Pharmacokinetics of α-amanitin in mice using liquid chromatography-high resolution mass spectrometry and in vitro drug–drug interaction potentials

References

• Abbott, N. L., K. L. Hill, A. Garrett, M. D. Carter, E. I. Hamelin, and R. C. Johnson. 2018. Detection of alpha-, beta-, and gamma-amanitin in urine by LC-MS/MS using 15N10-α-amanitin as the internal standard. Toxicon 152:71–77. doi:10.1016/j.toxicon.2018.07.025.
   PubMed Web of Science ®Google Scholar
• Ahmed, W. H. A., K. Gonmori, M. Suzuki, K. Watanabe, and O. Suzuki. 2010. Simultaneous analysis of α-amanitin, β-amanitin, and phalloidin in toxic mushrooms by liquid chromatography coupled to time-of-flight mass spectrometry. Forensic Toxicol. 28 (2):69–76. doi:10.1007/s11419-009-0089-7.
   Web of Science ®Google Scholar
• Alaraby, M., B. Annangi, M. Marcos, and A. Hernández. 2016. Drosophila melanogaster as a suitable in vivo model to determine potential side effects of nanomaterials: A review. J. Toxicol. Environ. Health part B 19 (2):65–104. doi:10.1080/10937404.2016.1166466.
   PubMed Web of Science ®Google Scholar
• Barman, B., S. Warjri, K. G. Lynrah, P. Phukan, and S. T. Mitchell. 2018. Amanita nephrotoxic syndrome: Presumptive first case report on the Indian subcontinent. Indian J. Nephrol. 28 (2):170–72. doi:10.4103/ijn.IJN_353_16.
   PubMed Web of Science ®Google Scholar
• Berger, K. J., and D. A. Guss. 2005. Mycotoxins revisited: Part I. J. Emerg. Med. 28 (1):53–62. doi:10.1016/j.jemermed.2004.08.013.
   PubMed Web of Science ®Google Scholar
• Caccialanza, G., C. Gandini, and R. Ponci. 1985. Direct, simultaneous determination of alpha-amanitin, beta-amanitin and phalloidine by high-performance liquid chromatography. J. Pharm. Biomed. Anal. 3 (2):179–85. doi:10.1016/0731-7085(85)80021-2.
   PubMed Web of Science ®Google Scholar
• Chen, X., B. Shao, C. Yu, Q. Yao, P. Ma, H. Li, B. Li, and C. Sun. 2021. Energy disorders caused by mitochondrial dysfunction contribute to α-amatoxin-induced liver function damage and liver failure. Toxicol. Lett. 336:68–79. doi:10.1016/j.toxlet.2020.10.003.
   PubMed Web of Science ®Google Scholar
• Choi, M.-K., and I.-S. Song. 2019. Interactions of ginseng with therapeutic drugs. Arch. Pharm.Res. 42 (10):862–78. doi:10.1007/s12272-019-01184-3.
   PubMed Web of Science ®Google Scholar
• Chung, W. C., S. C. Tso, and S. T. Sze. 2007. Separation of polar mushroom toxins by mixed-mode hydrophilic and ionic interaction liquid chromatography-electrospray ionization-mass spectrometry. J. Chromatogr. Sci. 45 (2):104–11. doi:10.1093/chromsci/45.2.104.
   PubMed Web of Science ®Google Scholar
• Defendenti, C., E. Bonacina, M. Mauroni, and L. Gelosa. 1998. Validation of a high performance liquid chromatographic method for alpha amanitin determination in urine. Forensic Sci. Int. 92 (1):59–68. doi:10.1016/S0379-0738(98)00006-1.
   PubMed Web of Science ®Google Scholar
• Diamond, G. L., W. C. Thayer, J. M. Klotzbach, and L. D. Ingerman. 2019. Urinary cadmium clearance, its relationship to glomerular filtration rate and implications for cadmium epidemiology. J. Toxicol. Environ. Health Part A 82 (23–24):1187–98. doi:10.1080/15287394.2019.1707947.
   PubMed Web of Science ®Google Scholar
• Diaz, J. H. 2018. Amatoxin-containing mushroom poisonings: Species, toxidromes, treatments, and outcomes. Wilderness Environ. Med. 29 (1):111–18. doi:10.1016/j.wem.2017.10.002.
   PubMed Web of Science ®Google Scholar
• Enjalbert, F., C. Gallion, F. Jehl, H. Monteil, and H. Faulstich. 1992. Simultaneous assay for amatoxins and phallotoxins in Amanita phalloides Fr. by high-performance liquid chromatography. J. Chromatogr. 598 (2):227–36. doi:10.1016/0021-9673(92)85052-U.
