Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.1.1. Reaction of Triphenylphosphonium Triflate with Halomethyloxiranes
2.1.2. Reaction of Triphenylphosphonium Triflate with Alkyl- and Acyl Glycidyl Ether
2.1.3. Synthesis of 3-Alkoxy(Iodo)-2-hydroxypropyl Triphenylphosphonium Iodides
2.1.4. Liposomal Systems Based on Amphiphilic Triflates of Acyloxypropylphosphonium and L-α-Phosphatidylcholine
2.2. Biology
2.2.1. Cytotoxicity
2.2.2. Induction of Apoptotic Effects by Lead Compounds
3. Materials and Methods
3.1. General
3.2. Chemistry
3.2.1. General Procedure for the Synthesis of 1-Chloro-3-alkoxypropan-2-ol (5a–d)
3.2.2. General Procedure for the Synthesis of 2-(Alkoxymethyl)oxirane (2f–j)
3.2.3. General Procedure for the Synthesis of 3-Alkoxy-1-iodopropan-2-ols (6a–d)
3.2.4. General Procedure for the Synthesis of Triphenylphosphonium Salts (3a–e, 3f–j)
3.2.5. General Procedure for the Synthesis of (3-Alkoxy-2-hydroxypropyl)triphenylphosphonium Iodide (4a–d)
3.2.6. Synthesis of 3d and 7
3.2.7. Preparation and Characterization Phosphorus-Containing Amphiphile Liposomes
Chemicals
Preparation and Characterization
In Vitro Rhodamine B Release Profile
Encapsulation Efficiency and Loading Capacity
3.3. Biology
3.3.1. Cell Toxicity Assay (MTT-Test)
3.3.2. Induction of Apoptotic Effects by Test Compounds (Flow Cytometry Assay)
Cell Culture
Cell Apoptosis Analysis
Mitochondrial Membrane Potential
Detection of Intracellular ROS
Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Composition | Ratio, w/w, % | Concentration of Rhodamine B, (%, w/w) | Zaverage (nm) | PdI | Z (mV) | EE, (%) | LC, (%) |
---|---|---|---|---|---|---|---|
PC * | 100 | – | 119 ± 2 | 0.12 ± 0.02 | −7.0 ± 2 | ||
PC/3k | 98/2 | – | 129 ± 1 | 0.14 ± 0.01 | +23.0 ± 2 | – | – |
PC/3k | 95/5 | – | 125 ± 1 | 0.16 ± 0.02 | +39.0 ± 3 | – | – |
PC/3k | 90/10 | – | 128 ± 1 | 0.16 ± 0.01 | +46.0 ± 3 | – | – |
PC/3l | 98/2 | – | 127 ± 0.5 | 0.11 ± 0.01 | +6.1 ± 0.1 | – | – |
PC/3l | 98/2 | – | 128 ± 0.5 | 0.12 ± 0.01 | +6.1 ± 0.1 | – | – |
PC/3l | 95/5 | – | 116 ± 0.2 | 0.07 ± 0.01 | +4.4 ± 0.1 | – | – |
PC/3l ** | 95/5 | – | 117 ± 0.2 | 0.09 ± 0.01 | +4.4 ± 0.1 | – | – |
PC/3l | 90/10 | – | 111 ± 0.5 | 0.08 ± 0.01 | +7.8 ± 0.2 | – | – |
PC/3l ** | 90/10 | – | 112 ± 0.5 | 0.09 ± 0.01 | +7.2 ± 0.2 | – | – |
PC | 100 | 0.1 | 121 ± 1 | 0.14 ± 0.01 | +20.5 ± 2 | 87 ± 1 | 1.74 |
PC ** | 100 | 0.1 | 122 ± 1 | 0.14 ± 0.01 | +12.0 ± 0.2 | – | – |
PC/3l | 98/2 | 0.1 | 113 ± 1 | 0.13 ± 0.01 | +21.0 ± 1 | 80 ± 1 | 1.6 |
PC/3l ** | 98/2 | 0.1 | 113 ± 1 | 0.08 ± 0.01 | +21.0 ± 0.1 | – | – |
PC/3l | 95/5 | 0.1 | 109 ± 1 | 0.16 ± 0.01 | +22.0 ± 1 | 93 ± 1 | 1.86 |
PC/3l ** | 95/5 | 0.1 | 109 ± 1 | 0.13 ± 0.01 | +22.0 ± 0.5 | – | – |
PC/3l | 90/10 | 0.1 | 110 ± 1 | 0.17 ± 0.01 | +26.0 ± 1 | 93 ± 1 | 1.86 |
PC/3l ** | 90/10 | 0.1 | 550 ± 50 | 0.4 ± 0.05 | +4.0 ± 0.5 | – | – |
Test Compound | Cancer Cell Lines | Normal Cell Lines | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
HuTu 80 a | PC3 b | M-HeLa c | MCF-7 d | A549 e | T98G f | WI38 g IC50 | |||||||
IC50 | SI | IC50 | SI | IC50 | SI | IC50 | SI | IC50 | SI | IC50 | SI | ||
