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Investigation of the relative cellular permeability of DNA-binding pyrrole-imidazole polyamides

Bo Liu1, Thomas Kodadek

  • 1Department of Internal Medicine, Division of Translational Research, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390, USA.

Journal of Medicinal Chemistry
|July 21, 2009
PubMed

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Basicity of Heterocyclic Aromatic Amines01:25

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).