Preparation and characterization of photoresponsive poly(methyl methacrylate) microspheres bearing phosphorylcholine‐analogous and spirooxazine moieties

Abstract

The photoresponsive copolymer microspheres [poly(MAIP-co-MMA)] were prepared from the emulsifier-free emulsion copolymerization of 2-[2-(methacryloyloxy) ethyldimethylammonio]-ethyl indolinonaphthooxazine phosphate (MAIP) and methyl methacrylate (MMA). From the kinetics of the copolymerization of MAIP and MMA, it was found that the initial rate of polymerization of MMA increased by the addition of a small amount of MAIP. From the X-ray photoelectron spectroscopy (XPS) measurements MAIP moiety was found to be located on the surface of a particle. The introduction of a MAIP moiety into poly(MMA) microspheres results in a decrease in the amount of bovine serum albumin (BSA) adsorbed. A photoresponsive adsorption of BSA on poly(MA1P-co-MMA) microspheres was observed with spirooxazine-merocyanine photoisomerization caused by UV irradiation.

Phospholipid Polymers

“…Other MPC derivatives with special functions have been reported (48)(49)(50)(51)(52). A photochromic spirobenzopyrane or azobenzene moiety is introduced at the terminus of the PC-like group (51).…”

“…A photochromic spirobenzopyrane or azobenzene moiety is introduced at the terminus of the PC-like group (51). An optically active monomer, 1-(2-methacryloyloxyethyl)carbamoyl-sn-glycero-3-phosphorylcholine (MCGPC), is synthesized with the reaction between L-α-glycerophosphorylcholine (GPC) and 2-methacryloyloxyethyl isocyanate (50).…”

Surface modified poly(methyl methacrylate) with 1-methyl- 2-methacrylamidoethyl phosphorylcholine moiety

“…Emulsifier-free emulsion polymerization and the purification of resulting polymer microspheres were carried out according to the method described in previous articles [4][5][6][7] , and the condition is given in Tab. 1.…”

“…These pH values are close to the respective isoelectric points of the protein, and the medium ionic strength (0,1) is also close to the ionic strength of human blood. This could be explained by the electrostatic interaction between protein molecule and the particles 6,7) . 4 shows the adsorption isotherm of protein on poly(MAPC-co-MMA) KPS f = 1 with f-potential = -29 mV, varying the initial concentration of protein from 5 to 50 mg N dm -3 as a typical instance.…”

“…We have studied the surface-modified polymer microspheres using the emulsion polymerization of various vinyl monomers in the presence of polymerizable phospholipid analogues such as MPC 4) , 2-(acryloyloxy)ethyl phosphorylcholine 5) , 2-[2-(methacryloyloxy)ethyldimethylammonio]-6-[4-(4methoxyphenylazo)phenoxy]hexyloxy phosphate 6) and 2-[2-(methacryloyloxy)ethyldimethylammonio]ethyl indolinonaphthooxazine 7) . We have studied the surface-modified polymer microspheres using the emulsion polymerization of various vinyl monomers in the presence of polymerizable phospholipid analogues such as MPC 4) , 2-(acryloyloxy)ethyl phosphorylcholine 5) , 2-[2-(methacryloyloxy)ethyldimethylammonio]-6-[4-(4methoxyphenylazo)phenoxy]hexyloxy phosphate 6) and 2-[2-(methacryloyloxy)ethyldimethylammonio]ethyl indolinonaphthooxazine 7) .…”