Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters
Abstract
:1. Introduction
2. Results
2.1. Synthesis and Characterization
2.2. Spectral Features and Photophysical Properties
2.3. In Vitro Assessment of Biological Activity
3. Materials and Methods
3.1. Synthesis
3.1.1. General
4-[5-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyloxy]benzaldehyde (1a)
4-[8-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)octyloxy]benzaldehyde (1b)
1,3,5,7-Tetramethyl-8-{4-[5-(phthalimidyl)pentyloxy]phenyl}-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (2a)
1,3,5,7-Tetramethyl-8-{4-[8-(phthalimidyl)octyloxy]phenyl}-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (2b)
2,6-Diiodo-1,3,5,7-tetramethyl-8-{4-[5-(phthalimidyl)pentyloxy]phenyl}-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (3a)
2,6-Diiodo-1,3,5,7-tetramethyl-8-{4-[8-(phthalimidyl)octyloxy]phenyl}-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (3b)
2,6-Dibromo-1,3,5,7-tetramethyl-8-{4-[5-(phthalimidyl)pentyloxy]phenyl}-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (4a)
2,6-Dibromo-1,3,5,7-Tetramethyl-8-{4-[8-(phthalimidyl)octyloxy]phenyl}-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (4b)
1,3,5,7-Tetramethyl-8-[4-(5-aminopentyloxy)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (5a)
1,3,5,7-Tetramethyl-8-[4-(8-aminooctyloxy)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (5b)
3.2. Photophysical Measurements
3.3. Photobleaching Experiments
3.4. Cell Culture and Sample Preparation
3.5. Cytotoxicity Experiments
3.6. Subcellular Localization
3.7. Real-Time Monitoring of Annexin V Binding and the Loss of Cell Membrane Integrity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Cpd. | X | λmax, nm (log ε) | λF, nm | ΦF (absol) | ΦF (relat)b | τF, ns | ΦΔc |
---|---|---|---|---|---|---|---|
2a | -H | 498 (4.77) | 507 | 0.52 | 0.49 | 3.27 | 0.036 |
3a | -I | 530 (4.36) | 546 | 0.022 | 0.024 | 0.17 | 0.77 |
4a | -Br | 525 (4.72) | 540 | 0.21 | 0.19 | 1.37 | 0.57 |
5a | -H | 498 (4.90) | 507 | 0.43 | 0.44 | 3.25 | 0.063 |
2b | -H | 498 (4.96) | 507 | 0.44 | 0.42 | 2.88 | 0.057 |
3b | -I | 530 (3.70) | 547 | 0.030 | 0.023 | 0.17 | 0.75 |
4b | -Br | 523 (4.04) | 538 | 0.23 | 0.22 | 1.54 | 0.56 |
5b | -H | 498 (4.00) | 507 | 0.50 | 0.47 | 3.22 | 0.071 |
Cpd. | X | EC50 (μM) | TC50 (μM) | TC50/EC50 | ||
---|---|---|---|---|---|---|
HeLa | SK-MEL-28 | SK-MEL-28 | SK-MEL-28 | |||
2a | -H | 3.60 ± 0.19 | 2.55 ± 0.14 | >10b | >3.92 | |
3a | -I | 0.14 ± 0.01 | 0.052 ± 0.01 | >10 b | >192 | |
4a | -Br | 0.21 ± 0.02 | 0.081 ± 0.023 | >10 b | >123 | |
5a | -H | 9.4 ± 0.70 | 3.6 ± 0.66 | >10 b | >2.78 | |
2b | -H | 2.4 ± 0.53 | 3.79 ± 0.20 | >10 b | >2.64 | |
3b | -I | 1.57 ± 0.33 | 1.23 ± 0.14 | >10 b | >8.13 | |
4b | -Br | 0.37 ± 0.07 | 0.22 ± 0.05 | >10 b | >45.5 | |
5b | -H | 1.57 ± 0.33 | 2.42 ± 0.46 | >10 b | >4.13 | |
Methylene blue c | 5.15 ± 1.93 | 22.7 ± 7.9 d | 4.4 d | |||
S3AlOHPc c | 2.07 ± 0.29 | 127 ± 7.8 d | 60 d | |||
Pp IX c | 0.80 ± 0.13 | >10 b,d | >10 d | |||
temoporfin c | 0.045 ± 0.007 | 20.6 ± 2.5 d | 460 d |
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Krzemien, W.; Rohlickova, M.; Machacek, M.; Novakova, V.; Piskorz, J.; Zimcik, P. Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters. Molecules 2021, 26, 4194. https://doi.org/10.3390/molecules26144194
Krzemien W, Rohlickova M, Machacek M, Novakova V, Piskorz J, Zimcik P. Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters. Molecules. 2021; 26(14):4194. https://doi.org/10.3390/molecules26144194
Chicago/Turabian StyleKrzemien, Wojciech, Monika Rohlickova, Miloslav Machacek, Veronika Novakova, Jaroslaw Piskorz, and Petr Zimcik. 2021. "Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters" Molecules 26, no. 14: 4194. https://doi.org/10.3390/molecules26144194