PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Purpurin 18 Derivatives
2.2. Singlet Oxygen Generation
2.3. Uptake and Intracellular Localization of the Compounds
2.4. Colocalization Study
2.5. Photo- and Dark Toxicity of the Compounds In Vitro
2.6. Evaluation of Cell Death
2.7. Molecular Docking of Purpurin 18 Derivatives with Human Serum Albumin
2.8. Logarithm of Partition Coefficients
3. Materials and Methods
3.1. Chemistry
3.1.1. General Methods and Materials
3.1.2. Synthesis of Purpurin Zinc Complex—Compound 2
3.1.3. Synthesis of Purpurin-PEG3-Boc Zinc Complex—Compound 3
3.1.4. Synthesis of Purpurin-PEG3-Amine Zinc Complex—Compound 4
3.2. Indirect Spectrophotometric Measurement of Singlet Oxygen Production
3.2.1. Data Measurement
3.2.2. Data Evaluation
3.3. Biology
3.3.1. Cell Lines and Cultivation Conditions
3.3.2. Cell Uptake of Purpurin 18 Derivatives
3.3.3. Determination of Intracellular Localization of Purpurin 18 Derivatives
3.3.4. Fluorescence Microscopy
3.3.5. Corrected Total Cell Fluorescence
3.3.6. Cell Lines and Cultivation Conditions
3.3.7. Cell Death Evaluation by Flow Cytometry
3.4. Theoretical Studies
3.4.1. Docking Into Human Serum Albumin
3.4.2. Calculation of the Logarithm of a Partition Coefficient
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
References
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Compound | Solvent | γ × 104 | ϕ |
---|---|---|---|
RB | PBS | 16.5 | 0.75 1 |
DMEM+FBS | 2.68 | 0.122 | |
1 | DMEM+FBS | 0.34 | 0.015 |
2 | DMEM+FBS | 1.23 | 0.056 |
3 | DMEM+FBS | 0.63 | 0.029 |
4 | DMEM+FBS | 0.81 | 0.037 |
Compound | CTCF × 103 |
---|---|
1 | 1.404 ± 0.134 |
2 | 1.593 ± 0.208 |
3 | 5.042 ± 0.263 |
4 | 6.643 ± 0.405 |
IC50 (µM) 1 | ||||||||
---|---|---|---|---|---|---|---|---|
Compound | 1 | 2 | 3 | 4 | ||||
Cell Line | Light | Dark | Light | Dark | Light | Dark | Light | Dark |
LNCAP | 0.34 ± 0.02 | >10 | 0.47 ± 0.03 | >10 | 0.04 ± 0.03 | 7.20 ± 0.08 | 0.02 ± 0.00 | >10 |
PC-3 | 0.16 ± 0.01 | >10 | 0.21 ± 0.01 | >10 | 2.33 ± 0.03 | >10 | 0.65 ± 0.00 | >10 |
U-2OS | 1.96 ± 0.01 | >10 | 7.01 ± 0.05 | >10 | 3.17 ± 0.05 | >10 | 1.83 ± 0.01 | >10 |
MIA PACA-2 | 1.51 ± 0.03 | >10 | 1.04 ± 0.03 | >10 | 1.12 ± 0.01 | >10 | 0.45 ± 0.05 | >10 |
MCF-7 | 1.62 ± 0.02 | >10 | 2.95 ± 0.01 | >10 | 2.00 ± 0.02 | >10 | 0.59 ± 0.03 | >10 |
HELA | 3.40 ± 0.02 | >10 | >10 | >10 | 0.06 ± 0.05 | 7.95 ± 0.06 | 0.02 ± 0.01 | >10 |
Ligands | Calculated Binding Energy (kcal/mol) |
---|---|
1 | −13.37 |
2 | −11.58 |
3 | −9.32 |
4 | −8.52 |
Compounds | Calculated logP |
---|---|
1 | 4.55 |
2 | 3.78 |
3 | 4.05 |
4 | 2.88 |
Ligand | Box Edge Size (Å) | |
---|---|---|
Small | Big | |
1 | 14 | 22 |
2 | 14 | 22 |
3 | 15 | 30 |
4 | 15 | 28 |
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Pavlíčková, V.; Rimpelová, S.; Jurášek, M.; Záruba, K.; Fähnrich, J.; Křížová, I.; Bejček, J.; Rottnerová, Z.; Spiwok, V.; Drašar, P.; et al. PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer. Molecules 2019, 24, 4477. https://doi.org/10.3390/molecules24244477
Pavlíčková V, Rimpelová S, Jurášek M, Záruba K, Fähnrich J, Křížová I, Bejček J, Rottnerová Z, Spiwok V, Drašar P, et al. PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer. Molecules. 2019; 24(24):4477. https://doi.org/10.3390/molecules24244477
Chicago/Turabian StylePavlíčková, Vladimíra, Silvie Rimpelová, Michal Jurášek, Kamil Záruba, Jan Fähnrich, Ivana Křížová, Jiří Bejček, Zdeňka Rottnerová, Vojtěch Spiwok, Pavel Drašar, and et al. 2019. "PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer" Molecules 24, no. 24: 4477. https://doi.org/10.3390/molecules24244477