Assessment of novel inhibitors of Helicoverpa aminopeptidases as anti-insect agents

Pest Management Science

Volumn 62, Issue 11, 2006, Pages 1098-1108

  Duncan, Ann Maree ^a   Ren, Hua ^a   Bound, Fleur ^a   Tully, Jon ^a   Chandler, David S ^b   Sandeman, R Mark ^a  

^a LA TROBE UNIVERSITY   (Australia)

^b NUFARM LIMITED   (Australia)

Author keywords

Aminopeptidase; Aminopeptidase inhibitor; Helicoverpa; Larval growth, insecticide

Indexed keywords

ACTINONIN; AMINOPEPTIDASE; DRUG DERIVATIVE; HYDROXAMIC ACID; INSECTICIDE; METHYLPHOSPHONIC ACID; ORGANOPHOSPHORUS COMPOUND; PHOSPHONIC ACID DERIVATIVE; PHTHALIMIDE DERIVATIVE; TETRALIN DERIVATIVE; VALINE; VALINE METHYL PHOSPHONATE;

ASSESSMENT METHOD; CROP PLANT; ENZYME ACTIVITY; INHIBITOR; INSECTICIDE; PEST SPECIES;

ANIMAL; ARTICLE; CHEMISTRY; DRUG ANTAGONISM; LARVA; MOTH;

AMINOPEPTIDASES; ANIMALS; HYDROXAMIC ACIDS; INSECTICIDES; LARVA; MOTHS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHONIC ACIDS; PHTHALIMIDES; TETRALONES; VALINE;

AUSTRALASIA; AUSTRALIA;

GOSSYPIUM HIRSUTUM; HELICOVERPA; HELICOVERPA ARMIGERA; HELICOVERPA PUNCTIGERA; INSECTA;

EID: 33750299054     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1286     Document Type: Article

References (30)

