Skip to main content
NCBI home page
Biochemical Journal logoLink to Biochemical Journal
. 1991 Jul 1;277(Pt 1):17–21. doi: 10.1042/bj2770017

Kinetic studies on protoporphyrinogen oxidase inhibition by diphenyl ether herbicides.

J M Camadro 1, M Matringe 1, R Scalla 1, P Labbe 1
PMCID: PMC1151185  PMID: 1854333

Abstract

Diphenyl ethers (DPEs) and related herbicides are powerful inhibitors of protoporphyrinogen oxidase, an enzyme involved in the biosynthesis of haems and chlorophylls. The inhibition kinetics of protoporphyrinogen oxidase of various origins by four DPEs, (methyl)-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (acifluorfen and its methyl ester, acifluorfen-methyl), methyl-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-chlorobenzoate (LS 820340) and methyl-5-[2-chloro-5-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (RH 5348), were studied. The inhibitions of the enzymes from maize (Zea mays) mitochondrial and etiochloroplastic membranes and mouse liver mitochondrial membranes were competitive with respect to the substrate, protoporphyrinogen IX, for all four molecules. The relative efficiencies of the inhibitors were: acifluorfen-methyl greater than LS 820340 much greater than RH 5348 greater than or equal to acifluorfen. The four molecules showed mixed-competitive type inhibition of the enzyme from yeast mitochondria where acifluorfen, a carboxylic acid, had the same inhibitory activity as its methyl ester, acifluorfen-methyl, and both were much greater than that of LS 820340 and RH 5348.

Full text

PDF
17

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Becerril J. M., Duke S. O. Protoporphyrin IX Content Correlates with Activity of Photobleaching Herbicides. Plant Physiol. 1989 Jul;90(3):1175–1181. doi: 10.1104/pp.90.3.1175. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. doi: 10.1016/0003-2697(76)90527-3. [DOI] [PubMed] [Google Scholar]
  3. Ensminger M. P., Hess F. D. Action Spectrum of the Activity of Acifluorfen-methyl, a Diphenyl Ether Herbicide, in Chlamydomonas eugametos. Plant Physiol. 1985 Feb;77(2):503–505. doi: 10.1104/pp.77.2.503. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Jacobs J. M., Jacobs N. J. Oxidation of protoporphyrinogen to protoporphyrin, a step in chlorophyll and haem biosynthesis. Purification and partial characterization of the enzyme from barley organelles. Biochem J. 1987 May 15;244(1):219–224. doi: 10.1042/bj2440219. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Jacobs N. J., Jacobs J. M. Assay for enzymatic protoporphyrinogen oxidation, a late step in heme synthesis. Enzyme. 1982;28(2-3):206–219. doi: 10.1159/000459103. [DOI] [PubMed] [Google Scholar]
  6. Labbe P., Camadro J. M., Chambon H. Fluorometric assays for coproporphyrinogen oxidase and protoporphyrinogen oxidase. Anal Biochem. 1985 Aug 15;149(1):248–260. doi: 10.1016/0003-2697(85)90502-0. [DOI] [PubMed] [Google Scholar]
  7. Matringe M., Camadro J. M., Labbe P., Scalla R. Protoporphyrinogen oxidase as a molecular target for diphenyl ether herbicides. Biochem J. 1989 May 15;260(1):231–235. doi: 10.1042/bj2600231. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Matringe M., Camadro J. M., Labbe P., Scalla R. Protoporphyrinogen oxidase inhibition by three peroxidizing herbicides: oxadiazon, LS 82-556 and M&B 39279. FEBS Lett. 1989 Mar 13;245(1-2):35–38. doi: 10.1016/0014-5793(89)80186-3. [DOI] [PubMed] [Google Scholar]
  9. Matringe M., Scalla R. Studies on the mode of action of acifluorfen-methyl in nonchlorophyllous soybean cells : accumulation of tetrapyrroles. Plant Physiol. 1988 Feb;86(2):619–622. doi: 10.1104/pp.86.2.619. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Orr G. L., Hess F. D. Mechanism of Action of the Diphenyl Ether Herbicide Acifluorfen-Methyl in Excised Cucumber (Cucumis sativus L.) Cotyledons : LIGHT ACTIVATION AND THE SUBSEQUENT FORMATION OF LIPOPHILIC FREE RADICALS. Plant Physiol. 1982 Feb;69(2):502–507. doi: 10.1104/pp.69.2.502. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Pardo A. D., Chereskin B. M., Castelfranco P. A., Franceschi V. R., Wezelman B. E. ATP requirement for mg chelatase in developing chloroplasts. Plant Physiol. 1980 May;65(5):956–960. doi: 10.1104/pp.65.5.956. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Urban-Grimal D., Labbe-Bois R. Genetic and biochemical characterization of mutants of Saccharomyces cerevisiae blocked in six different steps of heme biosynthesis. Mol Gen Genet. 1981;183(1):85–92. doi: 10.1007/BF00270144. [DOI] [PubMed] [Google Scholar]
  13. Witkowski D. A., Halling B. P. Accumulation of photodynamic tetrapyrroles induced by acifluorfen-methyl. Plant Physiol. 1988 Jul;87(3):632–637. doi: 10.1104/pp.87.3.632. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Witkowski D. A., Halling B. P. Inhibition of plant protoporphyrinogen oxidase by the herbicide acifluorfen-methyl. Plant Physiol. 1989 Aug;90(4):1239–1242. doi: 10.1104/pp.90.4.1239. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES