A pharmacophore model of tautomycin, an inhibitor of protein phosphatases 1 and 2A

Journal of Antibiotics

Volumn 50, Issue 10, 1997, Pages 801-807

  Ubukata, Makoto ^a   Koshino, Hiroyuki ^b   Yamasaki, Ciharu ^c   Fujita, Ken Ichi ^c   Isono, Kiyoshi ^d  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c JEOL LTD   (Japan)

^d TOKAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OKADAIC ACID; PHOSPHOPROTEIN PHOSPHATASE 1; PHOSPHOPROTEIN PHOSPHATASE 2A; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; TAUTOMYCIN;

DRUG STRUCTURE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0030727789     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.50.801     Document Type: Review

References (32)

1. POSADA, J. & J. A. COOPER: Molecular signal integration. Interplay between serine, threonine, and tyrosine phosphorylation. Mol. Biol. Cell 3: 583-592, 1992
2. CHENG, X.-C.; T. KIHARA, H. KUSAKABE, J. MAGAE, Y. KOBAYASHI, R.-P. FANG, R.-P., Z.-F. NI, Y.-C. SHENG, K. KO, I. YAMAGUCHI & K. ISONO: A new antibiotic, tautomycin. J. Antibiotics 40: 907-909, 1987
3. UBUKATA, M.; X.-C. CHENG & K. ISONO: The structure of tautomycin, a regulator of eukaryotic cell growth. J. Chem. Soc., Chem. Commun. 1990: 244-246, 1990
4. BIALOJAN, C. & A. TAKAI: Inhibitory effect of a marine sponge toxin, okadaic acid, on protein phosphatases: specificity and kinetics. Biochem. J. 256: 283-290, 1988
5. MAGAE, J.; H. OSADA, H. FUJIKI, C. SAIDO, K. SUZUKI, K. NAGAI, M. YAMASAKI & K. ISONO: Morphological changes of human myeloid leukemia K562 cells by a protein phosphatase inhibitor, tautomycin. Proc. Japan Acad. 66: 209-212, 1990
6. MACKINTOSH, C. & S. KLUMPP: Tautomycin from the bacterium Streptomyces verticillatus. Another potent and specific inhibitor of protein phosphatases 1 and 2A. FEBS Lett. 277: 137-140, 1990
7. SUGANUMA, M.; S. OKABE, E. SUEOKA, R. NISHIWAKI, A. KOMORI, N. UDA, K. ISONO & H. FUJIKI: Tautomycin: an inhibitor of protein phosphatases 1 and 2A but not a tumor promoter on mouse skin and in rat glandular stomach. J. Cancer Res. Clin. Oncol. 121: 621-627, 1995
8. SCHMITZ, F. J.; R. S. PRASAD, Y. GOPICHAND, H. B. HOSSAIN, D. VAN DER HELM & P. SCHMIDT: Acanthifolicin. a new episufide-containing polyether carboxylic acid from extracts of the marine sponge Pandaros acanthifolium. J. Am. Chem. Soc. 103: 2467-2469, 1981
9. TACHIBANA, K.; P. J. SCHEUER, Y. TSUKITANI, H. KIKUCHI, D. VAN ENGEN, J. CLARDY, Y. GOPICHAND & F. J. SCHMITZ: Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria. J. Am. Chem. Soc. 103: 2469-2471, 1981
10. QUINN, R. J.; C. TAYLOR, M. SUGANUMA & H. FUJIKI: The conserved acid-binding domain model of inhibitors of protein phosphatases 1 and 2A: molecular modeling aspects. BioMed. Chem. Lett. 13: 1029-1034, 1993
11. KURAMOTO, M.; T. ISHIDA, N. YAMADA, D. UEMURA, T. HAINO, K. YAMADA, Y. IJUIN & K. FUJITA: Structure-activity relationship of okadaic acid. 35th Symposium on the Chemistry of Natural Products. Symposium Papers., pp. 693-700, Kyoto, 1993
12. UBUKATA, M.; X.-C. CHENG, M. ISOBE & K. ISONO: Absolute configuration of tautomycin, a protein phosphatase inhibitor from a Streptomycete. J. Chem. Soc., Perkin Trans. 1 1993: 617-624, 1993
13. GRIESINGER, C.; O. W. SORENSEN & R. R. ERNST: Practical aspects of the E. COSY technique. Measurement of scalar spin-spin coupling constants in peptides. J. Magn. Reson. 75: 474-492, 1987
14. BOTHNER-BY, A. A.; R. L. STEPHENS, J.-M. LEE, C. D. WARREN & R. W. JEANLOZ: Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame. J. Am. Chem. Soc. 106: 811-813, 1984
