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Validation of a Microwave-Assisted Micellar Extraction Method for the Oxibendazole Determination in Soil Samples

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Validation of a Microwave-Assisted Micellar Extraction Method for the Oxibendazole Determination in Soil Samples Validation of a microwave-assisted micellar extraction method for the oxibendazole determination in soil samples María del Mar Gil-Díaz*1,2, Araceli Pérez-Sanz1, María Carmen Lobo1 1 IMIDRA Finca “El Encín” A-2 Km 38,2. 28800 Alcalá de Henares (Madrid) Spain. 2 Facultad de Veterinaria, UCM. Avda. Puerta de Hierro s/n. 28040 Madrid. Spain. Validación de un método de extracción micelar en microondas para la determinación de oxibendazole en muestras de suelo Validació d’un mètode d’extracció micel·lar en microones per a la determinació d’oxibendazole en mostres de sòl Recibido: 15 de junio de 2012; revisado: 5 de septiembre de 2012; aceptado: 13 de septiembre 2012 RESUMEN urine by grazing animals, or indirectly, when manure of treated farm animals are used as soil organic amendment. El oxibendazol es un fármaco veterinario utilizado como In this work, a simple, fast, reliable and sensitive method antihelmíntico para animales domésticos y de granja. Di- based on microwave-assisted micellar extraction (MAME) cho fármaco puede introducirse en el medio bien direc- procedure, using Genapol X-080 (0.5%) as surfactant, has tamente, a través de las heces o la orina, o bien indirec- been developed for the quantification of oxibendazole in tamente, cuando se utilizan residuos ganaderos como soil samples. Two classical methods, based on mecha- enmienda orgánica sobre suelos agrícolas. En este tra- nical shaking and ultrasonic assisted extraction followed bajo se ha desarrollado un método sencillo, rápido, fia- by solid phase extraction, were compared with the MAME ble y sensible basado en el proceso de extracción micelar procedure. Oxibendazole was determined by high-perfor- en microondas (MAME), usando Genapol X-080 (0.5%) mance liquid chromatography (HPLC) with fluorescence como surfactante, para la cuantificación de oxibendazol detector. In the optimization of the MAME procedure were en muestras de suelo. Dos métodos clásicos basados en evaluated four parameters: surfactant volume, stirring, agitación mecánica y por ultrasonidos seguidos de una irradiation power and extraction time. Optimum conditions extracción en fase sólida, fueron comparados con el pro- were 20 ml of Genapol X-080 (0.5%), irradiation power of ceso MAME. El oxibendazol fue determinado mediante 1000 W, extraction time of 2 minutes and stirring. At the- cromatografía liquida de alta eficacia (HPLC) con detector se MAME conditions, good recoveries (around 90%) were de fluorescencia. En la optimización del proceso MAME obtained, significantly higher than those found by classi- se evaluaron cuatro parámetros: volumen de surfactan- cal method (below 55%). Two different soils from Madrid te, agitación, potencia de irradiación y tiempo de extrac- (central Spain) were included in the study. Results confir- ción. Las condiciones óptimas fueron 20 ml de Genapol med the extraction effectiveness is strongly influenced by X-080 (0.5%), potencia de irradiación, 1000 W, tiempo de physico-chemical soil properties. extracción, 2 minutos y agitación. En estas condiciones del proceso MAME se obtuvieron buenas recuperaciones Keywords: benzimidazoles, antihelmintics, MAME, soil, (alrededor de 90%), significativamente superiores a las emerging pollutant. encontradas por el procedimiento clásico (por debajo de 55%). El método se aplicó a dos suelos de Madrid (centro de España). Los resultados confirmaron que las propieda- RESUM des físico-químicas del suelo influyen decisivamente en la eficacia de la extracción. L’oxibendazol és un fàrmac veterinari utilitzat com antihel- míntic per animals domèstics i de granja. Aquest fàrmac Palabras clave: benzimidazoles, antihelmínticos, MAME, pot introduir-se en el medi bé directament, a través de la suelo, contaminantes emergentes. femta o l’orina, o bé indirectament, quan s’utilitzen residus ramaders com esmena orgànica sobre sòls agrícoles. En SUMMARY Oxibendazole is a veterinary drug used as an antihelmin- *Corresponding author: [email protected]; mar.gil. tic for companion and farm animals. This drug may enter [email protected]; Phone 00 34 91 8879475; Fax 00 34 91 into the environment directly, via excretion of faeces and 8879474 AFINIDAD LXIX, 559, Julio - Septiembre 2012 197 aquest treball s’ha desenvolupat un mètode senzill, ràpid, fiable i sensible basat en el procés d’extracció micel·lar en microones (MAME), usant Genapol X-080 (0.5%) com ten- sioactiu, per a la quantificació d’oxibendazol en mostres de sòl. Dos mètodes clàssics basats en agitació mecàni- ca i ultrasons seguits d’una extracció en fase sòlida, van Figure 1. Chemical structure of oxibendazole. ser comparats amb el procés