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Volumn 3, Issue 5, 2012, Pages 387-391

Fungal bis-naphthopyrones as inhibitors of botulinum neurotoxin serotype a

Author keywords

[No Author keywords available]

Indexed keywords

BOTULINUM TOXIN A; CEPHALOCHROMIN; CHAETOCHROMIN A; PROTEINASE; PYRONE DERIVATIVE; SECALONIC ACID A; SKYRIN; TALARODERXINE A; TALARODERXINE B; UNCLASSIFIED DRUG;

EID: 84861082401     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200312s     Document Type: Article
Times cited : (21)

References (37)
  • 2
    • 84871920751 scopus 로고    scopus 로고
    • NIH Molecular Libraries Small Molecule Repository (): A collection of samples for high throughput biological screening distributed to the NIH Molecular Libraries Probe Production Centers Network. NCGC (NIH Chemical Genomics Center) is a member laboratory of this network.
    • NIH Molecular Libraries Small Molecule Repository (https://mlsmr.glpg. com/MLSMR-HomePage/centers.html): A collection of samples for high throughput biological screening distributed to the NIH Molecular Libraries Probe Production Centers Network. NCGC (NIH Chemical Genomics Center) is a member laboratory of this network.
  • 5
    • 52249109585 scopus 로고    scopus 로고
    • DOVIS 2.0: An efficient and easy to use parallel virtual screening tool based on AutoDock 4.0
    • Jiang, X; Kumar, K.; Hu, X.; Wallqvist, A.; Reifman, J. DOVIS 2.0: An efficient and easy to use parallel virtual screening tool based on AutoDock 4.0 Chem. Cent. J. 2008, 2, 1-7
    • (2008) Chem. Cent. J. , vol.2 , pp. 1-7
    • Jiang, X.1    Kumar, K.2    Hu, X.3    Wallqvist, A.4    Reifman, J.5
  • 6
    • 49649121294 scopus 로고    scopus 로고
    • Structure- and substrate-based inhibitor design for Clostridium botulinum neurotoxin serotype A
    • Kumaran, C.; Rawat, F.; Ludivico, M. L.; Swaminathan, S. Structure- and substrate-based inhibitor design for Clostridium botulinum neurotoxin serotype A J. Biol. Chem. 2008, 283, 18883-18891
    • (2008) J. Biol. Chem. , vol.283 , pp. 18883-18891
    • Kumaran, C.1    Rawat, F.2    Ludivico, M.L.3    Swaminathan, S.4
  • 7
    • 33947716119 scopus 로고    scopus 로고
    • Software news and update a semiempirical free energy force field with charge-based desolvation
    • DOI 10.1002/jcc.20634
    • 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 (Pubitemid 46506716)
    • (2007) Journal of Computational Chemistry , vol.28 , Issue.6 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4
  • 9
    • 0036022960 scopus 로고    scopus 로고
    • Further development and validation of empirical scoring functions for structure-based binding affinity prediction
    • DOI 10.1023/A:1016357811882
    • Wang, R.; Lai, L.; Wang, S. Further development and validation of empirical scoring functions for structure-based binding affinity prediction J. Comput.-Aided Mol. Des. 2002, 16, 11-26 (Pubitemid 34855041)
    • (2002) Journal of Computer-Aided Molecular Design , vol.16 , Issue.1 , pp. 11-26
    • Wang, R.1    Lai, L.2    Wang, S.3
  • 10
    • 12144257810 scopus 로고    scopus 로고
    • Derivation and validation of toxicophores for mutagenicity prediction
    • DOI 10.1021/jm040835a
    • Accelrys (www.accelrys.com), Pipeline Pilot ADMET-EXT-Mutagen Component, was used to model the data: Kazius, J.; McGuire, R.; Bursi, R. Derivation and validation of toxicophores for mutagenicity prediction. J. Med. Chem. 2005, 48, 312-320. (Pubitemid 40105270)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.1 , pp. 312-320
    • Kazius, J.1    McGuire, R.2    Bursi, R.3
  • 11
    • 27744582712 scopus 로고    scopus 로고
    • In silico screening of chemicals for bacterial mutagenicity using electrotopological E-state indices and MDL QSAR software
    • DOI 10.1016/j.yrtph.2005.09.001, PII S0273230005001686
