Tetramethylenedisulfotetramine: A Health Risk Compound and a Potential Chemical Warfare Agent
Abstract
:1. Introduction
2. Chemistry
3. Toxicokinetics and Toxicodynamics
4. Toxicity
5. Routes of Human Exposure
6. Biomedical Investigations
6.1. Biochemistry Examination
6.2. Electrocardiogram (ECG) Examination
6.3. Electroencephalogram (EEG) Examination
7. Analytical Investigations
8. Treatments
9. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Banks, C.N.; Yang, D.; Lein, P.J.; Rogawski, M.A. Tetramethylenedisulfotetramine. In Encyclopedia of Toxicology, 3rd ed.; Wexler, P., Ed.; Elsevier Inc.: Davis, CA, USA, 2014. [Google Scholar]
- Centers for Disease Control and Prevention (CDC). Poisoning by an Illegally Imported Chinese Rodenticide Containing Tetramethylenedisulfotetramine-New York City, 2002. Morb. Mortal. Wkly. Rep. 2003, 52, 199–201. [Google Scholar]
- Shakarjian, M.P.; Velíšková, J.; Stanton, P.K.; Velíšek, L. Differential antagonism of tetramethylenedisulfotetramine-induced seizures by agents acting at NMDA and GABA(A) receptors. Toxicol. Appl. Pharmacol. 2012, 265, 113–121. [Google Scholar] [CrossRef] [PubMed]
- Whitlow, K.S.; Belson, M.; Barrueto, F.; Nelson, L.; Henderson, A.K. Tetramethylenedisulfotetramine: Old Agent and New Terror. Ann. Emerg. Med. 2005, 45, 609–613. [Google Scholar] [CrossRef] [PubMed]
- Flannery, B.M.; Silverman, J.L.; Bruun, D.A.; Puhger, K.R.; McCoy, M.R.; Hammock, B.D.; Crawley, J.N.; Lein, P.J. Behavioral assessment of NIH Swiss mice acutely intoxicated with tetramethylenedisulfotetramine. Neurotoxicol. Teratol. 2015, 47, 36–45. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Li, J.M.; Gan, J.; Zeng, T.F.; Sander, J.W.; Zhou, D. Tetramethylenedisulfotetramine intoxication presenting with de novo Status Epilepticus: A case series. Neurotoxicology 2012, 33, 207–211. [Google Scholar] [CrossRef] [PubMed]
- Smith, K.J.; Skelton, H. Chemical warfare agents: Their past and continuing threat and evolving therapies part I of II. Skinmed 2003, 2, 215–221. [Google Scholar] [CrossRef] [PubMed]
- Shakarjian, M.P.; Ali, M.S.; Velíšková, J.; Stanton, P.K.; Heck, D.E.; Velíšek, L. Combined diazepam and MK-801 therapy provides synergistic protection from tetramethylenedisulfotetramine-induced tonic-clonic seizures and lethality in mice. Neurotoxicology 2015, 48, 100–108. [Google Scholar] [CrossRef] [PubMed]
- Esser, T.; Karu, A.E.; Toia, R.F.; Casida, J.E. Recognition of tetramethylenedisulfotetramine and related sulfamides by the brain GABA-gated chloride channel and a cyclodiene-sensitive monoclonal antibody. Chem. Res. Toxicol. 1991, 4, 162–167. [Google Scholar] [CrossRef] [PubMed]
- Barrueto, F.; Furdyna, P.M., Jr.; Hoffman, R.S.; Hoffman, R.J.; Nelson, L.S. Status epilepticus from an illegally imported Chinese rodenticide: “Tetramine”. J. Toxicol. Clin. Toxicol. 2003, 41, 991–994. [Google Scholar] [CrossRef] [PubMed]
- Mayer, B.P.; Albo, R.L.F.; Hok, S.; Valdez, C.A. NMR spectroscopic investigation of inclusion complexes between cyclodextrins and the neurotoxin tetramethylenedisulfotetramine. Magn. Reson. Chem. 2012, 50, 229–235. [Google Scholar] [CrossRef] [PubMed]
