A Hydrophobic Derivative of Ciprofloxacin as a New Photoinitiator of Two-Photon Polymerization: Synthesis and Usage for the Formation of Biocompatible Polylactide-Based 3D Scaffolds

• Published in: Polymers 2021-10, Vol.13 (19), p.3385
• Main Authors: Bardakova, Kseniia N., Faletrov, Yaroslav V., Epifanov, Evgenii O., Minaev, Nikita V., Kaplin, Vladislav S., Piskun, Yuliya A., Koteneva, Polina I., Shkumatov, Vladimir M., Aksenova, Nadezhda A., Shpichka, Anastasia I., Solovieva, Anna B., Kostjuk, Sergei V., Timashev, Peter S.
• Format: Article
• Language: English
• Subjects: Biocompatibility; Chemical synthesis; Efficiency; Fluorescence; Hydrophobicity; Lasers; Mechanical properties; Modulus of elasticity; Optical properties; Photocuring; Photoinitiators; Photons; Polyimide resins; Polylactic acid; Polymerization; Regeneration; Resins; Scaffolds; Thermal decomposition; Thermal stability; Tissue engineering; Toxicity
• ISSN: 2073-4360; 2073-4360
• DOI: 10.3390/polym13193385

A hydrophobic derivative of ciprofloxacin, hexanoylated ciprofloxacin (CPF-hex), has been used as a photoinitiator (PI) for two-photon polymerization (2PP) for the first time. We present, here, the synthesis of CPF-hex and its application for 2PP of methacrylate-terminated star-shaped poly (D,L-lactide), as well a systematic study on the optical, physicochemical and mechanical properties of the photocurable resin and prepared three-dimensional scaffolds. CPF-hex exhibited good solubility in the photocurable resin, high absorption at the two-photon wavelength and a low fluorescence quantum yield = 0.079. Structuring tests showed a relatively broad processing window and revealed the efficiency of CPF-hex as a 2PP PI. The prepared three-dimensional scaffolds showed good thermal stability; thermal decomposition was observed only at 314 °C. In addition, they demonstrated an increase in Young’s modulus after the UV post-curing (from 336 ± 79 MPa to 564 ± 183 MPa, which is close to those of a cancellous (trabecular) bone). Moreover, using CPF-hex as a 2PP PI did not compromise the scaffolds’ low cytotoxicity, thus they are suitable for potential application in bone tissue regeneration.