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Molecular Models of DAPI
This month’s Featured Molecule is DAPI (4′,6-diamidino-2-phenylindole), from the paper by Eamonn F. Healy (1). The utility of DAPI is a consequence of its being a minor-groove binder to DNA. A crystal structure of DAPI binding to the minor groove of a synthetic DNA has been determined, and the structure file made available through the RCSB Protein Data Bank (2, 3). That structure is also included in the Featured Molecules Collection, with the water molecules removed for the sake of clarity.
For many students this may be their first encounter with the binding of small molecules to DNA. Another example of such binding is the intercalation of the antibiotic actinomycin into DNA. The Department of Biology at the University of Hamburg maintains an excellent Web site showing both crystal and NMR structures of actinomycin intercalation (4). Observant students will also note in the structure of DAPI a theme that has appeared several times in our Featured Molecules, and that is the non-planarity of adjacent delocalized ring systems. In DAPI, it is a five-membered ring adjacent to a six-membered ring, and the observed departure from planarity is less than that in biphenyl. Students might be asked to explain that difference.
Literature Cited
- Healy, Eamonn F. J. Chem. Educ. 2007, 84, 1304–1307.
- RCSB PDB: Structure Explorer (accessed Jun 2007).
- Vlieghe, D.; Sponer, J.; Van Meervelt, L. Biochemistry 1999, 38, 16443–16451.
- Antibiotics: Actinomycin D—Structure Model (accessed Jun 2007).
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