Table 1. Binding parameters and techniques for the enantiodifferentiative study of chiral drugs with plasma protein.
| Chiral drugs | Proteins | Techniques | Protein binding (%) | Protein binding estimations Binding constants (K or logK or nK) | Enantioselectivity (ES) | Reference |
|---|---|---|---|---|---|---|
| Phenindamine E1 | Whole plasma | UF/AEKC | 2.5 | 30 | ||
| Phenindamine E2 | ||||||
| Trimeprazine E1 | 1.5 | |||||
| Trimeprazine E2 | ||||||
| Promethazine E1 | 1.4 | |||||
| Promethazine E2 | ||||||
| Rac-zopiclone | Total plasma | EKC | 47±4 | 31 | ||
| R-zopiclone | 49±6 | |||||
| S-zopiclone | 45±3 | |||||
| Nomifensine E1 | Total plasma | UF/EKC | 58±7 | 32 | ||
| Nomifensine E2 | 64±4 | |||||
| Brompheniramine E1 | HSA | UF/AEKC | (9.39±0.10)×102 (mol/L)−1 | 2.8 | 33 | |
| Brompheniramine E2 | (2.60±0.17)×103 (mol/L)−1 | |||||
| Chlorpheniramine E1 | (9.20±0.20)×102 (mol/L)−1 | 1.8 | ||||
| Chlorpheniramine E2 | (1.69±0.17)×103 (mol/L)−1 | |||||
| Hydroxyzine E1 | (5.30±0.5)×103 (mol/L)−1 | 1.2 | ||||
| Hydroxyzine E2 | (6.30±0.4)×103 (mol/L)−1 | |||||
| Orphenadrine E1 | (1.26±0.13)×103 (mol/L)−1 | 13.3 | ||||
| Orphenadrine E2 | (1.67±0.13)×103 (mol/L)−1 | |||||
| R-Amlodipine | HSA | ED/Flow | (9.91−11.2)×104 (mol/L)−1 | 34 | ||
| S-Amlodipine | Injection-CE | (9.02−10.4)×104 (mol/L)−1 | ||||
| R-Propafenone | HSA | UF/chiral HPLC | 2.05×103 (mol/L)−1 | 35 | ||
| S-Propafenone | 2.08×103 (mol/L)−1 | |||||
| R-Rotigotine | HSA | Partial filling | (17.6±0.6)×103 (mol/L)−1 | 36 | ||
| S-Rotigotine | -ACE | (8.90±0.3)×103 (mol/L)−1 | ||||
| R-Naproxen | HSA | EKC | (4.80±0.40)×105 (mol/L)−1 | 37 | ||
| S-Naproxen | (9.20±1.20)×105 (mol/L)−1 | |||||
| R-Naproxen-NHBu | (0.90±0.12)×105 (mol/L)−1 | |||||
| S-Naproxen-NHBu | (1.02±0.10)×105 (mol/L)−1 | |||||
| R-Naproxen-cRGD | (0.23±0.12)×105 (mol/L)−1 | |||||
| S-Naproxen-cRGD | (0.24±0.10)×105 (mol/L)−1 | |||||
| (−)-Tetrahydropalmatine | HSA | ED/HPLC-UV | 1.80×104 (mol/L)−1 | 38 | ||
| (+)-Tetrahydropalmatine | 2.20×104 (mol/L)−1 | |||||
| R-zopiclone | HSA | EKC | 36±8 | 3.09±0.19 (logK) | 1.95 | 31 |
| S-zopiclone | 47±6 | 3.38±0.19 (logK) | ||||
| S-etodolac | HSA | UF/chiral HPLC | 5.30×105 (mol/L)−1 | 6.06 | 39 | |
| R-etodolac | 0.87×105 (mol/L)−1 | |||||
| (−)Catechin | HSA | UF/CD-EKC | 64 | 3.47±0.06 (logK) | 1.5 | 40 |
| (+)Catechin | 53 | 3.28±0.16 (logK) | ||||
| Propanocaine E1 | HSA | UF/EKC | 48.7 | 3.20±0.16 (logK) | 1.5 | 41 |
| Propanocaine E2 | 60.1 | 3.40±0.14 (logK) | ||||
| R-Rotigotine | BSA | Partial filling | (9.40±0.4)×103 (mol/L)−1 | 36 | ||
| S-Rotigotine | -ACE | (7.30±0.2)×103 (mol/L)−1 | ||||
| R-Propranolol | AGP | Fluorescence | 2.62×105 (mol/L)−1 | 42 | ||
| S-Propranolol | Spectrophotometry | 8.57×105 (mol/L)−1 | ||||
| R-Propafenone | AGP | UF/chiral HPLC | 2.81×106 (mol/L)−1 | 35 | ||
| 9.74×103 (mol/L)−1 (n2K2) | ||||||
| S-Propafenone | 7.65×106 (mol/L)−1 | |||||
| 9.95×103 (mol/L)−1 (n2K2) | ||||||
| (−)-Tetrahydropalmatine | AGP | ED/HPLC-UV | 9.61×104 (mol/L)−1 | 38 | ||
| (+)-Tetrahydropalmatine | 14.6×104 (mol/L)−1 | |||||
| R-Mexiletine | AGP | UF/chiral HPLC | 31±2.8 | 43 | ||
| S-Mexiletine | 22±3.2 | |||||
| R-Propranolol | LDL | HPAC | (5.20±2.3)×105 (mol/L)−1 | 44 | ||
| R-Propranolol | (1.90±0.1)×105 (mol/L)−1 (n1K1) | |||||
| S-Propranolol | (2.70±0.2)×105 (mol/L)−1 (n1K1) |
E1 the first elute; E2 the second elute