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Quantification of Alpha-Amanitin in Biological Samples by HPLC Using Simultaneous UV

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Journal of Chromatography B, 997 (2015) 85–95 View metadata, citation and similar papers at core.ac.uk brought to you by CORE Contents lists available at ScienceDirect provided by Biblioteca Digital do IPB Journal of Chromatography B journal homepage: www.elsevier.com/locate/chromb Quantification of alpha-amanitin in biological samples by HPLC using simultaneous UV- diode array and electrochemical detection Juliana Garcia a,∗, Vera M. Costa a, Paula Baptista b, Maria de Lourdes Bastos a, Félix Carvalho a,∗ a REQUIMTE/Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Rua José Viterbo Ferreira n◦ 228, 4050-313 Porto, Portugal b CIMO/School of Agriculture, Polytechnic Institute of Braganc¸ a, Campus de Santa Apolónia, Apartado 1172, 5301-854 Braganc¸ a, Portugal article info abstract Article history: ␣-Amanitin is a natural bicyclic octapeptide, from the family of amatoxins, present in the deadly mush- Received 6 November 2014 room species Amanita phalloides. The toxicological and clinical interests raised by this toxin, require Received in revised form 27 May 2015 highly sensitive, accurate and reproducible quantification methods for pharmacokinetic studies. In the Accepted 4 June 2015 present work, a high-performance liquid chromatographic (HPLC) method with in-line connected diode- Available online 10 June 2015 array (DAD) and electrochemical (EC) detection was developed and validated to quantify ␣-amanitin in biological samples (namely liver and kidney). Sample pre-treatment consisted of a simple and unique Keywords: deproteinization step with 5% perchloric acid followed by centrifugation at 16,000 × g,4◦C, for 20 min. High-performance liquid chromatographic ␣ ≥ ␣ Diode-array The high recovery found for -amanitin ( 96.8%) makes this procedure suitable for extracting -amanitin Electrochemical from liver and kidney homogenates. The resulting supernatant was collected and injected into the HPLC. ␣-amanitin Mobile phase was composed by 20% methanol in 50 mM citric acid, and 0.46 mM octanessulfonic acid, adjusted to pH 5.5. The chromatographic runs took less than 22 min and no significant endogenous inter- ferences were observed at the ␣-amanitin retention time. Calibration curves were linear with regression coefficients higher than 0.994. The overall inter- and intra-assay precision did not exceed 15.3%. The present method has low interferences with simple and fast processing steps, being a suitable procedure to support in vivo toxicokinetic studies involving ␣-amanitin. In fact, the validated method was successfully applied to quantify ␣-amanitin in biological samples following intraperitoneal ␣-amanitin administration to rats. Moreover, human plasma was also used as matrix and the purposed method was adequate for detection of ␣-amanitin in that matrix. The results clearly indicate that the proposed method is suitable to investigate the pharmacokinetic and tissue distribution of ␣-amanitin. Additionally, the method will be very useful in the development of novel and potent antidotes against amatoxins poisoning and to improve the knowledge of ␣-amanitin toxicity. © 2015 Elsevier B.V. All rights reserved. 1. Introduction in this mushroom and is the main responsible for its toxic effects [1]. ␣-Amanitin produces hepatic and kidney failure, which result The main toxin of the amatoxins group, ␣-amanitin (Fig. 1)isa in a potentially fatal outcome in most of the human intoxication toxic bicyclic octapeptide present in the deadly mushroom species cases [2]. The underlying toxicity mechanisms of ␣-amanitin are Amanita phalloides. It represents up to 40% of the amatoxins present not completely understood, but it is well accepted that the inhi- bition of RNA polymerase II (RNAP II) is its main effect [3] . Other mechanisms also appear to be involved, including oxidative stress [4]. Abbreviations: HPLC, high-performance liquid chromatography; DAD, diode- So far, there is no specific and totally effective antidote array; EC, electrochemical; DNA, deoxyribonucleic acid; LOD, limit of detection; against A. phalloides poisoning. Benzylpenicillin, ceftazidime, N- LOQ, limit of quantification; LC, liquid chromatography; MS, mass spectrometry; acetylcysteine, and silybin are the most extensively used antidotes, RNA, ribonucleic acid; RNAP II, RNA polymerase II; RSD, relative standard deviation; SPE, solid phase extraction; UV, ultraviolet. however mortality remains high [5]. Currently, in vivo and in silico ∗ Corresponding authors. Fax: +351 22609339. studies are ongoing in search of effective antidotes, either directed E-mail addresses: jugarcia [email protected] (J. Garcia), [email protected] to the toxicokinetics or to the toxicodynamics of amatoxins [6–9] (F. Carvalho). http://dx.doi.org/10.1016/j.jchromb.2015.06.001 1570-0232/© 2015 Elsevier B.V. All rights reserved. 