| Name | protoporphyrinogen oxidase |
|---|---|
| Synonyms | Mutant protoporphyrinogen oxidase; VP; PPO; PPOX; Protoporphyrinogen oxidase; V290M; Protoporphyrinogen oxidases |
| Name | acifluorfen |
|---|---|
| CAS | 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 9007836 | Salonpaa P, Kottari S, Pelkonen O, Raunio H: Regulation of CYP 2 A 5 induction by porphyrinogenic agents in mouse primary hepatocytes. Naunyn Schmiedebergs Arch Pharmacol. 1997 Jan;355(1):8-13. Hepatocyte COH activity was increased also by the ferrochelatase inhibitor griseofulvin and the protoporphyrinogen oxidase inhibitor acifluorfen (about 9-fold induction). |
31(0,1,1,1) | Details |
| 9737859 | Arnould S, Takahashi M, Camadro JM: Stability of recombinant yeast protoporphyrinogen oxidase: effects of diphenyl ether-type herbicides and diphenyleneiodonium. Biochemistry. 1998 Sep 15;37(37):12818-28. Acifluorfen, a potent inhibitor that competes with the tetrapyrrole substrate, and to a lower extent FAD, the cofactor of the enzyme, protected the protein from thermal denaturation, raising the Tm to 50.5 +/- 0.5 degreesC (acifluorfen) and 46.5 +/- 0.5 degreesC (FAD). |
6(0,0,0,6) | Details |
| 8621563 | Camadro JM, Labbe P: Cloning and characterization of the yeast HEM14 gene coding for protoporphyrinogen oxidase, the molecular target of diphenyl ether-type herbicides. J Biol Chem. 1996 Apr 12;271(15):9120-8. Studies on protoporphyrinogen oxidase overexpressed in yeast and purified as wild-type enzyme showed that (i) the NH2-terminal mitochondrial targeting sequence of protoporphyrinogen oxidase is not cleaved during importation; (ii) the enzyme, as purified, had a typical flavin semiquinone absorption spectrum; and (iii) the enzyme was strongly inhibited by diphenyl ether-type herbicides and readily photolabeled by a diazoketone derivative of tritiated acifluorfen. |
4(0,0,0,4) | Details |
| 8288631 | Dailey TA, Meissner P, Dailey HA: Expression of a cloned protoporphyrinogen oxidase. . J Biol Chem. 1994 Jan 14;269(2):813-5. The diphenyl ether herbicide acifluorfen, which is a strong inhibitor of the eukaryotic enzyme, is only weakly inhibitory. |
4(0,0,0,4) | Details |
| 8554330 | Dailey TA, Dailey HA, Meissner P, Prasad AR: Cloning, sequence, and expression of mouse protoporphyrinogen oxidase. . Arch Biochem Biophys. 1995 Dec 20;324(2):379-84. The protein as expressed in E. coli is sensitive to inhibition by the diphenyl ether herbicide acifluorfen. |
4(0,0,0,4) | Details |
| 8771201 | Dailey TA, Dailey HA: Human protoporphyrinogen oxidase: expression, purification, and characterization of the cloned enzyme. Protein Sci. 1996 Jan;5(1):98-105. The enzyme does not use III as a substrate and is inhibited by micromolar concentrations of the herbicide acifluorfen. |
3(0,0,0,3) | Details |
| 9784236 | Corrigall AV, Siziba KB, Maneli MH, Shephard EG, Ziman M, Dailey TA, Dailey HA, Kirsch RE, Meissner PN: Purification of and kinetic studies on a cloned protoporphyrinogen oxidase from the aerobic bacterium Bacillus subtilis. Arch Biochem Biophys. 1998 Oct 15;358(2):251-6. B. subtilis protoporphyrinogen oxidase is not inhibited by the diphenyl ether herbicide acifluorfen at 100 microM and is weakly inhibited by methylacifluorfen at the same concentration. |
3(0,0,0,3) | Details |
| 12354210 | Kusaba A, Ansai T, Akifusa S, Nakahigashi K, Taketani S, Inokuchi H, Takehara T: Cloning and expression of a Porphyromonas gingivalis gene for protoporphyrinogen oxidase by complementation of a hemG mutant of Escherichia coli. Oral Microbiol Immunol. 2002 Oct;17(5):290-5. |
