QSAR modeling of antitubercular activity of diverse organic compounds

Tuberculosis (TB) is a worldwide infectious disease that has shown over time extremely high mortality levels. The urgent need to develop new antitubercular drugs is due to the increasing rate of appearance of multi-drug resistant strains to the commonly used drugs, and the longer durations of therapy and recovery, particularly in immuno-compromised patients. The major goal of the present study is the exploration of data from different families of compounds through the use of a variety of machine learning techniques so that robust QSAR-based models can be developed to further guide in the quest for new potent anti-TB compounds. Eight QSAR models were built using various types of descriptors (from ADRIANA.Code and Dragon software) with two publicly available structurally diverse data sets, including recent data deposited in PubChem. QSAR methodologies used Random Forests and Associative Neural Networks. Predictions for the external evaluation sets obtained accuracies in the range of 0.76-0.88 (for active/inactive classifications) and Q(2)=0.66-0.89 for regressions. Models developed in this study can be used to estimate the anti-TB activity of drug candidates at early stages of drug development (C) 2011 Elsevier B.V. All rights reserved.

Diptera of sanitary importance associated with composting of biosolids in Argentina

OBJECTIVE: Odorous compounds produced at the biosolids composting plant in Bariloche (NW Patagonia) attract a variety of insects, mainly belonging to the order Diptera. In order to characterize these flies, collected specimens were taxonomically identified, their community characteristics were described and their sanitary and synanthropic importance and autochthonous or introduced character were determined. METHODS: Sampling was performed from October 1999 until March 2000. Adults were collected using an entomological net, and larvae and puparia were obtained from the composting material and incubated to obtain adults. Richness, abundance and sex ratio were calculated. RESULTS: A total of 9 taxa of Diptera were identified: Sarconesia chlorogaster, Phaenicia sericata, Calliphora vicina, Cochliomya macellaria, Ophyra sp, Muscina stabulans, Musca domestica, Sarcophaga sp and Fannia sp. Specimens of Anthomyiidae, Acaliptratae and one larva of Eristalis tenax were also found. Ophyra sp. was the most abundant taxa. All the captured Diptera belonged to introduced taxa. Most of them are considered to be eusynanthropic and/or hemisynanthropic and have sanitary importance as they may cause myiasis and pseudomyiasis. The high number of females registered and the finding of immature stages indicated that flies can develop their complete life cycle on biosolid composting windrows. CONCLUSIONS: The characterization of flies obtained in this study may be useful for defining locations of urban or semi-urban composting facilities. It also highlights the importance of sanitary precautions at such plants.

Size distribution of polycyclic aromatic hydrocarbons in a roadway tunnel in Lisbon, Portugal

Atmospheric aerosols of four aerodynamic size ranges were collected using high volume cascade impactors in an extremely busy roadway tunnel in Lisbon (Portugal). Dust deposited on the tunnel walls and guardrails was also collected. Average particle mass concentrations in the tunnel atmosphere were more than 30 times higher than in the outside urban background air, revealing its origins almost exclusively from fresh vehicle emissions. Most of the aerosol mass was concentrated in submicrometer fractions (65%), and polycyclic aromatic hydrocarbons (PAH) were even more concentrated in the finer particles with an average of 84% of total PAH present in sizes smaller than 0.49 mu m. The most abundant PAH were methylated phenanthrenes, fluoranthene and pyrene. About 46% of the total PAH mass was attributed to lower molecular weight compounds (two and three rings), suggesting a strong influence of diesel vehicle emissions on the production of local particulate PAH. The application of diagnostic ratios confirmed the relevance of this source of PAH in the tunnel ambient air. Deposited dust presented PAH profiles similar to the coarser aerosol size range, in agreement with the predominant origin of coarser aerosol particles from soil dust resuspension and vehicle wear products. (c) 201 1 Elsevier Ltd. All rights reserved.

Supercritical carbon dioxide extraction of bioactive compounds from microalgae and volatile oils from aromatic plants

