A review of the mode of toxicity and relevance to humans of the triketone herbicide 2-(4-methylsulfonyl-2-nitrobenzoyl)-1,3-cyclohexanedione

References

• Burns RP, Gipson IK, Murray MJ. (1976). Keratopathy in tyrosinemia. Birth Defects, 12, 169–80
   Google Scholar
• Carmichael N, Bausen M, Boobis A, et al. (2011). Using mode of action information to improve regulatory decision making: an ECETOC/ILSR RF/HESI workshop overview. Crit Rev Toxicol, 41, 175–86
   PubMed Web of Science ®Google Scholar
• D’Eufemia PD, Finocchiaro R, Celli M, et al. (2009). Increased nitric oxide release by neutrophils of a patients with tyrosinemia type III. Biomed Pharmacother, 63, 359–61
   Google Scholar
• Ellaway CJ, Holme E, Standing S, et al. (2001). Outcome of tyrosinaemia type III. J Inherit Metab Dis, 24, 824–32
   Web of Science ®Google Scholar
• Ellis MK, Whitfield AC, Gowans LA, et al. (1995). Inhibition of 4-hydroxyphenylpyruvate dioxygenase by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione. Toxicol Appl Pharmacol, 133, 12–9
   PubMed Web of Science ®Google Scholar
• FDA. (2002) ORFADIN® capsules (nitisinone). Available from: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-232_Orfadin.cfmf [last accessed 15 Jan 2013].
   Google Scholar
• Gledhill AJ, Jones BK, Laird WJD. (2001). Metabolism of 2-(4-methylsulphonyl 1-2-nitrobenzolyl)-1,3-cyclohexanedione (mesotrione) in rat and mouse. Xenobiotica, 31, 733–47
   Web of Science ®Google Scholar
• Hall MG, Wilks MF, Provan WM, et al. (2001). Pharmacokinetcs and pharmacodynamics of NTBC (2-(2-nitro-4-fluoromethylbenzoyl)-1,3-cyclohexanedione) and mesotrione, inhibitors of 4-hydroxyphenyl pyruvate dioxygenase (HPPD) following a single dose to healthy male volunteers. Br J Clin Pharmacol, 52, 169–77
   PubMed Web of Science ®Google Scholar
• Henderson MJ, Faraj BT, Ali FM, Rudman D. (1981). Tyrosine transaminase activity in normal and cirrhotic liver. Dig Dis Sci, 26, 124–8
   Google Scholar
• Kretchmer N. (1959). Enzymic patterns during development. Paediatrics, 23, 606–17
   PubMed Web of Science ®Google Scholar
• Lee DL, Prisbylla MP, Cromartie TH, et al. (1997). The discovery and structural requirements of inhibitors of p-hydroxyphenylpyruvate dioxygenase. Weed Sci, 45, 601–9
   Web of Science ®Google Scholar
• Lindstedt S, Holme E, Lock EA, et al. (1992). Treatment of hereditart tyrosinaemia type I by inhibition of 4-hydroxyphenylpyruvate dioxygenase. Lancet, 340, 813–7
   PubMed Web of Science ®Google Scholar
• Lock EA, Ellis MK, Provan WM, Smith LL. (1994). The effect of NTBC on enzymes involved in tyrosine catabolism in the rat. Toxicologist, 14, 826–32
   Google Scholar
• Lock EA, Gaskin P, Ellis MK, et al. (2000). Tissue distribution of 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione (NTBC) and its effects on enzymes involved in tyrosine catabolism in the mouse. Toxicology, 144, 179–87
   PubMed Web of Science ®Google Scholar
• Lock EA, Gaskin P, Ellis MK, et al. (1996). Tissue distribution of 2-(2-nitro-4-trifluoromethylbenzoyl) cyclohexanedione (NTBC): effect on enzymes involved in tyrosine catabolism to ocular toxicity in the rat. Toxicol Appl Pharmacol, 141, 439–47
   PubMed Web of Science ®Google Scholar
• Lock EA, Smith LS. (2003). The role of mode of action studies in extrapolating to human risks in toxicology. Toxicol Lett, 140–141, 317–22
   Google Scholar
• Meek ME, Bucher JR, Cohen SM, et al. (2003). A framework for human relevance analysis on information on carcinogenic modes of action. Crit Rev Toxicol, 33, 591–654
   PubMed Web of Science ®Google Scholar
• Nixon D. (2001). Mesotrione (ZA1296) tyrosine-mediated toxicity in mice and rats. Health Effects Division (HED) Mechanism of Toxicity science assessment Review Committee, 27 March 2001
   Google Scholar
• OECD Guidelines for Testing of Chemicals. (1998). Test Guideline 408. Repeat dose 90 day oral toxicity study in rodents
   Google Scholar
• OECD Guidelines for Testing of Chemicals. (2001). Test Guideline 416. Two generation reproduction study
   Google Scholar
• OECD Guidelines for Testing of Chemicals. (2001). Test Guideline 414. Prenatal developmental toxicity study
   Google Scholar
• OECD Guidelines for Testing of Chemicals. (2009). Test Guideline 453. Combined chronic toxicity/carcinogenicity study
   Google Scholar
• Rich LF, Beard ME, Burns RP. (1973). Excess dietary tyrosine and corneal lesions. Exp Eye Res, 17, 87–97
   Google Scholar
• Ruetschi U, Cerone R, Perez-Cerda C, et al. (2000). Mutations in the 4-hyroxyohenylpyruvate dioxygenase gene (HPD) in patients with tyrosinemia type III. Hum Genet, 106, 654–62
   Google Scholar
• Scott CR. (2006). The genetic tyrosinemias. Am J Med Genet C, 142C, 121–6
   PubMed Web of Science ®Google Scholar
• Seed J, Carnet EW, Corley RA, et al. (2005). Overview: using mode of action and life stage information to evaluate the human relevance of animal toxicity data. Crit Rev Toxicol, 35, 663–72
   Web of Science ®Google Scholar
• Sunwannarat P, O’Brien K, Perry MB, et al. (2005). Use of nitisinone in patients with alkaptonuria. Metabolism, 54, 719–28
   Google Scholar
• Yang C, Pflugrath JW, Camper DL, et al. (2004). Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenases. Biochemistry, 43, 10414–23
   Google Scholar