| Name | cytochrome P450 monooxygenases |
|---|---|
| Synonyms | CYP M; CYP20A1; CYP20A1 protein; Cytochrome P450 family 20 subfamily A polypeptide 1; Cytochrome P450 monooxygenase; CYP20A1 proteins; Cytochrome P450 family 20 subfamily A polypeptide 1s; Cytochrome P450 monooxygenases |
| Name | piperonyl butoxide |
|---|---|
| CAS | 5-[[2-(2-butoxyethoxy)ethoxy]methyl]-6-propyl-1,3-benzodioxole |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 18615616 | Boonsuepsakul S, Luepromchai E, Rongnoparut P: Characterization of Anopheles minimus CYP6AA3 expressed in a recombinant baculovirus system. Arch Insect Biochem Physiol. 2008 Sep;69(1):13-21. Metabolism by cytochrome P450 monooxygenases is a major mechanism implicated in resistance of insects to insecticides, including pyrethroids. Deltamethrin degradation and formation of metabolites were -dependent and inhibited by piperonyl butoxide. |
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| 15880646 | Sevatdal S, Fallang A, Ingebrigtsen K, Horsberg TE: Monooxygenase mediated pyrethroid detoxification in sea lice (Lepeophtheirus salmonis). Pest Manag Sci. 2005 Aug;61(8):772-8. The results indicate that cytochrome P450 monooxygenases are involved in detoxification of pyrethroids in sea lice. 14C-Deltamethrin was absorbed in a lesser amount in a group of sea lice exposed to a mixture of the compound and PBO than in a group exposed to 14C-deltamethrin alone. |
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| 11603736 | Yang X, Zhu KY, Buschman LL, Margolies DC: Comparative susceptibility and possible detoxification mechanisms for selected miticides in banks grass mite and two-spotted spider mite (Acari: Tetranychidae). Exp Appl Acarol. 2001;25(4):293-9. On the other hand, the synergist piperonyl butoxide (PBO) increased the toxicities of bifenthrin and lambda-cyhalothrin by 6.0- and 2.6-fold, respectively, against BGM, and by 4.5- and 1.9-fold, respectively, against TSM. The significant synergism with these pyrethroids of all three tested synergists (except for DEM with lambda-cyhalothrin against TSM) suggests that esterases, glutathione S-transferases, and cytochrome P450 monooxygenases all play important roles in their detoxification. |
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| 18432628 | Krieger RI: Aldrin epoxidation and dihydroisodrin hydroxylation as probes of in vivo and in vitro oxidative metabolic capability of some caterpillars. Pest Manag Sci. 2008 Jun;64(6):622-7. Localization of relatively high concentrations of these cytochrome P450 monooxygenases in gut tissue of lepidoptera may represent an important means to minimize absorption of lipophilic foreign chemicals in food. In vivo studies to assess the significance of in vitro findings are feasible with substrates such as aldrin, dihydroisodrin (DHI) and oxidative methylenedioxyphenyl inhibitors such as piperonyl butoxide (PBO) or |
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| 19533589 | Wang D, Qiu X, Ren X, Zhang W, Wang K: Effects of spinosad on Helicoverpa armigera (Lepidoptera: Noctuidae) from China: tolerance status, synergism and enzymatic responses. Pest Manag Sci. 2009 Sep;65(9):1040-6. The toxicity of spinosad could be synergised by piperonyl butoxide (PBO) and triphenylphosphate (TPP), but not by diethyl maleate (DEM). Cytochrome P450 monooxygenase might be involved in the metabolism of, and hence resistance to, spinosad in this pest in China. |
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| 14680115 | Li AY, Davey RB, Miller RJ, George JE: Resistance to coumaphos and diazinon in Boophilus microplus (Acari: Ixodidae) and evidence for the involvement of an oxidative detoxification mechanism. J Med Entomol. 2003 Jul;40(4):482-90. Piperonyl butoxide (PBO) reduced coumaphos toxicity in susceptible strains, but synergized coumaphos toxicity in resistant strains. The results suggest that an enhanced cytochrome P450 monooxygenase (cytP450)-mediated detoxification mechanism may exist in the resistant strains, in addition to the cytP450-mediated metabolic pathway that activates coumaphos. |
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| 10918309 | David JP, Rey D, Cuany A, Amichot M, Meyran JC: Comparative ability to detoxify alder leaf litter in field larval mosquito collections. Arch Insect Biochem Physiol. 2000 Aug;44(4):143-50. The larvicidal effects of polyphenols from dietary alder leaf litter were investigated in different field collections of three detritivorous Aedes taxa (Ae. detritus, Ae. cataphylla, Ae. rusticus) and compared to the cytochrome P450 monooxygenase, glutathione S-transferase, and esterase activities. Furthermore, the role of P450 enzymes in the mechanism of resistance to alder polyphenols was suggested by the synergistic effect in vivo of piperonyl butoxide in the resistant Ae. rusticus. |
