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Virtual Screening Based on Ligand and Structure with in vitro Assessment of Neolignans against Trypanosoma cruzi
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Maia, Mayara S.

; Andrade, Rodrigo S.

; Sousa, Julyanne M. S.

; Sousa, Natália F.

; Rodrigues, Gabriela C. S.

; Menezes, Renata P. B.

; Silva, Marcelo S.

; Tavares, Josean F.

; Rodrigues, Klinger A. F.

; Scotti, Luciana

; Scotti, Marcus T.

Journal of the Brazilian Chemical Society

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mar 2023, Volume 34 N. 3 Pages 346 - 365

Abstract: En | Text: En | PDF: En

Chagas disease, caused by the parasite Trypanosoma cruzi, occurs most commonly in Latin America. As the treatment is highly toxic and ineffective in the chronic phase of the disease, alternative treatments are needed. Through quantitative structure-activity relationship modeling (QSAR) analysis using ligand-based and structure-based virtual screening methods, we predicted the trypanocidal potential of 47 neolignans against three targets, the enzymes cruzain, trypanothione reductase, and sterol 14-alpha demethylase. A combined analysis allowed for the selection of potent inhibitors against Trypanosoma cruzi. Of these compounds, two were isolated and shown to inhibit the growth of epimastigotes at concentrations of 9.64 and 8.72 µM, and trypomastigote forms at 4.88 and 2.73 µM. Therefore, the compounds (2R, 3R)-2,3-dihydro-2 (4 methoxyphenyl)-3-methyl-5-(E)-propenylbenzofuran (46) and ottomentosa (47) may be a good option of growth inhibitors for the parasite stages and warrant additional study.

https://doi.org/10.21577/0103-5053.20220113

DITERPENOS ENT-ABIETANOS DE Euphorbia phosphorea (EUPHORBIACEAE)
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Meireles, Roseana A. R.

; Abreu, Lucas S.

; Silva, Joanda Paolla R. e

; Cavalcanti, Andreza B. S.

; Menezes, Renata Priscila B. de

; Rodrigues, Gabriela Cristina S.

; Rodrigues Junior, Valnês S.

; Melo, José Iranildo M. de

; Kato, Massuo Jorge

; Costa, Vicente Carlos de O.

; Scotti, Marcus Tullius

; Tavares, Josean F.

Química Nova

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sep 2022, Volume 45 N. 9 Pages 1092 - 1097

Abstract: Pt | Text: Pt | PDF: Pt

Phytochemical study of the roots of Euphorbia phosphorea Mart. (Euphorbiaceae) was carried out through chromatographic techniques, resulting in the isolation of a new ent-abietane diterpene named 11β,12β-dihydroxy-ent-abieta-8(14),13(15)-dien-16,12α-olide (1), and of nine known ent-abietane diterpenes jolkinolide A (2), jolkinolide E (3), euphorin H (4), euphopilolide (5) jolkinolide F (6), ent-12-hydroxy-12[R]-abieta-8(14),13(15)-dien-16,12-olide (7), ent-11α-hydroxyabieta-8(14),13(15)-dien-16,12α-olide (8), 17-hydroxyjolkinolide B (9) and caudicifolin (10). The structures of all compounds were established using spectroscopic techniques such as 1D and 2D NMR, and the structure of the compound 1 was established also with MS, IR and ECD. All compounds were submitted to an in silico study through of a predictive model and then submitted to in vitro tests against Mycobacterium tuberculosis and M. smegmatis for evaluation of their antimycobacterial activity. Compounds 5 and 9 showed mycobacterial growth inhibition with MIC values of 62.5 μM against M. tuberculosis and M. smegmatis, respectively.

https://doi.org/10.21577/0100-4042.20170932

Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides
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Huang, Min-Fu N.

; Luis, José A. S.

; Silva, Alison P. da

; Rocha, Juliana C.

; Lima, Tatjana K. S.

; Scotti, Marcus T.

; Scotti, Luciana

; Oliveira, Rafael F. de

; Souza, Helivaldo D. S.

; Athayde-Filho, Petrônio F. de

; Barbosa-Filho, José M.