3a | 10.1 ± 0.8 | 4 | 45.0 ± 3.6 | ns | 66.7 ± 5.5 | ns | 56.1 ± 4.5 | ns | 64.4 ± 4.9 | ns | 64.3 ± 5.3 | ns | 37.5 ± 3.1 |
3b | 3.0 ± 0.1 | 5 | 23.3 ± 1.9 | ns | 30.1 ± 2.4 | ns | 34.0 ± 2.6 | ns | >100 | ns | 56.0 ± 4.5 | ns | 13.8 ± 1.1 |
3c | 19.1 ± 1.6 | 2.5 | 53.5 ± 4.2 | ns | 90.6 ± 8.6 | ns | 56.5 ± 4.5 | ns | >100 | ns | 52.1 ± 4.1 | ns | 47.3 ± 3.8 |
3d | 9.4 ± 0.7 | 4 | 39.1 ± 3.1 | ns | 50.0 ± 4.3 | ns | 88.6 ± 7.1 | ns | 74.2 ± 5.6 | ns | 64.0 ± 4.8 | ns | 35.2 ± 2.3 |
3f | 23.6 ± 1.8 | 1.5 | 55.2 ± 4.5 | ns | 56.2 ± 4.7 | ns | 60.7 ± 4.9 | ns | 39.0 ± 3.0 | ns | 60.4 ± 4.4 | ns | 35.6 ± 2.6 |
3g | 18.4 ± 1.5 | 1.6 | 48.9 ± 3.9 | ns | 63.7 ± 5.2 | ns | 66.8 ± 5.3 | ns | 42.2 ± 3.2 | ns | 62.9 ± 4.6 | ns | 30.1 ± 2.3 |
3h | 28.9 ± 2.1 | ns | 48.7 ± 3.7 | ns | 100 ± 8.6 | ns | 64.4 ± 5.0 | ns | 34.3 ± 2.6 | ns | 63.4 ± 4.8 | ns | 43.7 ± 3.5 |
3i | 7.1 ± 0.06 | 5 | 71.8 ± 6.6 | ns | 60.8 ± 5.2 | ns | 70.5 ± 5.6 | ns | 41.0 ± 3.3 | ns | 50.4 ± 4.0 | ns | 34.2 ± 2.7 |
3j | 0.5 ± 0.03 | 6.2 | 0.6 ± 0.05 | 5.2 | 1.1 ± 0.09 | 3 | 2.9 ± 0.2 | 1.1 | 3.7 ± 0.3 | ns | 1.7 ± 0.1 | 2 | 3.1 ± 0.2 |
3k | 3.5 ± 0.3 | 5 | 25.0 ± 2.0 | ns | 40.3 ± 3.5 | ns | 30.5 ± 2.5 | ns | 54.7 ± 4.4 | ns | 55.8 ± 4.7 | ns | 16.2 ± 1.3 |
PC/3k | 3.8 ± 0.4 | 7.5 | 27.0 ± 2.2 | 1.1 | 48.9 ± 38 | ns | 35.8 ± 2.8 | ns | 88.7 ± 7.3 | ns | >100 | ns | 28.4 ± 2.4 |
3l | 45.0 ± 3.5 | ns | 53.8 ± 4.4 | ns | 59.2 ± 5.1 | ns | 52.8 ± 4.2 | ns | 75.1 ± 5.7 | ns | 55.9 ± 5.0 | ns | 50.0 ± 3.9 |
PC/3l | 38.6 ± 3.1 | ns | 56.2 ± 4.5 | ns | 21.3 ± 1.7 | ns | 78.1 ± 6.2 | ns | >100 | ns | 64.7 ± 4.9 | ns | 26.8 ± 2.2 |
4a | 26.7 ± 2.1 | 1.4 | 50.3 ± 4.0 | ns | 57.3 ± 4.7 | ns | 75.7 ± 5.9 | ns | 36.0 ± 2.8 | ns | 55.3 ± 4.4 | ns | 36.5 ± 2.8 |
4b | 3.4 ± 0.3 | 7 | 42.4 ± 3.3 | ns | 68.4 ± 5.9 | ns | 60.3 ± 4.7 | ns | 39.1 ± 3.1 | ns | 49.7 ± 4.0 | ns | 22.9 ± 1.9 |
4c | 0.3 ± 0.02 | 12.3 | 0.7 ± 0.06 | 5.3 | 1.1 ± 0.09 | 3.4 | 2.7 ± 0.2 | 1.4 | 2.6 ± 0.2 | 1.4 | 2.0 ± 0.1 | 1.8 | 3.7 ± 0.3 |
4i | 5.0 ± 0.4 | 7 | 44.5 ± 3.5 | ns | 87.2 ± 7.9 | ns | 68.0 ± 5.5 | ns | 61.8 ± 5.0 | ns | >100 | ns | 34.2 |
Dox | 0.2 ± 0.01 | 4 | 1.4 ± 0.1 | ns | 2.1 ± 0.1 | ns | 0.4 ± 0.03 | 2 | 0.7 ± 0.5 | 1.1 | 2.0 ± 0.1 | ns | 0.8 ± 0.07 |
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Mironov, V.F.; Nemtarev, A.V.; Tsepaeva, O.V.; Dimukhametov, M.N.; Litvinov, I.A.; Voloshina, A.D.; Pashirova, T.N.; Titov, E.A.; Lyubina, A.P.; Amerhanova, S.K.; et al. Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties. Molecules 2021, 26, 6350. https://doi.org/10.3390/molecules26216350
Mironov VF, Nemtarev AV, Tsepaeva OV, Dimukhametov MN, Litvinov IA, Voloshina AD, Pashirova TN, Titov EA, Lyubina AP, Amerhanova SK, et al. Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties. Molecules. 2021; 26(21):6350. https://doi.org/10.3390/molecules26216350
Chicago/Turabian StyleMironov, Vladimir F., Andrey V. Nemtarev, Olga V. Tsepaeva, Mudaris N. Dimukhametov, Igor A. Litvinov, Alexandra D. Voloshina, Tatiana N. Pashirova, Eugenii A. Titov, Anna P. Lyubina, Syumbelya K. Amerhanova, and et al. 2021. "Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties" Molecules 26, no. 21: 6350. https://doi.org/10.3390/molecules26216350