Physicochemical Properties of a New PEGylated Polybenzofulvene Brush for Drug Encapsulation
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis
2.1.1. Ethyl 6-[2-(trimethylsilyl)ethynyl]-1-oxo-3-phenyl-1H-indene-2-carboxylate (2)
2.1.2. Ethyl 6-ethynyl-1-oxo-3-phenyl-1H-indene-2-carboxylate (3)
2.1.3. Ethyl 6-[1-(2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl)-1H-1,2,3-triazol-4-yl]-1-oxo-3-phenyl-1H-indene-2-carboxylate (4)
2.1.4. Ethyl 1-hydroxy-1-methyl-6-[1-(2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl)-1H-1,2,3-triazol-4-yl]-3-phenyl-1H-indene-2-carboxylate (5)
2.1.5. Ethyl 1-methylene-6-[1-(2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl)-1H-1,2,3-triazol-4-yl]-3-phenyl-1H-indene-2-carboxylate (6-MOEG-9-T-BF3k)
2.1.6. Poly[ethyl 1-methylene-6-[1-(2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl)-1H-1,2,3-triazol-4-yl]-3-phenyl-1H-indene-2-carboxylate] (poly-6-MOEG-9-T-BF3k)
2.2. X-ray Crystallography
2.3. Mass Spectrometry
2.4. SEC-MALS
2.5. Dynamic Light Scattering (DLS) Analysis and ζ Potential Measurements
2.6. Transmission Electron Microscopy (TEM)
2.7. Cytotoxicity Evaluation
3. Results and Discussion
3.1. Synthesis
3.2. NMR Spectroscopy Studies
3.3. MALDI-TOF Mass Spectrometry Characterization
3.4. Molecular Weight Distribution Characterization
3.5. Self-Aggregating Properties
3.6. Transmission Electron Microscopy Studies
3.7. Photophysical Characterization
3.8. Biocompatibility Evaluation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Polymer | Mp (kg/mol) a | MW (kg/mol) b | PDI c | Rg (nm) d |
---|---|---|---|---|
poly-6-MOEG-9-T-BF3k-SE | 5.14 | 6.05 | 1.5 | - |
poly-6-MOEG-9-T-BF3k-WA | 63.8 | 73.4 | 2.1 | 19.0 |
poly-6-MOEG-9-T-BF3k-FE | 488 | 752 | 2.5 | 41.3 |
poly-6-MOEG-9-TM-BF3k-GO e | 484 | 821 | 8.9 | 33.6 |
poly-6-MOEG-9-TM-BF3k-GT e | 193 | 358 | 3.9 | 15.5 |
poly-6-MOEG-9-BF3k | 527 | 456 | 1.8 | 20.8 |
Polymer Sample | Za (nm ± SD) | PDI ± SD | Zp (mV ± SD) |
---|---|---|---|
poly-6-MOEG-9-T-BF3k-FE | 166 ± 15 | 0.24 ± 0.02 | −26.0 ± 7.2 |
poly-6-MOEG-9-TM-BF3k-GT a | 245 ± 25 | 0.43 ± 0.04 | - |
poly-6-MOEG-9-TM-BF3k-GO a | 57 ± 6 | 0.38 ± 0.04 | −7.23 ± 1.5 |
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Paolino, M.; Reale, A.; Razzano, V.; Giuliani, G.; Donati, A.; Giorgi, G.; Boccia, A.C.; Mendichi, R.; Piovani, D.; Botta, C.; et al. Physicochemical Properties of a New PEGylated Polybenzofulvene Brush for Drug Encapsulation. Pharmaceutics 2019, 11, 444. https://doi.org/10.3390/pharmaceutics11090444
Paolino M, Reale A, Razzano V, Giuliani G, Donati A, Giorgi G, Boccia AC, Mendichi R, Piovani D, Botta C, et al. Physicochemical Properties of a New PEGylated Polybenzofulvene Brush for Drug Encapsulation. Pharmaceutics. 2019; 11(9):444. https://doi.org/10.3390/pharmaceutics11090444
Chicago/Turabian StylePaolino, Marco, Annalisa Reale, Vincenzo Razzano, Germano Giuliani, Alessandro Donati, Gianluca Giorgi, Antonella Caterina Boccia, Raniero Mendichi, Daniele Piovani, Chiara Botta, and et al. 2019. "Physicochemical Properties of a New PEGylated Polybenzofulvene Brush for Drug Encapsulation" Pharmaceutics 11, no. 9: 444. https://doi.org/10.3390/pharmaceutics11090444