- Ning, P.; He, Q.; Yu, F.; Feng, Z.; Deng, P.; Jia, T. Fifty two cases of acute tetramine poisoning. Chin. J. Ind. Hyg. Occup. Dis. 1997, 15, 108–109. [Google Scholar]
- Ge, X.; Li, X.; Guan, L.; Ma, P.; Wang, H. Study on the effect using haemoperfusion to treat tetramine poisoned patients. Chin. J. Ind. Hyg. Occup. Dis. 2002, 20, 403–404. [Google Scholar]
- Zhang, C.; Zhu, T.; Chen, X.; Hu, G.; Liu, D. The convulsive effects and mechanism of tetramethylenedisulfotetramine. J. Health Toxicol. 2001, 15, 5–7. [Google Scholar]
- Pressly, B.; Nguyen, H.M.; Wulff, H. GABAA receptor subtype selectivity of the proconvulsant rodenticide TETS. Arch. Toxicol. 2018, 92, 833–844. [Google Scholar] [CrossRef] [PubMed]
- Liu, T.; Fan, C.; Wu, G. Determination of tetramethylenedisulfotetramine in blood by gas chromatography. Clin. Chem. 1993, 39, 173–174. [Google Scholar] [PubMed]
- Zhu, C.H.; Liu, Y.; Deng, L.B. Detecting DNA damage of cell in rats using comet assay after tetramine poisoned. Fa Yi Xue Za Zhi 2005, 21, 27–29. [Google Scholar] [PubMed]
- Wang, Y.; Shen, L.H.; Chen, W.J.; Liu, M.; Li, F.; Liao, Z.G. Expressions of Bcl-2 and Caspase-3 in the internal organs of rats when tetramine was administered. Fa Yi Xue Za Zhi 2006, 22, 241–244. [Google Scholar] [PubMed]
- Zhi, C.H.; Liu, L.; Liu, Y. Study on ultra-structural pathological changes of rats poisoned by tetramine. Fa Yi Xue Za Zhi 2005, 21, 107–109. [Google Scholar] [PubMed]
- Cao, Z.; Hammock, B.D.; McCoy, M.; Ein, P.J.; Rogawski, M.A.; Pessah, I.N. Tetramethylenedisulfotetramine alters Ca2+ dynamics in cultured hippocampal neurons: Mitigation by NMDA receptor blockade and GABAA receptor positive modulation. Toxicol. Sci. 2012, 130, 362–372. [Google Scholar] [CrossRef] [PubMed]
- Bruun, D.A.; Cao, Z.; Inceoglu, B.; Vito, S.T.; Austin, A.T.; Hulsizer, S.; Hammock, B.D.; Tancredi, D.J.; Rogawski, M.A.; Pessah, I.N.; et al. Combined treatment with diazepam and allopregnanolone reverses tetramethylenedisulfotetramine (TETS)-induced calcium dysregulation in cultured neurons and protects TETS-intoxicated mice against lethal seizures. Neuropharmacology 2015, 95, 332–342. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Xiang, P.; Shen, M.; Bu, J.; Huang, Z. The stability of tetramine, morphine and meperidine in formalin solution. Forensic Sci. Int. 2001, 122, 159–162. [Google Scholar] [CrossRef]
- Rice, N.C.; Rauscher, N.A.; Langston, J.L.; Myers, T.M. Behavioral intoxication following voluntary oral ingestion of tetramethylenedisulfotetramine: Dose-dependent onset, severity, survival, and recovery. Neurotoxicology 2017, 63, 21–32. [Google Scholar] [CrossRef] [PubMed]
- Lauková, M.; Velíšková, J.; Velíšek, L.; Shakarjian, M.P. Developmental and sex differences in tetramethylenedisulfotetramine (TMDT)-induced syndrome in rats. Dev. Neurobiol. 2018, 78, 403–416. [Google Scholar] [CrossRef] [PubMed]
- Wu, G.H.; Huang, M.Y. Determination of the concentration of tetramethylenedisulfotetramine in human blood by GC FPD. J. Foren. Sci. 1992, 37, 1213–1215. [Google Scholar]
- Kim, J.H.; Lee, K.J.; Suzuki, T.; Kim, C.M.; Lee, J.Y.; Mok, J.S.; Lee, T.S. Identification of tetramine, a toxin in whelks, as the cause of a poisoning incident in Korea and the distribution of tetramine in fresh and boiled whelk (Neptunea intersculpta). J. Food Protect. 2009, 72, 1935–1940. [Google Scholar] [CrossRef]
