Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic receptors

Journal of Medicinal Chemistry

Volumn 45, Issue 13, 2002, Pages 2832-2840

  Zhang, Nanjing ^a   Tomizawa, Motohiro ^a   Casida, John E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANABASINE DERIVATIVE; AZIDOPYRIDINE DERIVATIVE; CHOLINERGIC RECEPTOR; IMIDACLOPRID; IMINOTHIOL; INSECTICIDE; N (5 AZIDO 6 CHLOROPYRIDIN 3 YLMETHYL) 2 IMINOTHIAZOLINE; N (5 AZIDO 6 CHLOROPYRIDIN 3 YLMETHYL) 2 NITROIMINOTHIAZOLINE; N (5 AZIDO 6 CHLOROPYRIDIN 3 YLMETHYL) 2 NITROMETHYLENEIMIDAZOLIDINE; NICOTINIC RECEPTOR; PYRIDINE DERIVATIVE; THIACLOPRID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; DROSOPHILA; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; INSECT CONTROL; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NONHUMAN; PHOTOAFFINITY LABELING; STRUCTURE ACTIVITY RELATION;

ANIMALS; AZIDES; BINDING SITES; BINDING, COMPETITIVE; CELL LINE; DROSOPHILA; IMIDAZOLES; IMINES; INSECTICIDES; MICE; PHOTOAFFINITY LABELS; PYRIDINES; RADIOLIGAND ASSAY; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 0037142378     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010508s     Document Type: Article

References (43)

1. Neonicotinoid insecticides: Molecular features conferring selectivity for insect versus mammalian nicotinic receptors
2. Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal nicotinic acetylcholine receptor
3. Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors
4. Imidacloprid, thiacloprid, and their imine derivatives up-regulate the α4β2 nicotinic acetylcholine receptor in M10 cells
5. Analgesic and toxic effects of neonicotinoid insecticides in mice
6. Nicotinic acetylcholine receptors in health and disease
7. Nicotinic receptor function: New perspectives from knockout mice
8. Characterization of bovine and human neuronal nicotinic acetylcholine receptors using monoclonal antibodies
9. A subtype of nicotinic cholinergic receptor in rat brain is composed of α4 and β2 subunits and is up-regulated by chronic nicotine treatment
10. Neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes have a pentameric quaternary structure
11. Pentameric structure and subunit stoichiometry of a neuronal nicotinic acetylcholine receptor
12. Neuronal nicotinic acetylcholine receptors as novel drug targets
13. Insect nicotinic acetylcholine receptors: Genes, structure, physiological and pharmacological properties
14. Structure and diversity of insect nicotinic acetylcholine receptors
15. 125I]neonicotinoid photoaffinity probe for the Drosophila nicotinic acetylcholine receptor
16. 125I]azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor
17. 5-Azidoimidacloprid and an acyclic analogue as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors
18. 3H]azidoneonicotinoid
19. Synthesis of chiral triamines and diamines from amino acids
20. Design and synthesis of a transferable farnesyl pyrophosphate analogue to Ras by protein farnesyltransferase
21. Directed lithiation of unprotected pyridinecarboxylic acids
22. The chemistry of 2-oxazolines (1985-present)
23. An oxazoline based approach to (S)-gossypol
24. A novel ring cleavage reaction of oxazolines
25. A new synthesis of azaphenanthrenes
26. Syntheses via 2-oxazolines. II. A versatile synthesis of aliphatic carboxylic acids and esters. Mono- and dialkylation of acids masked by a simple protecting group
27. Oxazolines. IX. Synthesis of homologated acetic acids and esters
28. 4
29. Chloronicotinyl insecticides. 8. Crystal and molecular structures of imidacloprid and analogous compounds
30. Stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen
31. Quantum chemical consideration of photostability of imidacloprid and related compounds
32. Synthesis and insecticidal evaluation of N-substituted 2-nitroiminoimidazolidines
33. Beiträge zur chemie der dithiocarbonsäureester und ketenmercaptale
34. The acid-catalyzed rearrangement of N-nitro-derivatives of 2-aminothiazole, I. Kinetics, solvent and substrate isotope effects in the acid-catalyzed rearrangement of 2-thiazolylnitroamines
35. An approach to a synthetic carboxylate-binding pocket based on β-avoparcin
36. Preparation of p-toluenesulfonyl azide. A cautionary note
37. Structural and pharmacological characterization of the major brain nicotinic acetylcholine receptor subtype stably expressed in mouse fibroblasts
38. Novel neonicotinoidagarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors
39. 50) of an enzyme reaction
40. Nicotine-induced increase in neuronal nicotinic receptors results from a decrease in the rate of receptor turnover