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- Biodegradation of chiral pharmaceuticals by an activated sludge consortium followed by a Chiral HPLC-FDPublication . Ribeiro, Ana R.; Castro, P. M. L.; Afonso, Carlos; Tiritan, MariaBiodegradation tends to be enantioselective in contrast to abiotic degradation and it is necessary enantioselective analytical methods to quantify the enantiomeric fraction of chiral pharmaceuticals in the environment for correct risk assessment. In this work, we developed HPLC-FD methods to follow the biodegradation of four beta-blockers: alprenolol , propranolol , metoprolol and atenolol and the antidepressant fluoxetine during 15 days in batch mode. The biodegradation assays were performed using AS from the aerated tanks of a municipal wastewater treatment plant with a singly compound supplementation and a mixture compound supplementation similar to those found in wastewater influents. Abiotic degradation in the presence of light and in the dark was evaluated. Either the low concentration or the mixture effects are situations closer to those found in the environment. The results indicate the higher degradation extents for the S-enantiomer forms, as is shown in Figure 1.
- Degradation of fluoroanilines by the wild strain Labrys portucalensisPublication . Amorim, Catarina L.; Carvalho, Maria F.; Afonso, Carlos M. M.; Castro, Paula M. L.Aromatic amine compounds, many of them with halogenated substituents, constitute a major class of environmental pollutants that have been released into soil and water due to extensive use in industries and agriculture. Biodegradation has been found to be a major route for the removal of this kind of toxic and recalcitrant pollutants from the environment. Whereas the degradation of mono- and dichlorinated anilines has been studied, very little is known about fluorinated anilines. Therefore, the objective of this study was to investigate, under aerobic conditions, the degradation of 2-, 3- and 4-fluoroaniline by a previously isolated pure bacterium, designated as strain F11. This microorganism, identified as Labrys portucalensis, was isolated from a contaminated site in northern Portugal and has the unique capacity to utilize fluorobenzene as a sole carbon and energy source,. The results of the biodegradation of 2-, 3- and 4-fluoroaniline by strain F11 showed that this microorganism is able to completely degrade 2- fluoroaniline and partially degrade 4-fluoroaniline, when these compounds are present as a sole carbon and energy source. Biodegradation of these two compounds also occurred, although at a lower rate, in the absence of an external nitrogen source in the culture medium. To our knowledge, this is the first study reporting the biodegradation of 2- and 4-fluoroaniline as a sole carbon and energy source by a pure microbial culture. C.L. Amorim and M.F. Carvalho wish to acknowledge a research grant from Fundação para a Ciência e Tecnologia (FCT), Portugal (Ref. SFRH/BD/47109/2008 and SFRH/BPD/44670/2008, respectively) and Fundo Social Europeu (III Quadro Comunitário de Apoio). This work was supported by the FCT Project - PTDC/BIO/67306/2006
- Microbial degradation of 17β -estradiol and 17α -ethinylestradiol followed by a validated HPLC-DAD methodPublication . Ribeiro, Ana R.; Carvalho, Maria F.; Afonso, Carlos M. M.; Tiritan, Maria E.; Castro, Paula M.L.This work aimed at studying the biodegradation of two estrogens, 17agr -estradiol (E2) and 17β -ethinylestradiol (EE2), and their potential metabolism to estrone (E1) by microbial consortia. The biodegradation studies were followed by High Performance Liquid Chromatography-Diode Array Detector (HPLC-DAD) using a specifically developed and validated method. Biodegradation studies of the estrogens (E2 and EE2) were carried out with activated sludge (consortium A, CA) obtained from a Wastewater Treatment Plant (WWTP) and with a microbial consortium able to degrade recalcitrant compounds, namely fluorobenzene (consortium B, CB). E2 was more extensively degraded than EE2 by CA whereas CB was only able to degrade E2. The addition of acetate as a supplementary carbon source led to a faster biodegradation of E2 and EE2. E1 was detected as a metabolite only during the degradation of E2. The 16S rRNA gene sequence analyses of strains recovered from the degrading cultures revealed the presence of the genera Pseudomonas, Chryseobacterium and Alcaligenes. The genera Pseudomonas and Chryseobacterium were retrieved from cultures supplied with E2 and EE2, while the genus Alcaligenes was found in the presence of E2, suggesting that they might be involved in the degradation of these compounds.