    • Contrera, J. F.; Matthews, E. J.; Kruhlak, N. L.; Benz, R. D. In silico screening of chemicals for bacterial mutagenicity using electrotopological E-state indices and MDL QSAR software Regul. Toxicol. Pharmacol. 2005, 43, 313-323 (Pubitemid 41616397)
    • (2005) Regulatory Toxicology and Pharmacology , vol.43 , Issue.3 , pp. 313-323
    • Contrera, J.F.1    Matthews, E.J.2    Kruhlak, N.L.3    Benz, R.D.4
  • 13
    • 4043167653 scopus 로고    scopus 로고
    • Data mining and machine learning techniques for the identification of mutagenicity inducing substructures and structure activity relationships of noncongeneric compounds
    • Helma, C.; Cramer, T.; Kramer, S.; De Raedt, L. Data mining and machine learning techniques for the identification of mutagenicity inducing substructures and structure activity relationships of noncongeneric compounds J. Chem. Inf. Comput. Sci. 2004, 44, 1402-1411
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1402-1411
    • Helma, C.1    Cramer, T.2    Kramer, S.3    De Raedt, L.4
  • 14
    • 4143122120 scopus 로고    scopus 로고
    • Classification of kinase inhibitors using a Bayesian model
    • DOI 10.1021/jm0303195
    • Xia, X.; Maliski, E., G.; Gallant, P.; Rogers, D. Classification of kinase inhibitors using a Bayesian model J. Med. Chem. 2004, 47, 4463-4470 (Pubitemid 39096834)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.18 , pp. 4463-4470
    • Xia, X.1    Maliski, E.G.2    Gallant, P.3    Rogers, D.4
  • 15
    • 1942475425 scopus 로고    scopus 로고
    • In silico models for the prediction of dose-dependent human hepatotoxicity
    • DOI 10.1023/B:JCAM.0000021834.50768.c6
    • Accelrys (www.accelrys.com), Pipeline Pilot ADMET-EXT-Hepatotoxic Component: Cheng, A.; Dixon, S. L. In silico models for the prediction of dose-dependent human hepatotoxicity. J. Comput.-Aided Mol. Des. 2003, 17, 811-823. (Pubitemid 38519138)
    • (2003) Journal of Computer-Aided Molecular Design , vol.17 , Issue.12 , pp. 811-823
    • Cheng, A.1    Dixon, S.L.2
  • 16
    • 4143122120 scopus 로고    scopus 로고
    • Classification of kinase inhibitors using a Bayesian model
    • DOI 10.1021/jm0303195
    • Three hundred eighty-two of the compounds are from the original training data, with the remaining 54 from the validation data. However, the modeling methodology described in that paper was not used; instead, modified Bayesian learning, described in Xia, X.; Maliski, E.; G.;Gallant, P.; Rogers, D. Classification of kinase inhibitors using a Bayesian model J. Med. Chem. 2004, 47, 4463-4470 was performed (Pubitemid 39096834)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.18 , pp. 4463-4470
    • Xia, X.1    Maliski, E.G.2    Gallant, P.3    Rogers, D.4
  • 17
    • 0041698413 scopus 로고    scopus 로고
    • Use of robust classification techniques for the pediction of human cytochrome P450 2D6 inhibition
    • Accelrys (), Pipeline pilot ADMET-EXT-CYP2D6-Inhibitor Component
    • Accelrys (www.accelrys.com), Pipeline pilot ADMET-EXT-CYP2D6-Inhibitor Component: Susnow, R., G.; Dixon, S. L. Use of robust classification techniques for the pediction of human cytochrome P450 2D6 inhibition. J. Chem. Inf. Comput. Sci. 2003, 43, 1308-1315.
    • (2003) J. Chem. Inf. Comput. Sci. , vol.43 , pp. 1308-1315
    • Susnow . R, G.1    Dixon, S.L.2
  • 18
    • 4143122120 scopus 로고    scopus 로고
    • Classification of kinase inhibitors using a Bayesian model
    • DOI 10.1021/jm0303195
    • Xia, X.; Maliski, E., G.; Gallant, P.; Rogers, D. Classification of kinase inhibitors using a Bayesian model J. Med. Chem. 2004, 47, 4463-4470 (Pubitemid 39096834)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.18 , pp. 4463-4470
    • Xia, X.1    Maliski, E.G.2    Gallant, P.3    Rogers, D.4
  • 19
    • 0023282885 scopus 로고