   PubMed Web of Science ®Google Scholar
• Fowler, S., P. N. Morcos, Y. Cleary, M. Martin-Facklam, N. Parrott, M. Gertz, and L. Yu. 2017. Progress in prediction and interpretation of clinically relevant metabolic drug-drug interactions: A minireview illustrating recent developments and current opportunities. Curr. Pharmacol. Rep. 3 (1):36–49. doi:10.1007/s40495-017-0082-5.
   PubMedGoogle Scholar
• Garcia, J., V. M. Costa, P. Baptista, L. Bastos Mde, and F. Carvalho. 2015b. Quantification of alpha-amanitin in biological samples by HPLC using simultaneous UV- diode array and electrochemical detection. J. Chromatogr. B 997:85–95. doi:10.1016/j.jchromb.2015.06.001.
   PubMed Web of Science ®Google Scholar
• Garcia, J., V. M. Costa, A. Carvalho, P. Baptista, P. G. de Pinho, M. D. Bastos, and F. Carvalho. 2015a. Amanita phalloides poisoning: Mechanisms of toxicity and treatment. Food Chem. Toxicol. 86:41–55. doi:10.1016/j.fct.2015.09.008.
   PubMed Web of Science ®Google Scholar
• Gicquel, T., S. Lepage, M. Fradin, O. Tribut, B. Duretz, and I. Morel. 2014. Amatoxins (alpha- and beta-Amanitin) and phallotoxin (Phalloidin) analyses in urines using high-resolution accurate mass LC-MS technology. J. Anal. Toxicol. 38 (6):335–40. doi:10.1093/jat/bku035.
   PubMed Web of Science ®Google Scholar
• Gonmori, K., K. Minakata, M. Suzuki, I. Yamagishi, H. Nozawa, K. Hasegawa, A. Wurita, K. Watanabe, and O. Suzuki. 2012. MALDI-TOF mass spectrometric analysis of α-amanitin, β-amanitin, and phalloidin in urine. Forensic Toxicol. 30 (2):179–84. doi:10.1007/s11419-012-0145-6.
   Web of Science ®Google Scholar
• Helfer, A. G., M. R. Meyer, J. A. Michely, and H. H. Maurer. 2014. Direct analysis of the mushroom poisons alpha- and beta-amanitin in human urine using a novel on-line turbulent flow chromatography mode coupled to liquid chromatography-high resolution-mass spectrometry/mass spectrometry. J. Chromatogr. A 1325:92–98. doi:10.1016/j.chroma.2013.11.054.
   PubMed Web of Science ®Google Scholar
• Jaeger, A., F. Jehl, F. Flesch, P. Sauder, and J. Kopferschmitt. 1993. Kinetics of amatoxins in human poisoning: Therapeutic implications. J. Toxicol.: Clin.Toxicol. 31 (1):63–80. doi:10.3109/15563659309000374.
   PubMed Web of Science ®Google Scholar
• Jeon, J. H., J. Lee, M. K. Choi, and I. S. Song. 2020. Pharmacokinetics of ginsenosides following repeated oral administration of red ginseng extract significantly differ between species of experimental animals. Arch. Pharm. Res. 43 (12):1335–46. doi:10.1007/s12272-020-01289-0.
   PubMed Web of Science ®Google Scholar
• Kang, Y. J., C. H. Lee, S. J. Park, H. S. Lee, M. K. Choi, and I. S. Song. 2021. Involvement of organic anion transporters in the pharmacokinetics and drug interaction of rosmarinic acid. Pharmaceutics 13 (1):83. doi:10.3390/pharmaceutics13010083.
   PubMed Web of Science ®Google Scholar
• Karlson-Stiber, C., and H. Persson. 2003. Cytotoxic fungi—an overview. Toxicon 42 (4):339–49. doi:10.1016/S0041-0101(03)00238-1.
   PubMed Web of Science ®Google Scholar
• Kaya, E., M. G. Surmen, K. O. Yaykasli, S. Karahan, M. Oktay, H. Turan, S. Colakoglu, and H. Erdem. 2014. Dermal absorption and toxicity of alpha amanitin in mice. Cutan. Ocul. Toxicol. 33 (2):154–60. doi:10.3109/15569527.2013.802697.
   PubMed Web of Science ®Google Scholar
• Kim, D., S. Kim, A.-Y. Na, C. H. Sohn, S. Lee, and H. S. Lee. 2021. Identification of decrease in TRiC proteins as novel targets of alpha-amanitin-derived hepatotoxicity by comparative proteome analysis. in vitro. Toxins 13 (3):197. doi:10.3390/toxins13030197.
