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Volumn 52, Issue 12, 2009, Pages 3735-3741

Nicotinic agonist binding site mapped by methionine- and tyrosine-scanning coupled with azidochloropyridinyl photoaffinity labeling

Author keywords

[No Author keywords available]

Indexed keywords

5 AZIDO 6 CHLOROPYRIDIN 3 YL DERIVATIVE; ACETYLCHOLINE; AMINO ACID; AZIDE; AZIDOEPIBATIDINE; BINDING PROTEIN; CHLORINE DERIVATIVE; EPIBATIDINE; INSECTICIDE; METHIONINE; NEONICOTINOID; NICOTINIC AGENT; NICOTINIC RECEPTOR; NICOTINOID; PYRIDINE DERIVATIVE; TOXIC SUBSTANCE; TYROSINE; UNCLASSIFIED DRUG;

EID: 67549084531     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900153c     Document Type: Article
Times cited : (16)

References (25)
  • 2
    • 29144435115 scopus 로고    scopus 로고
    • From ligand design to therapeutic efficacy: The challenge for nicotinic receptor research
    • DOI 10.1016/S1359-6446(05)03665-2, PII S1359644605036652
    • Cassels, B. K.; Bermúdez, I.; Dajas, F.; Abin-Carriquiry, J. A.; Wonnacott, S. From ligand design to therapeutic efficacy: the challenge for nicotinic receptor research. Drug Discovery Today 2005, 10, 1657-1665. (Pubitemid 41817614)
    • (2005) Drug Discovery Today , vol.10 , Issue.23-24 , pp. 1657-1665
    • Cassels, B.K.1    Bermudez, I.2    Dajas, F.3    Abin-Carriquiry, J.A.4    Wonnacott, S.5
  • 3
    • 23944472732 scopus 로고    scopus 로고
    • Nicotinic agonists, anatagonists, and modulators from natural sources
    • Daly, J. W. Nicotinic agonists, anatagonists, and modulators from natural sources. Cell. Mol. Neurobiol. 2005, 25, 513-552.
    • (2005) Cell. Mol. Neurobiol. , vol.25 , pp. 513-552
    • Daly, J.W.1
  • 4
    • 13844280231 scopus 로고    scopus 로고
    • Neonicotinoid insecticide toxicology: Mechanisms of selective action
    • Tomizawa, M.; Casida, J. E. Neonicotinoid insecticide toxicology: mechanisms of selective action. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 247-268.
    • (2005) Annu. Rev. Pharmacol. Toxicol. , vol.45 , pp. 247-268
    • Tomizawa, M.1    Casida, J.E.2
  • 5
    • 34547111135 scopus 로고    scopus 로고
    • Agents acting at the neuromuscular junction and autonomic ganglia
    • Brunton, L., Lazo, J. S., Parker, K. L., Eds.; McGraw-Hill: New York
    • Taylor, P. Agents acting at the neuromuscular junction and autonomic ganglia. In Goodman and Gilman's Pharmacological Basis of Therapeutics, 11th ed.; Brunton, L., Lazo, J. S., Parker, K. L., Eds.; McGraw-Hill: New York, 2006; pp 217-236.
    • (2006) Goodman and Gilman's Pharmacological Basis of Therapeutics, 11th Ed. , pp. 217-236
    • Taylor, P.1
  • 6
    • 44849128243 scopus 로고    scopus 로고
    • Cys-loop neuroreceptors: Structure to the rescue?
    • DOI 10.1021/cr078207z
    • Dougherty, D. A. Cys-loop neuroreceptors: structure to the rescue? Chem. Rev. 2008, 108, 1642-1653. (Pubitemid 351796402)
    • (2008) Chemical Reviews , vol.108 , Issue.5 , pp. 1642-1653
    • Dougherty, D.A.1
  • 7
    • 61749090098 scopus 로고    scopus 로고
    • Molecular recognition of neonicotinoid insecticides: The determinants of life or death
    • Tomizawa, M.; Casida, J. E. Molecular recognition of neonicotinoid insecticides: the determinants of life or death. Acc. Chem. Res. 2009, 42, 260-269.
    • (2009) Acc. Chem. Res. , vol.42 , pp. 260-269
    • Tomizawa, M.1    Casida, J.E.2
  • 8
    • 1842475289 scopus 로고    scopus 로고
    • Nicotine and carbamylcholine binding to nicotinic acetylcholine receptors as studied in AChBP crystal structures
    • DOI 10.1016/S0896-6273(04)00115-1, PII S0896627304001151
    • Celie, P. H. N.; van Rossum-Fikkert, S. E.; van Dijk, W. J.; Brejc, K.; Smit, A. B.; Sixma, T. K. Nicotine and carbamylcholine binding to nicotinic acetylcholine receptors as studied in AChBP crystal structures. Neuron 2004, 41, 907-914. (Pubitemid 38429734)
    • (2004) Neuron , vol.41 , Issue.6 , pp. 907-914
    • Celie, P.H.N.1    Van Rossum-Fikkert, S.E.2    Van Dijk, W.J.3    Brejc, K.4    Smit, A.B.5    Sixma, T.K.6
  • 9
    • 27144473613 scopus 로고    scopus 로고
    • Structures of Aplysia AChBP complexes with nicotinic agonists and antagonists reveal distinctive binding interfaces and conformations
    • DOI 10.1038/sj.emboj.7600828, PII 7600828
    • Hansen, S. B.; Sulzenbacher, G.; Huxford, T.; Marchot, P.; Taylor, P.; Bourne, Y. Structures of Aplysia AChBP complexes with nicotinic agonists and antagonists reveal distinctive binding interfaces and conformations. EMBO J. 2005, 24, 3635-3646. (Pubitemid 41509370)
    • (2005) EMBO Journal , vol.24 , Issue.20 , pp. 3635-3646
    • Hansen, S.B.1    Sulzenbacher, G.2    Huxford, T.3    Marchot, P.4    Taylor, P.5    Bourne, Y.6
  • 13
    • 44949241532 scopus 로고    scopus 로고
    • Atomic interactions of neonicotinoid agonists with AChBP: Molecular recognition of the distinctive electronegative pharmacophore