2(0,0,0,2) | Details |
| 16039600 | Shepherd M, Dailey HA: A continuous fluorimetric assay for protoporphyrinogen oxidase by monitoring accumulation. Anal Biochem. 2005 Sep 1;344(1):115-21. The Ki for acifluorfen, a diphenylether herbicide, was measured as 0.53 microM for the human enzyme. |
2(0,0,0,2) | Details |
| 8982084 | Narita S, Tanaka R, Ito T, Okada K, Taketani S, Inokuchi H: Molecular cloning and characterization of a cDNA that encodes protoporphyrinogen oxidase of Arabidopsis thaliana. Gene. 1996 Dec 5;182(1-2):169-75. Extracts of E. coli cells transformed with the Arabidopsis PPOX cDNA had high PPOX activity, and this activity was markedly inhibited by acifluorfen, a specific inhibitor of PPOX. |
2(0,0,0,2) | Details |
| 7713909 | Nishimura K, Taketani S, Inokuchi H: Cloning of a human cDNA for protoporphyrinogen oxidase by complementation in vivo of a hemG mutant of Escherichia coli. J Biol Chem. 1995 Apr 7;270(14):8076-80. |
2(0,0,0,2) | Details |
| 12231874 | Lee HJ, Duke MV, Duke SO: Cellular Localization of -Oxidizing Activities of Etiolated Barley (Hordeum vulgare L.) Leaves (Relationship to Mechanism of Action of Protoporphyrinogen Oxidase-Inhibiting Herbicides). Plant Physiol. 1993 Jul;102(3):881-889. The herbicide acifluorfen-methyl (AFM), at 1 [mu] M, inhibited Protox activity from crude etioplasts, purified etioplasts, microsomes, and PM by 58, 59, 23, and 0% in the absence of reductants. |
2(0,0,0,2) | Details |
| 7922145 | O'Connor N, Mornet R, Matringe M, Clair D, Scalla R, Fujimoto TT, Swithenbank C: Synthesis and properties of a photoaffinity labeling reagent for protoporphyrinogen oxidases, the target enzymes of diphenyl ether herbicides. Bioorg Med Chem. 1994 May;2(5):339-42. A diazoketone 3 has been synthesized in two steps from acifluorfen 1, a diphenyl ether herbicide. |
2(0,0,0,2) | Details |
| 8621504 | Dailey HA, Dailey TA: Protoporphyrinogen oxidase of Myxococcus xanthus. J Biol Chem. 1996 Apr 12;271(15):8714-8. The diphenyl ether herbicide acifluorfen at 1 microM strongly inhibits the enzyme's activity. |
2(0,0,0,2) | Details |
| 18834852 | Tan Y, Sun L, Xi Z, Yang GF, Jiang DQ, Yan XP, Yang X, Li HY: A capillary electrophoresis assay for recombinant Bacillus subtilis protoporphyrinogen oxidase. Anal Biochem. 2008 Dec 15;383(2):200-4. Epub 2008 Sep 20. The interaction between PPO and acifluorfen, a commercial PPO-inhibiting herbicide, was measured as the inhibition constant 186.9+/-9.3 miocroM EM, Cyrillic. |
2(0,0,0,2) | Details |
| 9578577 | Birchfield NB, Latli B, Casida JE: Human protoporphyrinogen oxidase: relation between the herbicide binding site and the flavin cofactor. Biochemistry. 1998 May 12;37(19):6905-10. Protox is the target of light-dependent peroxidizing herbicides and is inhibited at nanomolar levels by several chemical classes including tetrahydrophthalimides (discussed below) and diphenyl ethers (e.g., acifluorfen) usually with little selectivity between the mammalian and plant enzymes. |
1(0,0,0,1) | Details |
