Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Mitochondrial Affinity of Guanidine-rich Molecular Transporters Built on Monosaccharide Scaffolds: Stereochemistry and Lipophilicity

  • Lee, Woo-Sirl (Department of Chemistry, Pohang University of Science and Technology) ;
  • Kim, Wan-Il (Department of Life Science, Pohang University of Science and Technology) ;
  • Kim, Kyong-Tai (Department of Life Science, Pohang University of Science and Technology) ;
  • Chung, Sung-Kee (Department of Chemistry, Pohang University of Science and Technology)
  • Received : 2011.04.25
  • Accepted : 2011.05.24
  • Published : 2011.07.20
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Abstract

We synthesized eight G8 molecular transporters (MTs) based on 4 different monosaccharide scaffolds, and studied their biological properties with a special focus on possible mitochondrial targeting and tissue selectivity. The mitochondrial affinity of these MTs was found to be clearly related to the scaffold stereochemistry and also tenuously with the lipophilicity. It may be suggested that in the practical delivery strategy of drugs for the brain and mitochondrial diseases the BBB permeability and mitochondrial affinity should be considered as key parameters, and that an enhanced mitochondrial affinity appears possible by further research on the structure-property relationship of guanidine-rich molecular transporters.

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