- Takasaki, S.; Konta, T.; Shiomi, K.; Kubota, I. Tetramine poisoning. Neurologic symptoms in a dialysis patient after ingesting seafood. Am. J. Kidney Dis. 2009, 54, A37–A39. [Google Scholar] [PubMed]
- Deng, X.; Li, G.; Mei, R.; Sun, S. Long term effects of tetramine poisoning: An observational study. Clin. Toxicol. 2012, 50, 172–175. [Google Scholar] [CrossRef] [PubMed]
- Zhang, Y.; Su, M.; Tian, D.P. Tetramine poisoning: A case report and review of the literature. Forensic Sci. Int. 2011, 204, e24–e27. [Google Scholar] [CrossRef] [PubMed]
- Desneux, N.; Decourtye, A.; Delpuech, J. The sublethal effects of pesticides on beneficial arthropods. Annu. Rev. Entomol. 2007, 52, 81–106. [Google Scholar] [CrossRef] [PubMed]
- Voss, E.; Haskell, A.R.; Gartenberg, L. Reduction of tetramine toxicity by sedatives and anticonvulsants. J. Pharm. Sci. 1961, 50, 858–860. [Google Scholar] [CrossRef] [PubMed]
- Hager, J. Schwere Vergiftungen in einer Polstermöbelfabrik durch einen neuartigen hochtoxischen Giftstoff (Tetramethylendisulfotetramin). Dtsch. Med. Wochenschr. 1950, 75, 183–184. [Google Scholar]
- Li, Y.; Gao, Y.; Yu, X.; Peng, J.; Ma, F.; Nelson, L. Tetramine poisoning in China: Changes over a decade viewed through the media’s eye. BMC Public Health 2014, 14, 842. [Google Scholar] [CrossRef] [PubMed]
- Guan, F.Y.; Liu, Y.T.; Luo, Y.; Hu, X.Y.; Liu, F.; Li, Q.Y.; Kang, Z.W. GC/MS identification of tetramine in samples from human alimentary intoxication and evaluation of artificial carbonic kidneys for the treatment of the victims. J. Anal. Toxicol. 1993, 17, 199–201. [Google Scholar] [CrossRef] [PubMed]
- Zolkowska, D.; Banks, C.N.; Dhir, A.; Inceoglu, B.; Sanborn, J.R.; McCoy, M.R.; Bruun, D.A.; Hammock, B.D.; Lein, P.J.; Rogawski, M.A. Characterization of seizures induced by acute and repeated exposure to tetramethylenedisulfotetramine. J. Pharmacol. Exp. Ther. 2012, 341, 435–446. [Google Scholar] [CrossRef] [PubMed]
- Fraga, C.G.; Wahl, J.H.; Nunez, S.P. Profiling of volatile impurities in tetramethylenedisulfotetramine (TETS) for synthetic-route determination. Forensic Sci. Int. 2011, 210, 164–169. [Google Scholar] [CrossRef] [PubMed]
- Shakarjian, M.P.; Laukova, M.; Velíšková, J.; Stanton, P.K.; Heck, D.E.; Velíšek, L. Tetramethylenedisulfotetramine: pest control gone awry. Ann. N. Y. Acad. Sci. 2016, 1378, 68–79. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Barnych, B.; Vasylieva, N.; Joseph, T.; Hulsizer, S.; Nguyen, H.M.; Cajka, T.; Pessah, I.; Wulff, H.; Gee, S.J.; Hammock, B.D. Development of Tetramethylenedisulfotetramine (TETS) hapten library: Synthesis, electrophysiological studies, and immune response in rabbits. Chem.-Eur. J. 2017, 23, 8466–8472. [Google Scholar] [CrossRef] [PubMed]
- Zolkowska, D. Characterization of rodent model of tetramethylenedisulfotetramine (TETS)-induced seizures and potential treatment options. Pharmacol. Rep. 2013, 65, 258–260. [Google Scholar] [CrossRef]
- Wang, Y.; Zhao, J. Survey and development on determination of tetramine poisoning. Pesticides 2001, 8, 4. [Google Scholar]
