Novel guanidine-containing molecular transporters based on lactose scaffolds: lipophilicity effect on the intracellular organellar selectivity.
We have synthesized two lactose-based molecular transporters, each containing seven guanidine residues attached to the lactose scaffold through omega-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.
Biswas
Goutam
G
Department of Chemistry, Pohang University of Science and Technology, Pohang 790-784, Korea.
Jeon
Ock-Youm
OY
Lee
Woo Sirl
WS
Kim
Dong-Chan
DC
Kim
Kyong-Tai
KT
Lee
Suho
S
Chang
Sunghoe
S
Chung
Sung-Kee
SK
D019791:Guanidine / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D007785:Lactose / Q000737:chemistry* / Q000378:metabolism*; D015388:Organelles / Q000378:metabolism*; D012680:Sensitivity and Specificity
D007785:Lactose; D019791:Guanidine