86 J. Garcia et al. / J. Chromatogr. B 997 (2015) 85–95 Fig. 1. Chemical structure of ␣-amanitin. In both approaches, it is expected that the development of more with a Milli-Q Plus ultra-pure water purification system (Millipore, insightful analytical and physiological methodologies will provide Bedford, Massachusetts, USA). essential tools for achieving this purpose. ␣ Besides the toxicological interest in -amanitin, recent findings 2.2. Chromatographic conditions indicate that ␣-amanitin is emerging as an attractive new class of potent anticancer drug [10]. For this clinical application, ade- HPLC analysis was performed using a Waters 2690 separa- quate analytical methodologies are also required for the evaluation tion module (Waters, Milford, MA, USA), and a 250 mm × 4.6 mm, ␣ of -amanitin pharmacokinetics, both in pre-clinical and clinical Waters Spherisorb RP-18 (5 ␮m) ODS2 column. The mobile phase studies. (20% methanol in 50 mM citric acid, 0.46 mM octanessulfonic acid, The comprehensive characterization of antidotes in A. phal- adjusted to pH 5.5 with 10 M NaOH) was filtered through a 0.45 ␮m loides poisoning and the pharmacokinetics and toxicokinetic membrane (Millipore, Madrid, Spain) and degassed. An isocratic ␣ studies of -amanitin require highly sensitive, accurate and elution was performed at a flow rate of 1.0 mL/min, at room temper- reproducible quantification assays. Currently, there are several ature. Sample aliquots of 20 ␮L were injected. A Compaq computer high-performance liquid chromatography (HPLC)–ultraviolet (UV) fitted with Millenium32 software (Waters) processed the chro- [11–17], liquid chromatography (LC)–mass spectrometry (MS) matographic and spectral data. [18–20] and ultra performance liquid chromatography (UPLC)- For the spectroscopic and coulochemical analysis, a photodi- ␣ MS/MS [21] methods to determine -amanitin in mushrooms, liver ode array detector (Waters model 996) and/or a Colouchem II ␣ and biological fluids (Table 1). HPLC-MS methods for -amanitin (ESA, Chelmsford, USA) equipped with a guard cell (ESA 5020) and detection are accurate, sensitive, and specific; nevertheless HPLC- analytical cell (ESA 5011A) electrochemical detector were used. MS is an expensive technique and is not available in many In all the studies, both detectors were used, with the analytical laboratories. To date there are no published HPLC with electro- cell of the coulochemical detector placed after the photodiode ␣ chemical (EC) detection methods for the analysis of -amanitin in array detector. The electrochemical potential settings of Coulochem biological tissues. Hence, in this paper, we describe a simple acidic II detector were: guard cell, −550 mV, and analytical detector + extraction and HPLC methodology with in-line connected photodi- 500 mV, following a previous reported procedure [22]. A current ␣ ode array detection (DAD) and EC detection to quantify -amanitin of 5 ␮A full-scale was used. Ultraviolet-visible spectra were col- in rat liver and kidney. Moreover, we applied the validated method lected for all samples between from 230 to 400 nm. For quantitative ␣ to identify -amanitin in human plasma. The validated method analyses, chromatograms were integrated at 305 nm [15]. was successfully applied to quantify ␣-amanitin in plasma, liver and kidney tissues following intraperitoneal administration to rats. The new method provides the required high analytical sensitivity 2.3. Stock solution and calibration standards and reproducibility, with a simple and fast pretreatment, as it is ␣ required for advanced pharmacokinetic and toxicokinetic research. A stock solution of -amanitin was prepared in water Milli-Q and diluted to a final concentration of 1 mg mL−1. All stock solu- tions were stored of −20 ◦C. A set of eleven standards ranging from 0.025 ␮gmL−1 to 10 ␮gmL−1 were prepared at the moment of 2. Material and methods use by spiking the rat liver and kidney samples with appropriate amounts of ␣-amanitin. All calibration standards were prepared in 2.1. Reagents and chemicals triplicate. ␣-Amanitin (>99%), bovine serum albumin, and 1- 2.4. Animals and sample preparation octanesulfonic acid sodium salt were purchased from Sigma-Aldrich (St. Louis, MO, USA). Analytical HPLC grade The liver and kidney tissues were obtained from adult male methanol was obtained from Fisher Scientific (Waltham, Mas- Wistar rats. These animals were used as healthy controls in other sachusetts, USA). Sodium chloride (NaCl), potassium chloride experiments, where liver and kidney were not necessary. A mini- (KCl), sodium hydrogen phosphate (Na2HPO4), potassium dihy- mum number of animals was used in order to obtain valid results. drogen phosphate
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