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Micellar paclitaxel-initiated RAFT polymer conjugates with acid-sensitive behavior

(2017) ACS MACRO LETTERS . 6(3). p.272-276
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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 theC(2)' OH-group, direct acetalization was observed at either the C-2' or the C-7 OH-group of PTX. This yielded two regioisomers of acetal-based PTX-functionalized RAFT chain transfer agents (CTAs). Subsequent polymerization with N,N-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 in vitro biological performance, giving insights into the difference of the release mechanism between ester- and acetal-based PTX polymer conjugates.
Keywords
DRUG-DELIVERY, CREMOPHOR-EL, FORMULATION, ACTIVATION, EFFICACY, VEHICLES, PRODRUGS, ACETALS

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Chicago
Louage, Benoit, Mies J. van Steenbergen, Lutz Nuhn, Martijn Risseeuw, Izet Karalic, Johan Winne, Serge Van Calenbergh, Wim E Hennink, and Bruno De Geest. 2017. “Micellar Paclitaxel-initiated RAFT Polymer Conjugates with Acid-sensitive Behavior.” Acs Macro Letters 6 (3): 272–276.
APA
Louage, B., van Steenbergen, M. J., Nuhn, L., Risseeuw, M., Karalic, I., Winne, J., Van Calenbergh, S., et al. (2017). Micellar paclitaxel-initiated RAFT polymer conjugates with acid-sensitive behavior. ACS MACRO LETTERS , 6(3), 272–276.
Vancouver
1.
Louage B, van Steenbergen MJ, Nuhn L, Risseeuw M, Karalic I, Winne J, et al. Micellar paclitaxel-initiated RAFT polymer conjugates with acid-sensitive behavior. ACS MACRO LETTERS . 2017;6(3):272–6.
MLA
Louage, Benoit, Mies J. van Steenbergen, Lutz Nuhn, et al. “Micellar Paclitaxel-initiated RAFT Polymer Conjugates with Acid-sensitive Behavior.” ACS MACRO LETTERS 6.3 (2017): 272–276. Print.
@article{8542259,
  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 theC(2)' OH-group, direct acetalization was observed at either the C-2' or the C-7 OH-group of PTX. This yielded two regioisomers of acetal-based PTX-functionalized RAFT chain transfer agents (CTAs). Subsequent polymerization with N,N-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 in vitro biological performance, giving insights into the difference of the release mechanism between ester- and acetal-based PTX polymer conjugates.},
  author       = {Louage, Benoit and van Steenbergen, Mies J. and Nuhn, Lutz and Risseeuw, Martijn and Karalic, Izet and Winne, Johan and Van Calenbergh, Serge and Hennink, Wim E and De Geest, Bruno},
  issn         = {2161-1653},
  journal      = {ACS MACRO LETTERS },
  language     = {eng},
  number       = {3},
  pages        = {272--276},
  title        = {Micellar paclitaxel-initiated RAFT polymer conjugates with acid-sensitive behavior},
  url          = {http://dx.doi.org/10.1021/acsmacrolett.6b00977},
  volume       = {6},
  year         = {2017},
}

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