A discussion of the most interesting results obtained in our laboratories, during the supercritical CO(2) extraction of bioactive compounds from microalgae and volatile oils from aromatic plants, was carried out. Concerning the microalgae, the studies on Botryococcus braunii and Chlorella vulgaris were selected. Hydrocarbons from the first microalgae, which are mainly linear alkadienes (C(23)-C(31)) with an odd number of carbon atoms, were selectively extracted at 313 K increasing the pressure up to 30.0 MPa. These hydrocarbons are easily extracted at this pressure, since they are located outside the cellular walls. The extraction of carotenoids, mainly canthaxanthin and astaxanthin, from C. vulgaris is more difficult. The extraction yield of these components at 313 K and 35.0 MPa increased with the degree of crushing of the microalga, since they are not extracellular. On the other hand, for the extraction of volatile oils from aromatic plants, studies on Mentha pulegium and Satureja montana L were chosen. For the first aromatic plant, the composition of the volatile and essential oils was similar, the main components being the pulegone and menthone. However, this volatile oil contained small amounts of waxes, which content decreased with decreasing particle size of the plant matrix. For S. montana L it was also observed that both oils have a similar composition, the main components being carvacrol and thymol. The main difference is the relative amount of thymoquinone, which content can be 15 times higher in volatile oil. This oxygenated monoterpene has important biological activities. Moreover, experimental studies on anticholinesterase activity of supercritical extracts of S. montana were also carried out. The supercritical nonvolatile fraction, which presented the highest content of the protocatechuic, vanilic, chlorogenic and (+)-catechin acids, is the most promising inhibitor of the enzyme butyrylcholinesterase. In contrast, the Soxhlet acetone extract did not affect the activity of this enzyme at the concentrations tested. (C) 2011 Elsevier B.V. All rights reserved.

Trends in properties of para-substituted 3-(phenylhydrazo)pentane-2,4-diones

Trends between the Hammett's sigma(p) and related normal sigma(n)(p), inductive sigma(I), resonance sigma(R), negative sigma(-)(p) and positive sigma(+)(p) polar conjugation and Taft's sigma(o)(p) substituent constants and the N-H center dot center dot center dot O distance, delta(N-H) NMR chemical shift, oxidation potential (E-p/2(ox), measured in this study by cyclic voltammetry (CV)) and thermodynamic parameters (pK, Delta G(0), Delta H-0 and Delta S-0) of the dissociation process of unsubstituted 3-(phenylhydrazo)pentane-2,4-dione (HL1) and its para-substituted chloro (HL2), carboxy (HL3), fluoro (HL4) and nitro (HL5) derivatives were recognized. The best fits were found for sigma(p) and/or sigma(-)(p) in the cases of d(N center dot center dot center dot O), delta(N-H) and E-p/2(ox), showing the importance of resonance and conjugation effects in such properties, whereas for the above thermodynamic properties the inductive effects (sigma(I)) are dominant. HL2 exists in the hydrazo form in DMSO solution and in the solid state and contains an intramolecular H-bond with the N center dot center dot center dot O distance of 2.588(3)angstrom. It was also established that the dissociation process of HL1-5 is non-spontaneous, endothermic and entropically unfavourable, and that the increase in the inductive effect (sigma(I)) of para-substitutents (-H < -Cl < -COOH < -F < -NO2) leads to the corresponding growth of the N center dot center dot center dot O distance and decrease of the pK and of the changes of Gibbs free energy, of enthalpy and of entropy for the HL1-5 acid dissociation process. The electrochemical behaviour of HL1-5 was interpreted using theoretical calculations at the DFT/HF hybrid level, namely in terms of HOMO and LUMO compositions, and of reactivities induced by anodic and cathodic electron-transfers. Copyright (C) 2010 John Wiley & Sons, Ltd.

Diversidade e prospecção de fungos endofíticos de Begonia spp. encontradas na Mata Atlântica

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Marine cyanobacteria compounds with anticancer properties: a review on the implication of apoptosis

Marine cyanobacteria have been considered a rich source of secondary metabolites with potential biotechnological applications, namely in the pharmacological field. Chemically diverse compounds were found to induce cytoxicity, anti-inflammatory and antibacterial activities. The potential of marine cyanobacteria as anticancer agents has however been the most explored and, besides cytotoxicity in tumor cell lines, several compounds have emerged as templates for the development of new anticancer drugs. The mechanisms implicated in the cytotoxicity of marine cyanobacteria compounds in tumor cell lines are still largely overlooked but several studies point to an implication in apoptosis. This association has been related to several apoptotic indicators such as cell cycle arrest, mitochondrial dysfunctions and oxidative damage, alterations in caspase cascade, alterations in specific proteins levels and alterations in the membrane sodium dynamics. In the present paper a compilation of the described marine cyanobacterial compounds with potential anticancer properties is presented and a review on the implication of apoptosis as the mechanism of cell death is discussed.

