Miktoarm Amphiphilic Block Copolymer with Singlet Oxygen-Labile Stereospecific beta-Aminoacrylate Junction: Synthesis, Self-Assembly, and Photodynamically Triggered Drug Release

Cited 0 time in webofscience Cited 0 time in scopus
8 Viewed 0 Downloaded
Title
Miktoarm Amphiphilic Block Copolymer with Singlet Oxygen-Labile Stereospecific beta-Aminoacrylate Junction: Synthesis, Self-Assembly, and Photodynamically Triggered Drug Release
Author(s)
Saravanakumar, G; Park, H; Kim, J; Park, D; Pramanick, S; Kim, DH; Kim, WJ
Publication Date
2018-06
Journal
BIOMACROMOLECULES, v.19, no.6, pp.2202 - 2213
Publisher
AMER CHEMICAL SOC
Abstract
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(2) miktoarm block copolymers bearing a singlet oxygen (O-1(2))-labile regio and stereospecific beta-aminoacrylate linkage with 100% E-configuration at the junction via a combination of amino-yne click chemistry and ring opening polymerization. Using this strategy, a series of O-1(2)-responsive AB(2) amphiphilic miktoarm (MA) copolymers composed of hydrophilic polyethylene glycol (PEG) as the A constituent and hydrophobic polycaprolactone (PCL) as the B constituent (MA-PEG-b-PCL2) was synthesized by varying the block length of PCL. The self assembly characteristics of these well-defined MA-PEG-b-PCL2 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-b-PCL2 copolymer micelles. These coloaded micelles were taken up by human breast cancer (MDA-MB-231) cells. Upon red laser light irradiation, the O-1(2)-generated by the Ce6 induced photocleavage of the beta-aminoacrylate moiety, leading to the dissociation of the micellar structure and triggered intracellular drug release for effective therapy. Overall, rapid disassembly upon O-1(2) generation and subsequent controlled intracellular drug release suggested that these micelles bearing beta-aminoacrylate linkage have a huge potential for on-demand drug delivery. © 2018 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/5787
ISSN
1525-7797
Appears in Collections:
Center for Self-assembly and Complexity(복잡계 자기조립 연구단) > Journal Papers (저널논문)
Files in This Item:
Miktoarm Amphiphilic Block Copolymer with.pdfDownload

qrcode

  • facebook

    twitter

  • Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.
해당 아이템을 이메일로 공유하기 원하시면 인증을 거치시기 바랍니다.

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse