Siddique, Abu Bakkar Cho, Youngjun Kim, Yujin Bahng, Sung Hoon Kim, Sung Woo Lee, Jae Yeol Kang, Ho-Jung Kim, Sehoon Bae, You Han Kim, Jungahn 2024-01-20T07:34:30Z 2024-01-20T07:34:30Z 2021-09-05 2015-02-02 1022-1352 https://pubs.kist.re.kr/handle/201004/125777 A potent synthetic methodology is introduced to generate a useful intermediate for the preparation of smart' polymeric pro-drugs. Herein, living anionic block polymerization of ethylene oxide (EO) and N-phenylmaleimide (N-PMI), as well as the Gabriel process, are introduced. Hydrazinolysis of the resulting poly(ethylene oxide)-block-poly(N-PMI) (PEO-b-PN-PMI) using hydrazine under acidic conditions leads to the production of PEO-based frameworks with hydrazide (HZ) groups. The HZ groups are found to effect the formation of an acid-sensitive bond in reactions with medicines or drugs under neutral conditions (pH 7.2). The PEO-HZ intermediate, which shows a strong triplet splitting patterned chemical shift in the range = 6.5-8.5 ppm, represents the most powerful material employed for mass production of smart polymeric pro-drugs while controlling the drug-loading yield. Water-soluble smart polymeric pro-drugs, such as poly(ethylene oxide)-doxorubicin (PEO-HZ-Dox), poly(ethylene oxide)-methotrexate (PEO-HZ-MTX), and poly(ethylene oxide)-folate (PEO-HZ-FA) conjugates, show excellent acid-sensitive release profiles in water or alcohol at pH 4.5. English WILEY-V C H VERLAG GMBH N-SUBSTITUTED MALEIMIDES ANIONIC-POLYMERIZATION GABRIEL SYNTHESIS MICELLES NANOCARRIERS PEGYLATION COPOLYMERS HYDRAZIDE DELIVERY DESIGN pH-Sensitive Drug-Conjugates on Water-Soluble Polymer Frameworks Article 10.1002/macp.201400457 1 MACROMOLECULAR CHEMISTRY AND PHYSICS, v.216, no.3, pp.265 - 276 MACROMOLECULAR CHEMISTRY AND PHYSICS 216 3 265 276 scie scopus 000349216300002 2-s2.0-84922933977 Polymer Science Polymer Science Article N-SUBSTITUTED MALEIMIDES ANIONIC-POLYMERIZATION GABRIEL SYNTHESIS MICELLES NANOCARRIERS PEGYLATION COPOLYMERS HYDRAZIDE DELIVERY DESIGN acid-dependent drug-release living anionic block copolymerization PEO-drug conjugates poly(ethylene oxide)-based block copolymers