    • Talley, T. T.; Harel, M.; Hibbs, R. H.; Radić, Z.; Tomizawa, M.; Casida, J. E.; Taylor, P. Atomic interactions of neonicotinoid agonists with AChBP: molecular recognition of the distinctive electronegative pharmacophore. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 7606-7611.
    • (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 7606-7611
    • Talley, T.T.1    Harel, M.2    Hibbs, R.H.3    Radić, Z.4    Tomizawa, M.5    Casida, J.E.6    Taylor, P.7
  • 14
    • 0035902009 scopus 로고    scopus 로고
    • Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors
    • DOI 10.1038/35077011
    • Brejc, K.; van Dijk, W. J.; Klaassen, R. V.; Schuurmans, M.; van der Oost, J.; Smit, A. B.; Sixma, T. K. Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors. Nature 2001, 411, 269-276. (Pubitemid 32467026)
    • (2001) Nature , vol.411 , Issue.6835 , pp. 269-276
    • Brejc, K.1    Van Dijk, W.J.2    Klaassen, R.V.3    Schuurmans, M.4    Van Der Oost, J.5    Smit, A.B.6    Sixma, T.K.7
  • 16
    • 0037142378 scopus 로고    scopus 로고
    • Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic receptors
    • Zhang, N.; Tomizawa, M.; Casida, J. E. Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic receptors. J. Med. Chem. 2002, 45, 2832-2840.
    • (2002) J. Med. Chem. , vol.45 , pp. 2832-2840
    • Zhang, N.1    Tomizawa, M.2    Casida, J.E.3
  • 17
    • 0037328361 scopus 로고    scopus 로고
    • 5-Azidoepibatidine: An exceptionally potent photoaffinity ligand for neuronal α4β2 and α7 nicotinic acetylcholine receptors
    • Zhang, N.; Tomizawa, M.; Casida, J. E. 5-Azidoepibatidine: An exceptionally potent photoaffinity ligand for neuronal α4β2 and α7 nicotinic acetylcholine receptors. Bioorg. Med. Chem. Lett. 2003, 13, 525-527.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 525-527
    • Zhang, N.1    Tomizawa, M.2    Casida, J.E.3
  • 18
    • 3142652611 scopus 로고    scopus 로고
    • Acrylodan-conjugated cysteine side chains reveal conformational state and ligand site locations of the acetylcholine-binding protein
    • Hibbs, R. E.; Talley, T. T.; Taylor, P. Acrylodan-conjugated cysteine side chains reveal conformational state and ligand site locations of the acetylcholine-binding protein. J. Biol. Chem. 2004, 279, 28483-28491.
    • (2004) J. Biol. Chem. , vol.279 , pp. 28483-28491
    • Hibbs, R.E.1    Talley, T.T.2    Taylor, P.3
  • 19
    • 33646822242 scopus 로고    scopus 로고
    • Spectroscopic analysis of benzylidene anabaseine complexes with acetylcholine binding proteins as models for ligand-nicotinic receptor interactions
    • DOI 10.1021/bi060534y
    • Talley, T. T.; Yalda, S.; Ho, K.-Y.; Tor, Y.; Soti, F. S.; Kem, W. R.; Taylor, P. Spectroscopic analysis of benzylidene anabaseine complexes with acetylcholine binding proteins as models for ligand-nicotinic receptor interactions. Biochemistry 2006, 45, 8894-8902. (Pubitemid 44100685)
    • (2006) Biochemistry , vol.45 , Issue.29 , pp. 8894-8902
    • Talley, T.T.1    Yalda, S.2    Ho, K.-Y.3    Tor, Y.4    Soti, F.S.5    Kem, W.R.6    Taylor, P.7
  • 20
    • 0037109074 scopus 로고    scopus 로고
    • Structure and function in rhodopsin: High-level expression of rhodopsin with restricted and homogeneous N-glycosylation by a tetracycline-inducible N-acetylglucosaminyltransferase I-negative HEK293S stable mammalian cell line
    • Reeves, P. J.; Callewaeer, N.; Contreras, R.; Khorana, H. G. Structure and function in rhodopsin: High-level expression of rhodopsin with restricted and homogeneous N-glycosylation by a tetracycline-inducible N- acetylglucosaminyltransferase I-negative HEK293S stable mammalian cell line. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 13419-13424.
    • (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 13419-13424
    • Reeves, P.J.1    Callewaeer, N.2    Contreras, R.3    Khorana, H.G.4
  • 22
    • 0344778061 scopus 로고
    • Semi-analytical treatment of solvation for molecular mechanics and dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semi-analytical treatment of solvation for molecular mechanics and dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6129.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 23
    • 0029912748 scopus 로고    scopus 로고
    • Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids
    • Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J. Am. Chem. Soc. 1996, 118, 11225-11236.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11225-11236
    • Jorgensen, W.L.1    Maxwell, D.S.2    Tirado-Rives, J.3
  • 24
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 25
    • 33947716119 scopus 로고    scopus 로고
    • A semiempirical free energy force field with charge-based desolvation
    • Huey, R.; Morris, G. M.; Olson, A. J.; Goodsell, D. S. A semiempirical free energy force field with charge-based desolvation. J. Comput. Chem. 2007, 28, 1145-1152.
    • (2007) J. Comput. Chem. , vol.28 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.