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Novel Guanidine‐Containing Molecular Transporters Based on Lactose Scaffolds: Lipophilicity Effect on the Intracellular Organellar Selectivity
Author(s) -
Biswas Goutam,
Jeon OckYoum,
Lee Woo Sirl,
Kim DongChan,
Kim KyongTai,
Lee Suho,
Chang Sunghoe,
Chung SungKee
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801160
Subject(s) - intracellular , transporter , guanidine , linker , chemistry , lipophilicity , endocytic cycle , biochemistry , mitochondrion , microbiology and biotechnology , molecular motor , biophysics , biology , endocytosis , cell , gene , computer science , operating system
We have synthesized two lactose‐based molecular transporters, each containing seven guanidine residues attached to the lactose scaffold through ω‐aminocarboxylate linker chains of two different lengths, and have examined their cellular uptakes and intracellular and organellar localizations in HeLa cells, as well as their tissue distributions in mice. Both molecular transporters showed higher cellular uptake efficiencies than Arg8, and wide tissue distributions including the brain. Mitochondrial localization is of special interest because of its potential relevance to “mitochondrial diseases”. Interestingly, it has been found that the intracellular localization sites of the G7 molecular transporters—namely either mitochondria or lysosomes and endocytic vesicles—are largely determined by the linker chain lengths, or their associated lipophilicities.