15. UBUKATA, M.; X-C. CHENG, J. UZAWA & K. ISONO: Biosynthesis of the dialkylmaleic anhydride-containing antibiotics, tautomycin and tautomycetin. J. Chem. Soc. Perkin Trans 1 1995: 2399-2404, 1995
16. CHENG, X.-C.; M. UBUKATA & K. ISONO: The structure of tautomycin, a dialkylmaleic anhydride antibiotic. J. Antibiotics 43: 809-819, 1990
17. WIESLER, W. T.; J. T. VAZQUEZ & K. NAKANISHI: Pairwise additivity in exciton-coupled CD curves of multi-chromophoric systems. J. Am. Chem. Soc. 109: 5586-5592, 1987
18. ENDO, S.; H. WAKO, K. NAGAYAMA & N. GO: Computational aspects of the study of biological macromolecules by NMR spectroscopy. In NATO ASI series. Ed., J. C. HOCH et al., pp. 233-251, Plenum Press, New York, 1991
19. FUJITA, K.; M. FUJIWARA, C. YAMASAKI, T. MATSUURA, K. FURIHATA & H. SETO: Stereochemistry structure determination method used by computer. 38th Symposium on the Chemistry of Natural Products. Symposium papers., pp. 379-384, Sendai, 1996
20. SUGIYAMA, Y.; I. I. OHTANI, M. ISOBE, A. TAKAI, M. UBUKATA & K. ISONO: Molecular shape analysis and activity of tautomycin, a protein phosphatase inhibitor. BioMed. Chem. Lett. 6: 3-8, 1996
21. GOLDBERG, J.; H. HUANG, Y. KWON, P. GREENGARD, A. C. NAIRN & J. KURIYAN: Three-dimensional structure of the catalytic subunit of protein serine/threonine phosphatase-1. Nature 376: 745-753, 1995
22. TAKAI, A.; K. SASAKI, H. NAGAI, G. MIESKES, M. ISOBE, K. ISONO & T. YASUMOTO: Inhibition of specific binding of okadaic acid to protein phosphatase 2A by microcystin-LR, calyculin-A and tautomycin: method of analysis of interactions of tight-binding ligands with target protein. Biochem. J. 306: 657-665, 1995
23. SONODA, T.; K. KOBAYASHI, M. UBUKATA, H. OSADA & K. ISONO: Absolute configuration of epiderstatin, a new glutarimide antibiotic produced by Streptomyces pulveraceus. J. Antibiotics 45: 1963-1965, 1992
24. UBUKATA, M.; B. R. RANI, C.-B. CUI & H. OSADA: Preparation of optically active epiderstatin and its stereoisomers - Epiderstatin is not a real inhibitor of the mitogenic activity induced by epidermal growth factor -J. Antibiotics 48: 1176-1178, 1995
25. KATO, Y.; N. FUSETANI, S. MATUNAGA, K. HASHIMOTO, S. FUJITA & T. FURUYA: Calyculin A, a novel antitumor metabolite from the marine sponge Discodermia calyx. J. Am. Chem. Soc. 108: 2780-2781, 1986
26. INOUE, T.; H. KISHIMA, H. OTSUKA & T. NAKATANI: Type 2 helper T cell selective immunosuppressants. Japan Patent 18647, 23-Jul-96
27. ZHANG, L.; Z. ZHANG, F. LONG & E. Y. LEE: Tyrosine-272 is involved in the inhibition of protein phosphatase-I by multiple toxins. Biochemistry 35: 1606-1611, 1996
28. ARIZA, R. R.; S. M. KEYSE, J. G. MOGGS & R. D. WOOD: Reversible protein phosphorylation modulators nucleotide excision repair of damaged DNA by human cell extracts. Nucleic Acids Res 24: 433-440, 1996
29. ESCOUBAS, J. M.; M. LOMAS, J. LAROCHE & P. G. FALKOWSKI: Light intensity regulation of cab gene transcription is signaled by the redox state of the plastoquinone pool. Proc. Natl. Acad. Sci. U.S.A. 92: 10237-10241, 1995
30. 2+ channels in human vascular smooth muscle. FEBS Lett. 373: 30-34, 1995
31. KOVACS, C. S.; C. L. CHIK, B. LI, E. KARPINSKI & A. K. HO: Inhibition of serine/threonine protein phosphatases enhances agonist-stimulated cAMP accumulation in UMR 106 osteoblast-like cells. Mol. Cell Endocrinol. 110: 9-16, 1995
32. WONG, K.; X. B. LI & N. HUNCHUK: N-Acetylsphingosine (C2-ceramide) inhibited neutrophil superoxide formation and calcium influx. J. Biol. Chem. 270: 3056-3062, 1995