   PubMed Web of Science ®Google Scholar
• Kim, S., W. G. Choi, M. Kwon, S. Lee, Y. Y. Cho, J. Y. Lee, H. C. Kang, I. S. Song, and H. S. Lee. 2019. In vitro inhibitory effects of APINACA on human major cytochrome P450, UDP-glucuronosyltransferase enzymes, and drug transporters. Molecules 24 (16):3000. doi:10.3390/molecules24163000.
   Web of Science ®Google Scholar
• Kwon, M., J. H. Jeon, M. K. Choi, and I. S. Song. 2020. The development and validation of a novel “Dual Cocktail” probe for cytochrome P450s and transporter functions to evaluate pharmacokinetic drug-drug and herb-drug interactions. Pharmaceutics 12 (10):938. doi:10.3390/pharmaceutics12100938.
   Web of Science ®Google Scholar
• Leão, M. B., D. F. Gonçalves, G. M. Miranda, G. M. X. da Paixão, and C. L. Dalla Corte. 2019. Toxicological evaluation of the herbicide Palace® in Drosophila melanogaster. J. Toxicol. Environ. Health Part A 82 (22):1172–85. doi:10.1080/15287394.2019.1709109.
   PubMed Web of Science ®Google Scholar
• Lee, J. D., H. Y. Kim, J. J. Park, S. B. Oh, H. Goo, K. J. Cho, S. Kim, and K.-B. Kim. 2021. Metabolomics approach to biomarkers of dry eye disease using 1H-NMR in rats. J. Toxicol. Environ. Health Part A 84 (8):313–30. doi:10.1080/15287394.2020.1867274.
   PubMed Web of Science ®Google Scholar
• Lee, K.-B., D. Wang, S. J. Lippard, and P. A. Sharp. 2002. Transcription-coupled and DNA damage-dependent ubiquitination of RNA polymerase II. In Vitro. Proc. Nat. Acad. Sci. USA 99 (7):4239–44. doi:10.1073/pnas.072068399.
   PubMed Web of Science ®Google Scholar
• Letschert, K., H. Faulstich, D. Keller, and D. Keppler. 2006. Molecular characterization and inhibition of amanitin uptake into human hepatocytes. Toxicol. Sci. 91 (1):140–49. doi:10.1093/toxsci/kfj141.
   PubMed Web of Science ®Google Scholar
• Li, C., F. Wei, S. Muhammad, G. Yang, S. Wang, and X. Liu. 2017. A cost-effective LC–MS/MS method for identification and quantification of α-amanitin in rat plasma: Application to toxicokinetic study. J. Chromatogr. B. 1064:36–39. doi:10.1016/j.jchromb.2017.08.042.
   PubMed Web of Science ®Google Scholar
• Mas, A. 2005. Mushrooms, amatoxins and the liver. J. Hepatol.. 42 (2):166–69. doi:10.1016/j.jhep.2004.12.003.
   PubMed Web of Science ®Google Scholar
• Miranda, C. A., A. R. Guimarães, P. F. V. Bizerra, and F. E. Mingatto. 2020. Diazinon impairs bioenergetics and induces membrane permeability transition on mitochondria isolated from rat liver. J. Toxicol. Environ. Health Part A 83 (17–18):616–29. doi:10.1080/15287394.2020.1805078.
   PubMed Web of Science ®Google Scholar
• Mydlík, M., and K. Derzsiová. 2006. Liver and kidney damage in acute poisonings. 2006. BANTAO J. 4:30–33.
   Google Scholar
• Nielsen, D. S., N. E. Shepherd, W. Xu, A. J. Lucke, M. J. Stoermer, and D. P. Fairlie. 2017. Orally absorbed cyclic peptides. Chem. Rev. 117 (12):8094–128. doi:10.1021/acs.chemrev.6b00838.
   PubMed Web of Science ®Google Scholar
• Nomura, M., Y. Suzuki, R. Kaneko, T. Ogawa, H. Hattori, H. Seno, and A. Ishii. 2012. Simple and rapid analysis of amatoxins using UPLC–MS–MS. Forensic Toxicol. 30 (2):185–92. doi:10.1007/s11419-012-0146-5.
   Web of Science ®Google Scholar
• Pahl, A., C. Lutz, and T. Hechler. 2018. Amanitins and their development as a payload for antibody-drug conjugates. Drug Discov. Today Technol.. 30:85–89. doi:10.1016/j.ddtec.2018.08.005.
   PubMedGoogle Scholar
• Park, E., R. Park, J.-H. Jeon, -Y.-Y. Cho, J. Y. Lee, H. C. Kang, I.-S. Song, and H. S. Lee. 2020. Inhibitory effect of AB-PINACA, indazole carboxamide synthetic cannabinoid, on human major drug-metabolizing enzymes and transporters. Pharmaceutics 12 (11):1036. doi:10.3390/pharmaceutics12111036.