- Wu, Q.; Zhang, M.S.; Lan, Z.R. Simultaneous determination of fluoroacetamide and tetramine by gas chromatography. Chin. J. Chromatogr. 2002, 20, 381–382. [Google Scholar]
- Bolognesi, C. Genotoxicity of pesticides: A review of human biomonitoring studies. Mutat. Res. 2003, 543, 251–272. [Google Scholar] [CrossRef]
- Zeng, D.; Chen, B.; Yao, S.; Ying, J. Determination of tetramethylenedisulfotetramine in human urine with gas chromatograph-flame thermionic detection coupling with direct immersed solid-phase micro-extraction. Forensic Sci. Int. 2006, 159, 168–174. [Google Scholar] [CrossRef] [PubMed]
- Owens, J.; Hok, S.; Alcaraz, A.; Koester, C. Quantitative analysis of tetramethylenedisulfotetramine (tetramine) spiked into beverages by liquid chromatography-tandem mass spectrometry with validation by gas chromatography-mass spectrometry. J. Agric. Food Chem. 2009, 57, 4058–4067. [Google Scholar] [CrossRef] [PubMed]
- Luan, T.; Li, G.; Zhao, M.; Zhang, Z. Rapid detection of tetramethylenedisulfotetramine in human blood by solid-phase microextraction/gas chromatography. Anal. Chim. Acta 2000, 404, 329–334. [Google Scholar] [CrossRef]
- Shen, M.; Xiang, P. Rapid determination of tetramine in urine of rodenticide-poisoned person with SPME and GC/NPD. Chin. Pharm. J. 2000, 35, 341–343. [Google Scholar]
- Cao, Y.; Wei, Y. Analysis of tetramine in biological samples by GC-MS. Chem. Anal. Meas. 2001, 3, 8. [Google Scholar]
- Liang, G.; Wu, F. Simultaneous GC/MS determination of several organic poisons. Phys. Test. Chem. Anal. Part B Chem. Anal. 2001, 4, 15. [Google Scholar]
- Vasylieva, N.; Barnych, B.; Rand, A.; Inceoglu, B.; Gee, S.J.; Hammock, B.D. Sensitive immunoassay for detection and quantification of the neurotoxin, tetramethylenedisulfotetramine. Anal. Chem. 2017, 89, 5612–5619. [Google Scholar] [CrossRef] [PubMed]
- Li, Z.J.; Zeng, J.Y. Clinical analysis of 15 cases with tetramethylenedisulfotetramine. Bull. Hunan Med. Univ. 2001, 26, 65–66. [Google Scholar]
- Zhao, C.; Hwang, S.H.; Buchholz, B.A.; Carpenter, T.S.; Lightstone, F.C.; Yang, J.; Hammock, B.D.; Casida, J.E. GABAA receptor target of tetramethylenedisulfotetramine. Proc. Natl. Acad. Sci. USA 2014, 111, 8607–8612. [Google Scholar] [CrossRef] [PubMed] [Green Version]
© 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Patocka, J.; Franca, T.C.C.; Wu, Q.; Kuca, K. Tetramethylenedisulfotetramine: A Health Risk Compound and a Potential Chemical Warfare Agent. Toxics 2018, 6, 51. https://doi.org/10.3390/toxics6030051
Patocka J, Franca TCC, Wu Q, Kuca K. Tetramethylenedisulfotetramine: A Health Risk Compound and a Potential Chemical Warfare Agent. Toxics. 2018; 6(3):51. https://doi.org/10.3390/toxics6030051
Chicago/Turabian StylePatocka, Jiří, Tanos C. C. Franca, Qinghua Wu, and Kamil Kuca. 2018. "Tetramethylenedisulfotetramine: A Health Risk Compound and a Potential Chemical Warfare Agent" Toxics 6, no. 3: 51. https://doi.org/10.3390/toxics6030051
APA StylePatocka, J., Franca, T. C. C., Wu, Q., & Kuca, K. (2018). Tetramethylenedisulfotetramine: A Health Risk Compound and a Potential Chemical Warfare Agent. Toxics, 6(3), 51. https://doi.org/10.3390/toxics6030051