Dual 2-Hydroxypropyl-β-Cyclodextrin and 5,10,15,20-Tetrakis (4-Hydroxyphenyl) Porphyrin System as a Novel Chiral-Achiral Selector Complex for Enantioseparation of Aminoalkanol Derivatives with Anticancer Activity in Capillary Electrophoresis
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Reagents
2.2. Instrumentation
2.3. Sample Preparation
2.4. CE Conditions
3. Results and Discussion
3.1. Optimization
3.2. Method Development
3.3. Method Validation
3.4. Application of the CE Method for the Quantitation of I (S), I (R) and II (S), II (R) Enantiomers in Real Serum Samples
4. Conclusions
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compounds | Linearity Range | R2 | (RSD) [%] | LOD | LOQ | Regression Equation | (± SD) | |
---|---|---|---|---|---|---|---|---|
ng/mL | Mean | ng/mL | ng/mL | Mean | Slope | Intercept | ||
I(S) | 200–10000 | 0.9998 | 1.62 | 65.2 | 216.5 | y = 51.80x − 1425 | ±0.11 | ±5.41 |
I(R) | 200–10000 | 0.9979 | 2.17 | 65.6 | 217.8 | y = 51.81x − 1477 | ±0.12 | ±6.13 |
II(S) | 200–10000 | 0.9998 | 2.03 | 65.4 | 217.1 | y = 51.80x − 1415 | ±0.11 | ±5.50 |
II(R) | 200–10000 | 0.9969 | 2.23 | 65.7 | 218.1 | y = 49.68x − 994 | ±0.14 | ±7.04 |
Compounds | Added Amount | Observed Amount | %Recovery | %RSD | Compounds | Added Amount | Observed Amount | %Recovery | %RDS |
---|---|---|---|---|---|---|---|---|---|
Mean ± SD | Mean ± SD | ||||||||
(SL) | ng/mL | ng/mL | (S) | ng/mL | ng/mL | ||||
I (S) | 100 | 98.9 ± 3.5 | 98.9 | 3.5 | I (S) | 100 | 95.8 ± 5.3 | 95.8 | 5.5 |
500 | 495.2 ± 2.7 | 99.4 | 0.5 | 500 | 496.7 ± 3.4 | 99.3 | 0.7 | ||
1000 | 998.9 ± 1.2 | 99.9 | 0.1 | 1000 | 997.9 ± 2.2 | 99.8 | 0.2 | ||
I (R) | 100 | 97.8 ± 3.9 | 97.8 | 4.0 | I (R) | 100 | 94.9 ± 5.9 | 94.9 | 6.2 |
500 | 496.9 ± 3.1 | 99.4 | 0.6 | 500 | 497.1 ± 2.9 | 99.4 | 0.6 | ||
1000 | 997.7 ± 1.6 | 99.8 | 0.2 | 1000 | 996.8 ± 3.3 | 99.7 | 0.3 | ||
II (S) | 100 | 97.4 ± 3.7 | 97.4 | 3.8 | II (S) | 100 | 95.3 ± 4.9 | 95.3 | 5.1 |
500 | 495.0 ± 2.9 | 99.0 | 0.6 | 500 | 498.6 ± 1.4 | 99.7 | 0.3 | ||
1000 | 998.0 ± 1.5 | 99.8 | 0.2 | 1000 | 998.7 ± 1.3 | 99.9 | 0.1 | ||
II (R) | 100 | 97.6 ± 3.4 | 97.6 | 3.5 | II (R) | 100 | 94.6 ± 5.5 | 94.6 | 5.8 |
500 | 496.0 ± 2.9 | 99.2 | 0.6 | 500 | 496.5 ± 3.6 | 99.3 | 0.7 | ||
1000 | 997.0 ± 2.2 | 99.7 | 0.2 | 1000 | 997.1 ± 3.0 | 99.7 | 0.3 |
Compounds | Concentration | Intra-Day Precision (n = 6, Mean) | Inter-Dday Precision | ||||||
---|---|---|---|---|---|---|---|---|---|
ng/mL | Day-1 | Day-2 | Day-3 | (n = 18, mean) | |||||
tm/%RSD | PA/%RSD | tm/%RSD | PA/%RSD | tm/%RSD | PA/%RSD | tm/%RSD | PA/%RSD | ||
I (S) | 100 | 3.72/0.5 | 1116/1.0 | 3.79/0.5 | 1138/1.0 | 3.75/0.5 | 1093/1.0 | 3.75/1.1 | 1116/2.0 |
I (R) | 100 | 4.37/0.4 | 1150/1.0 | 4.39/0.7 | 1172/1.0 | 4.42/0.7 | 1138/1.0 | 4.39/0.7 | 1153/1.5 |
