title: Micelles consisting of choline phosphate-bearing calix[4]arene lipids.
abstract: We synthesized new calix[4]arene-based lipids, denoted by CPCaLn, bearing the choline phosphate (CP) group which is an inverse phosphoryl choline (PC) structure. Small-angle X-ray scattering and multi-angle light scattering coupled with field flow fractionation showed that these lipids form monodisperse micelles with a fixed aggregation number and diameters of 1.9 and 2.6 nm for lipids bearing C3 and C6 alkyl tails, respectively. Furthermore, when CPCaLn was mixed with the fluorescein isothiocyanate (FITC)-bearing lipids and added to cells, strong fluorescence was observed at 37 °C, but not at 4 °C, indicating that the micelles were taken up by the cells through endocytosis. Recent studies have shown that replacement of polymer-attached PC groups with CP groups markedly promotes cellular uptake, even though the surface charge is neutral. On the basis of the idea, CPCaLn micelles interacted with cells in the same way, suggesting that the micelles bearing CP groups are expected to use as carriers in the drug delivery system.
authors.affiliation: Graduate School of Engineering and Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan. sakurai@kitakyu-u.ac.jp.
authors.forename: Shota
authors.initials: S
authors.lastname: Fujii
authors.forename: Koichi
authors.initials: K
authors.lastname: Nishina
authors.forename: Shimpei
authors.initials: S
authors.lastname: Yamada
authors.forename: Shinichi
authors.initials: S
authors.lastname: Mochizuki
authors.forename: Noboru
authors.initials: N
authors.lastname: Ohta
authors.forename: Atsushi
authors.initials: A
authors.lastname: Takahara
authors.forename: Kazuo
authors.initials: K
authors.lastname: Sakurai
mesh_terms: D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry*; D002460:Cell Line; D004705:Endocytosis; D016650:Fluorescein-5-isothiocyanate / Q000737:chemistry; D006801:Humans; D008823:Micelles; D010743:Phospholipids / Q000737:chemistry*; D010767:Phosphorylcholine / Q000737:chemistry*; D055672:Static Electricity
chemical_list: D008823:Micelles; D010743:Phospholipids; D010767:Phosphorylcholine; D047250:Calixarenes; D016650:Fluorescein-5-isothiocyanate