Crystal structures of human HSP90alpha-complexed with dihydroxyphenylpyrazoles

Bioorg Med Chem Lett. 2005 Mar 1;15(5):1475-8. doi: 10.1016/j.bmcl.2004.12.087.

Abstract

A series of dihydroxyphenylpyrazole compounds were identified as a unique class of reversible Hsp90 inhibitors. The crystal structures for two of the identified compounds complexed with the N-terminal ATP binding domain of human Hsp90alpha were determined. The dihydroxyphenyl ring of the compounds fits deeply into the adenine binding pocket with the C2 hydroxyl group forming a direct hydrogen bond with the side chain of Asp93. The pyrazole ring forms hydrogen bonds to the backbone carbonyl of Gly97, the hydroxyl group of Thr184 and to a water molecule, which is present in all of the published HSP90 structures. One of the identified compounds (G3130) demonstrated cellular activities (in Her-2 degradation and activation of Hsp70 promoter) consistent with the inhibition of cellular Hsp90 functions.

MeSH terms

  • Cell Line
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Evaluation, Preclinical
  • HSP90 Heat-Shock Proteins / antagonists & inhibitors
  • HSP90 Heat-Shock Proteins / chemistry*
  • Humans
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Protein Structure, Tertiary
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology
  • Structure-Activity Relationship
  • Time Factors

Substances

  • G3129
  • G3130
  • HSP90 Heat-Shock Proteins
  • Pyrazoles

Associated data

  • PDB/1YC1
  • PDB/1YC3
  • PDB/1YC4