A simple and sensitive method for the determination of methylene blue and its analogues in fish muscle using UPLC-MS/MS

References

• ACD/MS Fragmenter 2021. version 2021.2.1, Advanced Chemistry Development, Inc. (ACD/Labs), Toronto, ON, Canada, www.acdlabs.com.
   Google Scholar
• Amelin VG, Korotkov AI, Andoralov AM. 2017. Simultaneous determination of dyes of different classes in aquaculture products and spices using HPLC–high-resolution quadrupole time-of-flight mass spectrometry. J Anal Chem. 72(2):183–190. doi:10.1134/S1061934817020034
   Web of Science ®Google Scholar
• Chen R-C, Wei K-J, Wang T-M, Yu Y-M, Li J-Y, Lee S-H, Wang W-H, Ren T-J, Tsai C-W. 2013. Simultaneous quantification of antibiotic dyes in aquatic products and feeds by liquid chromatography–tandem mass spectrometry. J Food Drug Anal. 21(4):339–346. doi:10.1016/j.jfda.2013.09.001
   Web of Science ®Google Scholar
• Dubreil E, Mompelat S, Kromer V, Guitton Y, Danion M, Morin T, Hurtaud-Pessel D, Verdon E. 2019. Dye residues in aquaculture products: targeted and metabolomics mass spectrometric approaches to track their abuse. Food Chem. 294:355–367. doi:10.1016/j.foodchem.2019.05.056
   PubMed Web of Science ®Google Scholar
• ECHA. 2023. https://www.echa.europa.eu/web/guest/information-on-chemicals/annex-iii-inventory/-/dislist/details/AIII-100.000.469.
   Google Scholar
• EURL. 2022. EURL guidance on minimum method performance requirements (MMPRs) for specific pharmacologically active substances in specific animal matrices.
   Google Scholar
• European Commission. 1996. Council directive 96/23/EC of 29 April 1996 on measures to monitor certain substances and residues thereof in live animals and animal products and repealing Directives 85/358/EEC and 86/469/EEC and Decisions 89/187/EEC and 91/664/EEC. Off J Eur Commun. L125:10–32.
   Google Scholar
• European Commission. 2002. Commission decision 2002/657/EC of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off J Eur Commun. L221:8–36.
   Google Scholar
• European Commission. 2010. Commission regulation EU No 37/2010 of 22 December 2009 on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin. Off J Eur Union. L15:1–72.
   Google Scholar
• European Commission. 2019. Commission Regulation (EU) 2019/1871 of 7 November 2019 on reference points for action for non-allowed pharmacologically active substances present in food of animal origin and repealing Decision 2005/34/EC. Off J Eur Union. L289:41–46.
   Google Scholar
• European Commission. 2021. Commission Implementing Regulation (EU) 2021/808 of 22 March 2021 on the performance of analytical methods for residues of pharmacologically active substances used in food-producing animals and on the interpretation of results as well as on the methods to be used for sampling and repealing Decisions 2002/657/EC and 98/179/EC. Off J Eur Union. L180:84–109.
   Google Scholar
• European Commission. 2022. Commission Delegated Regulation (EU) 2022/1644 of 7 July 2022 supplementing Regulation (EU) 2017/625 of the European Parliament and of the Council with specific requirements for the performance of official controls on the use of pharmacologically active substances authorised as veterinary medicinal products or as feed additives and of prohibited or unauthorised pharmacologically active substances and residues thereof. Off J Eur Union. L248:3–17.
   Google Scholar
• IARC. 2016. IARC Working group on the evaluation of carcinogenic risks to humans. Some drugs and herbal products. Lyon (FR ): International Agency for Research on Cancer; 2016. (IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, No. 108.).
   Google Scholar
• Kim SJ, Ha DJ, Koo TS. 2013. Simultaneous quantification of methylene blue and its major metabolite, azure B, in plasma by LC-MS/MS and its application for a pharmacokinetic study. Biomed Chromatogr. 28:518–524.
   PubMed Web of Science ®Google Scholar
• Kruve A, Rebane R, Kipper K, Oldekop M-L, Evard H, Herodes K, Ravio P, Leito I. 2015. Tutorial review on validation of liquid chromatography–mass spectrometry methods: part I. Anal Chim Acta. 870:29–44. doi:10.1016/j.aca.2015.02.017
   PubMed Web of Science ®Google Scholar
• Munns RK, Holland DC, Roybal JE, Meyer JG, Hurlbut JA, Long AR. 1992. Liquid chromatographic determination of methylene blue and its metabolites in milk. J AOAC Int. 75(5):796–800. doi:10.1093/jaoac/75.5.796
   Web of Science ®Google Scholar
• Noga EJ. 2010. Fish disease. Diagnosis and treatment. 2nd edition. Ames (IA): Wiley-Blackwell.
