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
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-lact...
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| Format: | Article |
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MDPI AG
2021-10-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/13/19/3385 |
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| author | Kseniia N. Bardakova Yaroslav V. Faletrov Evgenii O. Epifanov Nikita V. Minaev Vladislav S. Kaplin Yuliya A. Piskun Polina I. Koteneva Vladimir M. Shkumatov Nadezhda A. Aksenova Anastasia I. Shpichka Anna B. Solovieva Sergei V. Kostjuk Peter S. Timashev |
| author_facet | Kseniia N. Bardakova Yaroslav V. Faletrov Evgenii O. Epifanov Nikita V. Minaev Vladislav S. Kaplin Yuliya A. Piskun Polina I. Koteneva Vladimir M. Shkumatov Nadezhda A. Aksenova Anastasia I. Shpichka Anna B. Solovieva Sergei V. Kostjuk Peter S. Timashev |
| author_sort | Kseniia N. Bardakova |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T06:53:03Z |
| format | Article |
| id | doaj.art-762b6715c74545aa93afe8ec9bde530a |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T06:53:03Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-762b6715c74545aa93afe8ec9bde530a2023-11-22T16:39:52ZengMDPI AGPolymers2073-43602021-10-011319338510.3390/polym13193385A Hydrophobic Derivative of Ciprofloxacin as a New Photoinitiator of Two-Photon Polymerization: Synthesis and Usage for the Formation of Biocompatible Polylactide-Based 3D ScaffoldsKseniia N. Bardakova0Yaroslav V. Faletrov1Evgenii O. Epifanov2Nikita V. Minaev3Vladislav S. Kaplin4Yuliya A. Piskun5Polina I. Koteneva6Vladimir M. Shkumatov7Nadezhda A. Aksenova8Anastasia I. Shpichka9Anna B. Solovieva10Sergei V. Kostjuk11Peter S. Timashev12Institute of Photonic Technologies, Research Center “Crystallography and Photonics”, Russian Academy of Sciences, 2 Pionerskaya St., Troitsk, 108840 Moscow, RussiaResearch Institute for Physical Chemical Problems of the Belarusian State University, Minsk, Belarus 14 Leningradskaya St., 220030 Minsk, BelarusInstitute of Photonic Technologies, Research Center “Crystallography and Photonics”, Russian Academy of Sciences, 2 Pionerskaya St., Troitsk, 108840 Moscow, RussiaInstitute of Photonic Technologies, Research Center “Crystallography and Photonics”, Russian Academy of Sciences, 2 Pionerskaya St., Troitsk, 108840 Moscow, RussiaSemenov Federal Research Center of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., 119991 Moscow, RussiaResearch Institute for Physical Chemical Problems of the Belarusian State University, Minsk, Belarus 14 Leningradskaya St., 220030 Minsk, BelarusInstitute for Regenerative Medicine, Sechenov University, 8-2 Trubetskaya St., 119991 Moscow, RussiaResearch Institute for Physical Chemical Problems of the Belarusian State University, Minsk, Belarus 14 Leningradskaya St., 220030 Minsk, BelarusSemenov Federal Research Center of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., 119991 Moscow, RussiaWorld-Class Research Center “Digital Biodesign and Personalized Healthcare”, Sechenov University, 8-2 Trubetskaya St., 119991 Moscow, RussiaSemenov Federal Research Center of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., 119991 Moscow, RussiaResearch Institute for Physical Chemical Problems of the Belarusian State University, Minsk, Belarus 14 Leningradskaya St., 220030 Minsk, BelarusInstitute of Photonic Technologies, Research Center “Crystallography and Photonics”, Russian Academy of Sciences, 2 Pionerskaya St., Troitsk, 108840 Moscow, RussiaA 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.https://www.mdpi.com/2073-4360/13/19/3385two-photon polymerizationscaffoldphotoinitiatorciprofloxacinphotopolymerizationstar-shaped polylactide |
| spellingShingle | Kseniia N. Bardakova Yaroslav V. Faletrov Evgenii O. Epifanov Nikita V. Minaev Vladislav S. Kaplin Yuliya A. Piskun Polina I. Koteneva Vladimir M. Shkumatov Nadezhda A. Aksenova Anastasia I. Shpichka Anna B. Solovieva Sergei V. Kostjuk Peter S. Timashev 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 Polymers two-photon polymerization scaffold photoinitiator ciprofloxacin photopolymerization star-shaped polylactide |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | hydrophobic derivative of ciprofloxacin as a new photoinitiator of two photon polymerization synthesis and usage for the formation of biocompatible polylactide based 3d scaffolds |
| topic | two-photon polymerization scaffold photoinitiator ciprofloxacin photopolymerization star-shaped polylactide |
| url | https://www.mdpi.com/2073-4360/13/19/3385 |
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