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| 20232338 | Joussen N, Schuphan I, Schmidt B: Metabolism of methoxychlor by the P450-monooxygenase CYP6G1 involved in insecticide resistance of Drosophila melanogaster after expression in cell cultures of Nicotiana tabacum. Chem Biodivers. 2010 Mar;7(3):722-35. Cytochrome P450 monooxygenase CYP6G1 of Drosophila melanogaster was heterologously expressed in a cell suspension culture of Nicotiana tabacum. Furthermore, methoxychlor metabolism was inhibited by 43% after simultaneous addition of piperonyl butoxide (458 microg), whereas inhibition in the non-transgenic culture amounted to 92%. |
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| 11886776 | Tsagkarakou A, Pasteur N, Cuany A, Chevillon C, Navajas M: Mechanisms of resistance to organophosphates in Tetranychus urticae (Acari: Tetranychidae) from Greece. Insect Biochem Mol Biol. 2002 Apr;32(4):417-24. It is shown that S,S,S-tributyl phosphorotrithioate, a synergist that inhibits esterases and glutathione S-transferases, and piperonyl butoxide, a synergist that inhibits cytochrome P450 mediated monooxygenases, did not affect the level of methyl-parathion or methomyl resistance in RLAB and that resistance ratios to both insecticides did not change significantly in the presence of either synergist. The activity of two cytochrome P450 monooxygenase groups was compared. |
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| 14658506 | Li X, Zangerl AR, Schuler MA, Berenbaum MR: Cross-resistance to alpha-cypermethrin after xanthotoxin ingestion in Helicoverpa zea (Lepidoptera: Noctuidae). J Econ Entomol. 2000 Feb;93(1):18-25. Cytochrome P450 monooxygenases (P450) are membrane-bound hemoproteins that play important roles in conferring protection against both naturally occurring phytochemicals and synthetic organic insecticides. Administration of piperonyl butoxide, a P450 synergist, demonstrated that resistance to both xanthotoxin and alpha-cypermethrin is P450-mediated. |
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| 9465388 | Zhang L, Kasai S, Shono T: In vitro metabolism of pyriproxyfen by microsomes from susceptible and resistant housefly larvae. Arch Insect Biochem Physiol. 1998;37(3):215-24. Cytochrome P450 inhibitors, piperonyl butoxide (PB) and 2-propynyl 2,3,6-trichlorophenyl ether (PTPE), decreased the metabolic rates significantly in all three strains. This study confirmed that microsomal cytochrome P450 monooxygenases play an important role in the pyriproxyfen resistance of the housefly. |
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| 19800097 | Mori T, Nakamura K, Kondo R: Fungal hydroxylation of polychlorinated naphthalenes with migration by wood rotting fungi. Chemosphere. 2009 Nov;77(9):1230-5. Epub 2009 Oct 1. Significant inhibition of the degradation of DCNs and formation of their metabolic products was observed in incubation with the cytochrome P-450 monooxygenase inhibitor piperonyl butoxide. The formation of the dihydrodiol-like metabolites, migration and the experiment with P-450 inhibitor suggested that P. lindtneri provides metabolites via oxide intermediates of DCNs by a cytochrome P450 monooxygenase. |
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| 2372869 | Ruch RJ, Fransson R, Flodstrom S, Warngard L, Klaunig JE: Inhibition of hepatocyte gap junctional intercellular communication by endosulfan, chlordane and heptachlor. Carcinogenesis. 1990 Jul;11(7):1097-101. Concomitant treatment of the cells with inhibitors of cytochrome P450 monooxygenases (SKF-525A, piperonyl butoxide or did not alter the inhibition of GJIC by the cyclodienes, suggesting that cytochrome P450 metabolism was not involved in the inhibitory mechanism. |
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| 16032654 | Xu Q, Liu H, Zhang L, Liu N: Resistance in the mosquito, Culex quinquefasciatus, and possible mechanisms for resistance. Pest Manag Sci. 2005 Nov;61(11):1096-102. Resistance to permethrin in MAmCq (G1) and HAmCq (G3) was partially suppressed by piperonyl butoxide (PBO), S,S,S-tributylphosphorotrithioate (DEF) and diethyl (DEM), inhibitors of cytochrome P450 monooxygenases, hydrolases and glutathione S-transferases (GST), respectively, suggesting these three enzyme families are important in conferring permethrin resistance in both strains. |
