The Hsp90 Inhibitor Radicicol Interacts with the ATP-Binding Pocket of Bacterial Sensor Kinase PhoQ

Journal of Molecular Biology

Volumn 379, Issue 1, 2008, Pages 82-93

  Guarnieri, Michael T ^a   Zhang, Lingdi ^a   Shen, Jingping ^a   Zhao, Rui ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

ATP binding pocket; GHL inhibitor; PhoQ; radicicol; sensor kinase

Indexed keywords

ADENOSINE TRIPHOSPHATE; GELDANAMYCIN; HEAT SHOCK PROTEIN 90; NOVOBIOCIN; PHOSPHOTRANSFERASE; PROTEIN AMPPNP; RADICICOL; SENSOR KINASE PHOQ;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CRYSTALLOGRAPHY; DRUG BINDING; DRUG STRUCTURE; ENZYME ACTIVITY; ESCHERICHIA COLI; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN DOMAIN; PROTEIN FOLDING; SALMONELLA TYPHIMURIUM;

BACTERIA (MICROORGANISMS);

EID: 42749090538     PISSN: 00222836     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmb.2008.03.036     Document Type: Article

References (57)

1. J.A. Hoch T.J. Silhavy Two-Component Signal Transduction 1995 American Society for Microbiology Washington, DC
2. J.A. Hoch Two-component and phosphorelay signal transduction Curr. Opin. Microbiol. 3 2000 165 170
3. A.M. Stock V.L. Robinson P.N. Goudreau Two-component signal transduction Annu. Rev. Biochem. 69 2000 183 215
4. C. Chang R.C. Stewart The two-component system. Regulation of diverse signaling pathways in prokaryotes and eukaryotes Plant Physiol. 117 1998 723 731
5. J.J. Bijlsma E.A. Groisman Making informed decisions: regulatory interactions between two-component systems Trends Microbiol. 11 2003 359 366
6. L. Hancock M. Perego Two-component signal transduction in Enterococcus faecalis J. Bacteriol. 184 2002 5819 5825
7. J.B. Stock A.M. Stock J.M. Mottonen Signal transduction in bacteria Nature 344 1990 395 400
8. J.F. Barrett R.M. Goldschmidt L.E. Lawrence B. Foleno R. Chen J.P. Demers Antibacterial agents that inhibit two-component signal transduction systems Proc. Natl Acad. Sci. USA 95 1998 5317 5322
9. J.F. Barrett J.A. Hoch Two-component signal transduction as a target for microbial anti-infective therapy Antimicrob. Agents Chemother. 42 1998 1529 1536
10. K. Stephenson J.A. Hoch Virulence- and antibiotic resistance-associated two-component signal transduction systems of Gram-positive pathogenic bacteria as targets for antimicrobial therapy Pharmacol. Ther. 93 2002 293 305
11. K. Stephenson J.A. Hoch Two-component and phosphorelay signal-transduction systems as therapeutic targets Curr. Opin. Pharmacol. 2 2002 507 512
12. C. Tomomori T. Tanaka R. Dutta H. Park S.K. Saha Y. Zhu Solution structure of the homodimeric core domain of Escherichia coli histidine kinase EnvZ Nat. Struct. Biol. 6 1999 729 734
13. T. Tanaka S.K. Saha C. Tomomori R. Ishima D. Liu K.I. Tong NMR structure of the histidine kinase domain of the E. coli osmosensor EnvZ Nature 396 1998 88 92
14. A.M. Bilwes C.M. Quezada L.R. Croal B.R. Crane M.I. Simon Nucleotide binding by the histidine kinase CheA Nat. Struct. Biol. 8 2001 353 360
15. A. Marina C. Mott A. Auyzenberg W.A. Hendrickson C.D. Waldburger Structural and mutational analysis of the PhoQ histidine kinase catalytic domain. Insight into the reaction mechanism J. Biol. Chem. 276 2001 41182 41190
16. R. Dutta M. Inouye GHKL, an emergent ATPase/kinase superfamily Trends Biochem. Sci. 25 2000 24 28
17. P. Workman F. Burrows L. Neckers N. Rosen Drugging the cancer chaperone HSP90: combinatorial therapeutic exploitation of oncogene addiction and tumor stress Ann. N Y Acad. Sci. 1113 2007 202 216
