular interactions of the chosen classes of compounds with cyclodextrins and lipid bilayers, in relation to their solubilization and vectorization was also carried out. The updated examples herein illustrate how relevant and challenging the integration of electrochemistry, supramolecular and materials chemistry, biochemistry and medical knowledge for the design and development of redox-selective molecular approaches is. Many questions related to these fields are still unclear and the search for selectivity toward redox therapeutic agents remains of expanding interest. This review hopes to stimulate researchers to become more involved in this fruitful interface between electrochemistry and the life sciences. © 2015 Bentham Science Publishers.


Moura K.C.G.,Federal University of Rio de Janeiro | Carneiro P.F.,Federal University of Rio de Janeiro | Pinto M.D.C.F.R.,Federal University of Rio de Janeiro | Da Silva J.A.,Institute Quimica e Biotecnologia | And 8 more authors.
Bioorganic and Medicinal Chemistry | Year: 2012

Twenty-three naphthoimidazoles and six naphthoxazoles were synthesised and evaluated against susceptible and rifampicin- and isoniazid-resistant strains of Mycobacterium tuberculosis. Among all the compounds evaluated, fourteen presented MIC values in the range of 0.78 to 6.25 μg/mL against susceptible and resistant strains of M. tuberculosis. Five structures were solved by X-ray crystallographic analysis. These substances are promising antimycobacterial prototypes. © 2012 Elsevier Ltd. All rights reserved.


Da Silva Jr. E.N.,Federal University of Rio de Janeiro | Da Silva Jr. E.N.,University of Brasilia | Cavalcanti B.C.,Federal University of Ceará | Guimaraes T.T.,Federal University of Rio de Janeiro | And 10 more authors.
European Journal of Medicinal Chemistry | Year: 2011

Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 μM for some compounds. The β-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII).


Da Silva Jr. E.N.,University of Brasilia | De Deus C.F.,University of Brasilia | Cavalcanti B.C.,Federal University of Ceará | Pessoa C.,Federal University of Ceará | And 10 more authors.
Journal of Medicinal Chemistry | Year: 2010

Several 3-arylamino and 3-alkoxy-nor-β-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system),HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with IC50 below 2 μM. The arylamino para-nitro and the 2,4-dimethoxy substituted naphthoquinones showed the best cytoxicity profile, while the orthonitro and the 2,4-dimethoxy substituted ones were more selective than doxorubicin and similar to the precursor lapachones, thus emerging as promising new lead compounds in anticancer drug development. © 2009 American Chemical Society.


da Silva Junior E.N.,Federal University of Rio de Janeiro | da Silva Junior E.N.,University of Brasilia | Guimaraes T.T.,Federal University of Rio de Janeiro | Menna-Barreto R.F.S.,Instituto Oswaldo Cruz | And 10 more authors.
Bioorganic and Medicinal Chemistry | Year: 2010

In continuing our screening program of naphthoquinone activity against Trypanosoma cruzi, the aetiological agent of Chagas' disease, new β-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-β-lapachones, 3-alkoxy-nor-β-lapachones and imidazole anthraquinones were synthesised and evaluated against bloodstream trypomastigote forms of the parasite. Compounds 2,2-dimethyl-3-(2,4-dibromophenylamino)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione, IC50/24 h 24.9 ± 7.4 and 4-azido-3-bromo-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione with 23.4 ± 3.8 μM showed a trypanosomicidal activity higher than benznidazole. These results demonstrate the potential of naphthoquinone derivatives as novel structures for the development of alternative drugs for Chagas' disease. © 2010 Elsevier Ltd. All rights reserved.


Wender H.,Federal University of Rio Grande do Sul | De Oliveira L.F.,Federal University of Rio Grande do Sul | Feil A.F.,Federal University of Rio Grande do Sul | Lissner E.,Federal University of Rio Grande do Sul | And 4 more authors.
Chemical Communications | Year: 2010

The sputtering of Au targets onto castor oil generates stable spherical gold nanoparticles (AuNPs) of 2.4 to 3.8 nm. The AuNP size increases with the discharge voltage and the mechanism of nucleation and growth are related to the energy of the atoms/clusters ejected from the target. © 2010 The Royal Society of Chemistry.


PubMed | Institute Quimica e Biotecnologia
Type: Journal Article | Journal: Current topics in medicinal chemistry | Year: 2015

This review discusses the state of the art, challenges and perspectives in recent applications of electrochemistry in the life sciences. It deals mainly with the elucidation of molecular mechanisms of drug action, drug design and development, involving electron transfer, pharmaco-electrochemistry (the combination of electrochemical and pharmacological assays), and electrochemical studies of membrane models and drug delivery. It aims to shed light on the question: does electrochemistry really contribute to this area? It includes a general introduction for the use of electrochemistry in the life sciences, with a focus on how electrochemistry can uniquely provide both kinetic and thermodynamic information. A number of studies are reported in the literature and from the authors laboratories, including the investigation of biooxidative/bioreductive activation of pro-drugs, DNA alkylation, electrochemically- based release of reactive oxygen and nitrogen species, with a particular emphasis on quinones, ferrocifens and compounds with mixed-functionality. Within the context of drug delivery and bioavailability, the electrochemical investigation of supramolecular interactions of the chosen classes of compounds with cyclodextrins and lipid bilayers, in relation to their solubilization and vectorization was also carried out. The updated examples herein illustrate how relevant and challenging the integration of electrochemistry, supramolecular and materials chemistry, biochemistry and medical knowledge for the design and development of redox-selective molecular approaches is. Many questions related to these fields are still unclear and the search for selectivity toward redox therapeutic agents remains of expanding interest. This review hopes to stimulate researchers to become more involved in this fruitful interface between electrochemistry and the life sciences.

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