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PolyMPC–Doxorubicin Prodrugs

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Polymer Science & Engineering Department, 120 Governors Drive, University of Massachusetts, Amherst, Massachusetts 01003, United States
Pioneer Valley Life Sciences Institute, 3601 Main Street, Springfield, Massachusetts 01199, United States
Cite this: Bioconjugate Chem. 2012, 23, 9, 1753–1763
Publication Date (Web):August 10, 2012
Copyright © 2012 American Chemical Society

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    We demonstrate the conjugation of the cancer drug doxorubicin (DOX) to poly(methacryloyloxyethyl phosphorylcholine) (polyMPC), linked by hydrazone groups, using (1) a one-pot ATRP/click sequence, and (2) a post-polymerization conjugation strategy. While the one-pot method gave polyMPC–DOX conjugates in a facile single step, post-polymerization conjugation gave higher-molecular-weight polymers with very high DOX loadings. DOX release from the polyMPC backbone was pH-dependent (faster at pH 5.0 than at pH 7.4) owing to the hydrazone linkage. Half-life values of DOX release ranged from 2 to 40 h at pH 5.0. Cell culture experiments showed that highly loaded polyMPC–DOX conjugates exhibited higher intracellular drug accumulation and lower half-maximal inhibitory concentration (IC50) values, while a polymer with 30 wt % drug loading showed a maximum tolerated dose in the range of 30–50 mg/kg DOX equivalent weight in healthy mice.

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    NMR spectra of polymers (6-A, 7-A) and GPC chromatograms of the polymers (7-A,B,C,D), PD-10 column separation of conjugate 8-D2 and DOX, fluorescence spectra and HPLC chromatogram during the drug release studies, other drug release curves at pH 5.0, and fluorescence micrographs of MCF7 cells incubated with conjugates (8-B and 8-D). This material is available free of charge via the Internet at

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