Capillary electrophoresis and hollow fiber liquid‐phase microextraction for the enantioselective determination of albendazole sulfoxide after biotransformation of albendazole by an endophytic fungus

Abstract

Hollow fiber liquid-phase microextraction and CE were applied for the determination of albendazole sulfoxide (ASOX) enantiomers in liquid culture medium after a fungal biotransformation study. The analytes were extracted from 1 mL of liquid culture medium spiked with the internal standard (rac-hydroxychloroquine) and buffered with 0.50 mol/L phosphate buffer, pH 10. The analytes were extracted into 1-octanol impregnated in the pores of the hollow fiber, and into an acid acceptor solution inside the polypropylene hollow fiber. The electrophoretic separations were carried out in 0.05 mol/L tris(hydroxymethyl)aminomethane buffer, pH 9.3, containing 3.0% w/v sulfated-β-CD (S-β-CD) with a constant voltage of +15 kV and detection at 220 nm. The method was linear over the concentration range of 250-5000 ng/mL for each ASOX enantiomer. Within-day and between-day assay precision and accuracy for the analytes were studied at three concentration levels and the values of RSD% and relative error % were lower than 15%. The developed method was applied for the determination of ASOX after a biotransformation study employing the endophytic fungus Penicillium crustosum (VR4). This study showed that the endophytic fungus was able to metabolize the albendazole to ASOX enantioselectively. In addition, it was demonstrated that hollow fiber liquid-phase microextraction coupled to CE can be an excellent and environmentally friendly technique for the analysis of samples obtained in biotransformation studies.

Microbial Biotransformation of Gentiopicroside by the Endophytic Fungus Penicillium crustosum 2T01Y01

“…crustosum has been found commonly in food, feed, and plants (28)(29)(30); has a wide range of biological functions; and possesses multienzyme systems with significant region selectivity and stereoselectivity (13,31), which have already been used to biotransform natural products (32,33), chemicals (12,34,35), and endogenous materials (13) to change their structures and bioactivities.…”

“…The heteronuclear multiplebond correlation spectroscopy (HMBC) spectrum (Fig. 4A) showed correlations between CH 2 (3) and C(1) and C (12), between H-C(6) and C (8), between H-C(8) and C(11) and C (12), between H-C(9) and C(6) and C (12), and between the methyl group and C(6) and C(5), respectively. With these correlations, the constitution of compound 2 could be deduced.…”

“…isolated from the tea plant Camelia sinensis (11). It has been documented that Penicillium crustosum could enantioselectively metabolize albendazole to albendazole sulfoxide (12) and biotransform testosterone into five reduction products, 5␣-dihydrotestosterone, dihydrotestosterone, 3␣-hydroxy-5␤-androstan-17-one, 3␣-hydroy-5␣-androstan-17-one, 4-androstene-3,17-dione, and 5␣-androstane-3,17-dione (13).…”

Estudos de metabolismo in vitro de produtos naturais: biotransformação microbiana da piplartina

“…O fungo P. crustosum VR4 também já biotransformou outras substâncias de forma similar ao metabolismo humano, como os fármacos propranolol, tioridazina, e albendazol, produzindo principalmente derivados hidroxilados e sulfoxidados (BORGES et al, 2009c;BORGES et al, 2008;CARRÃO et al, 2011). Dessa forma, esse micro-organismo endofítico se destaca, e, por isso, vem sendo amplamente utilizado por nosso grupo de pesquisa e por colaboradores em estudos de metabolismo de produtos naturais e fármacos (BARTH, 2012, BORGES, 2010BORGES, 2008 Provavelmente o fungo C. echinulata ATCC 8688a apresenta outros mecanismos de defesa para se proteger da piplartina, uma vez que não foi necessário alterar a estrutura dessa substância para manter se vivo.…”

Avaliação de modelos químicos e microbiológicos para o estudo de (bio)transformações do antibiótico monensina A

“…Os experimentos de biotransformação foram realizados conforme procedimentos previamente descritos em nosso grupo de pesquisa (BARTH et al, 2012;BOCATO et al, 2012;CARRAO et al, 2011;HILARIO et al, 2012 Paralelamente aos estudos de biotransformação foram realizados controles contendo: 1) somente o meio de cultura e a MonA; 2) somente o meio de cultura com fungo sem a presença da MonA, com adição de 300 µL de DMF.…”