Biomimetic Chromatographic Studies Combined with the Computational Approach to Investigate the Ability of Triterpenoid Saponins of Plant Origin to Cross the Blood–Brain Barrier
Abstract
:1. Introduction
2. Results
2.1. Division of the Dataset for the QSAR Studies
2.2. BBB Descriptors Calculated In Silico
2.3. Chromatographic Biomimetic Studies
3. Discussion
4. Materials and Methods
4.1. Chemicals
4.2. Instrumentation
4.3. Chromatographic Conditions
4.4. Computer Programs
5. Conclusions
Supplementary Materials
Funding
Conflicts of Interest
References
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References | Drugs | BMC/IAM System | Biological Activity |
---|---|---|---|
[53] | Anticonvulsant drugs | Brij 35: 0.02 M; 0.04 M; 0.06 M; pH: 7.4 | Anticonvulsant properties |
[52] | Non-steroidal anti-inflammatory drugs | Brij 35: 0.02 M; 0.04 M; 0.06 M; pH: 7.4 | Anesthetic potency |
[48] | Local anesthetics | Brij 35: 0.02 M; 0.04 M; 0.06 M; pH: 7.4 | Anesthetic potency |
[72] | Barbiturates | Brij35: 0.02 M; 0.04 M; 0.06 M SDS: 0.05 M; 0.1 M; 0.15 M CTAB: 0.01 M; 0.02 M; 0.05 M pH: 3.5 and 7.4 | Hypnotic activity |
[73] | Catecholamines | SDS: 0.05 M; 0.1 M + MeOH, EtOH, 1-propanol, pentanol pH: 2–7 | β- andrenergic activity |
[74] | Benzodiazepines | Brij35: 0.02 M; 0.04 M; 0.06 M pH: 7.4 | Toxicity and anxiolytic activity |
[51] | Phenothiazines | Brij35: 0.02 M; 0.04 M; 0.06 M pH: 7.4 | Pharmacokinetics, preclinical pharmacology, and therapeutic efficacy parameters; antipsychotic potential |
[45] | Structurally diverse drugs | Brij35: 0.04 M pH: 7.4 and 6.5 | Oral absorption |
[75] | Fatty acids and polyphenols | Brij35: 0.04 M; 0.06 M; 0.08 M; 0.1 M; 0.12 M + acetonitrile CTAB: 0.04 M; 0.06 M; 0.08 M; 0.1 M; 0.12 M + acetonitrile SDS: 0.04 M; 0.06 M; 0.08 M; 0.1 M; 0.12 M + acetonitrile, dioxane, tetrahydrofuran, acetone pH: 7.4 | Oral, jejunum and Caco-2 absorption |
[76] | Structurally diverse drugs | Brij35: 0.04 M pH: 7.4 | BBB permeability |
[77] | Phenols | Brij35: 0.06 M; 0.08 M; 0.1 M; 0.12 M + isobutanol (5% v/v) pH: 7.4 | BBB permeability |
[78] | Non-steroidal anti-inflammatory drugs | Brij35: 0.04 M pH: 3.5–8 | Skin permeability |
[79] | Fatty acids and polyphenols | Brij35: 0.04 M; 0.06 M; 0.08 M; 0.1 M; 0.12 M + acetonitrile CTAB: 0.04 M; 0.06 M; 0.08 M; 0.1 M; 0.12 M + acetonitrile SDS: 0.04 M; 0.06 M; 0.08 M; 0.1 M; 0.12 M + acetonitrile, dioxane, tetrahydrofuran, acetone pH: 7.4 | Percutaneous absorption |
[80] | Anxiolytics, antihistamines, β-blockers, antiepileptics, antipsychotics | SDS: 0.07 M; 0.09 M pH: 7.4 | Protein drug binding properties |
[81] | Structurally diverse drugs | PBS or PBS-acetonitrile: 5–25% v/v pH: 7.4 | Cell permeability, human oral absorption, % plasma protein binding |
[82] | Novel β-hydroxy-β-aryl-alkanoic acids | Brij35: 0.04 M pH: 7.4 | Gastrointestinal absorption |
[83] | Structurally diverse drugs | Brij35: 0.04 M pH 7.4 | Blood to lung; blood to liver; blood to fat; blood to skin partition coefficients |
