polymers Article Photo- and Acid-Degradable Polyacylhydrazone– Doxorubicin Conjugates Maria Psarrou 1, Martha Georgia Kothri 2 and Maria Vamvakaki 1,3,* 1 Department of Materials Science and Technology, University of Crete, Vasilika Vouton, 700 13 Heraklion, Crete, Greece;
[email protected] 2 School of Medicine, University of Crete, Vasilika Vouton, 700 13 Heraklion, Crete, Greece;
[email protected] 3 Institute of Electronic Structure and Laser, Foundation for Research and Technology-Hellas, Vasilika Vouton, 700 13 Heraklion, Crete, Greece * Correspondence:
[email protected]; Tel.: +30-2810-545019 Abstract: Light-mediated polymer degradation has attracted considerable attention in various applications, including photo-patterning, tissue engineering and photo-triggered drug delivery. In this study, we report the synthesis and characterization of a new, linear, main-chain photo- and acid- degradable copolymer based on acylhydrazone linkages. The polymer was synthesized via a step- growth copolymerization of adipic acid dihydrazide with a bifunctional poly(ethylene glycol) bearing benzaldehyde end-groups, under mild acidic conditions, to afford a hydrophilic PEG-alt-adipic acid (PEG-alt-AA) alternating copolymer. The synthesized polymer was characterized by size exclusion chromatography, proton nuclear magnetic resonance and attenuated total reflection-Fourier transform infrared spectroscopies. The main-chain photo- and acid-induced degradation of the copolymer in dimethylsulfoxide and water, respectively, was verified by UV-vis spectroscopy at light intensities Citation: Psarrou, M.; Kothri, as low as 0.1 mW cm−2 at λ = 254 nm. Next, a model anticancer drug, doxorubicin (DOX), was M.G.; Vamvakaki, M. Photo- and Acid-Degradable Polyacylhydrazone– chemically linked to the polymer chain end(s) via acylhydrazone bond(s), resulting in amphiphilic Doxorubicin Conjugates.