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Despite their high potential to achieve controlled\/enhanced drug release, a systematic understanding of structural factors that affect their pH sensitivity remains challenging, particulary in the consruction of effective acid\u2010degradable shell\u2010sheddable nanoassemblies. Herein, the authors report the synthesis and acid\u2010responsive degradation through acid\u2010catalyzed hydrolysis of three acetal and ketal diols and identify benzaldehyde acetal (BzAA) exhibiting optimal hydrolysis profiles in targeted pH ranges to be a suitable candidate for junction acid\u2010labile linkage. The authors explore the synthesis and aqueous micellization of well\u2010defined poly(ethylene glycol)\u2010based block copolymer bearing BzAA linkage covalently attached to a polymethacrylate block for the formation of colloidally\u2010stable nanoassemblies with BzAA groups at core\/corona interfaces. Promisingly, the investigation on acid\u2010catalyzed hydrolysis and disassembly shows that the formed nanoassemblies meet the criteria for acid\u2010degradable shell\u2010sheddable nanoassemblies: slow degradation at tumoral pH = 6.5 and rapid disassembly at endo\/lysosomal pH = 5.0, while colloidal stability at physiological pH = 7.4. This work guides the design principle of acid\u2010degradable shell\u2010sheddable nanoassemblies bearing BzAA at interfaces, thus offering the promise to address the PEG dilemma and improve endocytosis in tumor\u2010targeting drug delivery.<\/jats:p>","DOI":"10.1002\/marc.202400097","type":"journal-article","created":{"date-parts":[[2024,3,18]],"date-time":"2024-03-18T19:25:18Z","timestamp":1710789918000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Design, Synthesis, and Acid\u2010Responsive Disassembly of Shell\u2010Sheddable Block Copolymer Labeled with Benzaldehyde Acetal Junction"],"prefix":"10.1002","volume":"45","author":[{"given":"Brandon","family":"Andrade\u2010Gagnon","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry Concordia University  Montreal QC H4B 1R6 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sofia Nieves","family":"Casillas\u2010Popova","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Concordia University  Montreal QC H4B 1R6 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arman Moini","family":"Jazani","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Concordia University  Montreal QC H4B 1R6 Canada"},{"name":"Department of Chemistry Carnegie Mellon University  4400 Fifth Avenue Pittsburgh PA 15213 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4220-308X","authenticated-orcid":false,"given":"Jung Kwon","family":"Oh","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Concordia University  Montreal QC H4B 1R6 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,4,8]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.progpolymsci.2006.09.004"},{"key":"e_1_2_8_1_2","doi-asserted-by":"publisher","DOI":"10.1007\/12_025"},{"key":"e_1_2_8_1_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.jconrel.2009.04.010"},{"key":"e_1_2_8_1_4","doi-asserted-by":"publisher","DOI":"10.1016\/j.jconrel.2011.04.028"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmat3776"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jconrel.2007.03.023"},{"key":"e_1_2_8_2_3","doi-asserted-by":"publisher","DOI":"10.1039\/C0SM00534G"},{"key":"e_1_2_8_2_4","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc32408c"},{"key":"e_1_2_8_2_5","doi-asserted-by":"publisher","DOI":"10.1039\/C8PY01808A"},{"key":"e_1_2_8_2_6","doi-asserted-by":"publisher","DOI":"10.1021\/acs.molpharmaceut.7b00284"},{"key":"e_1_2_8_2_7","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200803276"},{"key":"e_1_2_8_2_8","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs35469e"},{"key":"e_1_2_8_2_9","doi-asserted-by":"publisher","DOI":"10.1021\/ma201924h"},{"key":"e_1_2_8_2_10","doi-asserted-by":"publisher","DOI":"10.1021\/ma300094t"},{"key":"e_1_2_8_2_11","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2343"},{"key":"e_1_2_8_2_12","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.8b06104"},{"key":"e_1_2_8_2_13","doi-asserted-by":"publisher","DOI":"10.1039\/D0PY01408G"},{"key":"e_1_2_8_2_14","doi-asserted-by":"publisher","DOI":"10.1016\/j.progpolymsci.2023.101765"},{"key":"e_1_2_8_2_15","doi-asserted-by":"publisher","DOI":"10.1002\/wnan.1742"},{"key":"e_1_2_8_3_1","first-page":"4373","volume":"49","author":"Tannock I. 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