Synthesis of highly pH-responsive glucose poly(orthoester)

Lingyao Li, Yi Xu, Ian Milligan, Liye Fu, Emily A. Franckowiak, Wenjun Du

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

pH-Responsive polymers have great potential in biomedical applications, including the selective delivery of preloaded drugs to tissues with low pH values. These polymers usually contain acid-labile linkages such as esters and acetals/ketals. However, these linkages are only mildly pH-responsive with relatively long half-lives (t1/2). Orthoester linkages are more acid-labile, but current methods suffer from synthetic challenges and are limited to the availability of monomers. To address these limitations, a sugar poly(orthoester) was synthesized as a highly pH-responsive polymer. The synthesis was achieved by using 2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide as a difunctional AB monomer and tetra-n-butylammonium iodide (TBAI) as an effective promoter. Under optimal conditions, polymers with molecular weights of 6.9 kDa were synthesized in a polycondensation manner. The synthesized glucose poly(orthoester), wherein all sugar units were connected through orthoester linkages, was highly pH-responsive with a half-life of 0.9, 0.6, and 0.2 hours at pH 6, 5, and 4, respectively. We love sugar! The synthesis of sugar-based polymers, wherein all sugar units are connected by orthoester linkages, was achieved by polymerization of a glucose-based difunctional AB monomer (see scheme, left). When tetra-n-butylammonium iodide (TBAI) was used as a promoter, polymers with molecular weights up to 6.9 kDa were synthesized in a polycondensation manner. These polymers are highly pH-responsive with a half-life of 0.9 hours at pH 6.

Original languageEnglish
Pages (from-to)13699-13702
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number51
DOIs
StatePublished - Dec 16 2013

Keywords

  • carbohydrates
  • pH-responsive
  • poly(orthoester)
  • polymerization
  • tetra-n-butylammonium iodide

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