II (S) | 100 | 6.08/0.5 | 1003/ 0.9 | 6.12/0.5 | 1116/1.0 | 6.13/0.5 | 1071/1.0 | 6.11/0.5 | 1063/2.9 |
II (R) | 100 | 7.23/0.6 | 1195/1.1 | 7.28/0.5 | 1138/1.0 | 7.25/0.6 | 1161/1.0 | 7.25/0.4 | 1165/2.5 |
I (S) | 1000 | 3.61/0.3 | 12389/0.4 | 3.67/0.3 | 14247/0.5 | 3.65/0.3 | 13938/0.4 | 3.64/0.8 | 13525/0.5 |
I (R) | 1000 | 4.16/0.2 | 13938/0.4 | 4.25/0.2 | 14557/0.5 | 4.23/0.2 | 13628/0,4 | 4.21/1.2 | 14041/0.5 |
II (S) | 1000 | 5.90/0.2 | 9911/0.3 | 5.95/0.2 | 11770/0.4 | 5.98/0.3 | 11150/0.4 | 5.94/0.7 | 10944/0.4 |
II (R) | 1000 | 7.00/0.3 | 13628/0.4 | 7.04/0.3 | 13938/0.4 | 7.08/0.3 | 13318/0.4 | 7.04/0.6 | 13628/0.4 |
Spiked | Bench Top a | Freeze and Thaw b | Short Term c | ||||
---|---|---|---|---|---|---|---|
Concentration | |||||||
(ng/mL) | _________________ | ________________ | _________________ | ||||
Mean ± SD | Mean ± SD | Mean ± SD | |||||
Obtained | %RSD | Obtained | %RSD | Obtained | %RSD | ||
Concentration | Concentration | Concentration | |||||
(ng/mL) d | (ng/mL) d | (ng/mL) d | |||||
I (S) | 100 | 98.8 ± 3.2 | 3.2 | 91.2 ± 4.9 | 5.4 | 100.9 ± 4.9 | 4.9 |
1000 | 999.0 ± 1.3 | 0.1 | 994.1 ± 2.8 | 0.3 | 1001.2 ± 2.8 | 0.3 | |
I (R) | 100 | 97.3 ± 3.9 | 4.0 | 90.9 ± 5.0 | 5.5 | 100.1 ± 4.2 | 4.2 |
1000 | 998.6 ± 2.6 | 0.3 | 990.5 ± 3.3 | 0.3 | 1003.7 ± 3.3 | 0.3 | |
II (S) | 100 | 99.8 ± 1.5 | 1.5 | 96.2 ± 3.1 | 3.2 | 101.4 ± 3.9 | 3.8 |
1000 | 1000.0 ± 1.3 | 0.1 | 996.1 ± 3.8 | 0.4 | 1002.2 ± 2.9 | 0.3 | |
II (R) | 100 | 97.9 ± 2.9 | 3.0 | 94.3 ± 4.1 | 4.3 | 104.2 ± 3.7 | 3.6 |
1000 | 998.4 ± 2.6 | 0.3 | 991.3 ± 3.1 | 0.3 | 1002.7 ± 2.1 | 0.2 |
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Grodner, B.; Napiórkowska, M. Dual 2-Hydroxypropyl-β-Cyclodextrin and 5,10,15,20-Tetrakis (4-Hydroxyphenyl) Porphyrin System as a Novel Chiral-Achiral Selector Complex for Enantioseparation of Aminoalkanol Derivatives with Anticancer Activity in Capillary Electrophoresis. Molecules 2021, 26, 993. https://doi.org/10.3390/molecules26040993
Grodner B, Napiórkowska M. Dual 2-Hydroxypropyl-β-Cyclodextrin and 5,10,15,20-Tetrakis (4-Hydroxyphenyl) Porphyrin System as a Novel Chiral-Achiral Selector Complex for Enantioseparation of Aminoalkanol Derivatives with Anticancer Activity in Capillary Electrophoresis. Molecules. 2021; 26(4):993. https://doi.org/10.3390/molecules26040993
Chicago/Turabian StyleGrodner, Błażej, and Mariola Napiórkowska. 2021. "Dual 2-Hydroxypropyl-β-Cyclodextrin and 5,10,15,20-Tetrakis (4-Hydroxyphenyl) Porphyrin System as a Novel Chiral-Achiral Selector Complex for Enantioseparation of Aminoalkanol Derivatives with Anticancer Activity in Capillary Electrophoresis" Molecules 26, no. 4: 993. https://doi.org/10.3390/molecules26040993