Influence of hydrophobic structures on the plasma membrane permeability of lipidlike molecules.
A series of FITC-labeled hydrophobic molecules (1-8) were prepared, and their cellular uptakes have been investigated using cell-cycle-synchronized HeLa cells. The cellular membrane permeability of compounds strongly depended on both the chemical structure and the cell-cycle phase. In the G1/S phase, branched hydrocarbon-containing 3 and cis-olefin-containing 2 and 8 were efficiently internalized into cells by passive diffusion. In contrast, linear alkyl chain-containing 1 and 7 were retained on the membrane without rapid internalization. In the M phase, rapid permeation was suppressed for all molecules.
Niikura
Kenichi
K
Research Institute for Electronic Science, Hokkaido University, Kita21, Nishi10, Kita-Ku, Sapporo 001-0021, Japan. kniikura@poly.es.hokudai.ac.jp
Nambara
Katsuyuki
K
Okajima
Takaharu
T
Matsuo
Yasutaka
Y
Ijiro
Kuniharu
K
D002453:Cell Cycle; D002463:Cell Membrane Permeability; D016650:Fluorescein-5-isothiocyanate; D006367:HeLa Cells; D006801:Humans; D006838:Hydrocarbons / Q000737:chemistry / Q000493:pharmacokinetics*; D057927:Hydrophobic and Hydrophilic Interactions; D013329:Structure-Activity Relationship
D006838:Hydrocarbons; D016650:Fluorescein-5-isothiocyanate