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Drug-Initiated, Controlled Ring-Opening Polymerization for the Synthesis of Polymer-Drug Conjugates.

ABSTRACT: 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(?-valerolactone), poly(trimethylene carbonate), and poly(?-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.

SUBMITTER: Tong R

PROVIDER: S-EPMC3555138 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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Project description:Organocatalytic controlled/living ring-opening polymerization of cyclotrisiloxanes, such as hexamethylcyclotrisiloxane, 1,3,5-trimethyl-1,3,5-triphenylcyclotrisiloxane, 1,3,5-trimethyl-1,3,5-trivinylcyclotrisiloxane, and 1,3,5-trimethyl-1,3,5-tris(3,3,3-trifluoropropyl)cyclotrisiloxane, using water as an initiator and strong organic bases, such as amidines, guanidines, phosphazene bases, and proazaphosphatrane, as catalysts produced a variety of polysiloxanes with controlled number-average molecular weights (Mn = 2.64-102.3 kg mol-1), narrow polydispersity (? = 1.03-1.16), and well-defined symmetric structures. Controlled syntheses of statistical copolymers and triblock copolymers were achieved by copolymerizations of two cyclotrisiloxanes. Various terminal functionalities were successfully introduced by the end-capping reaction of propagating polysiloxanes using functional chlorosilanes. Kinetic investigations demonstrated that the polymerization proceeded through the initiator/chain-end activation mechanism, namely activations of water in the initiation reaction and of terminal silanols in propagating polysiloxanes in the propagation reaction. Catalytic activities of strong organic bases were revealed to depend on their Brønsted basicity and efficiency of the proton transfer in the initiation and propagation reactions. Guanidines possessing an R-N 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 C(N)-NH-R' unit, in particular 1,3-trimethylene-2-propylguanidine, showed excellent performance as a catalyst. In this system, even non-dehydrated solvents are usable for the polymerization.

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Drug-Initiated, Controlled Ring-Opening Polymerization for the Synthesis of Polymer-Drug Conjugates.

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