The two faces of potent antitumor duocarmycin-based drugs: A structural dissection reveals disparate motifs for DNA versus aldehyde dehydrogenase 1 affinity

Tanja Wirth, Galina F. Pestel, Vanessa Ganal, Thomas Kirmeier, Ingrid Schuberth, Theo Rein, Lutz F. Tietze, Stephan A. Sieber

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Duocarmycin-derived seco-cyclopropabenzindole (CBI) drugs have been shown to bind DNA and an aldehyde dehydrogenase (ALDH1A1) in lung cancer cells. The removal of the DNA-binding indole moiety results in a CBI compound that does not bind to DNA in whole cells but still exhibits remarkable cytotoxicity. This CBI compound has an increased affinity for ALDH1A1. Rh=rhodamine.

Original languageEnglish
Pages (from-to)6921-6925
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume52
Issue number27
DOIs
StatePublished - 1 Jul 2013

Keywords

  • aldehyde dehydrogenase 1
  • antitumor agents
  • cell biology
  • natural products
  • proteomics

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