Papers by Cláudia Maria Oliveira Simões
Marine Drugs, 2019
The marine sponge Raspailia bouryesnaultae, collected in South Brazil, was selected for detailed ... more The marine sponge Raspailia bouryesnaultae, collected in South Brazil, was selected for detailed investigation considering the results of a screening that pointed to an in vitro antiproliferative effect against non-small cells of human lung cancer (A549) and anti-herpes activity against Herpes Simplex virus type 1 (KOS and 29R strains) of ethanolic extracts. The fractionation and chemical investigation of the sponge’s hexanic fraction led to the isolation and structural elucidation of six clerodane diterpenes. The main component was identified as the already-reported raspailol (1), isolated from a sponge of the same genus collected in New Zealand. The structure of a new diterpene (2) with a rearranged skeleton was established by high-resolution mass spectrometry (HRMS) and 1D and 2D Nuclear magnetic resonance spectroscopy (NMR) experiments, and named here as raspadiene. Furthermore, four diterpenes were elucidated as isomers of clerodane diterpenes previously obtained from plants, n...
European Polymer Journal, 2018
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, Jan 14, 2018
Several beneficial effects on the skin have been reported for coumestrol (COU), such as protectio... more Several beneficial effects on the skin have been reported for coumestrol (COU), such as protection against photoaging and improvement of skin elasticity and thickness in postmenopausal women. However no reports on the effect of COU on wound healing were found. Nevertheless, COU has low aqueous solubility, which is a crucial limitation for biological tests. The present study was designed as a two-step experiment to evaluate the wound healing effect of COU. First, we used fibroblasts and the experimental in vitro artificial wound model, scratch assay, to compare the effects of COU free, dissolved in dimethyl sulfoxide (DMSO) or Dulbecco's modified Eagle's medium (DMEM), or associated with hydroxypropyl-β-cyclodextrin (HPβCD). The 50 μM (66.1%) and 10 μM (56.3%) COU/HPβCD association induced cell proliferation and migration in inflicted wounds. Subsequently, the in vivo wound healing experimental model (Wistar rats) revealed that COU/HPβCD incorporated into hypromellose (HPMC) ...
Industrial Crops and Products, 2017
Although various compounds from Ilex paraguariensis present high antioxidant activity, limitation... more Although various compounds from Ilex paraguariensis present high antioxidant activity, limitations in terms of chemical stability may be found, impacting on the formulation step. In this context, nanotechnology may be alternatively used to provide an additional protection for these compounds, avoiding degradative reactions. Different formulation parameters (eg. particle size, zeta potential, internal phase fraction) were assayed to maximize a local antioxidant action. Firstly, the extraction procedure for obtaining increased concentrations of antioxidant compounds was optimized. High stirring speed and ethanol as extractor liquid were defined as key parameters. Nanoparticles were prepared by double emulsion solvent evaporation technique. Polycaprolactonebased nanoparticles showed to be more stable than poly(lactic-co-glycolic acid)-based nanoparticles. Instead of poly(vinyl alcohol), Pluronic ® was selected as surfactant because it avoids aggregate formation and provides smaller particle size. While higher polymer content contributes positively to maintaining both reduced size particle and distribution, an increased extract concentration impacted negatively on these parameters. Stability studies were also performed using skin extracts and homogenates and confirmed that nanostructures provide an additional protection. Moreover, the incorporation of Ilex extract in nanoparticles significantly reduced the amount of chlorogenic acid permeated through the skin (no ex vivo permeation until 12 h for this system), extending its topical antioxidant effect.
Journal of Applied Microbiology, 2016
AAPS PharmSciTech, Jan 5, 2017
We have recently shown that coumestrol, an isoflavonoid-like compound naturally occurring in soyb... more We have recently shown that coumestrol, an isoflavonoid-like compound naturally occurring in soybeans, alfafa, and red clover, inhibited Herpes Simplex Virus types 1 (HSV-1) and 2 (HSV-2) replication. In this study, we designed coumestrol formulations in an attempt to enable its topical delivery to mucosa tissues. Physicochemical and microscopic examinations suggested that coumestrol was efficiently incorporated in positively-charged nanoemulsions dispersed in a hydroxyethylcellulose gel. The higher coumestrol flux through excised porcine esophageal mucosa was detected from nanoemulsions composed by a fluid phospholipid (dioleylphosphocholine, DOPC) in comparison with that of a rigid one (distearoylphosphocholine, DSPC) in two mucosa conditions (intact and injured). Such results were supported by confocal fluorescence images. Furthermore, the low IC50 values demonstrated an increasement in the antiviral inhibition against HSV-1 and HSV-2 after incorporation of coumestrol into nanoem...
