Improved performance by replacing iminodiacetic residues with glyceryl residues in symmetrically branched oligoglycerols

Synthesis of a symmetrically branched diglycerol (BGL002, involving one iminodiacetic residue) as a G2 dendron, and the tetradecaglycerol (BGL014, involving one iminodiacetic residue) as a G4 dendron, is described. Several members of the BGL family of G2–G4 dendrons were assembled, with G2 bearing f...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2011-08, Vol.21 (16), p.4724-4727
Hauptverfasser: Nemoto, Hisao, Ishihara, Atsushi, Araki, Takaaki, Katagiri, Ayato, Kamiya, Masaki, Matsushita, Tsuyoshi, Hattori, Hatsuhiko, Mimura, Yukiteru, Tomoda, Yutaka, Yamasaki, Motoo
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Sprache:eng
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Zusammenfassung:Synthesis of a symmetrically branched diglycerol (BGL002, involving one iminodiacetic residue) as a G2 dendron, and the tetradecaglycerol (BGL014, involving one iminodiacetic residue) as a G4 dendron, is described. Several members of the BGL family of G2–G4 dendrons were assembled, with G2 bearing four hydroxyl groups at the terminus region, G3 bearing eight, and G4 bearing sixteen. It is noteworthy that triglycerol (BGL003, including no iminodiacetic residue), has a water-solubility ten times higher than BGL002, and the liposome surrounded by BGL014 has a duration period in blood vessel roughly two times longer than the liposome surrounded by dodecaglycerol (BGL012, including three iminodiacetic residues).
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2011.06.064