We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Cyclic Hydrazide-Functionalized Poly(ethylene oxide) Frameworks for the Synthesis of pH-Cleavable Drug-Carriers and Their Applications for the Stabilization of Gold Nanoparticles.
- Authors
Geon Chang Lee; Donghwa Seo; Junggyu Kim; Siddique, Abu B.; Hyeonjong Park; Hyun Jun Kim; Ho-Jung Kang; Jae Yeol Lee; Jeewoo Lim; Jungahn Kim; Sehoon Kim
- Abstract
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 a,ω-positions bearing "smartness" are introduced. These heterobifunctional PEOs are synthesized via different functionalization approaches using t-butoxy PEO. Heterobifunctional PEOs, both a-luminol-ω-thiol PEO and a-thiol-ω-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 a-thiol-ω- 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 (1H NMR) spectroscopic, ultraviolet (UV)-visible spectroscopic, Fourier transform infrared (FT-IR), transmission electron microscopic (TEM), and size-exclusion chromatographic (SEC) analysis.
- Subjects
ETHYLENE oxide; GOLD nanoparticles; PROTON magnetic resonance; SULFHYDRYL group; CYCLIC groups; THIOLS
- Publication
Macromolecular Chemistry & Physics, 2019, Vol 220, Issue 12, p1
- ISSN
1022-1352
- Publication type
Article
- DOI
10.1002/macp.201900075