- Potential of ectomycorrhizal fungus Pisolithus tinctorius to tolerate and to degrade trifluoroacetate into fluoroformPublication . Franco, Albina R.; Ramos, Miguel A.; Cravo, Sara; Afonso, Carlos; Castro, Paula M. L.Trifluoroacetate (TFA) is a persistent fluorinated organic compound originated from the degradation of fluorinated compounds, such as HCFC and isoflurane, or as a side product from the thermolysis of fluoropolymers, like Teflon. TFA can reach soil through precipitation, where it persists in water and soil, and may contribute to forest decline. In this study, we assessed the capacity of P. tinctorius, an ectomycorrhizal fungus (ECMF), to tolerate and/or degrade TFA. In vitro studies in glucose-supplemented solid medium showed that the fungus tolerated up to 8.77 mM TFA. P. tinctorius also degraded 88.3 %, 89.9 %, and 42.1 % of 0.88, 2.39, and 4.39 mM TFA, respectively, in liquid cultures. No TFA accumulation was detected on the fungus mycelium, suggesting that TFA depletion was due to fungal degradation. Defluorination was not detected. A volatile compound with a structure and behavior compatible with fluoroform (CHF3), a potent greenhouse gas, was detected using GC-MS/MS, only in the gas phase of sealed P. tinctorius cultures supplied with TFA. Further confirmation of this compound is needed. Nevertheless, the study shows that P. tinctorius was capable to degrade TFA possibly through a similar pathway to that found on marine sediments. The results evidence the role of ECMF may play in the degradation of fluorinated organic compounds, enhancing their potential contribution on establishing tree growth in soils exposed to organic contamination.
- Chemical reactivity of paraquat with the previously validated antidote, sodium salicylatePublication . Dinis-Oliveira, Ricardo; Pinho, Paula Guedes de; Ferreira, António César Silva; Silva, Artur; Afonso, Carlos; Bastos, Maria de Lourdes; Remião, Fernando; Duarte, José Alberto
- Remoção de fluoroquinolonas do ambiente: biossorção a lamas ativadas e a grânulos aeróbiosPublication . Ferreira, Vanessa R. A.; Amorim, Catarina L.; Cravo, Sara M.; Tiritan, Maria E.; Castro, Paula M. L.; Afonso, Carlos M. M.Diversas matrizes ambientais, particularmente águas residuais, têm revelado a presença de antibióticos. Embora presentes em níveis vestigiais (ng.L-1 a µg.L-1,), estes compostos são pseudo-persistentes e, naquelas concentrações, podem também promover resistências nas populações bacterianas [1]. Estudos recentes de remoção de antibióticos com lamas ativadas (AS) e grânulos aeróbios (AGS) mostram a biossorção como processo dominante e eficaz na remoção destes micropoluentes [2,3]. O presente trabalho explorou a biossorção de três fluoroquinolonas (FQ) - ofloxacina (OFL), norfloxacina (NOR) e ciprofloxacina (CPF) - a AS e AGS. Com vista a uma melhor compreensão dos fenómenos que ocorrem durante o processo, foram estudados diversos parâmetros que condicionam a biossorção. As AS demonstraram melhor desempenho na remoção da OFL, NOR e CPF relativamente aos AGS. No entanto, nas concentrações estudadas, não foi possível promover a remoção total dos fármacos. A capacidade mais elevada de biossorção das AS foi atribuída à carga negativa da superfície da biossorção, representada por um potencial zeta de -25,65 mV, a pH 7. A OFL foi a FQ menos removida, tanto pelas AS como pelos AGS, porque a OFL a pH 7 está principalmente presente na forma aniónica, com uma pequena percentagem, na forma zwiteriónica. Em AGS verifica-se um aumento da biossorção da OFL, NOR e CPF em pH ácido (pH 4) e maior dessorção em pH alcalino (pH 8 a 9). Observou-se também que ocorre a destruição da estrutura granular dos AGS quando o pH do meio é igual ou inferior a 3. Os resultados obtidos neste estudo contribuem para uma utilização mais eficaz de AS e AGS na remoção de antibióticos fluoroquinolonas do ambiente.