81(1,1,1,1) | Details |
| 7908050 | Kumar GN, Walle UK, Walle T: Cytochrome P450 3A-mediated human liver microsomal taxol 6 alpha-hydroxylation. J Pharmacol Exp Ther. 1994 Mar;268(3):1160-5. The -dependency and the inhibitory effect of and piperonyl butoxide on taxol metabolism indicated the involvement of cytochrome P450 (CYP) monooxygenases. |
81(1,1,1,1) | Details |
| 18294710 | Weinstein JE, Garner TR: Piperonyl butoxide enhances the bioconcentration and photoinduced toxicity of fluoranthene and benzo [a] pyrene to larvae of the grass shrimp (Palaemonetes pugio). Aquat Toxicol. 2008 Apr 8;87(1):28-36. Epub 2008 Jan 16. Piperonyl butoxide (PBO) is a commonly used synergist in many pyrethroid formulations due to its ability to interfere with cytochrome P450 (CYP) monooxygenases. |
81(1,1,1,1) | Details |
| 17173346 | Bielza P, Espinosa PJ, Quinto V, Abellan J, Contreras J: Synergism studies with binary mixtures of pyrethroid, and organophosphate insecticides on Frankliniella occidentalis (Pergande). Pest Manag Sci. 2007 Jan;63(1):84-9. The major mechanism of resistance to most insecticides in Frankliniella occidentalis (Pergande) is metabolic, piperonyl butoxide (PBO) suppressible, mediated by cytochrome-P450 monooxygenases and conferring cross-resistance among insecticide classes. |
81(1,1,1,1) | Details |
| 10646973 | Li X, Berenbaum MR, Schuler MA: Molecular cloning and expression of CYP6B8: a xanthotoxin-inducible cytochrome P450 cDNA from Helicoverpa zea. Insect Biochem Mol Biol. 2000 Jan;30(1):75-84. Xanthotoxin, a plant allelochemical, induces alpha-cypermethrin insecticide tolerance in Helicoverpa zea (corn earworm); inhibition of tolerance by piperonyl butoxide implicates cytochrome P450 monooxygenases (P450s) in the detoxification of this insecticide. |
81(1,1,1,1) | Details |
| 8183245 | Chichester CH, Buckpitt AR, Chang A, Plopper CG: Metabolism and cytotoxicity of naphthalene and its metabolites in isolated murine Clara cells. Mol Pharmacol. 1994 Apr;45(4):664-72. Naphthalene-induced decreases in cell viability were blocked by preincubation of Clara cells with the cytochrome P450 monooxygenase inhibitor piperonyl butoxide. |
32(0,1,1,2) | Details |
| 18615705 | Yang ML, Zhang JZ, Zhu KY, Xuan T, Liu XJ, Guo YP, Ma EB: Mechanisms of organophosphate resistance in a field population of oriental migratory locust, Locusta migratoria manilensis (Meyen). Arch Insect Biochem Physiol. 2009 May;71(1):3-15. The susceptibilities to three organophosphate (OP) insecticides (malathion, chlorpyrifos, and phoxim), responses to three metabolic synergists [triphenyl (TPP), piperonyl butoxide (PBO), and diethyl (DEM)], activities of major detoxification enzymes [general esterases (ESTs), glutathione S-transferases (GSTs), and cytochrome P450 monooxygenases (P450s)], and sensitivity of the target enzyme acetylcholinesterase (AChE) were compared between a laboratory-susceptible strain (LS) and a field-resistant population (FR) of the oriental migratory locust, Locusta migratoria manilensis (Meyen). |
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| 19179004 | Marco-Urrea E, Perez-Trujillo M, Caminal G, Vicent T: Dechlorination of 1,2,3- and 1,2,4-trichlorobenzene by the white-rot fungus Trametes versicolor. J Hazard Mater. 2009 Jul 30;166(2-3):1141-7. Epub 2008 Dec 25. Cytochrome P450 monooxygenase appears to be involve in the first step of 1,2,4-TCB degradation, as evidenced by marked inhibition of both dechlorination and degradation of 1,2,4-TCB in the presence of the known cyt P450 inhibitors 1-aminobenzotriazole and piperonyl butoxide. |
31(0,1,1,1) | Details |
| 20069862 | Romero A, Potter MF, Haynes KF: Evaluation of piperonyl butoxide as a deltamethrin synergist for pyrethroid-resistant bed bugs. J Econ Entomol. 2009 Dec;102(6):2310-5. We used the cytochrome P450 monooxygenase (P450) inhibitor piperonyl butoxide (PBO) to assess the role of P450s in deltamethrin resistance in three field-collected bed bug strains, LA-1, CIN-1 and WOR-1. |
31(0,1,1,1) | Details |
| 15262281 | Yang Y, Wu Y, Chen S, Devine GJ, Denholm I, Jewess P, Moores GD: The involvement of microsomal oxidases in pyrethroid resistance in Helicoverpa armigera from Asia. Insect Biochem Mol Biol. 2004 Aug;34(8):763-73. The activities of cytochrome P450 monooxygenases from midguts of final instar larvae to p-nitroanisole (PNOD), ethoxycoumarin (ECOD), methoxyresorufin (MROD) significantly increased in all the resistant strains when compared with the susceptible strain. Selection with a mixture of fenvalerate and piperonyl butoxide (PBO) for 14 generations ('YGFP') resulted in resistance ratios of 2510, 2920 and 286. |
