Journal of Biological Control

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In silico Docking Studies on Cytochrome P450 Enzymes of Helicoverpa armigera (Hubner) and Trichogramma cacoeciae Marchal and Implications for Insecticide Detoxification


Affiliations
1 Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India
 

In silico docking of cytochrome P450 monooxygenase (CYP450) of an insect, Helicoverpa armigera (Hübner) and a parasitoid, Trichogramma cacoeciae Marchal was studied with two insecticides, monocrotophos and fenvalerate. The CYP450 sequences of H. armigera (CYP9A12), T. cacoeciae (CYP4G12) and a human microsomal sequence CYP3A4, as positive control were retrieved from NCBI’s GenBank database. The structure, as predicted by SOPMA, of CYP450 in H. armigera contained 78.7% helix and 43.3% sheets, while that of T. cacoeciae contained 60.6% helix and 68.5% sheets. The three-dimensional molecular models of CYP450 of H. armigera and T. cacoeciae indicated that 96.5 and 97.2% residues, respectively, were in the most favored region. The docking studies revealed that the binding energy of H. armigera was -3.50 and -7.65 kcal/mole compared to the binding energy of T. cacoeciae -2.96 and -5.28 kcal/mole for monocrotophos and fenvalerate, respectively, inferring stronger interaction of H. armigera CYP450 with the insecticides and thereby higher potential for resistance in H. armigera.

Keywords

Cytochrome P450, Helicoverpa armigera, Trichogramma cacoeciae, In silico Molecular Docking.
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  • Armes NJ, Jadhav DR, DeSouza KR. 1996. A survey of insecticides resistance in Helicoverpa armigera in the Indian subcontinent. Bull Ent Res. 86: 499–514.

  • Bachar O, Fischer D, Nussinov R, Wolfson HJ. 1993. A Computer vision based technique for 3-D sequence independent structural comparison of proteins. Protein Eng. 6: 279–288.

  • Baudry J, Li W, Pan L, Berenbaum MR, Schuler MA. 2003. Molecular docking of substrates and inhibitors in the catalytic site of CYP6B1, an insect cytochrome P450 monooxygenase. Protein Eng. 16: 577–587.

  • Baudry J, Rupasinghe S, Shuler MA. 2006. Classdependent sequence alignment strategy improves the structural and functional modeling of P450s. Protein Eng Des Sel. 19: 345–353.

  • Bikadi Z, Hazai E. 2009. Application of the PM6 semiempirical method to modeling proteins enhances docking accuracy of AutoDock. J Cheminf. 1: 15.

  • Bull DL, House VS. 1983. Effects of different insecticides on parasitism of host eggs by Trichogramma pretiosum Riley. Southwestern Entomol. 8: 46–53.

  • Cariño FA, Koener JF, Plapp Jr. FW, Feyereisen R. 1994. Constitutive over expression of the cytochrome P450 gene CYP6A1 in a house fly strain with metabolic resistance to insecticides. Insect Biochem Mol Biol. 24: 411–418.

  • Daborn PJ, Yen JL, Bogwitz MR, Le Goff G, Feil E, Jeffers S. 2002. A single p450 allele associated with insecticide resistance in Drosophila. Science 297: 2253–2256.

  • Daborn PJ, Lumb C, Boey A, Wong W, ffrench-Constant RH, Batterham P. 2007. Evaluating the insecticide resistance potential of eight Drosophila melanogaster cytochrome P450 genes by transgenic overexpression. Insect Biochem Mol Biol. 37: 512–519.

  • de Graaf C, Vermeulen NP, Feenstra KA. 2005. Cytochrome P450 insilico: an integrative modeling approach. J Med Chem. 48: 2725–2755.

  • Edgar RC. 2004. MUSCLE: multiple sequence alignment with high accuracy and high throughput. Nucleic Acids Res. 32, 1792–1797.

  • Feyereisen R, Insect P450 enzymes, Ann Rev Entomol. 44: 507–733.

