Immobilized Artificial Membrane HPLC Derived Parameters vs PAMPA-BBB Data in Estimating in Situ Measured Blood-Brain Barrier Permeation of Drugs

Molecular Pharmaceutics

Volumn 13, Issue 8, 2016, Pages 2808-2816

  Grumetto, Lucia ^a   Russo, Giacomo ^a   Barbato, Francesco ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

blood brain barrier; immobilized artificial membrane; in situ brain perfusion; parallel artificial membrane permeability assay; quantitative structure properties relationships

Indexed keywords

AMINOPHENAZONE; AMITRIPTYLINE; BUSPIRONE; CAFFEINE; CARBAMAZEPINE; CHLORAMBUCIL; CHLORPROMAZINE; CIMETIDINE; CODEINE; DIAZEPAM; DILTIAZEM; DIPHENHYDRAMINE; DOMPERIDONE; DOXORUBICIN; FLUINDOSTATIN; FLUOXETINE; FLUPHENAZINE; FLURBIPROFEN; HALOPERIDOL; HYDROCORTISONE; HYDROXYZINE; IBUPROFEN; INDOMETACIN; LIDOCAINE; LORATADINE; NAPROXEN; PHENAZONE; PHENYTOIN; THEOPHYLLINE; UNINDEXED DRUG; ARTIFICIAL MEMBRANE;

ARTICLE; ARTIFICIAL MEMBRANE; BLOOD BRAIN BARRIER; BRAIN PERFUSION; CHEMICAL STRUCTURE; DRUG PENETRATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZATION; LIPOPHILICITY; MOUSE; NONHUMAN; PH; PRIORITY JOURNAL; RAT; STATIC ELECTRICITY; SURFACE AREA; ANIMAL; CAT; CHEMICAL PHENOMENA; DOG; GUINEA PIG; METABOLISM; PROCEDURES;

ANIMALS; BLOOD-BRAIN BARRIER; CATS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOGS; GUINEA PIGS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MEMBRANES, ARTIFICIAL; MICE; RATS;

EID: 84980037570     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.6b00397     Document Type: Article

References (32)