| 12758057 | Krijt J, Psenak O, Vokurka M, Chlumska A, Fakan F: Experimental hepatic uroporphyria induced by the diphenyl-ether herbicide fomesafen in male DBA/2 mice. Toxicol Appl Pharmacol. 2003 May 15;189(1):28-38. However, feeding of the protoporphyrinogen oxidase-inhibiting herbicide fomesafen (0.25% in the diet for 18 weeks) induced hepatic uroporphyria in male DBA/2N mice (liver content up to 150 nmol/g, control animals 1 nmol/g), whereas fomesafen-treated male C57BL/6N mice displayed only a slight elevation of liver porphyrins (approximately 5 nmol/g). A similar uroporphyria was induced by the herbicide formulation Blazer, containing a structurally related herbicide acifluorfen, when fed to DBA/2N mice at a dose corresponding to 0.25% of acifluorfen in the diet. |
1(0,0,0,1) | Details |
| 19266155 | Sun L, Wen X, Tan Y, Li H, Yang X, Zhao Y, Wang B, Cao Q, Niu C, Xi Z: Site-directed mutagenesis and computational study of the Y366 active site in Bacillus subtilis protoporphyrinogen oxidase. Amino Acids. 2009 Sep;37(3):523-30. Epub 2009 Mar 6. Y366E shows large resistance (K (i) = 153.94 microM) to acifluorfen. |
1(0,0,0,1) | Details |
| 19944166 | Qin X, Sun L, Wen X, Yang X, Tan Y, Jin H, Cao Q, Zhou W, Xi Z, Shen Y: Structural insight into unique properties of protoporphyrinogen oxidase from Bacillus subtilis. J Struct Biol. 2010 Apr;170(1):76-82. Epub 2009 Nov 26. Bacillus subtilis PPO (bsPPO) is unique among PPO family members in that it is a soluble monomer, is inefficiently inhibited by the herbicide acifluorfen (AF) and has broader substrate specificity than other PPO enzymes. |
1(0,0,0,1) | Details |
| 17714436 | Froissard M, Belgareh-Touze N, Dias M, Buisson N, Camadro JM, Haguenauer-Tsapis R, Lesuisse E: Trafficking of siderophore transporters in Saccharomyces cerevisiae and intracellular fate of ferrioxamine B conjugates. Traffic. 2007 Nov;8(11):1601-16. Epub 2007 Aug 20. Ferrioxamine B coupled to an inhibitor of mitochondrial protoporphyrinogen oxidase (acifluorfen) could not reach its target unless the cells were disrupted, confirming the tight compartmentalization of siderophores within cells. |
0(0,0,0,0) | Details |
| 1425694 | Matringe M, Mornet R, Scalla R: Characterization of [3H] acifluorfen binding to purified pea etioplasts, and evidence that protoporphyrinogen oxidase specifically binds acifluorfen. Eur J Biochem. 1992 Nov 1;209(3):861-8. |
407(5,5,5,7) | Details |
| 16666913 | Witkowski DA, Halling BP: Inhibition of Plant Protoporphyrinogen Oxidase by the Herbicide Acifluorfen-Methyl. Plant Physiol. 1989 Aug;90(4):1239-1242. |
112(1,2,2,2) | Details |
| 7849556 | Sinclair PR, Gorman N, Walton HS, Sinclair JF, Jacobs JM, Jacobs NJ: accumulation in cultured hepatocytes treated with the diphenyl ether herbicide, acifluorfen. Cell Mol Biol (Noisy-le-grand). 1994 Nov;40(7):891-7. Diphenyl ether (DPE) herbicides such as acifluorfen inhibit both the plant and mammalian forms of protoporphyrinogen oxidase, a heme biosynthetic enzyme. |
112(1,2,2,2) | Details |
| 7697001 | Corrigall AV, Hift RJ, Adams PA, Kirsch RE: Inhibition of mammalian protoporphyrinogen oxidase by acifluorfen. . Biochem Mol Biol Int. 1994 Dec;34(6):1283-9. |
112(1,2,2,2) | Details |
| 15815918 | Soldatova O, Apchelimov A, Radukina N, Ezhova T, Shestakov S, Ziemann V, Hedtke B, Grimm B: An Arabidopsis mutant that is resistant to the protoporphyrinogen oxidase inhibitor acifluorfen shows regulatory changes in tetrapyrrole biosynthesis. Mol Genet Genomics. 2005 Jun;273(4):311-8. Epub 2005 Apr 7. Several Arabidopsis mutants of the ecotype Dijon were isolated that show resistance to the herbicide acifluorfen, which inactivates protoporphyrinogen oxidase (PPOX), an enzyme of tetrapyrrole biosynthesis. |
112(1,2,2,2) | Details |