Journal of the Brazilian Chemical Society

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apr 2021, Volume 32 N. 4 Pages 712 - 721

Abstract: En | Text: En | PDF: En

This study describes a virtual screening performed for two series of selenides (28 compounds), derived from N-phenylacetamides chlorides and 7-chloro-quinoline, to determine their potential for leishmanicidal activity against Leishmania amazonensis and Leishmania donovani. Seven compounds were predicted as potential leishmanicides; therefore, they were synthesized from elemental selenium, as a precursor for the production of NaHSe, and subsequent reactions with 4,7-dichloro-quinoline and N-phenylacetamides chlorides were performed. The compounds were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and sent for in vitro cytotoxicity tests against L. amazonensis and were found to be active and selective, and two compounds presented half-maximal inhibitory concentrations (IC50) of 5.67 and 10.81 µg mL-1. They also presented good interaction energies in the docking study, suggesting that may exert their effects by inhibiting the N-myristoyltransferase and O-acetylserine sulfhydrylase enzymes in parasites.

https://doi.org/10.21577/0103-5053.20200223 183 downloads

Antifungal activity and mechanism of action of 2-chloro-N -phenylacetamide: a new molecule with activity against strains of Aspergillus flavus
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FERREIRA, ELBA S.

; CORDEIRO, LAÍSA V.

; SILVA, DANIELE DE F.

; SOUZA, HELIVALDO D.S.

; ATHAYDE-FILHO, PETRÔNIO F. DE

; BARBOSA-FILHO, JOSÉ MARIA

; SCOTTI, LUCIANA

; LIMA, EDELTRUDES O.

; CASTRO, RICARDO D. DE

Anais da Academia Brasileira de Ciências

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2021, Volume 93 elocation e20200997

Abstract: En | Text: En | PDF: En

Abstract Aspergillus genus causes many diseases, and the species Aspergillus flavus is highly virulent. Treatment of aspergillosis involves azole derivatives such as voriconazole and polyenes such as amphotericin B. Due to an increase in fungal resistance, treatments are now less effective; the search for new compounds with promising antifungal activity has gained importance. The aims of this study were to evaluate the effects of the synthetic amide 2-chloro-N-phenylacetamide (A1Cl) against strains of Aspergillus flavus and to elucidate its mechanism of action. Thus, the minimum inhibitory concentration, minimum fungicidal concentration, conidial germination, associations with antifungal agents, cell wall activities, membrane activities and molecular docking were evaluated. A1Cl presented antifungal activity against Aspergillus flavus strains with a minimum inhibitory concentration of between 16 and 256 μg/mL and a minimum fungicidal concentration between 32 and 512 μg/mL. The minimum inhibitory concentration of A1Cl also inhibited conidial germination, but when associated with amphotericin B and voriconazole, it promoted antagonistic effects. Binding to ergosterol on the fungal plasma membrane is the likely mechanism of action, along with possible inhibition of DNA synthesis through the inhibition of thymidylate synthase. It is concluded that the amide 2-chloro-N-phenylacetamide has promising antifungal potential.

https://doi.org/10.1590/0001-3765202120200997 82 downloads

Virtual Screening of Secondary Metabolites of the Family Velloziaceae J. Agardh with Potential Antimicrobial Activity
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Pinheiro, Anderson A. V.

; Barros, Renata P. C.

; Assis, Edileuza B. de

; Maia, Mayara S.

; Araújo, Diego I. A. F. de

; Sales, Kaio A.

; Scotti, Luciana

; Tavares, Josean F.

; Scotti, Marcus T.

; Silva, Marcelo S. da

Journal of the Brazilian Chemical Society

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oct 2020, Volume 31 N. 10 Pages 2114 - 2119

Abstract: En | Text: En | PDF: En

The objective of this work was to carry out a bibliographic survey of secondary metabolites isolated from the Velloziaceae family, creating a bank of compounds. After the bank was created, four prediction models for potentially active compounds against pathogenic microorganisms (Candida albicans, Escherichia coli, Pseudomonas aeruginosa and Salmonella sp.) were obtained trying to identify which metabolites would be more active against the strains. Four sets of compounds with known activity for microorganisms were selected for the construction of predictive models from the CHEMBL database. Another bank with 163 unique molecules isolated from the Velloziaceae family was built. The Volsurf+ v.1.0.7 software obtained the molecular descriptors and Knime 3.5 generated the in silico model. The performances of the internal and external tests were also analyzed. The study contributed through the virtual screening of a bank of metabolites to select several compounds with potential antimicrobial activity, highlighting the biflavonoid amentoflavone which showed potential activity against the four strains.

https://doi.org/10.21577/0103-5053.20200112 284 downloads

Pyrimidine Derivatives: QSAR Studies of Larvicidal Activity against Aedes aegypti
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Monte, Zenaide S.