   Web of Science ®Google Scholar
• Song, I. S., H. U. Jeong, M. K. Choi, M. Kwon, Y. Shin, J. H. Kim, and H. S. Lee. 2020. Interactions between cyazofamid and human drug transporters. J. Biochem. Mol. Toxicol. 34 (4):e22459. doi:10.1002/jbt.22459.
   PubMed Web of Science ®Google Scholar
• Stump, A. D., S. E. Jablonski, L. Bouton, and J. A. Wilder. 2011. Distribution and mechanism of α-amanitin tolerance in mycophagous drosophila (Diptera: Drosophilidae). Environ. Entomol. 40 (6):1604–12. doi:10.1603/EN11136.
   PubMed Web of Science ®Google Scholar
• Sun, J., Y. M. Niu, Y. T. Zhang, H. J. Li, Y. Yin, Y. Z. Zhang, P. B. Ma, J. Zhou, L. Huang, H. S. Zhang, et al.. 2018. Toxicity and toxicokinetics of Amanita exitialis in beagle dogs. Toxicon 143:59–67. doi:10.1016/j.toxicon.2018.01.008.
   PubMed Web of Science ®Google Scholar
• Tanahashi, M., R. Kaneko, Y. Hirata, M. Hamajima, T. Arinobu, T. Ogawa, and A. Ishii. 2010. Simple analysis of α-amanitin and β-amanitin in human plasma by liquid chromatography-mass spectrometry. Forensic Toxicol. 28 (2):110–14. doi:10.1007/s11419-010-0098-6.
   Web of Science ®Google Scholar
• US FDA. Bioanalytical method validation: Guidance for industry. Accessed April 6, 2020 . https://www.fda.gov/media/70858/download
   Google Scholar
• Vetter, J. 1998. Toxins of. Amanita Phalloides. Toxicon 36 (1):13–24. doi:10.1016/S0041-0101(97)00074-3.
   PubMed Web of Science ®Google Scholar
• Wang, H., Y. Wang, -F.-F. Shi, S. Zhang, W.-T. Fang, L.-M. Qi, N. Wang, C. Huang, H.-Q. Fang, and H.-J. Li. 2020. A case report of acute renal failure caused by Amanita neoovoidea poisoning in Anhui Province, eastern China. Toxicon 173:62–67. doi:10.1016/j.toxicon.2019.11.007.
   PubMed Web of Science ®Google Scholar
• White, J., S. A. Weinstein, L. D. Haro, R. Bedry, A. Schaper, B. H. Rumack, and T. Zilker. 2019. Mushroom poisoning: A proposed new clinical classification. Toxicon 157:53–65. doi:10.1016/j.toxicon.2018.11.007.
   PubMed Web of Science ®Google Scholar
• Wieland, T. 1983. The toxic peptides from Amanita mushrooms. Int. J. Pept. Protein Res. 22 (3):257–76. doi:10.1111/j.1399-3011.1983.tb02093.x.
   PubMedGoogle Scholar
• Xu, X. M., Z. Meng, J. S. Zhang, Q. Chen, and J. L. Han. 2020. Analytical method development for alpha-amanitin and beta-amanitin in plasma at ultra-trace level by online solid phase extraction-high performance liquid chromatography-triple quadrupole mass spectrometry and its application in poisoning events. J. Pharm. Biomed. Anal. 190:113523. doi:10.1016/j.jpba.2020.113523.
   PubMed Web of Science ®Google Scholar
• Ye, Y., and Z. Liu. 2018. Management of Amanita phalloides poisoning: A literature review and update. J. Crit. Care. 46:17–22. doi:10.1016/j.jcrc.2018.03.028.
   PubMed Web of Science ®Google Scholar
• Yun, Y. E., and A. N. Edginton. 2019. Model qualification of the PK-Sim® pediatric module for pediatric exposure assessment of CYP450 metabolized compounds. J. Toxicol. Environ. Health Part A 82 (14):789–814. doi:10.1080/15287394.2019.1652215.
   PubMed Web of Science ®Google Scholar
• Yun, Y. E., and A. N. Edginton. 2021. Evaluation of models for predicting pediatric fraction unbound in plasma for human health risk assessment. J. Toxicol. Environ. Health Part A 84 (2):67–83. doi:10.1080/15287394.2020.1835761.
   PubMed Web of Science ®Google Scholar
• Zhang, L., Y. D. Zhang, P. Zhao, and S. M. Huang. 2009. Predicting drug-drug interactions: An FDA perspective. Am. Assoc. Pharmaceut. Sci. J. 11:300–06.
   Google Scholar