Protoporphyrinogen Oxidase of Mouse and Maize: Target Site Selectivity and Thiol Effects on Peroxidizing Herbicide Action

Birchfield, Norman B.; Casida, John E.

doi:10.1006/pest.1997.2260

Cited by 14 publications

(9 citation statements)

References 15 publications

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“…These include the diphenyl ethers, N ‐aryltetrahydropthalimides, oxadiazon and flumioxazin. These herbicides are potent inhibitors of PROTOX from both plants and animals 44…”

Section: Porphyrin Biosynthesismentioning

confidence: 99%

Herbicide safety relative to common targets in plants and mammals

Shaner

2003

Pest Management Science

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Most modern herbicides have low mammalian toxicity. One of the reasons for this safety is that the target site for the herbicides is not often present in mammals. There are approximately 20 mechanisms of action that have been elucidated for herbicides. Of these, some do share common target sites with mammals. The mechanisms include formation of free radicals, protoporphyrinogen oxidase (PROTOX), glutamine synthetase (GS) and 4-hydroxyphenylpyruvate dioxygenase (HPPD). PROTOX, HPPD and GS inhibitors have been shown to inhibit these enzymes in both plants and mammals and there are measurable effects in mammalian systems. However, the consequences of inhibiting a common target site in plants can be quite different than in animals. What may be a lethal event in plants, eg inhibition of HPPD, can have a beneficial effect in mammals, eg treatment for tyrosinemia type I. These chemicals also have low mammalian toxicity due to rapid metabolism and/or excretion of the herbicide from mammalian systems.

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“…These include the diphenyl ethers, N ‐aryltetrahydropthalimides, oxadiazon and flumioxazin. These herbicides are potent inhibitors of PROTOX from both plants and animals 44…”

Section: Porphyrin Biosynthesismentioning

confidence: 99%

Herbicide safety relative to common targets in plants and mammals

Shaner

2003

Pest Management Science

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“…They also demonstrated that oxyfluorfen interacts with photosynthetic electron transport of isolated thylakoids to produce hydroxyl and/or alkoxyl radicals, whereas the other DPhE herbicides, such as acifluorfen, acifluorfenmethyl, nitrofen and nitrofluorfen, have less interaction with the thylakoids to produce oxygen radicals. It has also been reported that binding affinities of peroxidizing herbicides to Protox vary (Nicolaus et al 1995) and considerable variation was observed in the affinities of DPhE herbicides to different substrates (Armbruster et al 1993;Birchfield and Casida 1997;Rio et al 1998). These findings led us to propose that hydroxyl and alkoxyl radicals may be involved in the mechanism of cellular damage, and oxyfluorfen and acifluorfen may have differential responses to plants.…”

Section: Introductionmentioning

confidence: 93%

Responses of MxPPO overexpressing transgenic tall fescue plants to two diphenyl-ether herbicides, oxyfluorfen and acifluorfen

et al. 2008

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We generated transgenic tall fescue (Festuca arundinacea Schreb. cv. Kentucky-31) plants harboring a synthetic Myxococcus xanthus protoporphyrinogen oxidase (MxPPO) gene through Agrobacterium-mediated gene transfer. Successful integration of the transgene into the genome of transgenic plants confirmed by polymerase chain reaction (PCR) and Southern blot analysis, and the functional expression of the MxPPO gene at the mRNA level in transgenic lines was validated by Northern blot analysis. Responses of transgenic and non-transgenic tall fescue plants to diphenyl-ether herbicides such as oxyfluorfen and acifluorfen have been evaluated in respect of various physiological and biochemical parameters. Differential responses were observed in chlorophyll content, in vivo H 2 O 2 deposition and lipid peroxidation in both transgenic and non-transgenic plants exposed to oxyfluorfen or acifluorfen. Isozyme profiles of four antioxidantenzymes, including peroxidase (POD), catalase (CAT), superoxide dismutase (SOD) and ascorbate peroxidase (APX), were also investigated in transgenic and nontransgenic plants using native PAGE analysis. Compared to the transgenic lines, higher staining activities of the examined antioxidant-enzymes observed in non-transgenic plants subjected to 100 lM of oxyfluorfen or acifluorfen suggests that non-transgenic plants are unable to prevent the photodynamic induced oxidative stress caused by herbicides. In addition, both transgenic and non-transgenic plants exposed to oxyfluorfen exhibited proportionally increased band-staining patterns in contrast to acifluorfen, which suggests that oxyfluorfen has relatively greater or more rapid effects on leaves than acifluorfen.

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“…For the potential biological activity, pharmaceutical utility and biological effects of cyclic imides, see: Adomat & Bö ger (2000); Bö ger & Wakabayashi (1995); Birchfield & Casida (1997);Cechinel Filho, Nunes, Calixto & Yunes (1995); Cechinel Filho, de Campos, Corrê a, Yunes & Nunes (2003); Ló pez et al (2003); Lima et al (1999); Sami et al (2000); Wang et al (2000); Watanabe et al (1998).…”

Section: Related Literaturementioning

confidence: 99%

“…Some of these effects appear to be related to the size and electrophilic characteristics of substituent groups on the imide ring, which can modify its steric properties (Cechinel et al, 1995;Lima et al, 1999;López et al, 2003). Beside these interesting biological effects, some cyclic imides, e.g., chlorophthalim (Adomat & Böger, 2000), N-aryltetrahydrophthalimide (Birchfield & Casida, 1997) and N-(4-chloro-2-fluoro-5propargyloxy)-phenyl-3,4,5,6-tetrahydrophthalimide (Watanabe et al, 1998) are peroxidizing herbicides, a class of herbicides that inhibit protoporphyrinogen IX oxidase, a key enzyme of heme and chlorophyll biosynthesis (Böger & Wakabayashi, 1995). In the course of our studies of cyclic imides, we have synthesized the title compound (I) and here present its structure (Fig.…”

Section: S1 Commentmentioning

confidence: 99%