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Saravanakumar, Gurusamy,Lee, Junseok,Kim, Jihoon,Kim, Won Jong The Royal Society of Chemistry 2015 Chemical communications Vol.51 No.49
<P>Herein, we report a biocompatible amphiphilic block copolymer micelle bearing a singlet oxygen-sensitive vinyldithioether cleavable linker at the core–shell junction, which undergoes singlet oxygen-mediated photocleavage in the presence of visible light. The micelle facilitates the light-responsive release of singlet oxygen and an anticancer drug for enhanced photodynamic therapy.</P> <P>Graphic Abstract</P><P>This communication demonstrates the enhanced photodynamic therapy by means of singlet oxygen sensitive micelle, photosensitizer and anticancer drug. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c5cc01937k'> </P>
Saravanakumar, Gurusamy,Park, Hyeongmok,Kim, Jinhwan,Park, Dongsik,Pramanick, Swapan,Kim, Dae Heon,Kim, Won Jong American Chemical Society 2018 Biomacromolecules Vol.19 No.6
<P>Incorporation of a desired stimuli-responsive unit in a stereospecific manner at the specific location within a nonlinear block copolymer architecture is a challenging task in synthetic polymer chemistry. Herein, we report a facile and versatile method to synthesize AB<SUB>2</SUB> miktoarm block copolymers bearing a singlet oxygen (<SUP>1</SUP>O<SUB>2</SUB>)-labile regio and stereospecific β-aminoacrylate linkage with 100% <I>E</I>-configuration at the junction via a combination of amino-yne click chemistry and ring opening polymerization. Using this strategy, a series of <SUP>1</SUP>O<SUB>2</SUB>-responsive AB<SUB>2</SUB> amphiphilic miktoarm (MA) copolymers composed of hydrophilic polyethylene glycol (PEG) as the A constituent and hydrophobic polycaprolactone (PCL) as the B constituent (MA-PEG-<I>b</I>-PCL<SUB>2</SUB>) was synthesized by varying the block length of PCL. The self-assembly characteristics of these well-defined MA-PEG-<I>b</I>-PCL<SUB>2</SUB> copolymers in an aqueous condition were studied by solvent displacement and thin-film hydration method, and their morphologies were investigated using transmission electron microscopy. The copolymers formed spherical, cylindrical, or lamella morphologies, depending on the chain length and preparation conditions. A hydrophobic photosensitizer chlorin e6 (Ce6) and anticancer drug doxorubicin (DOX) were efficiently encapsulated into the hydrophobic core of MA-PEG-<I>b</I>-PCL<SUB>2</SUB> copolymer micelles. These coloaded micelles were taken up by human breast cancer (MDA-MB-231) cells. Upon red laser light irradiation, the <SUP>1</SUP>O<SUB>2</SUB>-generated by the Ce6 induced photocleavage of the β-aminoacrylate moiety, leading to the dissociation of the micellar structure and triggered intracellular drug release for effective therapy. Overall, rapid disassembly upon <SUP>1</SUP>O<SUB>2</SUB> generation and subsequent controlled intracellular drug release suggested that these micelles bearing β-aminoacrylate linkage have a huge potential for on-demand drug delivery.</P> [FIG OMISSION]</BR>
THAVASYAPPANTHAMBI,Gurusamy Saravanakumar,추준욱,허로운,고혜원,VEERASIKKUGOPAL DEEPAGAN,김종호,박재형 한국고분자학회 2013 Macromolecular Research Vol.21 No.1
An amphiphilic diblock copolymer bearing the reduction-sensitive linker, composed of poly(ethylene glycol) (PEG) and hydrophobic poly(γ-benzyl L-glutamate) (PBLG), was prepared as the potential carrier of doxorubicin (DOX) via a facile synthetic method in the presence of a shell-sheddable PEG macroinitiator (PEG-SS-NH2). Owing to its amphiphilic nature, the copolymer (PEG-SS-PBLG) formed spherical micelles (137 nm in diameter)in aqueous conditions. The micelles were stable under the physiologic condition (pH 7.4) and were readily cleaved in the presence of glutathione (GSH), a tripeptide reducing the disulfide bond in the cytoplasm of the cell. DOX,chosen as a model anticancer drug, was effectively encapsulated into the hydrophobic core of the micelle with high loading efficiency (>75%). The micelle released DOX completely within 18 h at 10 mM GSH mimicking the intracellular condition, whereas only 34% of the drug was released from the micelle at 2 μM GSH. In vitro cytotoxicity tests revealed that DOX-loaded reduction-sensitive micelles are more toxic to SCC7 cells than reduction-insensitive control micelles. These results suggest that PEG-SS-PBLG is the promising carrier for the intracellular delivery of DOX.