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Micellar Paclitaxel-Initiated RAFT Polymer Conjugates with Acid-Sensitive Behavior. | LitMetric

Micellar Paclitaxel-Initiated RAFT Polymer Conjugates with Acid-Sensitive Behavior.

ACS Macro Lett

Laboratory of Pharmaceutical Technology, Department of Pharmaceutics, Ghent University, Ottergemsesteenweg 460, 9000 Ghent, Belgium.

Published: March 2017

AI Article Synopsis

  • Researchers developed acid-sensitive paclitaxel (PTX)-polymer conjugates using a grafting-from-drug RAFT method, which involved linking PTX through cyclic or linear acetal moieties.
  • Two regioisomers of acetal-based PTX-functionalized RAFT chain transfer agents (CTAs) were created, showcasing different attachment points on the PTX molecule.
  • The resulting amphiphilic PTX-polymer conjugates demonstrated similar polymer characteristics but varied in PTX release rates, highlighting the distinct biological performance and release mechanisms between ester- and acetal-based conjugates.

Article Abstract

Acid-sensitive paclitaxel (PTX)-polymer conjugates were designed by applying a grafting-from-drug RAFT approach. PTX was linked through either a cyclic or a linear, acid-sensitive acetal moiety. Relative to direct esterification of PTX, which occurred regioselectively at the C' OH-group, direct acetalization was observed at either the C' or the C OH-group of PTX. This yielded two regioisomers of acetal-based PTX-functionalized RAFT chain transfer agents (CTAs). Subsequent polymerization with ,-dimethylacrylamide (DMA) resulted in amphiphilic highly defined, acetal-based PTX-polymer conjugates with nearly identical features in terms of polymer definition and micellar self-assembly behavior, but with distinct PTX release kinetics and absence of burst release. This was further reflected by their biological performance, giving insights into the difference of the release mechanism between ester- and acetal-based PTX-polymer conjugates.

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Source
http://dx.doi.org/10.1021/acsmacrolett.6b00977DOI Listing

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