   Google Scholar
• Park H, Kim J, Kang HS, Cho BH, Oh JH. 2020. Multi-residue analysis of 18 dye residues in animal products by liquid chromatography-tandem mass spectrometry. J Fd Hyg Safety. 35(2):109–117. doi:10.13103/JFHS.2020.35.2.109
   Google Scholar
• Reyns T, Belpaire C, Geeraerts C, Van Loco J. 2014. Multi-dye residue analysis of triarylmethane, xanthene, phenothiazine and phenoxazine dyes in fish tissues by ultra-performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 953-954:92–101. doi:10.1016/j.jchromb.2014.02.002
   PubMed Web of Science ®Google Scholar
• Tarbin JA, Chan D, Stubbings G, Sharman M. 2008. Multiresidue determination of triarylmethane and phenothiazine dyes in fish tissues by LC-MS/MS. Anal Chim Acta. 625(2):188–194. doi:10.1016/j.aca.2008.07.018
   PubMed Web of Science ®Google Scholar
• Thesnaar L, Bezuidenhout JJ, Petzer A, Petzer JP, Cloete TT. 2021. Methylene blue analogues: in vitro antimicrobial minimum inhibitory concentrations and in silico pharmacophore modelling. Eur J Pharm Sci. 157:105603. doi:10.1016/j.ejps.2020.105603
   PubMed Web of Science ®Google Scholar
• Tkaczyk A, Mitrowska K, Posyniak A. 2020. Synthetic organic dyes as contaminants of the aquatic environment and their implications for ecosystems: a review. Sci Total Environ. 717:137222. doi:10.1016/j.scitotenv.2020.137222
   PubMed Web of Science ®Google Scholar
• Touchais G, Bessiral M, Hurtaud-Pessel D, Verdon E, Dubreil E. 2021. Development and applicability of a multi-residue method for dyes, including new residue markers, to detect drug misuse in aquaculture. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 38(8):1332–1349. doi:10.1080/19440049.2021.1914869
   PubMed Web of Science ®Google Scholar
• Turnipseed SB, Roybal JE, Plakas SM, Pfenning AP, Hurlbut JA, Long AR. 1997. Determination of methylene blue in channel catfish (Ictalurus punctatus) tissue by liquid chromatography with visible detection. J AOAC Int. 80(1):31–35. doi:10.1093/jaoac/80.1.31
   PubMed Web of Science ®Google Scholar
• Vennerstrom JL, Makler MT, Angerhofer CK, Williams JA. 1995. Antimalarial dyes revisited: xanthenes, azines, oxazines, and thiazines. Antimicrob Agents Chemother. 39(12):2671–2677. doi:10.1128/AAC.39.12.2671
   PubMed Web of Science ®Google Scholar
• Verdon E, Andersen WC. 2017. Chemical analysis of non-antimicrobial veterinary drug residues in food. Chapter 9. Certain Dyes as Pharmacologically Active Substances in Fish Farming and Other Aquaculture Products. Hoboken (NJ): John Wiley & Sons, Inc.; p. 497–548.
   Google Scholar
• Wang Y, Huang X, Lv X, Sun J, Zheng R, Hu K. 2020. The metabolism of methylene blue and Its derivatives in Japanese eel (Anguilla japonica). J Ocean Univ China. 19(3):653–658. doi:10.1007/s11802-020-4166-1
   Web of Science ®Google Scholar
• Xu JZ, Dai L, Wu B, Ding T, Zhu JJ, Lin H, Chen HL, Shen CY, Jiang Y. 2009. Determination of methylene blue residues in aquatic products by liquid chromatography-tandem mass spectrometry. J Sep Sci. 32(23-24):4193–4199. doi:10.1002/jssc.200900364
   PubMed Web of Science ®Google Scholar
• Xu YJ, Tian XH, Zhang XZ, Gong XH, Liu HH, Zhang HJ, Huang H, Zhang LM. 2012. Simultaneous determination of malachite green, crystal violet, methylene blue and the metabolite residues in aquatic products by ultra-performance liquid chromatography with electrospray ionization tandem mass spectrometry. J Chromatogr Sci. 50(7):591–597. doi:10.1093/chromsci/bms054
   PubMed Web of Science ®Google Scholar
• Zhang X, Hui Y, Fang C, Wang Y, Han F, Lou X, Fodjo EK, Cai Y, Kong C. 2021. Determination of methylene blue and its metabolite residues in aquatic products by high-performance liquid chromatography–tandem mass spectrometry. Molecules. 26(16):4975. doi:10.3390/molecules26164975
   PubMed Web of Science ®Google Scholar