title: "Bitter-Sweet" Polymeric Micelles Formed by Block Copolymers from Glucosamine and Cholic Acid.
abstract: Natural compounds glucosamine and cholic acid have been used to make acrylic monomers which are subsequently used to prepare amphiphilic block copolymers by reversible addition-fragmentation chain transfer (RAFT) polymerization. Despite the striking difference in polarity and solubility, three diblock copolymers consisting of glucosamine and cholic acid pendants with different hydrophilic and hydrophobic chain lengths have been synthesized without the use of protecting groups. They are shown to self-assemble into polymeric micelles with a "bitter" bile acid core and "sweet" sugar shell in aqueous solutions, as evidenced by dynamic light scattering and transmission electron microscopy. The critical micelle concentration varies with the hydrophobic/hydrophilic ratio, ranging from 0.62 to 1.31 mg/L. Longer chains of polymers induced the formation of larger micelles in range of 50-70 nm. These micelles can solubilize hydrophobic compounds such as Nile Red in aqueous solutions. Their loading capacity mainly depends upon the hydrophobic/hydrophilic ratio of the polymers, and may be also related to the length of the hydrophilic block. These polymeric micelles allowed for a 10-fold increase in the aqueous solubility of paclitaxel and showed no cytotoxicity below the concentration of 500 mg/L. Such properties make these polymeric micelles interesting reservoirs for hydrophobic molecules and drugs for biomedical applications.
authors.affiliation: Département de Chimie, Université de Montréal , C.P. 6128, Succ. Centre-ville, Montreal, QC H3C 3J7, Canada.
authors.forename: Kun
authors.initials: K
authors.lastname: Zhang
authors.affiliation: Département de Chimie, Université de Montréal , C.P. 6128, Succ. Centre-ville, Montreal, QC H3C 3J7, Canada.
authors.forename: Yong-Guang
authors.initials: YG
authors.lastname: Jia
authors.affiliation: Département de Chimie, Université de Montréal , C.P. 6128, Succ. Centre-ville, Montreal, QC H3C 3J7, Canada.
authors.forename: I-Huang
authors.initials: IH
authors.lastname: Tsai
authors.affiliation: Département de Chimie, Université de Montréal , C.P. 6128, Succ. Centre-ville, Montreal, QC H3C 3J7, Canada.
authors.forename: Satu
authors.initials: S
authors.lastname: Strandman
authors.affiliation: School of Materials Science and Engineering, South China University of Technology , Guangzhou, China.
authors.forename: Li
authors.initials: L
authors.lastname: Ren
authors.affiliation: School of Materials Science and Engineering, South China University of Technology , Guangzhou, China.
authors.forename: Liangzhi
authors.identifier: 0000-0002-2297-8013
authors.initials: L
authors.lastname: Hong
authors.affiliation: School of Materials Science and Engineering, South China University of Technology , Guangzhou, China.
authors.forename: Guangzhao
authors.initials: G
authors.lastname: Zhang
authors.affiliation: Institute of Polymer Chemistry, Nankai University , Tianjin, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Guan
authors.affiliation: Institute of Polymer Chemistry, Nankai University , Tianjin, China.
authors.forename: Yongjun
authors.identifier: 0000-0002-1079-4137
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Département de Chimie, Université de Montréal , C.P. 6128, Succ. Centre-ville, Montreal, QC H3C 3J7, Canada.
authors.forename: X X
authors.identifier: 0000-0003-0828-299X
authors.initials: XX
authors.lastname: Zhu
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D019826:Cholic Acid / Q000737:chemistry*; D004337:Drug Carriers / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008823:Micelles; D010078:Oxazines / Q000737:chemistry; D017239:Paclitaxel / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry; D058105:Polymerization; D011108:Polymers / Q000737:chemistry*
chemical_list: D004337:Drug Carriers; D008823:Micelles; D010078:Oxazines; D011108:Polymers; D011092:Polyethylene Glycols; D019826:Cholic Acid; D005944:Glucosamine; C044808:nile red; D017239:Paclitaxel