| 7798202 | Camadro JM, Thome F, Brouillet N, Labbe P: Purification and properties of protoporphyrinogen oxidase from the yeast Saccharomyces cerevisiae. J Biol Chem. 1994 Dec 23;269(51):32085-91. The mixed inhibition by acifluorfen-methyl previously reported for the membrane-bound protoporphyrinogen oxidase (Camadro, J.M., Matringe, M., Scalla, R., and Labbe, P. (1991) Biochem. |
85(1,1,1,5) | Details |
| 2775186 | Matringe M, Camadro JM, Labbe P, Scalla R: Protoporphyrinogen oxidase as a molecular target for diphenyl ether herbicides. Biochem J. 1989 May 15;260(1):231-5. Acifluorfen-methyl was strongly inhibitory to protoporphyrinogen oxidase activities whatever their origins [concn. causing 50% inhibition (IC50) = 4 nM for the corn etioplast enzyme]. |
84(1,1,1,4) | Details |
| 17046834 | Corradi HR, Corrigall AV, Boix E, Mohan CG, Sturrock ED, Meissner PN, Acharya KR: Crystal structure of protoporphyrinogen oxidase from Myxococcus xanthus and its complex with the inhibitor acifluorfen. J Biol Chem. 2006 Dec 15;281(50):38625-33. Epub 2006 Oct 17. |
82(1,1,1,2) | Details |
| 16668383 | Sherman TD, Becerril JM, Matsumoto H, Duke MV, Jacobs JM, Jacobs NJ, Duke SO: Physiological Basis for Differential Sensitivities of Plant Species to Protoporphyrinogen Oxidase-Inhibiting Herbicides. Plant Physiol. 1991 Sep;97(1):280-287. Little difference was found between in vitro acifluorfen inhibition of protoporphyrinogen oxidase (Protox) of plastid preparations of mustard, cucumber, and morning glory, three species with large differences in their susceptibility at the tissue level. |
82(1,1,1,2) | Details |
| 1404247 | Jacobs JM, Sinclair PR, Gorman N, Jacobs NJ, Sinclair JF, Bement WJ, Walton H: Effects of diphenyl ether herbicides on accumulation by cultured hepatocytes. J Biochem Toxicol. 1992 Summer;7(2):87-95. In vitro enzyme studies of hepatic mitochondria isolated from rat and chick embryos demonstrated that protoporphyrinogen oxidase, the penultimate enzyme of heme biosynthesis, was inhibited by low concentrations of acifluorfen, nitrofen, or acifluorfen methyl with the latter being the most potent inhibitor. |
82(1,1,1,2) | Details |
| 2146157 | Varsano R, Matringe M, Magnin N, Mornet R, Scalla R: Competitive interaction of three peroxidizing herbicides with the binding of [3H] acifluorfen to corn etioplast membranes. FEBS Lett. 1990 Oct 15;272(1-2):106-8. The specific binding of the herbicide acifluorfen 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid to corn etioplast membranes is competitively inhibited by the substrate of protoporphyrinogen oxidase. |
82(1,1,1,2) | Details |
| 7575589 | Prasad AR, Dailey HA: Generation of resistance to the diphenyl ether herbicide acifluorfen by MEL cells. Biochem Biophys Res Commun. 1995 Oct 4;215(1):186-91. The diphenyl ether herbicide acifluorfen has been shown to act by inhibition of the terminal enzyme of the biosynthetic pathway, protoporphyrinogen oxidase (E.C. 1.3.3.4) (PPO), in plant and animal cells. |
81(1,1,1,1) | Details |
| 17459329 | Tripathy BC, Mohapatra A, Gupta I: Impairment of the photosynthetic apparatus by oxidative stress induced by photosensitization reaction of Biochim Biophys Acta. 2007 Jun;1767(6):860-8. Epub 2007 Mar 19. Treatment with the herbicide acifluorfen- (AF-Na), an inhibitor of protoporphyrinogen oxidase, caused an accumulation of (Proto IX) , light-induced necrotic spots on the cucumber cotyledon within 12-24 h, and photobleaching after 48-72 h of light exposure. |