; Navarro, Daniela M. A. F.

; Aguiar, Júlio C. R. O. F.

; Nascimento, Jessica S.

; Scotti, Marcus T.

; Scotti, Luciana

; Barros, Renata P. C.

; Santos, Aline C. S.

; Pereira, Valéria R. A.

; Falcão, Emerson P. S.

; Melo, Sebastião J.

Journal of the Brazilian Chemical Society

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jul 2020, Volume 31 N. 7 Pages 1531 - 1540

Abstract: En | Text: En | PDF: En

The present study investigated the activity of pyrimidine derivatives against Aedes aegypti. Two compounds, 3c and 3d showed excellent larvicide activity. Additionally, quantitative structure-activity relationship (QSAR) models were built using multiple-linear regression and partial least squares with descriptors generated from Dragon and VolSurf+ software, respectively. The best model is obtained with multiple linear regression (MLR), leading to a robust model. Moreover, the QSAR model is validated by means of some internal validation techniques in order to check its reliability, quality and robustness for predicting the larvicidal activity against A. aegypti. The models confirmed that the three-dimensional structure of molecules, steric properties, hydrophobic polar surface area, log partition (logP) and a simple pattern of substituent groups as methyl, methoxy, and succinimide in the pyrimidine derivatives are responsible for the larvicidal activity of the pyrimidine derivatives. Even more, the activity decreases by an electron-withdrawing group in R1 and increases when it is replaced by an aromatic ring activator group. These findings will aid in further studies of new pyrimidine derivatives active against Aedes aegypti.

https://doi.org/10.21577/0103-5053.20200039 283 downloads

Dual-band System composed by a Photonics-based Radar and a Focal-Point/Cassegrain Parabolic Antenna
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Brandão, T. H.

; Filgueiras, H.R.D.

; Alves, A. A. C.

; Scotti, F.

; Melo, S.

; Bogoni, A.

; Arismar Cerqueira Jr., S.

Journal of Microwaves, Optoelectronics and Electromagnetic Applications

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oct 2018, Volume 17 N. 4 Pages 567 - 578

Abstract: En | Text: En | PDF: En

Abstract This work reports a dual-band radar system composed of aphotonics-based transceiver and a unique dual-band antenna. The proposed antenna consists of an integration of conventional focal-point and Cassegrain parabolic antennas in the same structure, ensured by using a subreflector based on a frequency selective surface. Numerical and experimental results in terms of the antenna reflection coefficient, radiation pattern and gain are reported with excellent agreement over both frequency ranges. The innovative dual-band photonics-based radar transceiver operates simultaneously in the S- and X-bands. The radar system has been properlyvalidated by multiple detections of helicopters and airplanes in real conditions.

https://doi.org/10.1590/2179-10742018v17i41545 1693 downloads

Zornioside, a dihydrochalcone C-glycoside, and other compounds from Zornia brasiliensis
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Nascimento, Yuri M.

; Abreu, Lucas S.

; Lima, Ramon L.

; Silva, Anne Dayse S.

; Costa, Vicente Carlos O.

; Melo, José Iranildo M.

; Scotti, Marcus Tulius

; Sobral, Marianna V.

; Araujo, Silvany S.

; G. Filho, Manoel Adrião

; Silva, Marcelo S.

; Tavares, Josean F.

Revista Brasileira de Farmacognosia

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apr 2018, Volume 28 N. 2 Pages 192 - 197

Abstract: En | Text: En | PDF: En

ABSTRACT The secondary metabolites of the aerial parts of Zornia brasiliensis Vogel, Fabaceae, and the biological activity of one of these secondary metabolites were characterized in this study. A phytochemical investigation was performed using chromatographic techniques including analytical and preparative reverse-phase HPLC column sequences, which resulted in the isolation of fourteen compounds: one previously undescribed C-glycosylated dihydrochalcone (zornioside), one cyclitol (D-pinitol), one glycosylated megastigmane (roseoside) and eleven phenolic compounds: 7-methoxyflavanone, 7,4'-dimethoxyisoflavone, medicarpin, 2'-4'-dihydroxychalcone, onionin, isoorientin-3'-O-methyl ether, isovitexin, glycosylated (Z)-O-coumaric acid, glycosylated (E)-O-coumaric acid, dihydromelilotoside, and isoorientin. The structures of the isolated compounds were determined based on 1D and 2D-NMR, HRESIMS, IR and CD spectroscopic analyses. The cytotoxic activity of zornoside was assessed against tumor cell lines (MCF-7, HCC1954, T-47D, 4T1, HL60), and a non-tumor cell line (RAW264.7) using MTT assay. The compound zornioside was selectively cytotoxic for HL60 leukemia cells (IC50: 37.26 µM).

https://doi.org/10.1016/j.bjp.2018.02.003 621 downloads

Chemometric analysis of ESIMS and NMR data from Piper species
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Yamaguchi, Lydia F.

