Lee, Geon Chang Seo, Donghwa Kim, Junggyu Siddique, Abu B. Park, Hyeonjong Kim, Hyun Jun Kang, Ho-Jung Lee, Jae Yeol Lim, Jeewoo Kim, Jungahn Kim, Sehoon 2024-01-19T20:01:50Z 2024-01-19T20:01:50Z 2021-09-02 2019-06 1022-1352 https://pubs.kist.re.kr/handle/201004/119947 In this paper, two different types of poly(ethylene oxide) (PEO) frameworks with different functional groups such as the thiol group and cyclic hydrazide in the alpha,omega-positions bearing "smartness" are introduced. These heterobifunctional PEOs are synthesized via different functionalization approaches using t-butoxy PEO. Heterobifunctional PEOs, both alpha-luminol-omega-thiol PEO and alpha-thiol-omega-cyclic hydrazide PEO, are prepared by chain-end functionalization of the reactive t-butoxy PEOs. The chain-end luminol as a cyclic hydrazide is found to be effective to yield pH-responsive prodrugs from the reaction with doxorubicin (Dox) yielding corresponding Dox-tethered PEO. The active t-butoxy PEO-initiated block copolymerization of N-phenylmaleimide (N-PMI) in acetone yields a block copolymer controlled in the 3- to 5-units range of the N-PMI group. The deprotection of the t-butoxy group, followed by tosylation, thioacetylaton, and the Gabriel process, provides corresponding alpha-thiol-omega-cyclic hydrazide PEO. The functionality yields are almost quantitative (over 98 mol%). Polymeric prodrugs such as Dox-tethered PEO and folate-conjugated PEO are successfully employed for the stabilization of gold (Au) nanoparticles. The resulting products are characterized by a combination of proton nuclear magnetic resonance (H-1 NMR) spectroscopic, ultraviolet (UV)-visible spectroscopic, Fourier transform infrared (FT-IR), transmission electron microscopic (TEM), and size-exclusion chromatographic (SEC) analysis. English WILEY-V C H VERLAG GMBH QUANTUM DOTS DELIVERY MUCUS WATER CHEMILUMINESCENCE DENSITY Cyclic Hydrazide-Functionalized Poly(ethylene oxide) Frameworks for the Synthesis of pH-Cleavable Drug-Carriers and Their Applications for the Stabilization of Gold Nanoparticles Article 10.1002/macp.201900075 1 MACROMOLECULAR CHEMISTRY AND PHYSICS, v.220, no.12 MACROMOLECULAR CHEMISTRY AND PHYSICS 220 12 scie scopus 000477760200008 2-s2.0-85065774716 Polymer Science Polymer Science Article QUANTUM DOTS DELIVERY MUCUS WATER CHEMILUMINESCENCE DENSITY cyclic hydrazide gold nanoparticles pH-sensitive linkers prodrugs smart poly(ethylene oxide)