VIRUS Reviews & Research, 2001
Biocatalysis and Agricultural Biotechnology, 2015
Abstract Ultrasound-assisted system is promising for chemical synthesis. This study aimed the pro... more Abstract Ultrasound-assisted system is promising for chemical synthesis. This study aimed the production of ascorbyl oleate catalyzed by lipase Novozym® 435 in organic solvent using ultrasound-assisted system. Different organic solvents and solvent concentration were tested at 70 °C using 1:9 M ratio ascorbic acid:oleic acid. The solubility was evaluated by visual analysis after 40 min of stirring substrates and solvent. By this procedure, 20 mL of tert-butanol was defined as the best solvent for the reaction. The maximized conditions for ascorbyl oleate production in the ultrasound-assisted system were determined by evaluating the temperature, enzyme concentration and molecular sieves influence in the kinetics reaction. At the end of reaction the best conditions obtained for the maximal ascorbyl oleate conversion was molar ratio ascorbic acid:oleic acid, 1:9, 20 mL tert-butanol, 70 °C, 5 wt% Novozym® 435, 20 wt% molecular sieve, 100% ultrasound power and 12 h reaction, resulting in 87% of ascorbyl oleate conversion. Without the use of molecular sieve, the kinetic study pointed the maximized experimental condition conversions of 66% after 3 h of reaction.
Química Nova, 2015
In this study, nifedipine (NFP)-loaded polymeric nanocapsules were prepared and characterised wit... more In this study, nifedipine (NFP)-loaded polymeric nanocapsules were prepared and characterised with a view to protect the drug from degradation. Nanocapsule suspensions were prepared using two different surfactants (pluronic F68 and polyvinyl alcohol). Physicochemical stability and in vivo antihypertensive effect were evaluated. The particle size, zeta potential and entrapment efficiency remained constant during a period of 28 days of exposure under light irradiation. A smaller particle size and a higher zeta potential were obtained for the nanocapsules prepared with Pluronic F68 as surfactant. The solid drug and the nanocapsules were submitted to light exposure for 28 days. After this period of time, the percentage of drug remaining in the PF68NFP and PVANFP nanocapsules was 28.1% and 21.3%, respectively. In contrast, the solid drug was completely degraded after 4 days, suggesting that the nanocapsule suspensions promoted significant protection of the drug against light exposure. In addition, in vivo studies were carried out, which demonstrated that the formulations with polyvinyl alcohol exhibited a very rapid onset of action after oral administration in rats and led to faster drug release. The nanoparticles developed can be considered as an alternative for improving NFP stability in liquid formulations.
Industrial Crops and Products, 2014
Topical administration of flavonoids from Achyrocline satureioides extracts provides a promising ... more Topical administration of flavonoids from Achyrocline satureioides extracts provides a promising opportunity in the treatment of various skin disorders. This study describes the simultaneous incorporation of quercetin, luteolin and 3-O-Methylquercetin (3-O-MQ) from liquid or dried ethanolic extracts into topical nanoemulsions by a spontaneous emulsification procedure. By using of liquid plant extract (up to 1% of extract dry residue), this procedure resulted in monodispersed nanoemulsions exhibiting a droplet size at a 200 nm range, as attested by transmission electron microscopy. Flavonoids seem to be located in the oil phase of nanoemulsions since they are not detected in the water phase after separation on ultrafiltration membranes. Similar results were obtained when freeze-or spray-dried ethanolic extracts were used. Regardless of the extract type, 3-O-MQ release rate was influenced by the extract content into nanoemulsion achieving approximately 90% released after 8 h of kinetics. First order model provides the most satisfactory fitting of the release data from extracts-nanoemulsions. Higher amount of 3-O-MQ was found in the porcine ear skin after topical application of nanoemulsions containing the extract before drying procedures. The involvement of others extract compounds in 3-O-MQ retention can be suggested. Such results indicate that nanoemulsions are potential carriers for skin delivery of Achyrocline satureioides flavonoids.
Phytochemistry, 2013
Polyacetylenes constitute an underexplored and unstable class of compounds that are found mainly ... more Polyacetylenes constitute an underexplored and unstable class of compounds that are found mainly in the Apiaceae, Araliaceae and Asteraceae families. Vernonia scorpioides (Lam.) Pers., Asteraceae is a lianous neotropical herb that usually grows in soils that have been deforested and are of poor quality. It is used in folk medicine for the treatment of several skin conditions. This study addresses the characterisation of eight polyacetylenes isolated from the leaves of V. scorpioides. Their structures were established on the basis of 1D and 2D NMR spectroscopy and MS analysis. Ab initio calculations including solvent effects were employed to aid the elucidation of the absolute configurations of the compounds. The in vitro antiproliferative and anti-herpetic activities of the polyacetylenes were determined. The isolated compounds presented no inhibitory effect against a human cell line of non-small cell lung cancer, but presented a mild non-selective in vitro antiviral activity, although their corresponding glycosides were inactive.