; Freitas, Giovana C.

; Yoshida, Nidia C.

; Silva, Renata A.

; Gaia, Anderson M.

; Silva, Adalberto M.

; Scotti, Marcus T.

; Emerenciano, Vicente de P.

; Guimarães, Elsie F.

; Floh, Eny I. S.

; Colombo, Carlos A.

; Siqueira, Walter J.

; Kato, Massuo J.

Journal of the Brazilian Chemical Society

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dec 2011, Volume 22 N. 12 Pages 2371 - 2382

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

O perfil metabólito baseado na aplicação de análises multivariadas (análise de componentes principais, PCA) dos dados de espectrometria de massas com ionização electrospray (ESIMS) no modo positivo e de ressonância magnética nuclear (RMN) do ¹H de extratos brutos de espécies de Piper destacou algumas espécies caracterizadas pela produção de lignanas (P. solmsianum, P. truncatum e P. cernuum), neolignanas (P. regnellii) e cromenos (P. gaudichaudianum). Análises específicas em conjunto de espécies caracterizadas morfologicamente por apresentarem inflorescências pêndulas e globosas (P. caldense, P. carniconnectivum, P. bowiei e P. permucronatum) ou em espécies que produzem amidas indicaram o potencial mais significativo para tais análises como critério para estudos fitoquímicos posteriores. Análises intraespecíficas de plântulas das espécies P. solmsianum, P. regnellii e P. gaudichaudianum indicaram uma composição química nas folhas baseada na presença dos fenilpropanóides dilapiol e apiol, diferentemente do que produzem as plantas adultas. No caso das espécies que produzem amidas, a composição apresentou-se relativamente constante independentemente do estágio de desenvolvimento.

The metabolomic profiling based on the application of multivariate analysis (principal component analysis, PCA) of positive mode electrospray ionization mass spectrometric (ESIMS) and ¹H nuclear magnetic resonance (NMR) data of crude extracts highlighted some species characterized by lignans (P. solmsianum, P. truncatum and P. cernuum), neolignans (P. regnellii) and chromenes (P. gaudichaudianum). A specific analysis focusing on species having pendant and globular inflorescences (P. caldense, P. carniconnectivum, P. bowiei and P. permucronatum) or amides-producing species indicated higher potential of the methodology in determining similarities and establishing priorities for further phytochemical investigation. Such intraspecific analysis applied to analyzed seedling leaves of the P. solmsianum, P. regnellii and P. gaudichaudianum species revealed the production of dillapiole and apiole instead of lignans, neolignans or prenylated benzoic acid, produced by the adult leaves, respectively. In case of amides-producing species, a similar profile was observed regardless the developmental stage.

4247 downloads

10.

Self-organizing maps and VolSurf approach to predict aldose reductase inhibition by flavonoid compounds
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Scotti, Luciana

; Fernandes, Mariane B.

; Muramatsu, Eric

; Pasqualoto, Kerly F. M.

; Emereciano, Vicente de P.

; Tavares, Leoberto C.

; Silva, Marcelo Sobral da

; Scotti, Marcus T.

Revista Brasileira de Farmacognosia

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feb 2011, Volume 21 N. 1 Pages 170 - 180

Abstract: En | Text: En | PDF: En

Aldose Reductase (AR) is the polyol pathway key enzyme which converts glucose to sorbitol. High glucose availability in insulin resistant tissues in diabetes leads into an accumulation of sorbitol, which has been associated with typical chronic complications of this disease, such as neuropathy, nephropathy and retinopathy. In this study, 71 flavonoids AR inhibitors were subjected to two methods of SAR to verify crucial substituents. The first method used the PCA (Principal Component Analysis) to elucidate physical and chemical characteristics in the molecules that would be essential for the activity, employing VolSurf descriptors. The rate obtained explained 53% of the system total variance and revealed that a hydrophobic-hydrophilic balance in the molecules is required, since very polar or nonpolar substituents decrease the activity. Artificial Neural Networks (ANNs) was also employed to determine key substituents by evaluating substitution patterns, using NMR data. This study had a high success rate (85% accuracy in the training set and 88% accuracy in the test set) and showed polihydroxilations are essential for high activity and methoxylations and glicosilations primarily at positions C7, C3' and C4' decrease the activity.

