A novel mechanism for adenylyl cyclase inhibition from the crystal structure of its complex with catechol estrogen

J Biol Chem. 2005 Sep 9;280(36):31754-9. doi: 10.1074/jbc.M507144200. Epub 2005 Jul 7.

Abstract

Catechol estrogens are steroid metabolites that elicit physiological responses through binding to a variety of cellular targets. We show here that catechol estrogens directly inhibit soluble adenylyl cyclases and the abundant trans-membrane adenylyl cyclases. Catechol estrogen inhibition is non-competitive with respect to the substrate ATP, and we solved the crystal structure of a catechol estrogen bound to a soluble adenylyl cyclase from Spirulina platensis in complex with a substrate analog. The catechol estrogen is bound to a newly identified, conserved hydrophobic patch near the active center but distinct from the ATP-binding cleft. Inhibitor binding leads to a chelating interaction between the catechol estrogen hydroxyl groups and the catalytic magnesium ion, distorting the active site and trapping the enzyme substrate complex in a non-productive conformation. This novel inhibition mechanism likely applies to other adenylyl cyclase inhibitors, and the identified ligand-binding site has important implications for the development of specific adenylyl cyclase inhibitors.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Adenosine Triphosphate / metabolism
  • Adenylyl Cyclase Inhibitors*
  • Adenylyl Cyclases / chemistry*
  • Adenylyl Cyclases / metabolism
  • Binding Sites
  • Crystallography, X-Ray
  • Cyanobacteria / enzymology*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / metabolism
  • Estrogens, Catechol / chemistry*
  • Estrogens, Catechol / metabolism
  • Humans
  • Protein Structure, Tertiary

Substances

  • Adenylyl Cyclase Inhibitors
  • Enzyme Inhibitors
  • Estrogens, Catechol
  • Adenosine Triphosphate
  • Adenylyl Cyclases

Associated data

  • PDB/2BW7