Jiagao Cheng

East China University of Science and Technology, Shanghai, Shanghai Shi, China

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Publications (39)116.64 Total impact

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    ABSTRACT: Insecticide resistance is a critical problem for pest control and management. For Bemisia tabaci, striking high metabolic resistance (generally conferred by CYP6CM1) was observed for imidacloprid (IMI) and most of other neonicotinoid members. However, dinotefuran (DIN) displayed very low resistance factors, which indicated distinct metabolic properties. Here, molecular modeling methods were applied to explore the different resistance features of IMI versus DIN within the Q type of CYP6CM1. It was found that Arg225 played crucial roles in the binding of IMI-CYP6CM1vQ with a cation-π interaction and two stable H-bonds, however, such interactions were all absent in DIN-CYP6CM1vQ system. The stable binding of IMI with CYP6CM1vQ would facilitate the following metabolic reaction, while the weak binding of DIN might disable its potential metabolism, which should be an important factor for their distinct resistance levels. The findings might facilitate in future design of the anti-resistance neonicotinoid molecules.
    No preview · Article · Jan 2016 · Journal of Agricultural and Food Chemistry
  • Zhiping Xu · Lina Shi · Danping Jiang · Jiagao Cheng · Xusheng Shao · Zhong Li
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    ABSTRACT: Incorporating the photoisomerizable azobenzene into imidacloprid produced a photoswitchable insecticidal molecule as the first neonicotinoid example of remote control insecticide performance with spatiotemporal resolution. The designed photoswitchable insecticides showed distinguishable activity against Musca both in vivo and in vitro upon irradiation. Molecular docking study further suggested the binding difference of the two photoisomers. The generation of these photomediated insecticides provides novel insight into the insecticidal activity facilitating further investigation on the functions of insect nicotinic acetylcholine receptors and opens a novel way to control and study insect behavior on insecticide poisoning using light.
    No preview · Article · Oct 2015 · Scientific Reports
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    ABSTRACT: Tetraheterocyclic tetrahydroindeno[1',2':4,5]pyrrolo[1,2-a]imidazol-5(1H)-one derivatives as novel neonicotinoid candidates were designed and prepared by selective etherification, chlorination and esterification of ninhydrin-heterocyclic ketene aminals adducts. Some of the designed compounds showed excellent insecticidal activity against cowpea aphids (Aphis craccivora), brown planthopper (Nilaparvata lugens) and armyworm (Mythimna separata). In particular, the activity against armyworm (Mythimna separata) improved a lot in contrast with imidacloprid and cycloxaprid. The research here provides a novel neonicotinoid chemotype for further development.
    No preview · Article · Jan 2015 · Journal of Agricultural and Food Chemistry
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    ABSTRACT: To study the influence of the ring sizes, 37 novel seven-membered azabrigded neonicotinoid analogues were synthesized by reactions of nitromethylene analogues, succinaldehyde, and aniline hydrochlorides. Most of titled compounds presented higher insecticidal activities than that of imidacloprid (IMI), cycloxaprid (CYC), and eight-membered compounds against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker) and brown planthopper (Nilaparvata lugens), which indicated that introducing the structure of seven-membered azabridge, could significantly improve the insecticidal activities of neonicotinoid analogues. Molecular docking study showed that introducing methyl group into position 2 of phenyl ring could shortened the distance between the molecular and the specific residues, which could be the reason that position 2 was the key site to get high insecticidal activities compounds.
    No preview · Article · Oct 2014 · Journal of Agricultural and Food Chemistry
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    ABSTRACT: Fipronil, which targets on GABAA receptors (GABAARs), is the first phenylpyrazole insecticide widely used in crops protection and public hygiene. However, its high toxicity on fishes deeply limited its applications. In the present study, a series of computational methods including the homology modeling, docking and molecular dynamics simulation studies were integrated to explore the binding difference of fipronil with GABAARs from fruitfly and zebrafish systems. It was found that, in zebrafish system, the H-bond between 6'Thr and fipronil exerted key effects on the recognition of fipronil, which was absent in fruitfly system. On the other hand, in fruitfly system, strong electrostatic interaction between 2'Ala and fipronil was favorable to the binding of fipronil, while was detrimental to the binding in zebrafish system. These findings marked the binding difference of fipronil with different GABAARs, which might be helpful in designing selective insecticides against pests instead of fishes.