MAME. L’oxibendazol va ser determinat mitjançant cromatografia líquida d’alta eficàcia It is necessary to develop new analytical methods to detect (HPLC) amb detector de fluorescència. A la optimització veterinary medicines at low concentrations and to estimate del procés MAME es van avaluar quatre paràmetres: vo- their environmental impact. In general, the extraction of lum de tensioactiu, agitació, potència d’irradiació i temps veterinary medicines in soil samples is based on classical d’extracció. Les condicions òptimes van ser 20 ml de Ge- processes of shaking with organic solvents followed by an napol X-080 (0.5%), potència d’irradiació, 1000 W, temps additional cleanup step through a solid phase extraction d’extracció, 2 minuts i agitació. En aquestes condicions (SPE) column [3,4,10]. Soxhlet extraction is another del procés MAME es van obtenir bones recuperacions (al method frequently used to extract organic pollutants from voltant de 90%), significativament superiors a les que es soil samples; the major disadvantages are large volumes troben amb el procediment clàssic (per sota de 55%). El of organic solvent usage (300-500 ml) and long extraction mètode es va aplicar a dos sòls de Madrid (centre d’Espa- times (up to 24-48 hours) [11-12]. In microwave-assisted nya). Els resultats van confirmar que les propietats fisico- extraction (MAE), the soil is treated with an organic solvent químiques del sòl influeixen decisivament en l’eficàcia de and heated with microwave energy. MAE has been applied l’extracció. to extract different organic compounds from soil samples. The extraction efficiency is comparable to that of the Paraules clau: benzimidazols, antihelmíntics, MAME, sòl, classical techniques, such as soxhlet, ultrasonic assisted contaminants emergents. extraction or liquid-liquid extraction and other more recent ones such as SFE (supercritical fluid extraction) or PLE (pressurized liquid extraction) [11-14]. The use INTRODUCTION of micellar media combined with the microwave energy, called microwave-assisted micellar extraction (MAME), Veterinary medicines are widely used in treating cattle and offers advantages such as low toxicity, low cost, and can be released into the environment, either directly in fae- friendly to the environment [11,12,15]. MAME has been ces or urine or indirectly after the application of the ma- applied successfully to extract organic contaminants nure as organic fertilizer. Numerous veterinary medicines such as pesticides [12,16], PAHs [17], PCBs [18], and such as hormones, antibiotics and antiparasitics have pharmaceuticals [19] from soil and sediment samples. been detected in soil, surface water and groundwater [1- To our knowledge, there are not data related with 3]. As emerging contaminants, the faeces-borne drugs determination of oxibendazole in soil samples. A MAME are suspected of causing adverse effects in both humans method for determination of two benzimidazole fungicides and wildlife. It is therefore necessary to develop analytical chemically similar to oxibendazole has been developed methods to determine drugs in environmental samples. In in sandy soil samples [12]. The aim of this study was to the past few years, several studies on the potential impact develop and validate a simple method for the extraction of veterinary medicines on the environment and on animal of oxibendazole in two soil samples with different health have been conducted [4,5]. characteristics using MAME technology followed by liquid Benzimidazoles (mebendazole, fenbendazole, oxfendazole, chromatographic determination. oxibendazole, albendazole and triclabendazole) are one of the main groups of antihelmintics used clinically because of their broad spectrum of activity, wide safety Material AND METHODS margin and effectiveness against adults, larvae and eggs [6]. All benzimidazoles share the same central structure Chemical with 1,2-diaminobezene. Oxibendazole (Figure 1) is of Oxibendazole (Dr. Ehrenstorfer, Augsburg, Germany) was particular interest since its effectiveness against certain used as the standard reference material (purity = 98.5%) gastrointestinal parasites that are resistant to other (see Figure 1 for structure). A stock solution of oxibenda- benzimidazoles [7]. After administration, benzimidazoles zole at concentration of 125 μg/ml and prepared in metha- are absorbed into the bloodstream and transported to nol was stored at -18 ºC. Working standard solutions at different parts of the body [6]. Then, benzimidazoles can 12.5 μg/ml was prepared from stock solution by adding be partially metabolized and excreted through faeces and acetonitrile. The non-ionic surfactant Genapol X-080 (Oli- urine. In the particular case of oxibendazole, the most goethylene glycol monoalkyl ether) was obtained from persistent metabolite is the parent drug [8,9]. Gokbulut et Fluka (Sigma-Aldrich Chemie, Steinheim, Germany). Ace- al. [8] detected
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