The mechanism of topoisomerase I poisoning by a camptothecin analog

Proc Natl Acad Sci U S A. 2002 Nov 26;99(24):15387-92. doi: 10.1073/pnas.242259599. Epub 2002 Nov 8.

Abstract

We report the x-ray crystal structure of human topoisomerase I covalently joined to double-stranded DNA and bound to the clinically approved anticancer agent Topotecan. Topotecan mimics a DNA base pair and binds at the site of DNA cleavage by intercalating between the upstream (-1) and downstream (+1) base pairs. Intercalation displaces the downstream DNA, thus preventing religation of the cleaved strand. By specifically binding to the enzyme-substrate complex, Topotecan acts as an uncompetitive inhibitor. The structure can explain several of the known structure-activity relationships of the camptothecin family of anticancer drugs and suggests that there are at least two classes of mutations that can produce a drug-resistant enzyme. The first class includes changes to residues that contribute to direct interactions with the drug, whereas a second class would alter interactions with the DNA and thereby destabilize the drug-binding site.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Crystallography, X-Ray
  • DNA / chemistry*
  • DNA / metabolism
  • DNA Topoisomerases, Type I / chemistry
  • DNA Topoisomerases, Type I / genetics
  • DNA Topoisomerases, Type I / metabolism
  • Drug Resistance, Neoplasm
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Hydrogen Bonding
  • Intercalating Agents / chemistry
  • Intercalating Agents / pharmacology*
  • Macromolecular Substances
  • Models, Molecular
  • Molecular Structure
  • Mutation
  • Neoplasm Proteins / antagonists & inhibitors*
  • Neoplasm Proteins / chemistry
  • Neoplasm Proteins / genetics
  • Neoplasm Proteins / metabolism
  • Peptide Fragments / chemistry
  • Peptide Fragments / metabolism
  • Peptide Fragments / physiology
  • Protein Binding
  • Protein Conformation
  • Recombinant Fusion Proteins / chemistry
  • Recombinant Fusion Proteins / metabolism
  • Recombinant Fusion Proteins / physiology
  • Structure-Activity Relationship
  • Topoisomerase I Inhibitors*
  • Topotecan / chemistry
  • Topotecan / pharmacology*

Substances

  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Intercalating Agents
  • Macromolecular Substances
  • Neoplasm Proteins
  • Peptide Fragments
  • Recombinant Fusion Proteins
  • Topoisomerase I Inhibitors
  • Topotecan
  • DNA
  • DNA Topoisomerases, Type I

Associated data

  • PDB/1K4S
  • PDB/1K4T