Marine drugs, Jan 4, 2014
Five new polyoxygenated marine steroids-punicinols A-E (1-5)-were isolated from the gorgonian Lep... more Five new polyoxygenated marine steroids-punicinols A-E (1-5)-were isolated from the gorgonian Leptogorgia punicea and characterized by spectroscopic methods (IR, MS, 1H, 13C and 2-D NMR). The five compounds induced in vitro cytotoxic effects against lung cancer A549 cells, while punicinols A and B were the most active, with IC50 values of 9.7 μM and 9.6 μM, respectively. The synergistic effects of these compounds with paclitaxel, as well as their effects on cell cycle distribution and their performance in the clonogenic assay, were also evaluated. Both compounds demonstrated significant synergistic effects with paclitaxel.
Revista Brasileira de Farmacognosia, 2011
The exploration of marine environment represents a promising strategy in the search for new activ... more The exploration of marine environment represents a promising strategy in the search for new active antiviral compounds. The isolation and characterization of the nucleosides spongothymidine and spongouridine from the sponge Cryptotethia crypta used as models for the synthesis of ara-A (vidarabine), that has been used therapeutically against herpetic encephalitis, was the most important contribution since the late 1970s. This paper describes the in vitro antiviral evaluation of 26 organic extracts obtained from eleven octocoral species and fi fteen marine sponges. Cytotoxicity was evaluated on Vero cells by MTT assay and the antiviral activity was tested against Herpes Simplex Virus type 1 (HSV-1, KOS strain) by plaque number reduction assay. Results were expressed as 50% cytotoxic (CC50) and 50% inhibitory (IC50) concentrations, respectively, in order to calculate the selectivity index (SI= CC50/IC50) of each extract. Among the tested marine octocoral species, only three extracts showed antiviral activity, but with low selectivity indices (≤3.0). Among the tested marine sponges, eight extracts showed SI values higher than 2.0, and three can be considered promising (Aka cachacrouense, Niphates erecta and Dragmacidon reticulatum) with SI values of 5.0, 8.0 and 11.7, respectively, meriting complementary studies in order to identify the bioactive components of these sponge extracts, which are in course now.
Molecules, 2013
This manuscript describes the evaluation of anti-infective potential in vitro of organic extracts... more This manuscript describes the evaluation of anti-infective potential in vitro of organic extracts from nine sponges, one ascidian, two octocorals, one bryozoan, and 27 seaweed species collected along the Brazilian coast. Antimicrobial activity was tested against Staphylococcus aureus (ATCC 25923), Enterococcus faecalis (ATCC 29212), Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 25922) and Candida albicans (ATCC 10231) by the disk diffusion method. Antiprotozoal activity was evaluated against Leishmania braziliensis (MHOM/BR/96/LSC96-H3) promastigotes and Trypanosoma cruzi (MHOM/BR/00/Y) epimastigotes by MTT assay. Activity against intracellular amastigotes of T. cruzi and L. brasiliensis in murine macrophages was also evaluated. Antiviral activity was tested against Herpes Simplex Virus type 1 (HSV-1, KOS strain) by the plaque number reduction assay (IC 50). Cytotoxicity on VERO cells was evaluated by the MTT assay (CC 50). The results were expressed as SI = CC 50 /IC 50. The most promising antimicrobial results were obtained against S. aureus and C. albicans with Dragmacidon reticulatum. Among the seaweeds, only Osmundaria obtusiloba showed moderate activity against P. aeruginosa. Concerning antiprotozoal activity, Bugula neritina, Carijoa riseii, Dragmaxia anomala and Haliclona (Halichoclona) sp. showed the most interesting results, mainly against extracellular promastigote forms of L. braziliensis (66, 35.9, 97.2, and 43.6% inhibition, respectively). Moreover, six species of seaweeds Anadyomene saldanhae, Caulerpa cupressoides, Canistrocarpus cervicornis, Dictyota sp., Ochtodes secundiramea, and Padina sp. showed promising results against L. braziliensis (87.9, 51.7, 85.9, 93.3, 99.7, and 80.9% inhibition, respectively), and only Dictyota sp. was effective against T. cruzi (60.4% inhibition). Finally, the antiherpes activity was also evaluated, with Haliclona (Halichoclona) sp. and Petromica citrina showing the best results (SI = 11.9 and SI > 5, respectively). All the active extracts deserve special attention in further studies to chemically characterize the bioactive compounds, and to perform more refined biological assays.
