A study of neolignan compounds with biological activity against Paracoccidioides brasiliensis by using quantum chemical and chemometric methods

Camargo, Ademir J.; Honório, Káthia Maria; Mercadante, Ricardo; Molfetta, Fábio Alberto de; Alves, Cláudio Nahum; Silva, Albérico Borges Ferreira da

doi:10.1590/s0103-50532003000500017

Cited by 26 publications

(16 citation statements)

References 20 publications

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“…Recently, we successfully used molecular descriptors in structure-activity relationship (SAR) studies of neolignan compounds with antischitosomal activity, 20,21 antifungal activity, 37 and synthetic neolignans with biological activity against Escherichia coli 34 and Paracoccidiodes brasiliensis. 36 These descriptors are successful and well accepted. [38][39][40][41][42][43][44][45] Our purpose is to investigate, in a qualitative way, the structure activity relationship of neolignan compounds using quantum chemical descriptors.…”

Section: 35mentioning

confidence: 99%

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Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Nascimento¹,

Santos²,

Santos³

et al. 2010

J. Braz. Chem. Soc.

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A síntese e a estrutura cristalina por difração de raios-X de dois análogos de neolignanas, 2-(4-clorofenil)-1-feniletanona (20) e 2-[tio(4-clorofenil)]-1-(3,4-dimetoxifenil)propan-1-ona (12) são descritas. O composto 12 apresenta atividade intracelular contra Leishmania donovani e Leishmania amazonensis de amastigotas que causam a leishmaniose tegumentar e visceral. Além disso, a teoria do funcional de densidade (DFT) com o funcional híbrido B3LYP foi empregado para calcular um conjunto de descritores moleculares para dezenove análogos sintéticos de neolignanas com atividades antileishmaniose. Posteriormente, a análise discriminante stepwise foi realizada para investigar possíveis relações entre a estrutura molecular e atividades biológicas. Por meio dessa análise os compostos foram classificados em dois grupos ativos e inativos de acordo com seu grau de atividade biológica, e as propriedades mais importantes foram as cargas de alguns átomos, a afinidade eletrônica e o ClogP.The synthesis and X-ray crystal diffraction structure of two analogues of neolignans, 2-(4-chlorophenyl)-1-phenylethanone (20) and 2-[(4-chlorophenyl)thio]-1-(3,4-dimethoxyphenyl) propan-1-one (12) is described. The compound 12 presents activity against intracellular Leishmania donovani and Leishmania amazonensis amastigotes that cause cutaneous and visceral leishmaniasis. In addition, the density functional theory (DFT) with the B3LYP hybrid functional was employed to calculate a set of molecular descriptors for nineteen synthetic analogues of neolignans with antileishmanial activities. Afterwards, the stepwise discriminant analysis was performed to investigate possible relationship between the molecular descriptors and biological activities. Through this analysis the compounds were classified into two groups active and inactive according to their degree of biological activities, and the more important properties were charges on some key atoms, electronic affinity and ClogP.

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Section: 35mentioning

confidence: 99%

“…36 Usually, neolignans are organic dimmers derived from oxidative coupling of allyl and propenyl phenols. 16,22 Previous studies have evaluated the antileishmanials activities of twenty-two sulfur and oxygen synthetic analogues of neolignans against parasite species that cause cutaneous and visceral Leishmaniasis.…”

Section: 35mentioning

confidence: 99%

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Nascimento¹,

Santos²,

Santos³

et al. 2010

J. Braz. Chem. Soc.

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“…Redundancy analysis (RDA) is a method of multivariate analysis and its central purpose is to reduce the dimensions of a set of data that presents a large number of interrelated variables while retaining as much of the variation of this set as possible (CAMARGO et al, 2003). Multivariate analysis has been used for the study of fish populations by a number of authors, among them Pihl and Wennhagem (2002); Pessanha and Araújo (2003); Veja-Cendejas and Santillana (2004); Tuya et al (2005); Azevedo et al (2007) and Vaz et al (2007).…”

