Novel Antitumor Agents Based on Fluorescent Benzofurazan Derivatives and Mesoporous Silica
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Compounds
2.2. Characterization of Materials
2.3. Antioxidant Activity of the SBA-15-NBD Derivatives
2.4. Biological Activity Results
2.4.1. SBA-15-NBD Derivatives Induced a Selective Antiproliferative Effect in Melanoma Cells
2.4.2. Evaluation of Cell Morphology and Conjugated Nanoparticles Internalization
2.4.3. SBA-15-NBD Derivatives Induced a Reduction of Melanoma Clonogenic Survival
2.4.4. Tumor Cells Undergo Mitotic Catastrophe after Exposure to Nanoparticles
2.4.5. Benzofurazan Derivates Linked to SBA-15 Induced a Cytotoxic Antitumoral Effects in Melanoma Spheroids
3. Materials and Methods
3.1. Materials
3.2. Characterization Methods
3.3. Synthesis of the Materials
3.3.1. Synthesis of SBA-15
3.3.2. Synthesis of SBA-15-Cl
3.3.3. Synthesis of [4-hydrazinyl-7-nitrobenz-[2,1,3-d]-oxadiazole (NBDH)
3.3.4. Synthesis of N1-(7-nitrobenzo[c] [1,2,5] oxadiazol-4-yl) benzene- 1,2-diamine (NBD-PD)
3.3.5. Synthesis of SBA-15 Functionalized with Nitrobenzofurazan Derivatives
3.4. Antioxidant Activity of the SBA-15-NBD Derivatives
3.5. Measurement of Fluorescence Spectra
3.6. Biological Evaluation Procedures
3.6.1. Cell Cultures
3.6.2. Cytotoxicity and Proliferation Determination
3.6.3. Cells Morphology, Cytoskeleton Evaluation and Nanoparticles Internalization
3.6.4. Clonogenic Assay
3.6.5. Viability Assay on Melanoma Spheroids
3.6.6. Morphological Evaluation of Different Types of Cell Death (Apoptosis, Mitotic Catastrophe and Senescence)
3.6.7. Statistics
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Sample | SBET (m2g−1) | Vtotal (cm3g−1) | Average Pore Size (nm) |
---|---|---|---|
SBA-15 | 778.9 | 1.177 | 6.04 |
SBA-Cl | 631.6 | 1.018 | 6.01 |
SBA-NBDH | 562.0 | 0.944 | 6.04 |
SBA-NBD-PD | 587.2 | 0.972 | 6.06 |
Sample | d100 (nm) | d110 (nm) | d200 (nm) | d201 (nm) | d300 (nm) |
---|---|---|---|---|---|
SBA-15 | 10.4 | 5.9 | 5.2 | 3.8 | 3.4 |
SBA-NBDH | 10.1 | 5.7 | 5.1 | - | - |
SBA-NBD-PD | 10.4 | 5.9 | 5.2 | - | - |
Sample | C1s (%) | O1s (%) | Si 2p(%) | N1s (%) | Cl 2p |
---|---|---|---|---|---|
SBA-15 | 3.4 | 85.76 | 10.77 | - | - |
SBA-Cl | 4.27 | 84.54 | 10.55 | - | 0.64 |
SBA-NBDH | 6.4 | 83.28 | 10.04 | 0.28 | - |
SBA-NBD-PD | 8.74 | 81.32 | 9.5 | 0.44 | - |
Cells/IC50 | IC50 (µg/mL) SBA-NBDH | IC50 (µg/mL) SBA-NBD-PD | Selectivity Index (SBA-NBDH) | Selectivity Index (SBA-NBD-PD) |
---|---|---|---|---|
BJ cells | 138.63 | 136.13 | - | - |
B16 cells | 120.12 | 114.11 | 1.15 | 1.19 |
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Tudose, M.; Culita, D.C.; Baratoiu-Carpen, R.D.; Mitran, R.-A.; Kuncser, A.; Romanitan, C.; Popescu, R.C.; Savu, D.I. Novel Antitumor Agents Based on Fluorescent Benzofurazan Derivatives and Mesoporous Silica. Int. J. Mol. Sci. 2022, 23, 15663. https://doi.org/10.3390/ijms232415663
Tudose M, Culita DC, Baratoiu-Carpen RD, Mitran R-A, Kuncser A, Romanitan C, Popescu RC, Savu DI. Novel Antitumor Agents Based on Fluorescent Benzofurazan Derivatives and Mesoporous Silica. International Journal of Molecular Sciences. 2022; 23(24):15663. https://doi.org/10.3390/ijms232415663
Chicago/Turabian StyleTudose, Madalina, Daniela C. Culita, Rodica D. Baratoiu-Carpen, Raul-Augustin Mitran, Andrei Kuncser, Cosmin Romanitan, Roxana Cristina Popescu, and Diana Iulia Savu. 2022. "Novel Antitumor Agents Based on Fluorescent Benzofurazan Derivatives and Mesoporous Silica" International Journal of Molecular Sciences 23, no. 24: 15663. https://doi.org/10.3390/ijms232415663