    • Chaetochromins B, C and D, bis(naphtho-gamma-pyrone) derivatives from Chaetomium gracile
    • Koyama, K.; Natori, S. Chaetochromins B, C and D, bis(naphtho-gamma- pyrone) derivatives from Chaetomium gracile Chem. Pharm. Bull. 1987, 35, 578-584
    • (1987) Chem. Pharm. Bull. , vol.35 , pp. 578-584
    • Koyama, K.1    Natori, S.2
  • 20
    • 0023605728 scopus 로고
    • Absolute configurations of chaetochromin A and related bis(naphtha-γ-pyrone) mold metabolites
    • Koyama, K.; Natori, S.; Iitaka, Y. Absolute configurations of chaetochromin A and related bis(naphtha-γ-pyrone) mold metabolites Chem. Pharm. Bull. 1987, 35, 4049-4055
    • (1987) Chem. Pharm. Bull. , vol.35 , pp. 4049-4055
    • Koyama, K.1    Natori, S.2    Iitaka, Y.3
  • 21
    • 79551684116 scopus 로고    scopus 로고
    • Chaetomium mycotoxins with antiinsectan or antifungal activity
    • In; Proceedings of International Symposium of Mycotoxicology '99, Chiba, Japan. Mycotoxins: Supplement 99; Kumagai, S. Matsumoto Printing Co. Tokyo, Japan
    • Wicklow, D. T.; Dowd, P. F.; Gloer, J. B. Chaetomium mycotoxins with antiinsectan or antifungal activity. In Mycotoxin Contamination: Health Risk and Prevention Project; Proceedings of International Symposium of Mycotoxicology '99, Chiba, Japan. Mycotoxins: Supplement 99; Kumagai, S., Ed.; Matsumoto Printing Co.: Tokyo, Japan, 2000; pp 267-271.
    • (2000) Mycotoxin Contamination: Health Risk and Prevention Project , pp. 267-271
    • Wicklow, D.T.1    Dowd, P.F.2    Gloer, J.B.3
  • 22
    • 0026716644 scopus 로고
    • Isolation and structures of antibacterial binaphtho-α-pyrones, talaroderxines A and B, from Talaromyces derxii
    • Suzuki, K.; Nozawa, K.; Nakajima, S.; Udagawa, S.; Kawai, K. Isolation and structures of antibacterial binaphtho-α-pyrones, talaroderxines A and B, from Talaromyces derxii Chem. Pharm. Bull. 1992, 40, 1116-1119
    • (1992) Chem. Pharm. Bull. , vol.40 , pp. 1116-1119
    • Suzuki, K.1    Nozawa, K.2    Nakajima, S.3    Udagawa, S.4    Kawai, K.5
  • 23
    • 38249037504 scopus 로고
    • Secalonic acid A, a vivotoxin in pink root-infected onion
    • Steffens, J. C.; Robeson, D. J. Secalonic acid A, a vivotoxin in pink root-infected onion Phytochemistry 1987, 26, 1599-1602
    • (1987) Phytochemistry , vol.26 , pp. 1599-1602
    • Steffens, J.C.1    Robeson, D.J.2
  • 24
    • 0015779192 scopus 로고
    • Fungal metabolites. Part I. Stereochemical features and mass spectrometry of secalonic acids
    • Howard, C. C.; Johnstone, R. A. W. Fungal metabolites. Part I. Stereochemical features and mass spectrometry of secalonic acids J. Chem. Soc. Perkin Trans. I 1973, 2440-2444
    • (1973) J. Chem. Soc. Perkin Trans. i , pp. 2440-2444
    • Howard, C.C.1    Johnstone, R.A.W.2
  • 27
    • 0344953656 scopus 로고
    • Pigments of fungi, part 8. Bisanthraquinones from Dermocybe austroveneta
    • Gill, M.; Gimenez, A.; McKenzie, R. W. Pigments of fungi, part 8. Bisanthraquinones from Dermocybe austroveneta J. Nat. Prod. 1988, 51, 1251-1256
    • (1988) J. Nat. Prod. , vol.51 , pp. 1251-1256
    • Gill, M.1    Gimenez, A.2    McKenzie, R.W.3
  • 28
    • 0028254615 scopus 로고
    • Coupled anthraquinones from the toadstool Dermocybe icterinoides
    • Antonowitz, A.; Gill, M.; Morgan, P. M.; Yu, J. Coupled anthraquinones from the toadstool Dermocybe icterinoides Phytochemistry 1994, 37, 1679-1683
    • (1994) Phytochemistry , vol.37 , pp. 1679-1683
    • Antonowitz, A.1    Gill, M.2    Morgan, P.M.3    Yu, J.4
  • 29
    • 0025088805 scopus 로고
    • Supplemental observations on atropisomerism of fungal bis(naphtho-γ-pyrone)s
    • Koyama, K.; Aida, S.; Natori, S. Supplemental observations on atropisomerism of fungal bis(naphtho-γ-pyrones) Chem. Pharm. Bull. 1990, 38, 2259-2261 (Pubitemid 20338194)