Section: Introductionmentioning

confidence: 99%

Spatial and temporal distribution of fish in Palmas bay, Ubatuba, Brazil

2010

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A B S T R A C TThe aim of this study was to analyze the distribution and abundance of the fish fauna of Palmas bay on Anchieta Island in southeastern Brazil. Specimens were caught in the summer and winter of 1992, using an otter trawl at three locations in the bay. The specimens were caught in both the nighttime and daytime. Data on the water temperature and salinity were recorded for the characterization of the predominant water mass in the region, and sediment samples were taken for granulometric analysis. A total of 7 656 specimens (79 species), with a total weight of approximately 300 kg, were recorded. The most abundant species were Eucinostomus argenteus, Ctenosciaena gracilicirrhus, Haemulon steindachneri, Eucinostomus gula and Diapterus rhombeus, which together accounted for more than 73% of the sample. In general, the ecological indices showed no differences in the composition of species for the abiotic variables analyzed. The multivariate analysis showed that the variations in the distribution of the fish fauna were mainly associated with intra-annual differences in temperature and salinity, resulting from the presence of South Atlantic Central Water (SACW) in the area during the summer. The analysis also showed an association with the type of bottom and a lesser association with respect to the night/day periods. R E S U M OEste estudo teve como objetivo analisar a composição e a abundância da fauna de peixes provenientes da enseada Palmas em Ubatuba, costa sudeste do Brasil. Os espécimes foram obtidos no verão e no inverno de 1992, utilizando-se uma rede de arrasto de fundo em três locais da enseada. Os arrastos foram realizados no período noturno e no período diurno. Foram obtidos dados de temperatura e salinidade da água para caracterização da massa de água predominante na região e amostras do sedimento para análise granulométrica. Foram capturadas 79 espécies de Actinopterygii, representadas por 7 656 indivíduos com peso total aproximado de 300 kg. As espécies mais abundantes foram Eucinostomus argenteus, Ctenosciaena gracilicirrhus, Haemulon steindachneri, Eucinostomus gula e Diapterus rhombeus e representaram mais de 73% da amostra. Os índices ecológicos utilizados, de uma maneira geral, não mostraram diferenças na composição das espécies quanto às variáveis abióticas analisadas. A análise multivariada empregada mostrou que as variações encontradas na distribuição da fauna de peixes foram associadas principalmente às diferenças intraanuais de temperatura e salinidade, relacionadas à presença da Água Central do Atlântico Sul no verão na área de estudo. A análise também mostrou uma associação em relação ao tipo de fundo e uma menor associação em relação aos períodos do ciclo noite/dia.

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“…The best descriptors to discriminate the two classes are those with large values of Fisher weights. Therefore, the descriptors with higher values were selected for PCA analysis, 26,27 an unsupervised classification method that reduces the dimensionality of a data set, explaining the variance-covariance structure. This is achieved through linear transformations of the original data set of variables into a smaller number of uncorrelated significant principal components (PCs).…”

Section: Methodsmentioning

confidence: 99%

Structure-activity relationship study of rutaecarpine analogous active against central nervous system cancer

Martins

Napolitano

Camargo

et al. 2012

J. Braz. Chem. Soc.

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Com o objetivo de relacionar os descritores geométricos e eletrônicos dos derivados análogos da rutaercarpina com a atividade biológica contra o câncer do sistema nervoso central (CNS), cálculos de química quântica molecular em nível B3LYP/6-31(d) e análise estatística foram realizados para os 21 derivados análogos da rutaecarpina. Dos 86 descritores moleculares calculados, 5 foram selecionados na construção do modelo de análises de componentes principais (PCA). A componente PC1, a qual responde por 46,11% da variância total dos dados, foi capaz sozinha de discriminar completamente os compostos em duas classes: ativos e inativos. Todos os descritores moleculares selecionados pelo modelo PCA são parâmetros eletrônicos. A análise de agrupamento hierárquico (HCA) foi também aplicada aos descritores selecionados pelo modelo PCA. Baseado nos 5 descritores selecionados é possível sugerir novos derivados ativos da rutaercarpina para serem sintetizados. Além disso, um modelo de mínimos quadrados parciais para análise discriminante (PLS-DA) supervisionado foi construído e aplicado com sucesso na discriminação dos análogos à rutaercarpina, o qual foi validado usando um conjunto independente de compostos.In order to relate the geometric and electronic descriptors of the rutaecarpine analogous to their biological activity against cancer of the central nervous system (CNS), molecular quantum chemical calculations at B3LYP/6-31(d) level and statistical analysis were carried out for 21 rutaecarpine analogous. Out of the 86 molecular descriptors calculated, 5 were selected to build the principal component analysis (PCA) model. The PC1 component that accounts for 46.11% of the total variance of the data was alone able to discriminate completely the compounds into two classes: active and inactive. All molecular descriptors selected by PCA model are electronic parameters. The hierarchical cluster analysis (HCA) was also applied on the selected descriptors. Based on the 5 electronic descriptors selected, it is possible to suggest new compounds to be synthesized with activity against CNS cancer. In addition to that, a supervised partial least squares discriminant analysis (PLS-DA) model was built and successfully applied to discriminate rutaecarpine analogues, being validated through an independent test set and considered robust to overfitting.Keywords: central nervous system cancer, quinazoline-beta-carboline-5-one, B3LYP, rutaecarpine analogous Introduction Brain tumors are rare, but their incidence and mortality rates have been increasing over the past decades in several countries, especially among older people.1-3 Although very little about brain tumors is known, it is believed that genetic factors, hormonal and environmental factors are related to the evolution of this disease. 4,5 The central nervous system (CNS) comprises the brain and spinal cord. Patients who experience personality changes, apathy, early dementia, constant headache or even depression can have a brain tumor. 6,7 Data from the American Cancer Society (ACS) sh...

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A study of neolignan compounds with biological activity against Paracoccidioides brasiliensis by using quantum chemical and chemometric methods

Cited by 26 publications

References 20 publications

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Spatial and temporal distribution of fish in Palmas bay, Ubatuba, Brazil

Structure-activity relationship study of rutaecarpine analogous active against central nervous system cancer

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