- Fármacos quirais em diferentes matrizes ambientais: ocorrência, remoção e toxicidadePublication . Ribeiro, Ana R.; Afonso, Carlos; Castro, Paula M. L.; Tiritan, Maria E.In recent decades, the occurrence of pharmaceuticals in the environment has been widely reported due to their high frequency and recalcitrance in many cases. Concerning the chiral pharmaceuticals (CPs) in environmental matrices, the stereochemistry is often neglected and enantiomers are determined together as unique molecules. However, it is well known that CPs might have enantioselective toxicity, rendering important to assess the occurrence and degradation processes of single enantiomers in the environment, namely during biological treatment in wastewater treatment plants (WWTPs). The development of analytical methods to qualitatively and quantitatively evaluate the enantiomers of CPs is crucial for determining enantiomeric fraction (EF). The EF is the most important parameter in studies involving enantiomers and enantioselective processes and fundamental in biodegradation studies and wastewater monitoring. This review summarizes the analytical methods used to determine EF of CPs in environmental matrices and/or during biodegradation processes. The occurrence of CPs in the environment and their biodegradation are reviewed and future trends in the area outlined.
- Enantioselective Degradation of Enantiomers of Fluoxetine Followed by HPLC- FDPublication . Ribeiro, Ana R.; Maia, Alexandra S.; Moreira, Irina S.; Afonso, Carlos; Castro, Paula M.L.; Tiritan, Maria E.Environmental fate assessment of chiral pharmaceuticals is an important issue and little information is known about enantioselectivity in the environment. This kind of information is important for regulamentation of pharmaceutical industry and chiral switching processes. Fluoxetine (FLX), an anti-depressant worldwide used, is a chiral pharmaceutical prescribed in racemic form, and its main metabolite norfluoxetine (NFLX) is also chiral. In this study, enantioselective degradation of rac-FLX and degradation of its enantiomers separately, in a minimal salts medium inoculated by a bacterium consortium was examined both at light and dark conditions. Theassays were performed in a shaker at aerobic and ambient temperature conditions. The analytical method used was an enantioselective HPLC-FD method using a vancomycin-based chiral stationary phase in reversed mode to monitor enantiomers of FLX and NFLX. No degradation of enantiomers of FLX in the abiotic controls was observed. In theall assays (R)-FLX was degraded faster and totally until day 24th while (S)-FLX remained up to 20% of its initial concentration until the end of the experiment (38 days). NFLX wasdetected in all biotic experiments.
- Pé diabéticoPublication . Afonso, Carlos; Carvalho, P.; Xavier, A.; Dias, Vanessa; Alves, Paulo
- Mineralization of 4-fluorocinnamic acid by a Rhodococcus strainPublication . Amorim, Catarina L.; Ferreira, António César Silva; Carvalho, M.F.; Afonso, Carlos M. M.; Castro, Paula M.L.A bacterial strain capable of aerobic degradation of 4-fluorocinnamic acid (4-FCA) as the sole source of carbon and energy was isolated from a biofilm reactor operating for the treatment of 2-fluorophenol. The organism, designated as strain S2, was identified by 16S rRNA gene analysis as a member of the genus Rhodococcus. Strain S2 was able to mineralize 4-FCA as sole carbon and energy source. In the presence of a conventional carbon source (sodium acetate [SA]), growth rate of strain S2 was enhanced from 0.04 to 0.14 h−1 when the culture medium was fed with 0.5 mMof 4- FCA, and the time for complete removal of 4-FCA decreased from 216 to 50 h.When grown in SA-supplemented medium, 4-FCA concentrations up to 1 mM did not affect the length of the lag phase, and for 4-FCA concentrations up to 3 mM, strain S2 was able to completely remove the target fluorinated compound. 4-Fluorobenzoate (4-FBA) was transiently formed in the culture medium, reaching concentrations up to 1.7 mM when the cultures were supplemented with 3.5mMof 4-FCA. Trans,trans-muconate was also transiently formed as a metabolic intermediate. Compounds with molecular mass compatible with 3-carboxymuconate and 3-oxoadipate were also detected in the culture medium. Strain S2 was able to mineralize a range of other haloorganic compounds, including 2- fluorophenol, to which the biofilm reactor had been exposed. To our knowledge, this is the first time that mineralization of 4-FCA as the sole carbon source by a single bacterial culture is reported.
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