    • (1990) Chemical and Pharmaceutical Bulletin , vol.38 , Issue.8 , pp. 2259-2261
    • Koyama, K.1    Aida, S.2    Natori, S.3
  • 30
    • 78149435273 scopus 로고    scopus 로고
    • Computing relative free energies of solvation using Single Reference Thermodynamic Integration augmented with Hamiltonian Replica Exchange. computing relative free energies of solvation using Single Reference Thermodynamic Integration augmented with Hamiltonian Replica Exchange
    • Khavrutskii, I. V.; Wallqvist, A. Computing relative free energies of solvation using Single Reference Thermodynamic Integration augmented with Hamiltonian Replica Exchange. computing relative free energies of solvation using Single Reference Thermodynamic Integration augmented with Hamiltonian Replica Exchange J. Chem. Theory Comput. 2010, 6, 3427-3441
    • (2010) J. Chem. Theory Comput. , vol.6 , pp. 3427-3441
    • Khavrutskii, I.V.1    Wallqvist, A.2
  • 31
    • 80052807977 scopus 로고    scopus 로고
    • Improved binding free energy predictions from Single-Reference Thermodynamic Integration augmented with Hamiltonian Replica Exchange
    • Khavrutskii, I. V.; Wallqvist, A. Improved binding free energy predictions from Single-Reference Thermodynamic Integration augmented with Hamiltonian Replica Exchange J. Chem. Theory Comput. 2011, 7, 3001-3011
    • (2011) J. Chem. Theory Comput. , vol.7 , pp. 3001-3011
    • Khavrutskii, I.V.1    Wallqvist, A.2
  • 32
    • 76149120388 scopus 로고    scopus 로고
    • AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading
    • Trott, O.; Olson, A. J. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 2010, 31, 455-461
    • (2010) J. Comput. Chem. , vol.31 , pp. 455-461
    • Trott, O.1    Olson, A.J.2
  • 33
    • 68549131981 scopus 로고
    • Oral toxicity of chaetochromin, a new mycotoxin produced by Chaetomium virescens, to mice
    • Ohtsubo, K. Oral toxicity of chaetochromin, a new mycotoxin produced by Chaetomium virescens, to mice Proc. Jpn. Assoc. Mycotoxicol. 1980, 28-29
    • (1980) Proc. Jpn. Assoc. Mycotoxicol. , pp. 28-29
    • Ohtsubo, K.1
  • 34
    • 85005000970 scopus 로고
    • Exencephaly in mice induced by feeding chaetochromin-containing diet
    • Ito, Y.; Ohtsubo, K. Exencephaly in mice induced by feeding chaetochromin-containing diet Proc. Jpn. Assoc. Mycotoxicol. 1982, 22-23
    • (1982) Proc. Jpn. Assoc. Mycotoxicol. , pp. 22-23
    • Ito, Y.1    Ohtsubo, K.2
  • 35
    • 0023389039 scopus 로고
    • Teratogenicity of oral chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp., to mice embryo
    • Ito, Y.; Ohtsubo, K. Teratogenicity of oral chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp., to mice embryo Bull. Environ. Contam. Toxicol. 1987, 39, 299-303
    • (1987) Bull. Environ. Contam. Toxicol. , vol.39 , pp. 299-303
    • Ito, Y.1    Ohtsubo, K.2
  • 36
    • 0023723836 scopus 로고
    • Cytotoxicity and antitumor activities of fungal bis(naphtho-γ- pyrone) derivatives
    • Koyama, K.; Ominato, K.; Natoria, S.; Tashiro, T.; Tsuruo, T. Cytotoxicity and antitumor activities of fungal bis(naphtho-γ-pyrone) derivatives J. Pharmacobio-Dyn. 1988, 11, 630-635
    • (1988) J. Pharmacobio-Dyn. , vol.11 , pp. 630-635
    • Koyama, K.1    Ominato, K.2    Natoria, S.3    Tashiro, T.4    Tsuruo, T.5
  • 37
    • 85010151336 scopus 로고
    • Myocardial and hepatic necrosis and bone marrow suppression in mice induced by single administration of chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp
    • Ohtsubo, K. Myocardial and hepatic necrosis and bone marrow suppression in mice induced by single administration of chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp J. Toxicol. Pathol. 1989, 2, 163-174
    • (1989) J. Toxicol. Pathol. , vol.2 , pp. 163-174
    • Ohtsubo, K.1


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