The chitin crystallite in arthropod cuticle

Neville, A. C.; Parry, David; Woodhead-Galloway, John

doi:10.1242/jcs.21.1.73

Cited by 155 publications

(39 citation statements)

References 16 publications

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“…Chitin, a long-chain polymer composed of β-1,4-linked N -acetyl- d -glucosamines (GlcNAc), is a vital structural component of insects . As well as being important for insect growth and development, it also supports the integrity of the cuticle that is secreted by the epidermal cells.…”

Section: Introductionmentioning

confidence: 99%

Structure-Based Virtual Screening, Compound Synthesis, and Bioassay for the Design of Chitinase Inhibitors

Dong

Jiang

Liu

et al. 2018

J. Agric. Food Chem.

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Chitinases play a vital part in the molting phase of insect pests. Inhibiting their activities by the use of drug-like small chemical molecules is thought to be an efficient strategy in pesticide design and development. On the basis of the crystal structure of OfChtI, a chitinase indispensable for the molting of the insect pest Ostrinia furnacalis (Asian corn borer), here we report a chemical fragment and five variant compounds as inhibitors of OfChtI obtained from a library of over 200 000 chemicals by a structure-based-virtual-screening approach. The compounds were synthesized with high atom economy and tested for their OfChtI-inhibitory activities in a bioassay. Compound 3 showed preferential inhibitory activity with a K value of 1.5 μΜ against OfChtI. Analysis of the structure-activity relationships of the compounds provided insight into their interactions with the enzyme active site, which may inform future work in improving the potencies of their inhibitory activities.

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Section: Introductionmentioning

confidence: 99%

Structure-Based Virtual Screening, Compound Synthesis, and Bioassay for the Design of Chitinase Inhibitors

Dong

Jiang

Liu

et al. 2018

J. Agric. Food Chem.

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“…Chitin is the second most abundant polymer in nature after cellulose and is present in the extracellular matrix of animal organisms in the form of a nanofibril building block. Chitin is found in squid pens, insect cuticles, or crustacean shells in the form of long fibrils of small diameter (∼3 nm) surrounded by a sheath of protein. − The primary role of chitin fibrils in organisms is the mechanical function because of their axial stiffness and strength. This is due to an extended chitin polymer chain conformation in the fibrils.…”

Section: Introductionmentioning

confidence: 99%

High-Strength Nanostructured Film Based on β-Chitin Nanofibrils from Squid Illex argentinus Pens by 2,2,6,6-Tetramethylpiperidin-1-yl Oxyl-Mediated Reaction

Engström

et al. 2021

ACS Sustainable Chem. Eng.

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2,2,6,6-Tetramethylpiperidin-1-yl oxyl (TEMPO)-oxidized β-chitin nanofibrils (T-ChNF) are novel nanofibrils of high strength and stiffness and can also enhance the adsorption of chitosan in materials for biomedical applications. This study presents the preparation, structure, and properties of T-ChNF based on squid pens. Our nanofibrils have a zeta potential of −25.3 mV at neutral pH and a carboxylic content of 0.17 mmol/g, making hydrocolloid suspension stable at alkaline and neutral pH. It was demonstrated that positively charged chitosan could be adsorbed on the negatively charged surface of T-ChNF, leading to charge neutralization. The key to strong squid pen T-ChNF is the initial raw squid chitin properties and the high degree of acetylation (DA = 99.9%). The T-ChNF diameter is ∼4.4 nm, and the length is in the micrometer range. The length and diameter are similar to those of squid pen β-chitin fibrils prepared under mild conditions. These qualities of fibrils resulted in high-strength (176 MPa) chitin films prepared using the rapid vacuum filtration and drying technique. T-ChNF-based films are ductile, flexible, and transparent.

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“…Chitin, a major component of the insect cuticle, is a straight chain polymer of N -acetyl- d -glucosamine (GlcNAc), linked by β-1,4-glucosidic bonds . Glycoside-hydrolase family 18 (GH18) chitinases participate in the molting stage and can hydrolyze chitin to chitosan oligosaccharides. , Of ChtI, a member of GH18 chitinases, was first found from Ostrinia furnacalis (Asian corn borer).…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Activity of Novel Heptacyclic Pyrazolamide Derivatives: A New Candidate of Dual-Target Insect Growth Regulators

Jiang

Jin

Dong

et al. 2020

J. Agric. Food Chem.

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Insect growth regulators (IGRs) can cause abnormal growth and development in insects, resulting in incomplete metamorphosis or even death of the larvae. Ecdysone receptor (EcR) and chitinase in insects play indispensable roles in the molting process. Ecdysone analogues and chitinase inhibitors are considered as potential IGRs. In order to find new and highly effective IGR candidates, based on the structure–activity relationship and molecular docking results of the active compound 6i (3-(tert-butyl)-N-(4-(tert-butyl)phenyl)-1-phenyl-1H-pyrazole-5-carboxamide) discovered in our previous work, we changed the t-butyl group on the pyrazole ring into heptacycle to enhance the hydrophobicity. Consequently, a series of novel heptacyclic pyrazolamide derivatives were designed and synthesized. The bioassay results demonstrated that some compounds showed obvious insecticidal activity. Especially, D-27 (N-(4-(tert-butyl)phenyl)-2-phenyl-2,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-5-carboxamide) showed good activities against Plutella xylostella (LC50, 51.50 mg·L–1) and Mythimna separata (100% mortality at 2.5 mg·L–1). Furthermore, protein validation indicated that D-27 acts not only on the EcR but also on chitinase Of ChtI. Molecular docking and molecular dynamics simulation explained the vital factors in the interaction between D-27 and receptors. D-27 may be a new lead candidate with a dual target in which Of ChtI shall be the main one. This work created a new starting point for discovering a novel type of IGRs.

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The chitin crystallite in arthropod cuticle

Cited by 155 publications

References 16 publications

Structure-Based Virtual Screening, Compound Synthesis, and Bioassay for the Design of Chitinase Inhibitors

Structure-Based Virtual Screening, Compound Synthesis, and Bioassay for the Design of Chitinase Inhibitors

High-Strength Nanostructured Film Based on β-Chitin Nanofibrils from Squid Illex argentinus Pens by 2,2,6,6-Tetramethylpiperidin-1-yl Oxyl-Mediated Reaction

Design, Synthesis, and Biological Activity of Novel Heptacyclic Pyrazolamide Derivatives: A New Candidate of Dual-Target Insect Growth Regulators

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