18. E. McDonald K. Jones P.A. Brough M.J. Drysdale P. Workman Discovery and development of pyrazole-scaffold Hsp90 inhibitors Curr. Top. Med. Chem. 6 2006 1193 1203
19. M.K. Hadden D.J. Lubbers B.S. Blagg Geldanamycin, radicicol, and chimeric inhibitors of the Hsp90 N-terminal ATP binding site Curr. Top. Med. Chem. 6 2006 1173 1182
20. Y.L. Janin Heat shock protein 90 inhibitors. A text book example of medicinal chemistry? J. Med. Chem. 48 2005 7503 7512
21. G. Chiosis B. Lucas H. Huezo D. Solit A. Basso N. Rosen Development of purine-scaffold small molecule inhibitors of Hsp90 Curr. Cancer Drug Targets 3 2003 371 376
22. S. Soga Y. Shiotsu S. Akinaga S.V. Sharma Development of radicicol analogues Curr. Cancer Drug Targets 3 2003 359 369
23. L. Neckers Development of small molecule Hsp90 inhibitors: utilizing both forward and reverse chemical genomics for drug identification Curr. Med. Chem. 10 2003 733 739
24. O.K. Kim K. Ohemeng J.F. Barrett Advances in DNA gyrase inhibitors Expert Opin. Investig. Drugs 10 2001 199 212
25. P.G. Besant M.V. Lasker C.D. Bui C.W. Turck Inhibition of branched-chain alpha-keto acid dehydrogenase kinase and Sln1 yeast histidine kinase by the antifungal antibiotic radicicol Mol. Pharmacol. 62 2002 289 296
26. C.M. Parry Antimicrobial drug resistance in Salmonella enterica Curr. Opin. Infect. Dis. 16 2003 467 472
27. E.J. Threlfall I.S. Fisher C. Berghold P. Gerner-Smidt H. Tschape M. Cormican Antimicrobial drug resistance in isolates of Salmonella enterica from cases of salmonellosis in humans in Europe in 2000: results of international multi-centre surveillance Euro Surveill. 8 2003 41 45
28. E.A. Groisman The pleiotropic two-component regulatory system PhoP–PhoQ J. Bacteriol. 183 2001 1835 1842
29. S.I. Miller J.J. Mekalanos Constitutive expression of the phoP regulon attenuates Salmonella virulence and survival within macrophages J. Bacteriol. 172 1990 2485 2490
30. P.I. Fields E.A. Groisman F. Heffron A Salmonella locus that controls resistance to microbicidal proteins from phagocytic cells Science 243 1989 1059 1062
31. J.E. Galan R. Curtiss 3rd Virulence and vaccine potential of phoP mutants of Salmonella typhimurium Microb. Pathog. 6 1989 433 443
32. S.I. Miller A.M. Kukral J.J. Mekalanos A two-component regulatory system (phoP phoQ) controls Salmonella typhimurium virulence Proc. Natl Acad. Sci. USA 86 1989 5054 5058
33. W.L. DeLano The PyMOL User's Manual 2002 DeLano Scientific Palo Alto, CA
34. Y. Song D. Peisach A.A. Pioszak Z. Xu A.J. Ninfa Crystal structure of the C-terminal domain of the two-component system transmitter protein nitrogen regulator II (NRII; NtrB), regulator of nitrogen assimilation in Escherichia coli Biochemistry 43 2004 6670 6678
35. A.M. Bilwes L.A. Alex B.R. Crane M.I. Simon Structure of CheA, a signal-transducing histidine kinase Cell 96 1999 131 141
36. E. Nowak S. Panjikar J.P. Morth R. Jordanova D.I. Svergun P.A. Tucker Structural and functional aspects of the sensor histidine kinase PrrB from Mycobacterium tuberculosis Structure 14 2006 275 285
37. S.M. Roe C. Prodromou R. O'Brien J.E. Ladbury P.W. Piper L.H. Pearl Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin J. Med. Chem. 42 1999 260 266
38. A.C. Wallace R.A. Laskowski J.M. Thornton LIGPLOT: a program to generate schematic diagrams of protein–ligand interactions Protein Eng. 8 1995 127 134
39. R.C. Stewart R. VanBruggen D.D. Ellefson A.J. Wolfe TNP-ATP and TNP–ADP as probes of the nucleotide binding site of CheA, the histidine protein kinase in the chemotaxis signal transduction pathway of Escherichia coli Biochemistry 37 1998 12269 12279