    No preview · Article · Oct 2014 · Journal of Agricultural and Food Chemistry
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    ABSTRACT: The cis- and trans-configurational isomers 3 are designed and investigated as chemdosimeter for CN ions for the first time. The cis-3 reveals a NIR absorbance at 717 nm (vs trans-3, 620 nm), and such configurational difference can be attributed to the acidity as well as position of binding site (CH group). A probable sensing mechanism involving cyanide-driven carbanion electron transfer oxidation is proposed.
    Full-text · Article · Oct 2014 · Chemical Communications
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    ABSTRACT: Ninhydrin and heterocyclic ketene aminals (HKAs) are versatile building blocks in organic chemistry. Reactions of ninhydrin with HKAs initially produced the kinetic products indeno[1,2-b]pyrrol-4(1H)-one derivatives, which could further isomerize to thermodynamic counterparts indeno[2,1-b]pyrrol-8(1H)-ones. The isomerization showed a strong solvent dependency and occurred through a decomposition–reconstruction pathway. This is the first example of isomerization of ninhydrin-constructed products. The conversion between kinetic and thermodynamic control may be applicable to similar reactions involving ninhydrin or HKAs.
    No preview · Article · Oct 2014 · European Journal of Organic Chemistry
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    ABSTRACT: Chiral nucleophilic catalysts, 6-aryl-phenyl-dihydroimidazoquinolines (PIQs), were designed, synthesised and applied to the kinetic resolution of arylalkyl carbinols with very high selectivity (S) factors (up to 530). Density functional theory calculations indicate that multiple noncovalent interactions play a key role in chiral recognition between 6-aryl-PIQ catalysts and chiral secondary alcohol substrates.
    No preview · Article · Jul 2014 · Catalysis Science & Technology
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    ABSTRACT: Molecular aggregation state of bioactive compounds plays a key role in bio-interactive procedure. Diverse aggregation states of bioactive compounds contribute to different biological or chemical properties. Water-bridge, as the simple hetero-molecular aggregation, has been found bridging the binding between many bioactive compounds and their targets through hydrogen bonding network, e.g. in the recognition of neonicotinoids with insect nAChRs. To better understanding the roles of water-bridge on bioactivities of compounds, an approach of hetero-dimeric aggregation with water was proposed. Quantitative structure-activity relationship (QSAR) and pharmacophore modeling investigations were applied on 19 neonicotinoids, as well as their aggregates with water. The aggregate-based CoMSIA, PHASE and linear QSAR models presented better statistical significance and predictabilities than the monomer ones, which indicated that the bioactivities correlated with the aggregate properties and water bridged hydrogen bond of the active site. All results revealed the essential roles of water-bridge in ligand recognition, which should be considered in future ligand design and optimization.
    No preview · Article · Apr 2014 · Chinese Journal of Chemistry
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    Yinbo Chen · Jie Fan · Shuang Xia · Jiagao Cheng · Xiaoyong Xu · Zhong Li
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    ABSTRACT: Six novel neonicotinoid analogues with bicyclic ring system were designed and synthesized, and their structures were characterized by 1H NMR, 13C NMR, HRMS and single crystal X-ray diffraction analysis. Preliminary bioassays showed that five target compounds 6a, 6c-6f exhibited good insecticidal activities against cowpea aphids (Aphis craccivora) at 500 mg·L-1. Docking study was applied to investigate the effect of the bicyclic ring system of the target compound 6a on the biological activity, and compared with mode of action of imidacloprid (IMI) and compound 6a. It was found that the only π-π stacking interaction was found between the plane of pyridine of the target compounds 6a and the aromatic side chain of Tyr 147, which was different binding mode with that of IMI.
    Preview · Article · Feb 2014 · Chinese Journal of Organic Chemistry
  • Renbo Xu · Rui Xia · Ming Luo · Xiaoyong Xu · Xusheng Shao · Jiagao Cheng · Zhong Li
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    ABSTRACT: Three series of novel azabridge neonicotinoid analogues were designed and Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde and primary amine hydrochlorides (aliphatic amines, phenylhydrazines and anilines). Most of eight-membered azabridge compounds presented higher insecticidal activities than oxabridge compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridge compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge-atoms from O to N could lead to entirely different conformations, which might be the important influential factors of the bioactivities.
