title: Influence of hydrophobic structures on the plasma membrane permeability of lipidlike molecules.
abstract: 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.
authors.affiliation: Research Institute for Electronic Science, Hokkaido University, Kita21, Nishi10, Kita-Ku, Sapporo 001-0021, Japan. kniikura@poly.es.hokudai.ac.jp
authors.forename: Kenichi
authors.initials: K
authors.lastname: Niikura
authors.forename: Katsuyuki
authors.initials: K
authors.lastname: Nambara
authors.forename: Takaharu
authors.initials: T
authors.lastname: Okajima
authors.forename: Yasutaka
authors.initials: Y
authors.lastname: Matsuo
authors.forename: Kuniharu
authors.initials: K
authors.lastname: Ijiro
mesh_terms: 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
chemical_list: D006838:Hydrocarbons; D016650:Fluorescein-5-isothiocyanate