Predicting and improving the membrane permeability of peptidic small molecules.

@article{Rafi2012PredictingAI,
  title={Predicting and improving the membrane permeability of peptidic small molecules.},
  author={Salma B Rafi and Brian R. Hearn and Punitha Vedantham and Matthew P. Jacobson and Adam R. Renslo},
  journal={Journal of medicinal chemistry},
  year={2012},
  volume={55 7},
  pages={3163-9}
}
We evaluate experimentally and computationally the membrane permeability of matched sets of peptidic small molecules bearing natural or bioisosteric unnatural amino acids. We find that the intentional introduction of hydrogen bond acceptor-donor pairs in such molecules can improve membrane permeability while retaining or improving other favorable drug-like properties. We employ an all-atom force field based method to calculate changes in free energy associated with the transfer of the peptidic… CONTINUE READING
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Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space

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