81(1,1,1,1) | Details |
| 2369128 | Jacobs JM, Jacobs NJ, Borotz SE, Guerinot ML: Effects of the photobleaching herbicide, acifluorfen-methyl, on oxidation in barley organelles, soybean root mitochondria, soybean root nodules, and bacteria. Arch Biochem Biophys. 1990 Aug 1;280(2):369-75. The photobleaching herbicide, acifluorfen-methyl (AFM), has been reported to be an inhibitor of the heme and chlorophyll biosynthetic enzyme protoporphyrinogen oxidase (Protox) in several plant species. |
81(1,1,1,1) | Details |
| 10631251 | Lermontova I, Grimm B: Overexpression of plastidic oxidase leads to resistance to the diphenyl-ether herbicide acifluorfen. Plant Physiol. 2000 Jan;122(1):75-84. Therefore, overproduction of protoporphyrinogen oxidase neutralizes the herbicidal action, prevents the accumulation of the substrate and consequently abolishes the light-dependent phytotoxicity of acifluorfen. |
38(0,1,2,3) | Details |
| 1537847 | Matringe M, Camadro JM, Block MA, Joyard J, Scalla R, Labbe P, Douce R: Localization within chloroplasts of protoporphyrinogen oxidase, the target enzyme for diphenylether-like herbicides. J Biol Chem. 1992 Mar 5;267(7):4646-51. Protoporphyrinogen oxidase specific activity was 7-8 times higher in envelope membranes than in thylakoids, in good agreement with the number of [3H] acifluorfen binding sites in each membrane system: 21 and 3 pmol/mg protein, respectively, in envelope membranes and thylakoids. |
37(0,1,1,7) | Details |
| 7758461 | Camadro JM, Matringe M, Thome F, Brouillet N, Mornet R, Labbe P: Photoaffinity labeling of protoporphyrinogen oxidase, the molecular target of diphenylether-type herbicides. Eur J Biochem. 1995 May 1;229(3):669-74. The diazoketone derivative of tritiated acifluorfen was used to specifically photolabel yeast protoporphyrinogen oxidase. |
34(0,1,1,4) | Details |
| 11020479 | Mesenholler M, Matthews EK: A key role for the mitochondrial benzodiazepine receptor in cellular photosensitisation with delta-aminolaevulinic acid. Eur J Pharmacol. 2000 Oct 13;406(2):171-80. chelation enhanced the accumulation of photo-active whereas 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxam ide (PK11195), dipyridamole, or 7-(dimethylcarbamoloxy)-6-phenylpyrrolo-[2,1-d] benzothiazepi ne (DPB), competitive ligands of the mitochondrial benzodiazepine receptor, all diminished accumulation, as did acifluorfen, a mitochondrial protoporphyrinogen oxidase inhibitor. |
31(0,1,1,1) | Details |
| 16668371 | Jacobs JM, Jacobs NJ, Sherman TD, Duke SO: Effect of Diphenyl Ether Herbicides on Oxidation of to in Organellar and Plasma Membrane Enriched Fractions of Barley. Plant Physiol. 1991 Sep;97(1):197-203. Protoporphyrinogen oxidase activity in the barley root mitochondrial fraction and etioplast extracts was more than 90% inhibited by assay in the presence of the diphenyl ether herbicide acifluorfen methyl, but the activity in the plasma membrane enriched fraction exhibited much less inhibition by this herbicide (12 to 38% inhibition) under the same assay conditions. |
34(0,1,1,4) | Details |
| 1854333 | Camadro JM, Matringe M, Scalla R, Labbe P: Kinetic studies on protoporphyrinogen oxidase inhibition by diphenyl ether herbicides. Biochem J. 1991 Jul 1;277 ( Pt 1):17-21. 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]- (LS 820340) and methyl-5-[2-chloro-5-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid (RH 5348), were studied. |
33(0,1,1,3) | Details |