3(0,0,0,3) | Details |
| 9076527 | Kotze AC: Cytochrome P450 monooxygenase activity in Haemonchus contortus (Nematoda). Int J Parasitol. 1997 Jan;27(1):33-40. Larval activities were -dependent, suppressed by (CO) and piperonyl butoxide, and induced (up to 60-fold) by exposure to phenobarbital. |
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| 19125173 | Pasay C, Arlian L, Morgan M, Gunning R, Rossiter L, Holt D, Walton S, Beckham S, McCarthy J: The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides. PLoS Negl Trop Dis. 2009;3(1):e354. Epub 2009 Jan 6. METHODOLOGY/PRINCIPAL FINDINGS: To determine the role of metabolic degradation as a mechanism for acaricide resistance in scabies mites, PBO (piperonyl butoxide), DEF (S,S,S-tributyl phosphorotrithioate) and DEM (diethyl were first tested for synergistic activity with permethrin in a bioassay of mite killing. Then, to investigate the relative role of specific metabolic pathways inhibited by these synergists, enzyme assays were developed to measure esterase, glutathione S-transferase (GST) and cytochrome P450 monooxygenase (cytochrome P450) activity in mite extracts. |
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| 16937654 | Johnson RM, Wen Z, Schuler MA, Berenbaum MR: Mediation of pyrethroid insecticide toxicity to honey bees (Hymenoptera: Apidae) by cytochrome P450 monooxygenases. J Econ Entomol. 2006 Aug;99(4):1046-50. To test the role of metabolic detoxification in mediating the relatively low toxicity of tau-fluvalinate compared with more toxic pyrethroid insecticides, we examined the effects of piperonyl butoxide (PBO), S,S,S-tributylphosphorotrithioate (DEF), and diethyl (DEM) on the toxicity of these pyrethroids. |
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| 19937914 | Feng Y, Wu Q, Wang S, Chang X, Xie W, Xu B, Zhang Y: Cross-resistance study and biochemical mechanisms of thiamethoxam resistance in B-biotype Bemisia tabaci (Hemiptera: Aleyrodidae). Pest Manag Sci. 2010 Mar;66(3):313-8. Piperonyl butoxide (PBO) and triphenyl (TPP) exhibited significant synergism on thiamethoxam effects in the TH-R strain (3.14- and 2.37-fold respectively). Biochemical assays showed that cytochrome P450 monooxygenase activities increased 1.21- and 1.68-fold respectively, and carboxylesterase activity increased 2.96-fold in the TH-R strain. |
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| 11681686 | Sanchez-Arroyo H, Koehler PG, Valles SM: Effects of the synergists piperonyl butoxide and S,S,S-tributyl phosphorotrithioate on propoxur pharmacokinetics in Blattella germanica (Blattodea: Blattellidae). J Econ Entomol. 2001 Oct;94(5):1209-16. Treatment of adult male German cockroaches with the cytochrome P450 monooxygenase inhibitor, PBO, or the esterase inhibitor, DEF, increased propoxur toxicity by 2- and 6.8-fold, respectively, implicating hydrolysis as a major detoxification route of propoxur in the German cockroach. |
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| 16830213 | Zeng RS, Niu G, Wen Z, Schuler MA, Berenbaum MR: Toxicity of to Helicoverpa zea and bioactivation by cytochrome P450 monooxygenases. J Chem Ecol. 2006 Jul;32(7):1459-71. Epub 2006 Jun 1. That cytochrome P450 monooxygenases (P450s) are involved in the bioactivation of aflatoxin in this species is evidenced by the effects of piperonyl butoxide (PBO), a known P450 inhibitor, on toxicity; whereas no fourth instars pupated in the presence of 1 mug/g in the diet, the presence of 0.1% PBO increased the pupation rate to 71.7%. |
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| 19883652 | Guo L, Zeng XY, Wang DY, Li GQ: metabolism in the Asian corn borer, Ostrinia furnacalis (Guenee) (Lepidoptera: Pyralidae). J Insect Physiol. 2010 Mar;56(3):260-5. Epub 2009 Nov 11. Toxicity of was enhanced by 4-methylpyrazole, 3-amino-1,2,4-triazole and piperonyl butoxide, and toxicity of was increased by 3-amino-1,2,4-triazole and piperonyl butoxide. These data indicate that alcohol dehydrogenase, and probably catalase and cytochrome P450 monooxygenase oxidize to catalase and cytochrome P450 monooxygenase catalyze to water and and carboxylesterase may have a minor effect. |
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