    No preview · Article · Dec 2013 · Journal of Agricultural and Food Chemistry
  • Wei Zhang · Shuang Xia · Jinjin Ye · Yun Tang · Zhong Li · Weiping Zhu · Jiagao Cheng
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    ABSTRACT: Pharmacophore modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) studies have been carried out on 5-(4-piperidyl)-3-isoxazolol (4-PIOL) analogs as GABAA receptor antagonists in this study. The best pharmacophore hypothesis generated by PHASE was ADHPR.6, which comprised a hydrogen bond acceptor (A), a hydrogen bond donor (D), a hydrophobic group (H), a positively charged group (P), and an aromatic ring (R). The pharmacophore model provided a good alignment for the further 3D-QSAR analyses, which presented a good R 2 value of 0.943, 0.930, and 0.916 for atom-based QSAR model, CoMFA model, and CoMSIA model, respectively. All QSAR models presented good statistical significance and predictivity, the corresponding Q 2 values for each 3D-QSAR model are 0.794, 0.569, and 0.637, respectively. Both pharmacophore and CoMSIA results showed that the hydrophobic sites are the key structural feature for GABAA receptor antagonists with high activities.
    No preview · Article · Dec 2013 · Medicinal Chemistry Research
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    ABSTRACT: The neonicotinoids with a nitroconjugated system had excellent bioactivity, which could rival imidacloprid, and has been previously reported. However, the photodegradation and hydrolysis of this series of neonicotinoids was very quick according to our further investigation, which can't be developed as pesticide further. The approach to further enhance the conjugation was tried not only to increase the bioactivities but also improve the stability in water and in the sun. A substituted phenyl group was introduced into the furan ring of compound 3, thirteen novel neonicotinoids analogues with higher conjugation system were designed and synthesized. The target molecular structures have been confirmed based on satisfactory analytical and spectral data. All compounds presented significant insecticidal activities on cowpea aphid (Aphis craccivora), cotton aphid (Aphis gossypii) and brown planthopper (Nilaparvatalugens). The stability test exhibited that the stability of novel analogues in water and under the mercury lamp has been improved significantly compared with compound 3.
    No preview · Article · Nov 2013 · Journal of Agricultural and Food Chemistry
  • Ying Yang · Wei Zhang · Jiagao Cheng · Yun Tang · Yanqing Peng · Zhong Li
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    ABSTRACT: Ligands binding at the benzodiazepine site of GABAA receptor play important pharmacological roles in clinical application. In this study, ligand‐based pharmacophore modeling, 3D‐QSAR analysis, and Bayesian model studies have been performed on a set of 84 diverse ligands binding at the benzodiazepine site. The results showed the best pharmacophore hypothesis AADHR.4, which included two hydrogen acceptors (A), one hydrogen donor (D), one hydrophobic group (H), and one aromatic ring (R). Atom‐based 3D‐QSAR model was built, and it showed good statistical significance (R 2 = 0.936) and excellent predictive ability (Q 2 = 0.821). Moreover, Bayesian model was developed and used to identify the key molecular features which are good or bad for the ligand binding activity. All the results from the pharmacophore, 3D‐QSAR, and Bayesian modeling studies revealed that a hydrogen‐bond donor (e.g., N‐H) and a hydrophobic group (e.g., Br) are critical structural features for the ligands binding at the benzodiazepine site.
    No preview · Article · Jan 2013 · Chemical Biology & Drug Design
  • Ying Yang · Wei Zhang · Jiagao Cheng · Yun Tang · Yanqing Peng · Zhong Li
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    ABSTRACT: Ligands binding at the benzodiazepine (BZD) site of GABA(A) receptor play important pharmacological roles in clinical application. In the present study, ligand-based pharmacophore modeling, 3D-QSAR analysis and Bayesian model studies have been performed on a set of 84 diverse ligands binding at the BZD site. The results showed the best pharmacophore hypothesis AADHR.4, which included two hydrogen acceptors (A), one hydrogen donor (D), one hydrophobic group (H) and one aromatic ring(R). Atom-based 3D-QSAR model was built and showed good statistically significance (R(2) =0.936) and excellent predictive ability (Q(2) =0.821). Moreover, Bayesian model was developed and used to identify the key molecular features which are good or bad for the ligand binding activity. All the results from the pharmacophore, 3D-QSAR and Bayesian modeling studies, revealed that a hydrogen-bond donor (e.g. N-H) and a hydrophobic group (e.g. Br) are critical structural features for the ligands binding at the BZD site. © 2012 John Wiley & Sons A/S.