Antimicrobial activity of pyrazine and quinoxaline N,N’-dioxide heterocyclic compounds

The nitrogen heterocyclic organic compounds 1,4 dioxide pyrazine and quinoxaline derivatives have been widely studied due to their potential use as synthetic drugs. The thermochemical study of three N,N´-dioxides: 2,3,5-trimethylpyrazine-1,4-dioxide, tetramethylpyrazine-1,4-dioxide and 6-chloro-2,3-dimethilquinoxaline 1,4-dioxide has been recently developed in order to establish relationships among the energetical, structural and reactivity properties [4,5]. Several studies have reported their pharmacological activity, particularly as antimicrobial agents [1,2,3]. It has also been established a relation between energetical and structural properties and biological activity, once these compounds present N – oxide bonds, increasing their oxidative capacity. The present work reports the study of antimicrobial activity for those compounds against the bacteria Geobacillus stearothermophylus, Staphylococcus aureus, Streptococcus agalactiae, Escherichia coli and also against the yeasts Saccharomyces cerevisiae PYCC 4072, Candida albicans PYCC3436T, Candida tropicalis PYCC, Issatchenka Orientalis PYCC. The determination of the minimal inhibitory concentration (MIC), points to an antimicrobial activity and the preliminary results indicate that these compounds may be potential candidates as antimicrobial drugs with clinical, agriculture or food industries applications.

Py-GC/MS(FID) assessed behavior of polysaccharides during kraft delignification of Eucalyptus globulus heartwood and sapwood

Eucalyptus globulus heartwood, sapwood and their delignified samples by kraft pulping at 130, 150 and 170 degrees C along time were characterized in respect to total carbohydrates by Py-GC/MS(FID). No significant differences between heartwood and sapwood were found in relation to pyrolysis products and composition. The main wood carbohydrate derived pyrolysis compounds were levoglucosan (25.1%), hydroxyacetaldehyde (12.5%), 2-oxo-propanal (10.3%) and acetic acid (8.7%). Levoglucosan decreased during the early stages of delignification and increased during the bulk and residual phases. Acetic acid decreased hydroxyacetaldehyde and 2-oxo-propanal increased, and 2-furaldehyde and hydroxypropanone remained almost constant during delignification. The C/L ratio was 3.2 in wood and remained rather constant in the first pulping periods until a loss of 15-25% in carbohydrate and 60% in lignin. Afterwards it increased sharply until 44 that correspond to the removal of 25-35% of carbohydrates and 95% of lignin. The pulping reactive selectivity to lignin vs. polysaccharides was the same for sapwood and heartwood. (C) 2013 Elsevier B.V. All rights reserved.

Compounds identified on hexane and dichloromethane extracts of Salicornia ramosissima

3rd Portuguese Meeting on Medicinal Chemistry and 1st Portuguese-Spanish-Brazilian Meeting on Medicinal Chemistry, Aveiro, 28-30 Novembro 2012.

Synthesis and antioxidant activity of new xanthone-type compounds

3rd Portuguese Meeting on Medicinal Chemistry and 1st Portuguese-Spanish-Brazilian Meeting on Medicinal Chemistry, Aveiro, 28-30 Novembro 2012.

Purification and structural characterization of compounds isolated from Cystoseira abies-marina

6th Spanish-Portuguese-Japanese Organic Chemistry Symposium, Lisboa, de 18 a 20 de Julho de 2012 (Poster Communication).

Some aromatic compounds from dichloromethane extract of Salicornia ramosissima.

6th Spanish-Portuguese-Japanese Organic Chemistry Symposium, Lisboa, de 18 a 20 de Julho de 2012 (Poster Communication).

Organic compounds isolated from Juniperus brevifolia bark

10º Encontro Nacional de Química Orgânica e 1º Simpósio Luso-Brasileiro de Química Orgânica, Lisboa, 4-6 Setembro de 2013

Nanofiltration of Cork Wastewaters and Their Possible Use in Leather Industry as Tanning Agents

Cork processing wastewater is a very complex mixture of vegetal extracts and has, among other natural compounds, a very high content of phenolic/tannic colloidal matter that is responsible for severe environmental problems. In the present work, the concentration of this wastewater by nanofiltration was investigated with the aim of producing a cork tannin concentrate to be utilized in tanning. Permeation results showed that the permeate fluxes are controlled by both osmotic pressure and fouling/gel layer phenomena, leading to a rapid decrease of permeate fluxes with the concentration factor. The rejection coefficients to organic matter were higher than 95%, indicating that nanofiltration has a very good ability to concentrate the tannins and produce a permeate stream depleted from organic matter. The cork tannin concentrate obtained by nanofiltration and evaporation had total solids concentration of 34.8 g/l. The skins tanned by this concentrate were effectively converted to leather with a shrinking temperature of 7 degrees C.