X-Ray diffraction analyses of the natural isoquinoline alkaloids Berberine and Sanguinarine complexed with double helix DNA d(CGTACG)

Chem Commun (Camb). 2011 May 7;47(17):4917-9. doi: 10.1039/c1cc10971e. Epub 2011 Mar 22.

Abstract

The first crystal structures of Berberine and Sanguinarine intercalated with a d(CGTACG)(2) DNA sequence were obtained by X-ray diffraction analysis at 2.3 Å resolution. Both drugs join the end of two "two-molecules" DNA units, stacked in a non-classic intercalation site formed by six bases. Sanguinarine interacts with d(CGTACG)(2) DNA in its iminium form.

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / metabolism
  • Benzophenanthridines / chemistry
  • Benzophenanthridines / metabolism*
  • Berberine / chemistry
  • Berberine / metabolism*
  • Binding Sites
  • Crystallization
  • Crystallography, X-Ray
  • DNA / chemistry
  • DNA / metabolism*
  • Intercalating Agents / chemistry
  • Intercalating Agents / metabolism
  • Isoquinolines / chemistry
  • Isoquinolines / metabolism*
  • Models, Molecular
  • Nucleic Acid Conformation
  • Oligodeoxyribonucleotides / chemistry
  • Oligodeoxyribonucleotides / metabolism
  • X-Ray Diffraction

Substances

  • Anti-Infective Agents
  • Benzophenanthridines
  • Intercalating Agents
  • Isoquinolines
  • Oligodeoxyribonucleotides
  • Berberine
  • DNA
  • sanguinarine

Associated data

  • PDB/3NP6
  • PDB/3NX5