[84] | Newly-synthesized 17-β-carboxamide steroids | Brij35: 0.04 M pH: 5.5 and 7.5 | Skin and corneal permeability |
[85] | Structurally diverse drugs | Brij35: 0.04 M pH: 7.4–7.7 | Ocular tissue permeability |
[86] | Structurally diverse drugs | Brij35: 0.04 M pH: 7.4 | BBB permeability |
[87] | Benzophenone ultraviolet filters | Brij35: 0.01 M; 0.02 M; 0.03 M pH: 7.4 and 6.5 | Ecotoxicity and skin permeability |
[65] | Structurally diverse pesticides | Phosphate-buffered saline (PBS) or PBS-acetonitrile: 5–25% v/v pH: 7.4 | Ecotoxicity |
[61] | Structurally diverse compounds | Buffer- MeOH: 70:30 v/v pH: 7.4 | BBB permeability |
[66] | Structurally diverse drugs | PBS or PBS-acetonitrile: 5–25% v/v pH: 7.4 | Bioconcentration factor |
[88] | Structurally diverse drugs | Acetonitrile-buffer pH: 7.4 | Interactions between the solutes and the immobilized phospholipid membranes |
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[63] | Newly-synthesized drug-like compounds | Acetonitrile-buffer pH 7.4 | Blood–brain barrier permeation |
[89] | Newly synthesized antiproliferative and analgesic active compounds | Acetonitrile-buffer pH 7.4 | Lipophilicity |
Name | Structure |
---|---|
Arjunic acid | |
Akebia saponin D | |
Bacoside A | |
Platycodin D |
Name | logBB | logPS | logPSFubrain | Fu | Fb |
---|---|---|---|---|---|
Arjunic acid | 0.14 | −3.2 | −4.9 | 0.012 | 0.02 |
Akebia saponin D | 0.32 | −4.4 | −5.7 | 0.12 | 0.06 |
Bacoside A | 0.03 | −3.6 | −4.5 | 0.14 | 0.13 |
Platycodin D | <−2 | −3.6 | −9.0 | 0.52 | 0.98 |
Name | LogPow (Octanol/Water) | logPhw (Heptane/Hater) | logPcw (Cyclohexane /Water) | Molecular Weight (MW) (g/mol) | Topological Polar Surface Area (TPSA) (Å2) | Polarizability |
---|---|---|---|---|---|---|
Arjunic acid | 5.2 | 4.179 | 4.029 | 488.70 | 97.99 | 54.15 |
Akebia saponin D | 0.8 | −9.919 | −9.932 | 929.10 | 294.98 | 91.23 |
Bacoside A | 2.8 | −7.553 | −7.110 | 768.97 | 215.83 | 78.66 |
Platycodin D | −3.7 | −24.512 | −24.704 | 1225.32 | 453.28 | 114.32 |
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Stępnik, K. Biomimetic Chromatographic Studies Combined with the Computational Approach to Investigate the Ability of Triterpenoid Saponins of Plant Origin to Cross the Blood–Brain Barrier. Int. J. Mol. Sci. 2021, 22, 3573. https://doi.org/10.3390/ijms22073573
Stępnik K. Biomimetic Chromatographic Studies Combined with the Computational Approach to Investigate the Ability of Triterpenoid Saponins of Plant Origin to Cross the Blood–Brain Barrier. International Journal of Molecular Sciences. 2021; 22(7):3573. https://doi.org/10.3390/ijms22073573
Chicago/Turabian StyleStępnik, Katarzyna. 2021. "Biomimetic Chromatographic Studies Combined with the Computational Approach to Investigate the Ability of Triterpenoid Saponins of Plant Origin to Cross the Blood–Brain Barrier" International Journal of Molecular Sciences 22, no. 7: 3573. https://doi.org/10.3390/ijms22073573