title: 2-Nitrobenzyl Borate Based Photolabile Linker for Breakable Polymer Vesicles.
abstract: Fluorescent photolabile groups undergoing convenient synthesis and fast cleavage are being explored because of their increasing utility in both synthetic and biological chemistry. Herein, a model photosensitive poly(ethylene glycol)-lipid of NP-B-PEG with a 2-nitrobenzyl 2-pyridinylmethyl borate hydrophobic tail is synthesized. The (1) H-NMR and absorption spectra analysis of NP-B-PEG upon 365 nm irradiation in water supports a rapid photocleavage of nitrobenzyl borate with the concomitant hydrolysis of 2-pyridinylmethyl borate. It is also shown that the borate tail hydrolyzes slowly in water. Fortunately, when the polymer aqueous solution is loaded with the hydrophobic doxorubicin (DOX), the borate hydrolysis can be much retarded. The phototriggered experiment shows a two-stage DOX release: first, the slow leakage as a result of the photocleavage of 2-nitrobenzyl borate before the vesicle disintegration; second, the quick DOX precipitation from the disintegrated vesicles induced by the speeding up hydrolysis of 2-pyridinylmethyl borate.
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi, 710062, P. R. China.
authors.forename: Ruidong
authors.initials: R
authors.lastname: Cheng
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi, 710062, P. R. China.
authors.forename: Jiangang
authors.initials: J
authors.lastname: Chen
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi, 710062, P. R. China.
authors.forename: Zhaotie
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi, 710062, P. R. China.
authors.forename: Zhongwen
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi, 710062, P. R. China.
authors.forename: Jinqiang
authors.initials: J
authors.lastname: Jiang
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D004317:Doxorubicin / Q000737:chemistry*; D004337:Drug Carriers / Q000737:chemistry*; D004339:Drug Compounding; D065546:Drug Liberation; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D008823:Micelles; D015394:Molecular Structure; D055668:Photochemical Processes; D011092:Polyethylene Glycols / Q000737:chemistry*; D014466:Ultraviolet Rays
chemical_list: D000970:Antineoplastic Agents; D001593:Benzyl Compounds; D001881:Borates; D004337:Drug Carriers; D008823:Micelles; D011092:Polyethylene Glycols; D004317:Doxorubicin
keywords: 2-nitrobenzyl; PEG-lipid; borate; photolabile; polymer vesicles