2385 downloads Cited 1 time in SciELO

11.

II Diretriz de Avaliação Perioperatória da Sociedade Brasileira de Cardiologia
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Feitosa, Alina Coutinho Rodrigues

; Marques, André Coelho

; Caramelli, Bruno

; Ayub, Beatriz

; Polanczyk, Carisi A.

; Jardim, Carlos

; Vieira, Carolina L. Zilli

; Pinho, Claudio

; Calderaro, Daniela

; Gualandro, Danielle Menosi

; Iezzi, Denise

; Ikeoka, Dimas T.

; Schreen, Dirk

; D'Amico, Elbio Antonio

; Pfeferman, Elcio

; Lima, Emerson Quintino de

; Burdmann, Emmanuel de A.

; Pachon, Enrique

; Machado, Fabio Santana

; Galas, Filomena Regina Barbosa Gomes

; Paula, Flávio Jota de

; Carvalho, Francine Corrêa de

; Feitosa-Filho, Gilson Soares

; Prado, Gustavo Faibischew

; Lopes, Heno F.

; Lima, José Jaime Galvão de

; Marchini, Julio Flavio Meirelles

; Fornari, Luciana S.

; Drager, Luciano F.

; Vacanti, Luciano Janussi

; Hajjar, Ludhmila Abrahão

; Rohde, Luis Eduardo P.

; Gowdak, Luís Henrique

; Cardoso, Luiz Francisco

; Vieira, Marcelo Luiz Campos

; Monachini, Maristela C.

; Macatrão, Milena

; Yu, Pai Ching

; Villaça, Paula Ribeiro

; Farsky, Pedro Silvio

; Lopes, Renato Delascio

; Bagnatori, Renato Scotti

; Heinisch, Roberto Henrique

; Gualandro, Sandra F. Menosi

; Accorsi, Tarso Augusto Duenhas

; Ávila, Walkiria Samuel

; Mathias Jr., Wilson

Arquivos Brasileiros de Cardiologia

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2011, Volume 96 N. 3 Pages 1 - 68

Abstract: Pt | Text: Pt | PDF: Pt

53329 downloads

12.

A Study on out-of-phase current pulses of the double wire MIG/MAG process with insulated potentials on coating applications: part I
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Motta, Marcelo F.

; Dutra, Jair Carlos

; Gohr Jr, Raul

; Scotti, Américo

Journal of the Brazilian Society of Mechanical Sciences and Engineering

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jun 2007, Volume 29 N. 2 Pages 202 - 206

Abstract: En | Text: En | PDF: En

The part 1 of this work presents a study about the use of the out-of-phase current pulses technology applied to the Double Wire MIG/MAG welding process with Insulated Potentials on welded coating. High-speed digital back-lighted images were recorded to evaluate the influence of the levels of out-of-phase current pulses on the behavior of both metallic transfer modes and voltaic arcs configurations. The results showed that, with the electrodes positioned side by side and the mean currents below the transition current, the out-of-phasing parameter setting reduces the deviations of the arcs and changes the paths of the droplets. However, no significant effect was noticed on bead finishing or arc stability.

2961 downloads

13.

A Study on out-of-phase current pulses of the double wire MIG/MAG process with insulated potentials on coating applications: part II
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Motta, Marcelo F.

; Dutra, Jair Carlos

; Gohr Jr, Raul

; Scotti, Américo

Journal of the Brazilian Society of Mechanical Sciences and Engineering

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jun 2007, Volume 29 N. 2 Pages 207 - 210

Abstract: En | Text: En | PDF: En

This paper presents a continuation of a study carried out on the use of the out-of-phase current pulses technology applied to the Double Wire MIG/MAG welding process with Insulated Potentials on welded coatings. In the first part it was reported how the level of out-phase pulsed current acts on arc configuration, droplet paths, bead finishing and arc stability. The objective now is to show the effect on the bead geometry caused by changes in arc and metal transfer. Beads were deposited on plate in a flat position and out-of-phase levels were varied. The results showed that, with the electrodes positioned side by side and mean currents below the transition current, the lag time between out-of-phase current pulses have a remarkable influence on the penetration profile of the weld bead.

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