Modes of Action of Chitin Synthesis Inhibitors

Marks, Edwin P.; Leighton, Terrance; Leighton, Frances

doi:10.1016/b978-0-12-177120-1.50015-1

Cited by 32 publications

(9 citation statements)

References 70 publications

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“…The exact biochemical lesion inflicted by these inhibitors is not known. Among the suggestions forwarded were 1) enhanced activities of phenoloxidase and chitinase [66]; 2) inhibition of proteases which convert the inactive zymogenic chitin synthase into an active enzyme [67]; 3) inhibition of DNA synthesis [68]; 4) inhibition of influx of nucleosides [69]; 5) interference with the insect hormonal balance [70]; and 6) inhibition of the speculative GlcNAc transporter [64]. Some of the suggested mechanisms of action such as 1, 3, and 4 have been regarded as secondary effects [3].…”

Section: Chitin From Polymer To Microfibrilmentioning

confidence: 99%

Chitin synthesis and degradation as targets for pesticide action

Cohen

1993

Arch Insect Biochem Physiol

139

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Various pesticides are being used to destabilize, perturb, or inhibit crucial biochemical and physiological targets related to metabolism, growth, development, nervous communication, or behavior in pestiferous organisms. Chitin is an eukaryotic extracellular aminosugar biopolymer, massively produced by most fungal systems and by invertebrates, notably arthropods. Being an integral supportive component in fungal cell wall, insect cuticle, and nematode egg shell, chitin has been considered as a selective target for pesticide action. Throughout the elaborate processes of chitin formation and deposition, only the polymerization events associated with the cell membrane compartment are so far available for chemical interference. Currently, the actinomycetes-derived nucleoside peptide fungicides such as the polyoxins and the insecticidal benzoylaryl ureas have reached commercial pesticide status. The polyoxins and other structurally-related antibiotics like nikkomycins are strong competitive inhibitors of the polymerizing enzyme chitin synthase. The exact biochemical lesion inflicted by the benzoylaryl ureas is still elusive, but a post-polymerization event, such as translocation of chitin chains across the cell membrane, is suggested. Hydrolytic degradation of the chitin polymer is essential for hyphal growth, branching, and septum formation in fungal systems as well as for the normal molting of arthropods. Recently, insect chitinase activity was strongly and specifically suppressed by allosamidin, an actimomycetes-derived metabolite. In part, the defense mechanism in plants against invasion of pathogens is associated with induced chitinases. Chitin, chitosan, and their oligomers are able to act as elicitors which induce enhanced levels of chitinases in various plants. Lectins which bind to N-acetyl-D-glucosamine strongly interfere with fungal and insect chitin synthases. Plant lectins with similar properties may be involved in plant-pathogen interaction inter alia by suppressing fungal invasion.

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Section: Chitin From Polymer To Microfibrilmentioning

confidence: 99%

Chitin synthesis and degradation as targets for pesticide action

Cohen

1993

Arch Insect Biochem Physiol

139

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“…The major problem in answering this question has been that so far neither DFB nor any other benzoylurea-type chemicals have shown inhibitory properties toward any of the enzymes associated with chitin synthesis when tested in vitro (Cohen, 2001). Furthermore, DFB does not inhibit chitin synthesis in yeast (Marks et al, 1982), unlike other chitin synthesis inhibitors such as polyoxin D (Endo et al, 1970), which is effective in inhibiting chitin synthesis both in insects and yeast. Clearly DFBtype chemicals act on an arthropod-specific cuticular component that is vital to chitin synthesis in vivo.…”

Section: Introductionmentioning

confidence: 97%

“…It has been well established that diflubenzuron (DFB) inhibits chitin synthesis in vivo and that such action constitutes the main insecticidal mechanism of this compound (Marks et al, 1982;Verloop and Ferrell, 1977). However, the precise molecular mechanism of its action has not been elucidated.…”

Section: Introductionmentioning

confidence: 99%

Significance of the sulfonylurea receptor (SUR) as the target of diflubenzuron in chitin synthesis inhibition in Drosophila melanogaster and Blattella germanica

Abo-Elghar

Fujiyoshi

Matsumura

2004

Insect Biochemistry and Molecular Biology

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“…Chitin synthetase (CS) is a preferred target in the rational design of selective fungicides and insecticides (Marks et al, 1982;Hajjar, 1985; Kramer and Koga, 1986). Nikkomycin Z (NZ) (Figure 1), a fermentation product of Streptomyces tendae (Dáhn et al, 1976), and some closely related nucleoside peptide antibiotics (Hori et al, 1971; Kobinata et al, 1980) are the most potent known inhibitors of CS of fungi (Gow and Selitrennikoff, 1984;Furter and Rast, 1985) and insects (Cohen and Casida, 1980).…”

Section: Introductionmentioning

confidence: 99%

Tritritionikkomycin Z, [uracil-5-3H,pyridyl-2,4-3H2]: radiolabeling of a potent inhibitor of fungal and insect chitin synthetase

Ando¹,

Tecle²,

Toia³

et al. 1990

J. Agric. Food Chem.

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Nikkomycin Z (NZ) (a potent fungicide, insecticide, miticide, and inhibitor of fungal and insect chitin synthetase) was converted to a mixture of specific mono-, di-, and tribromo derivatives (BrNZ, Br2NZ, and BrgNZ, respectively) on reaction with N-bromosuccinimide in jV^V-dimethylformamide. Substitution by bromine occurred first at the 2-position of the 3-hydroxypyridyl moiety, second at the 5-position of the uracil moiety, and finally at the 4-position of the 3-hydroxypyridyl moiety as observed both for NZ and for mixtures of uridine and 3-hydroxy-6-methylpyridine as model compounds representative of the moieties of NZ. Following fractionation of the various bromonikkomycin derivatives by HPLC, their structures were assigned by NMR, MS, and UV analyses. Catalytic reductive debromination of Br3NZ with tritium gas over palladium on carbon gave [uroctZ-5-3H,pyrid>'Z-2,4-3H2]NZ. This material has sufficiently high specific activity (~60 Ci/mmol) and suitable positions of labeling to study its uptake, distribution, metabolism, and possible target site interactions in fungal and insect systems.

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Modes of Action of Chitin Synthesis Inhibitors

Cited by 32 publications

References 70 publications

Chitin synthesis and degradation as targets for pesticide action

Chitin synthesis and degradation as targets for pesticide action

Significance of the sulfonylurea receptor (SUR) as the target of diflubenzuron in chitin synthesis inhibition in Drosophila melanogaster and Blattella germanica

Tritritionikkomycin Z, [uracil-5-3H,pyridyl-2,4-3H2]: radiolabeling of a potent inhibitor of fungal and insect chitin synthetase

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