Journal of Food Science, 2002
The goal of this work was to examine the use of cell culture and immunofluorescence assays to det... more The goal of this work was to examine the use of cell culture and immunofluorescence assays to detect viable rotaviruses in artificially seeded oyster meat and to determine if the method for oyster extracts preparation affects the viability of the viruses. Oyster tissues were seeded with rotavirus SA11, followed by tissue extract preparation. For cytopathogenicity assays (CPE), non-cytotoxic dilutions of seeded oyster extracts were inoculated in MA 104 cells. For immunofluorescence assays (IFA) the monoclonal antibody Mab M60 anti-VP7 capsid glycoprotein of rotavirus was used. For CPE tests, no significant difference between the oyster extracts inoculated with rotavirus before and after extract preparation was detected. Similar results have been observed in IFA assays and the recoveries of viable rotavirus obtained were close to 100%.
Caderno de farmácia. …, 1985
Page 1. Caderno de Farmácia, v. 1, n. 1, p. 45-54, 1985. http://www.ufrgs.br/farmacia/cadfar digi... more Page 1. Caderno de Farmácia, v. 1, n. 1, p. 45-54, 1985. http://www.ufrgs.br/farmacia/cadfar digitalizado do original: Caderno de Farmácia, v. 1, n. 1, p. 45-54, 1985. ESTUDOS FARMACOLÓGICOS PRELIMINARES DAS RAÍZES DO LIMONIUM BRASILIENSE (BOISS.) ...
Archives of Pharmacal Research, 2013
Solid dispersions of saquinavir mesylate containing either Gelucire® 44/14 or poly(ethylene glyco... more Solid dispersions of saquinavir mesylate containing either Gelucire® 44/14 or poly(ethylene glycol) (PEG) 4000, or mixtures of each carrier with Tween 80 or polyvinyl pyrrolidone (PVP) K30 were prepared in order to enhance the drug dissolution rate. These systems were prepared by the melting method and characterized by X-ray powder diffraction, microscopical techniques, and Raman spectroscopy aiming to establish a relationship between physicochemical and dissolution properties under different cooling conditions. Modifications in degree of crystalline order/disorder over time were observed in preparations with both carriers. Overall, formulations cooled and stored at -20 °C showed less variation in dissolution rates than those at 25 °C. Although Tween 80 has enhanced the known self-emulsifying properties of Gelucire® 44/14, its combination with PEG 4000 displayed miscibility problems. The addition of PVP K30 was not the most effective approach in enhancing the dissolution in early steps; however, the drug dissolution was stable after 7 days of storage at 25 °C. The combination of PEG 4000 and PVP K30 maintained the dissolution properties for 60 and 90 days at 25 °C/95% relative humidity and 40 °C/75% (f₂ values >50), respectively.
Antiviral Research, 2011
Sulfated polysaccharides are good candidates for drug discovery in the treatment of herpetic infe... more Sulfated polysaccharides are good candidates for drug discovery in the treatment of herpetic infections. Agaricus brasiliensis (syn A. subrufescens, A. blazei) is a Basidiomycete fungus native to the Atlantic forest region of Southeastern Brazil. Herein we report the chemical modification of a polysaccharide extracted from A. brasiliensis mycelia to obtain its sulfated derivative (MI-S), which presented a promising inhibitory activity against HSV-1 [KOS and 29R (acyclovir-resistant) strains] and HSV-2 strain 333, with selectivity indices (SI = CC50/IC50) higher than 439, 208, and 562, respectively. The mechanisms underlying this inhibitory activity were scrutinized by plaque assay with different methodological strategies. MI-S had no virucidal effects, but inhibited HSV-1 and HSV-2 attachment, penetration, and cell-to-cell spread, as well as reducing the expression of HSV-1 ICP27, UL42, gB, and gD proteins. MI-S also presented synergistic antiviral effect with acyclovir. These results suggest that MI-S presents multiple modes of anti-HSV action.
Investigational New Drugs, 2016
Cucurbitacins and their derivatives are triterpenoids that are found in various plant families, a... more Cucurbitacins and their derivatives are triterpenoids that are found in various plant families, and are known for their pharmacological and biological activities, including anti-cancer effects. Lung cancer represents a major public health problem, with non-small-cell lung cancer (NSCLC) being the most frequent and aggressive type of lung cancer. The objective of this work was to evaluate four cucurbitacins (CUCs) for their cytotoxic activity, effects on apoptosis induction, cell cycle progression, anti-migratory, and anti-invasive effects on the human NSCLC cell line (A549 cells). Our findings showed that these CUCs could suppress human NSCLC cell growth in vitro through their effects on the PI3Kinase and MAPK pathways, which lead to programmed cell death induction, as well as inhibition of cell migration and cell invasion. Additionally, these effects culminate in apoptosis induction and G2/M cell cycle arrest by modulating cyclin B1 expression, and in the mitigation of strategic steps of lung cancer metastasis, including migration and invasion of A549 cells. These results suggest that two natural (DDCB and CB) and two novel semisynthetic derivatives of cucurbitacin B (ACB and DBCB) could be considered as promising compounds with antitumor potential.
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Papers by Cláudia Maria Oliveira Simões