    No preview · Article · Dec 2012 · Chemical Biology & Drug Design
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    ABSTRACT: The structure-based design and synthesis of a series of novel neonicotinoid analogues are described. The novel neonicotinoid analogues were designed based upon the reaction of enamine derivatives with electron-withdrawing β-substituents with electrophilic thiocyanogen reagents. These compounds were characterized by spectroscopic methods. Bioassays indicated that some of the synthesized compounds exhibited excellent bioactivity against cowpea aphids (Aphis craccivora). The LC₅₀ values of compounds 7, 9,12, 13, 15, 17, 19, 20 and commercial imidacloprid were 0.01567, 0.00974, 0.02494, 0.01893, 0.02677, 0.01778, 0.0220, 0.02447 and 0.03502 mmol L⁻¹, respectively, which suggested that they could be used as leads for future development of new insecticides.
    Preview · Article · Dec 2012 · Molecules
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    ABSTRACT: Twenty nine novel N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N′-phenyl ureas were designed and synthesized, and their structures were confirmed by proton nuclear magnetic resonance (1H NMR), infra red spectroscopy (IR) and high-resolution mass spectroscopy (HRMS). Compounds V-9, V-11, V-12, V-15, V-19, V-21, V-22 and V-24 exhibit excellent activity against Culex pipiens pallens. Compounds V-12 and V-22 present good insecticidal activity against Plutella xylostella L. Their median lethal concentrations (LC50) are 164.15 and 89.69 mg·L−1, respectively. Compound V-11 also has potential wide spectrum of fungicide activity. Its median effective concentrations (EC50) detected from 3.82 µg·mL−1 against Physalospora piricola to 31.60 µg·mL−1 against Cercospora arachidicola. Compounds V-15 and V-24 show outstanding induction activities as same as positive controls TDL and ningnanmycin, furthermore V-24 has the highest induction activity of 41.85%±4.43%. To elucidate the structure activity relationship in these compounds, a 3D-QSAR model has been built. The established model showed a reliable predicting ability with q2 values of 0.643 and r2 values of 0.982.
    No preview · Article · Oct 2012 · Chinese Journal of Chemistry
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    ABSTRACT: A novel fluorescent probe for peroxynitrite, PN(600), was rationally designed on the basis of a unique fluorophore assembly approach. PN(600) is a green-emitting coumarin derivative. Upon oxidation by peroxynitrite, PN(600) is transformed into a highly fluorescent red-emitting resorufin derivative via an orange-emitting intermediate. This three-channel signaling capability enables PN(600) to differentiate peroxynitrite from other reactive oxygen and nitrogen species, including hypochlorite and hydroxyl radical. Moreover, PN(600) is membrane-permeable and compatible with common TRITC filter sets and displays low cytotoxicity. Therefore, PN(600) is a promising candidate for in vitro peroxynitrite imaging.
    No preview · Article · Sep 2012 · Journal of the American Chemical Society
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    Wenwen Zhang · Yefeng Fan · Tao Yu · Zhiping Xu · Xiaoyong Xu · Jiagao Cheng · Zhong Li
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    ABSTRACT: Eight novel neonicotinoids N-oxide analogues were designed and synthesized. All the compounds have been identified by 1H NMR and HRMS. The N-oxide analogues exhibit high insecticidal activity against cowpea aphids (Aphis craccivora) at 250 mg·L−1. The influence of N-oxide formation on the biological activity was elucidated by computational chemical study, and it indicated that the water bridge hydrogen bonding network was broken due to the influence of the O atom connected with the pyridine ring.
    Preview · Article · Feb 2012 · Chinese Journal of Chemistry
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    ABSTRACT: On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the π-π interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral ((1)H NMR, (13)C NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids ( Aphis craccivora ). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.
    No preview · Article · Sep 2011 · Journal of Agricultural and Food Chemistry

Publication Stats

367 Citations
116.64 Total Impact Points

Institutions

  • 2006-2015
    • East China University of Science and Technology
      • School of Pharmacy
      Shanghai, Shanghai Shi, China
  • 2007
    • Shanghai Institutes for Biological Sciences
      Shanghai, Shanghai Shi, China
  • 2006-2007
    • Chinese Academy of Sciences
      • • Drug Discovery and Design Center
      • • State Key Laboratory of Drug Research
      Peping, Beijing, China