40. S. Soga S.V. Sharma Y. Shiotsu M. Shimizu H. Tahara K. Yamaguchi Stereospecific antitumor activity of radicicol oxime derivatives Cancer Chemother. Pharmacol. 48 2001 435 445
41. T. Agatsuma H. Ogawa K. Akasaka A. Asai Y. Yamashita T. Mizukami Halohydrin and oxime derivatives of radicicol: synthesis and antitumor activities Bioorg. Med. Chem. 10 2002 3445 3454
42. V. Hellwig A. Mayer-Bartschmid H. Muller G. Greif G. Kleymann W. Zitzmann Pochonins A–F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata J. Nat. Prod. 66 2003 829 837
43. S. Barluenga P. Lopez E. Moulin N. Winssinger Modular asymmetric synthesis of pochonin C Angew. Chem., Int. Ed. Engl. 43 2004 3467 3470
44. K. Yamamoto R.M. Garbaccio S.J. Stachel D.B. Solit G. Chiosis N. Rosen S.J. Danishefsky Total synthesis as a resource in the discovery of potentially valuable antitumor agents: cycloproparadicicol Angew. Chem., Int. Ed. Engl. 42 2003 1280 1284
45. N. Proisy S.Y. Sharp K. Boxall S. Connelly S.M. Roe C. Prodromou Inhibition of Hsp90 with synthetic macrolactones: synthesis and structural and biological evaluation of ring and conformational analogs of radicicol Chem. Biol. 13 2006 1203 1215
46. Z.Q. Yang X. Geng D. Solit C.A. Pratilas N. Rosen S.J. Danishefsky New efficient synthesis of resorcinylic macrolides via ynolides: establishment of cycloproparadicicol as synthetically feasible preclinical anticancer agent based on Hsp90 as the target J. Am. Chem. Soc. 126 2004 7881 7889
47. E. Moulin V. Zoete S. Barluenga M. Karplus N. Winssinger Design, synthesis, and biological evaluation of HSP90 inhibitors based on conformational analysis of radicicol and its analogues J. Am. Chem. Soc. 127 2005 6999 7004
48. M. Arai K. Yamamoto I. Namatame H. Tomoda S. Omura New monordens produced by amidepsine-producing fungus Humicola sp, FO-2942 J. Antibiot. (Tokyo) 56 2003 526 532
49. K. Takehana S. Sato T. Kobayasi T. Maeda A radicicol-related macrocyclic nonaketide compound, antibiotic LL-Z1640-2, inhibits the JNK/p38 pathways in signal-specific manner Biochem. Biophys. Res. Commun. 257 1999 19 23
50. V. Lamour L. Hoermann J.M. Jeltsch P. Oudet D. Moras Crystallization of the 43 kDa ATPase domain of Thermus thermophilus gyrase B in complex with novobiocin Acta Crystallogr., Sect. D: Biol. Crystallogr. 58 2002 1376 1378
51. R.C. Schnur M.L. Corman Tandem [3,3]-sigmatropic rearrangements in an ansamycin—stereospecific conversion of an ( S )-allylic alcohol to an ( S )-allylic amine derivative J. Org. Chem. 59 1994 2581 2584
52. F. Delaglio S. Grzesiek G.W. Vuister G. Zhu J. Pfeifer A. Bax NMRPipe: a multidimensional spectral processing system based on UNIX pipes J. Biomol. NMR 6 1995 277 293
53. W.F. Vranken W. Boucher T.J. Stevens R.H. Fogh A. Pajon M. Llinas The CCPN data model for NMR spectroscopy: development of a software pipeline Proteins 59 2005 687 696
54. J.W. Pflugrath The finer things in X-ray diffraction data collection Acta Crystallogr., Sect. D: Biol. Crystallogr. 55 1999 1718 1725
55. N.C.C. Project The CCP4 Suite: Programs for Protein Crystallography Acta Crystallogr., Sect. D: Biol. Crystallogr. 50 1994 760 763
56. T.A. Jones J.Y. Zou S.W. Cowan Kjeldgaard Improved methods for building protein models in electron density maps and the location of errors in these models Acta Crystallogr. A 47 Pt 2 1991 110 119
57. A.T. Brunger P.D. Adams G.M. Clore W.L. DeLano P. Gros R.W. Grosse-Kunstleve Crystallography and NMR system: A new software suite for macromolecular structure determination Acta Crystallogr., Sect. D: Biol. Crystallogr. 54 Pt 5 1998 905 921