Journal
MACROMOLECULES
Volume 45, Issue 5, Pages 2225-2232Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ma202581d
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Funding
- NSF [DMR-0748834]
- NIH [1DP2OD007246-01]
- Midwest Cancer Nanotechnology Training Center, University of Illinois at Urbana-Champaign (UIUC)
- Siteman Center for Cancer Nanotechnology Excellence (SCCNE, Washington University)-Center for Nanoscale Science and Technology (CNST, UIUC)
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [0748834] Funding Source: National Science Foundation
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Paclitaxel, a polyol chemotherapeutic agent, was covalently conjugated through its 2'-OH to polylactide with 100% regioselectivity via controlled polymerization of lactide mediated by paclitaxel/(BDI-II)ZnN(TMS)(2) (BDI-II = 2-((2,6-diisopropylphenyl)amino)-4-((2,6-diisopropylphenyl)imino)-2-pentene). The steric bulk of the substituents on the N-aryl groups of the BDI ligand drastically affected the regiochemistry of coordination of the metal catalysts to paclitaxel and the subsequent ring-opening polymerization of lactide. The drug-initiated, controlled polymerization of lactide was extended, again with 100% regioselectivity, to docetaxel, a chemotherapeutic agent that is even more structurally complex than paclitaxel. Regioselective incorporation of paclitaxel (or docetaxel) to other biopolymers (i.e., poly(delta-valerolactone), poly(trimethylene carbonate), and poly(epsilon-caprolactone)) was also achieved through drug/(BDI-II)ZnN(TMS)(2)-mediated controlled polymerization. These drug-polylactide conjugates with precisely controlled structures are expected to be excellent building blocks for drug delivery, coating, and controlled-release applications.
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