  • Jalali SK, Singh SP, Venkatesan T, Murthy KS, Lalitha Y. 2006. Development of endosulfan tolerant strain of an egg parasitoid Trichogramma chilonis Ishii (Hymenoptera: Trichogrammatidae). Indian J Exp Biol. 44: 584–590.

  • Jones RT, Bakker SE, Stone D, Shuttleworth SN, Boundy S, McCart C, Daborn PJ, ffrench-Constant RH, van den Elsen JM. 2010. Homology modelling of Drosophila cytochrome P450 enzymes associated with insecticide resistance. Pest Mgmt Sci. 66: 1106–1115.

  • Korytko PJ, Scott JG. 1998. CYP6D1 protects thoracic ganglia of houseflies from the neurotoxic insecticide cypermethrin. Arch Insect Biochem Physiol. 37: 57–63.

  • Kranthi KR, Jadhav DR, Kranthi S, Wanjari RR, Ali SS, Russell DA. 2002. Insecticide resistance in five major insect pests of cotton in India. Crop Prot. 21: 449-460.

  • Laskowski RA, MacArthur MW, Moss DS, Thornton JM. 1993. PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Cryst. 26: 283-291.

  • Li LY. 1994. Worldwide use of Trichogramma for biological control on different crops: a survey. In: Wajnberg, E. and Hassan, SA. (Eds.), Biological control with egg parasitoids, CAB International, Wallingford, UK, pp. 37–44.

  • Liu N, Scott JG. 1998. Increased transcription of CYP6D1 causes cytochrome P450-mediated insecticide resistance in house fly. Insect Biochem Mol Biol. 28: 531–535.

  • Lopez JD, Morrison RK. 1985. Parasitization of Heliothis spp. eggs after augmentative releases of Trichogramma pretiosum Riley. Southwestern Entomol. 8: 110–138.

  • Maitra S, Dombrowski SM, Waters LC, Ganguly R. 1996. Three second chromosome-linked clustered Cyp6 genes show differential constitutive and barbitalinduced expression in DDT-resistant and susceptible strains of Drosophila melanogaster. Gene 180: 165–171.

  • Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. 1998. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comp Chem. 19: 1639–1662.

  • Panigrahi SK. 2008. Strong and weak hydrogen bonds in protein-ligand complexes of kinases: a comparative study. Amino Acids 34: 617–633.

  • Patil R, Das S, Stanley A, Yadav L, Sudhakar A, Varma AK. 2010. Optimized hydrophobic interactions and hydrogen bonding at the target-ligand interface leads the pathways of drug-designing. PLoS One 5: e12029.

  • Pedra JHF, Mclntyre LM, Scharf ME, Pittendrigh BR. 2004. Genome-wide transcription profile of field and laboratory-selected dichlorodiphenyltrichloroethane (DDT)-resistant Drosophila. Proc Nat Acad Sci USA. 101: 7034–7039.

  • Pittendrigh B, Aronstein K, Zinkovsky E, Andreev O, Campbell B, Daly J, Trowell S, ffrench-Constant RH. 1997. Cytochrome P450 genes from Helicoverpa armigera: expression in a pyrethroid – susceptible and – resistant strain. Insect Biochem Mol Biol. 27: 507–512.

  • Ramachandran GN, Ramakrishnan C, Sasisekharan V. 1963. Stereochemistry of polypeptide chain configurations. J Mol Biol. 7: 95–99.

  • Ranson H, Jensen B, Vulule JM, Wang X, Hemingway J, Collins FH. 2000a. Identification of a point mutation in the voltage-gated sodium channel gene of Kenyan Anopheles gambiae associated with resistance to DDT and pyrethroids. Insect Mol Biol. 9: 491–497.

  • Ranson H, Jensen B, Wang X, Prapanthadara L, Hemingway J, Collins FH. 2000b. Genetic mapping of two loci affecting DDT resistance in the malaria vector Anopheles gambiae. Insect Mol Biol. 9: 499–507.

