Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

Name imidacloprid
CAS

Reference List

PubMed Abstract RScore(About this table)
18510975 Karunker I, Benting J, Lueke B, Ponge T, Nauen R, Roditakis E, Vontas J, Gorman K, Denholm I, Morin S: Over-expression of cytochrome P450 CYP6CM1 is associated with high resistance to imidacloprid in the B and Q biotypes of Bemisia tabaci (Hemiptera: Aleyrodidae). Insect Biochem Mol Biol. 2008 Jun;38(6):634-44. Epub 2008 Mar 29.
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19391582 Shi X, Dick RA, Ford KA, Casida JE: Enzymes and inhibitors in neonicotinoid insecticide metabolism. . J Agric Food Chem. 2009 Jun 10;57(11):4861-6.

Neonicotinoid insecticide metabolism involves considerable substrate specificity and regioselectivity of the relevant CYP450, aldehyde oxidase, and phase II enzymes.
Imidacloprid (IMI), CLO, and several of their metabolites do not give detectable N-glucuronides but 5-hydroxy-IMI, 4,5-diol-IMI, and 4-hydroxythiacloprid are converted to O-glucuronides in vitro with mouse liver microsomes and UDP-glucuronic acid or in vivo in mice.
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14635178 Rauch N, Nauen R: Identification of biochemical markers linked to neonicotinoid cross resistance in Bemisia tabaci (Hemiptera: Aleyrodidae). Arch Insect Biochem Physiol. 2003 Dec;54(4):165-76.

Target site resistance to imidacloprid using [(3) H] imidacloprid in nicotinic acetylcholine receptor (nAChR) binding assays could not be detected in any of these highly resistant strains.
The impact of metabolizing enzymes such as esterases, glutathione S-transferases, and cytochrome P450-dependent monooxygenases in neonicotinoid resistance was studied biochemically with artificial substrates.
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15720138 Dick RA, Kanne DB, Casida JE: Identification of aldehyde oxidase as the neonicotinoid nitroreductase. Chem Res Toxicol. 2005 Feb;18(2):317-23.

Imidacloprid (IMI), the prototypical neonicotinoid insecticide, is used worldwide for crop protection and flea control on pets.
It is both oxidatively metabolized by cytochrome P450 enzymes and reduced at the nitroguanidine moiety by a previously unidentified cytosolic "neonicotinoid nitroreductase", the subject of this investigation.
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17598550 Sims SR, Appel AG: Linear alcohol ethoxylates: insecticidal and synergistic effects on German cockroaches (Blattodea: Blattellidae) and other insects. J Econ Entomol. 2007 Jun;100(3):871-9.

The insecticidal activity of Tomadol 23-1 was synergized by coapplication with a sublethal amount of piperonyl butoxide, indicating the involvement of cytochrome P450 microsomal monooxygenases in insect metabolism of AEO surfactants.
Significant synergism was demonstrated in combinations of Tomadol 23-1 and chlorfenapyr, clothianidin, imidacloprid, thiamethoxam, and pyrethrum.
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11810226 Daborn P, Boundy S, Yen J, Pittendrigh B, ffrench-Constant R: DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid. Mol Genet Genomics. 2001 Dec;266(4):556-63. Epub 2001 Oct 5.

The genomic sequence in this interval shows a cluster of cytochrome P450 genes, one of which, Cyp6g1, is over-expressed in all resistant strains examined.
1(0,0,0,1) Details
12230409 Schulz-Jander DA, Leimkuehler WM, Casida JE: Neonicotinoid insecticides: reduction and cleavage of imidacloprid nitroimine substituent by liver microsomal and cytosolic enzymes. Chem Res Toxicol. 2002 Sep;15(9):1158-65.

Only a portion of the microsomal reduction and cleavage of the nitroimine substituent is attributable to a CYP450 enzyme.
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12826097 Le Goff G, Boundy S, Daborn PJ, Yen JL, Sofer L, Lind R, Sabourault C, Madi-Ravazzi L, ffrench-Constant RH: Microarray analysis of cytochrome P450 mediated insecticide resistance in Drosophila. Insect Biochem Mol Biol. 2003 Jul;33(7):701-8.

We show that all three DDT selected P450s can confer resistance to the neonicotinoid imidacloprid but that Cyp6a8 confers no cross-resistance to malathion.
1(0,0,0,1) Details
12084621 Schulz-Jander DA, Casida JE: Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction. Toxicol Lett. 2002 Jun 7;132(1):65-70.
83(1,1,1,3) Details
19562662 Wang Z, Yao M, Wu Y: Cross-resistance, inheritance and biochemical mechanisms of imidacloprid resistance in B-biotype Bemisia tabaci. Pest Manag Sci. 2009 Nov;65(11):1189-94.

It is shown that enhanced detoxification mediated by cytochrome-P450-dependent monooxygenases contributes to imidacloprid resistance to some extent in the NJ-Imi strain.
31(0,1,1,1) Details
19716416 Karunker I, Morou E, Nikou D, Nauen R, Sertchook R, Stevenson BJ, Paine MJ, Morin S, Vontas J: Structural model and functional characterization of the Bemisia tabaci CYP6CM1vQ, a cytochrome P450 associated with high levels of imidacloprid resistance. Insect Biochem Mol Biol. 2009 Oct;39(10):697-706. Epub 2009 Aug 27.
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