1. Zalucki MP, Daglish G, Firempong S and Twine A, The biology and ecology of Heliothis armigera (Hübner) and H. punctigera Wallengren (Lepidoptera: Noctuidae) in Australia: What do we know? Aust J Zool 34:779-814 (1986).
2. Matthews M, Heliothine Moths of Australia: a Guide to Pest Bollworms and Related Noctuid Groups. CSIRO Publishing, Melbourne (1999).
3. Heckel DG, Gahan LJ, Gould F, Daly JC and Trowell S, Genetics of Heliothis and Helicoverpa resistance to chemical insecticides and to Bacillus thuringiensis. Pestic Sci 51:251-258 (1997).
4. Broadway RM and Duffey SS, Plant proteinase inhibitors: mechanism of action and effect on the growth and digestive physiology of larval Heliothis zea and Spodoptera exiqua. J Insect Physiol 32:827833 (1986).
5. McManus MT and Burgess EPJ, Effects of the soybean (Kunitz) trypsin inhibitor on growth and digestive proteases of larvae of Spodoptera litura. J Insect Physiol 41:731-738 (1995).
6. Burgess EPJ, Main CA, Stevens PS, Christeller JT, Gatehouse AMR and Laing WA, Effects of protease inhibitor concentration and combinations on the survival, growth and gut enzyme activities of the black field cricket, Teleogryllus commodus. J Insect Physiol 40:803-911 (1994).
7. Reed BJ, Chandler DS and Sandeman RM, Aminopeptidases as potential targets for the control of the Australian sheep blowfly, Lucilia cuprina. Internat J Parasitol 29:839-850 (1999).
8. Johnston KA, Gatehouse JA and Anstee JH, Effects of soybean protease inhibitors on the growth and development of larval Helicoverpa armigera. J Insect Physiol 39:657-664 (1993).
9. Terra WR and Ferreira C, Insect digestive enzymes: properties, compartmentalization and function. Comp Biochem Physiol 109B:1-62 (1994).
10. Christeller JT, Laing WA, Markwick NP and Burgess EPJ, Midgut protease activities in 12 phytophagous Lepidopteran larvae: dietary and protease inhibitor interactions. Insect Biochem Mol Biol 22:735-746 (1992).
11. Gatehouse LN, Shannon AL, Burgess EPJ and Christeller JT, Characterization of major midgut proteinase cDNAs from Helicoverpa armigera larvae and changes in gene expression in response to four proteinase inhibitors in the diet. Insect Biochem Mol Biol 27:929-944 (1997).
12. Broadway RM, Dietary proteinase inhibitors alter complement of midgut proteases. Arch Insect Biochem Physiol 32:39-53 (1996).
13. Emmerling M, Chandler D and Sandeman M, Molecular cloning of cDNAs encoding aminopeptidases from the midgut of Helicoverpa punctigera, the Australian native budworm. Insect Biochem Mol Biol 31:899-907 (2001).
14. Wang P, Zhang X and Zhang J, Molecular characterization of four midgut aminopeptidase N isozymes from the cabbage looper, Trichoplusia ni. Insect Biochem Mol Biol 35:611-620 (2005).
15. Miyachi H, Kato M, Kato F and Hashimoto Y, Novel potent nonpeptide aminopeptidase N inhibitors with a cyclic imide skeleton. J Med Chem 41:263-265 (1998).
16. Schalk C, d'Orchymont H, Jauch M-F and Tarnus C, 3-Amino-2-tetralone derivatives: novel potent and selective inhibitors of aminopeptidase-M (EC3.4.11.2). Arch Biochem Biophys 311:42-46 (1994).
17. Umezawa H, Aoyagi T, Tanaka T, Suda H, Okuyama A, Naganawa H, et al, Production of actinonin, an inhibitor of aminopeptidase M, by actinomycetes. J Antibiot 38:1629-1630 (1985).
18. Chan WW, Dennis P, Demmer W and Brand K, Inhibition of leucine aminopeptidase by amino acid hydroxamates. J Biol Chem 257:7955-7957 (1982).
19. Baker JO, Wilkes SH, Bayliss ME and Prescott JM, Hydroxamates and aliphatic boronic acids: marker inhibitors for aminopeptidase. Biochemistry 22:2098-2103 (1983).
20. Giannousis PP and Bartlett PA, Phosphorus amino acid analogues as inhibitors of leucine aminopeptidase. J Med Chem 30:1603-1609 (1987).
21. Spengler J and Burger K, An efficient synthesis of N- phosphinoylmethylamino acids and some of their derivatives. J Chem Soc Perkin Trans 1:2091-2095 (1998).
22. Teakle RE and Jensen JM, Heliothis punctigera, in Handbook of Insect Rearing, ed. by Singh P and Moore RF. Elsevier, Amsterdam, pp. 313-322 (1985).
23. Sandeman RM, Chandler DS, Duncan A-M and Hay PM, Insecticide and method for controlling insects. International Patent PCT/AU02/00389, priority date March 2002 (2002).
24. Lawrence PK and Koundal KR, Plant protease inhibitors in control of phytophagous insects. Electronic J Biotech 5:93-109 (2002).
25. Ortego F, Farinos GP, Ruiz M, Marco V and Castanera P, Characterization of digestive proteases in the weevil Aubeonymus mariaefranciscae and effects of proteinase inhibitors on larval development and survival. Entomologia Experimentalis et Applicata 88:265-274 (1998).
26. Bown DP, Wilkinson HS and Gatehouse JA, Midgut carboxypeptidase from Helicoverpa armigera (Lepidoptera: Noctuidae) larvae: enzyme characterisation, cDNA cloning and expression. Insect Biochem Mol Biol 28:739-749 (1998).
27. Nakanishi K, Yaoi K, Nagino Y, Hara H, Kitami M, Atsumi S, et al, Aminopeptidase N isoforms from the midgut of Bombyx mori and Plutella xylostella - their classification and the factors that determine their binding specificity to Bacillus thuringiensis Cry1A toxin. FEBS Lett 519:215-220.
28. Herrero S, Gechev T, Bakker PL, Moar WJ and de Maagd RA, Bacillus thuringiensis Cry1Ca-resistant Spodoptera exigua lacks expression of one of four Aminopeptidase N genes. BMC Genomics 6:96 (2005).
29. Bown DP, Wilkinson HS and Gatehouse JA, Differentially regulated inhibitor-sensitive and insensitive protease genes from the phytophagous insect pest, Helicoverpa armigera, are members of complex multigene families. Insect Biochem Mol Biol 27:625-638 (1997).
30. Mathe G, Bestatin, an aminopeptidase inhibitor with a multi-pharmacological function. Biomed Pharmacother 45:49-54 (1991).