  • Rocher A, Marchand-Geneste N. 2008. Homology modeling of the Apis melifera nicotinic acetylcholine receptor (nAChR) and docking of imidacloprid and fipronil insecticides and their metabolites. SAR and QSAR in Environ Res. 19: 245–261.

  • Sabourault C, Guzov VM, Koener JF, Claudianos C, Plapp Jr. FW, Feyereisen R. 2001. Overproduction of a P450 that metabolizes diazinon is linked to a loss of function in the chromosome 2 ali-esterase (MdalphaE7) gene in resistant house flies. Insect Mol Biol. 10: 609–618.

  • Scott JG. 1999. Cytochromes P450 and insecticide resistance. Insect Biochem Mol Biol. 29: 757–777.

  • Shen J, Wu Y. 1995. Resistance to Helicoverpa armigera to insecticides and its management. China Agricultural Press, Beijing, China, pp. 1–88.

  • Solis FJ, Wets R.J-B. 1998. Minimization by random search techniques. Maths Operation Res. 6: 19–30.

  • Tares S, Berge JB, Amichot M. 2000. Cloning and expression of cytochrome P450 genes belonging to the CYP4 family and to a novel Family, CYP48, in two hymenopteran insects, Trichogramma cacoeciae and Apis mellifera. Biochem Biophys Re. Commun. 268: 677–682.

  • Wheelock GD, Scott JG. 1992. Anti-P450I pr antiserum inhibits specific monooxygenase activities in LPR housefly microsomes. J Exp Zool. 264: 153–158.

  • Yang Y, Yue L, Chen S, Wu Y. 2008. Functional expression of Helicoverpa armigera CYP912 and CYP9A14 in Saccharomyces cerevisiae. Pesticide Biochem Physiol. 92: 101–105.

  • Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, Johnson EF. 2004. The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05A° resolution. J Biol Chem. 279: 38091–38094.


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  • In silico Docking Studies on Cytochrome P450 Enzymes of Helicoverpa armigera (Hubner) and Trichogramma cacoeciae Marchal and Implications for Insecticide Detoxification

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Authors

K. P. Dhanya
Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India
Madhusmita Panda
Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India
S. K. Jalali
Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India
N. K. Krishna Kumar
Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India
R. Gandhi Gracy
Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India
T. Venkatesan
Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India
M. Nagesh
Molecular Entomology Laboratory, National Bureau of Agriculturally Important Insects, Post Bag No. 2491, H. A. Farm Post, Bellary Road, Hebbal, Bangalore 560 024, Karnataka, India

Abstract


In silico docking of cytochrome P450 monooxygenase (CYP450) of an insect, Helicoverpa armigera (Hübner) and a parasitoid, Trichogramma cacoeciae Marchal was studied with two insecticides, monocrotophos and fenvalerate. The CYP450 sequences of H. armigera (CYP9A12), T. cacoeciae (CYP4G12) and a human microsomal sequence CYP3A4, as positive control were retrieved from NCBI’s GenBank database. The structure, as predicted by SOPMA, of CYP450 in H. armigera contained 78.7% helix and 43.3% sheets, while that of T. cacoeciae contained 60.6% helix and 68.5% sheets. The three-dimensional molecular models of CYP450 of H. armigera and T. cacoeciae indicated that 96.5 and 97.2% residues, respectively, were in the most favored region. The docking studies revealed that the binding energy of H. armigera was -3.50 and -7.65 kcal/mole compared to the binding energy of T. cacoeciae -2.96 and -5.28 kcal/mole for monocrotophos and fenvalerate, respectively, inferring stronger interaction of H. armigera CYP450 with the insecticides and thereby higher potential for resistance in H. armigera.

Keywords


Cytochrome P450, Helicoverpa armigera, Trichogramma cacoeciae, In silico Molecular Docking.

References