1. Van Bree, J. B.; De Boer, A. G.; Danhof, M.; Breimer, D. D. Drug Transport across the Blood - Brain Barrier. I. Anatomical and Physiological Aspects Pharm. Weekbl. 1992, 14 (5) 305-310 10.1007/BF01977618
2. Keaney, J.; Campbell, M. The Dynamic Blood-Brain Barrier FEBS J. 2015, 282 (21) 4067-4079 10.1111/febs.13412
3. Bickel, U. How to Measure Drug Transport across the Blood-Brain Barrier NeuroRx 2005, 2 (1) 15-26 10.1602/neurorx.2.1.15
4. Lundquist, S.; Renftel, M.; Brillault, J.; Fenart, L.; Cecchelli, R.; Dehouck, M.-P. Prediction of Drug Transport through the Blood-Brain Barrier in Vivo: A Comparison between Two in Vitro Cell Models Pharm. Res. 2002, 19 (7) 976-981 10.1023/A:1016462205267
5. Grumetto, L.; Carpentiero, C.; Barbato, F. Lipophilic and Electrostatic Forces Encoded in IAM-HPLC Indexes of Basic Drugs: Their Role in Membrane Partition and Their Relationships with BBB Passage Data Eur. J. Pharm. Sci. 2012, 45 (5) 685-692 10.1016/j.ejps.2012.01.008
6. Grumetto, L.; Carpentiero, C.; Di Vaio, P.; Frecentese, F.; Barbato, F. Lipophilic and Polar Interaction Forces between Acidic Drugs and Membrane Phospholipids Encoded in IAM-HPLC Indexes: Their Role in Membrane Partition and Relationships with BBB Permeation Data J. Pharm. Biomed. Anal. 2013, 75, 165-172 10.1016/j.jpba.2012.11.034
7. Grumetto, L.; Russo, G.; Barbato, F. Indexes of Polar Interactions between Ionizable Drugs and Membrane Phospholipids Measured by IAM-HPLC: Their Relationships with Data of Blood-Brain Barrier Passage Eur. J. Pharm. Sci. 2014, 65, 139-146 10.1016/j.ejps.2014.09.015
8. Tsinman, O.; Tsinman, K.; Sun, N.; Avdeef, A. Physicochemical Selectivity of the BBB Microenvironment Governing Passive Diffusion-Matching with a Porcine Brain Lipid Extract Artificial Membrane Permeability Model Pharm. Res. 2011, 28 (2) 337-363 10.1007/s11095-010-0280-x
9. Di, L.; Kerns, E. H.; Fan, K.; McConnell, O. J.; Carter, G. T. High Throughput Artificial Membrane Permeability Assay for Blood-Brain Barrier Eur. J. Med. Chem. 2003, 38 (3) 223-232 10.1016/S0223-5234(03)00012-6
10. Abraham, M. H. Scales of Solute Hydrogen-Bonding-Their Construction and Application to Physicochemical and Biochemical Processes Chem. Soc. Rev. 1993, 22 (2) 73-83 10.1039/cs9932200073
11. Avdeef, A. Absorption and Drug Development; John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2012; pp 625-663.
12. Müller, J.; Esso, K.; Dargó, G.; Könczöl, á.; Balogh, G. T. Tuning the Predictive Capacity of the PAMPA-BBB Model Eur. J. Pharm. Sci. 2015, 79, 53-60 10.1016/j.ejps.2015.08.019
13. Bicker, J.; Alves, G.; Fortuna, A.; Soares-Da-Silva, P.; Falcão, A. A New PAMPA Model Using an in-House Brain Lipid Extract for Screening the Blood-Brain Barrier Permeability of Drug Candidates Int. J. Pharm. 2016, 501 (1-2) 102-111 10.1016/j.ijpharm.2016.01.074
14. Braumann, T.; Weber, G.; Grimme, L. H. Quantitative Structure-activity Relationships for Herbicides J. Chromatogr. A 1983, 261, 329-343 10.1016/S0021-9673(01)87961-9
15. Wishart, D. S.; Knox, C.; Guo, A. C.; Shrivastava, S.; Hassanali, M.; Stothard, P.; Chang, Z.; Woolsey, J. DrugBank: A Comprehensive Resource for in Silico Drug Discovery and Exploration Nucleic Acids Res. 2006, 34 (Suppl. 1) D668-D672 10.1093/nar/gkj067
16. Avdeef, A. Absorption and Drug Development; John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2012; pp 201-209.
17. Lombardo, F.; Shalaeva, M. Y.; Tupper, K. A.; Gao, F.; Abraham, M. H. ElogP(oct): A Tool for Lipophilicity Determination in Drug Discovery J. Med. Chem. 2000, 43 (15) 2922-2928 10.1021/jm0000822
18. Biobyte Clog P; Claremont, CA.
19. Gambaro, V.; Argo, A.; Cippitelli, M.; Dell'Acqua, L.; Farè, F.; Froldi, R.; Guerrini, K.; Roda, G.; Rusconi, C.; Procaccianti, P. Unexpected Variation of the Codeine/morphine Ratio Following Fatal Heroin Overdose J. Anal. Toxicol. 2014, 38 (5) 289-294 10.1093/jat/bku016
20. Drug-Membrane Interactions and Pharmacodynamics. In Methods and Principles in Medicinal Chemistry; Seydel, J. K.; Wiese, M., Eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2002; Vol. 15, 217 - 289.
21. Barbato, F.; La Rotonda, M. I.; Quaglia, F. Interactions of Nonsteroidal Antiinflammatory Drugs with Phospholipids: Comparison between Octanol/buffer Partition Coefficients and Chromatographic Indexes on Immobilized Artificial Membranes J. Pharm. Sci. 1997, 86 (2) 225-229 10.1021/js960233h
22. Drug Bioavailability; van de Waterbeemd, H.; Testa, B., Eds.; Methods and Principles in Medicinal Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008; Vol. 40.
23. Barbato, F.; La Rotonda, M. I.; Quaglia, F. Chromatographic Indexes on Immobilized Artificial Membranes for Local Anesthetics: Relationships with Activity Data on Closed Sodium Channels Pharm. Res. 1997, 14 (12) 1699-1705 10.1023/A:1012119527214
24. Barbato, F.; Caliendo, G.; La Rotonda, M. I.; Morrica, P.; Silipo, C.; Vittoria, A. Relationships between Octanol-Water Partition Data, Chromatographic Indices and Their Dependence on pH in a Set of Beta-Adrenoceptor Blocking Agents Farmaco 1990, 45 (6) 647-663
25. Aravagiri, M.; Yuwiler, A.; Marder, S. R. Distribution after Repeated Oral Administration of Different Dose Levels of Risperidone and 9-Hydroxy-Risperidone in the Brain and Other Tissues of Rat Psychopharmacology (Berl) 1998, 139 (4) 356-363 10.1007/s002130050726
26. Govers, H.; Ruepert, C.; Stevens, T.; van Leeuwen, C. J. Experimental Determination and Prediction of Partition Coefficients of Thioureas and Their Toxicity to Chemosphere 1986, 15 (4) 383-393 10.1016/0045-6535(86)90532-1
27. Tetko, I. V.; Gasteiger, J.; Todeschini, R.; Mauri, A.; Livingstone, D.; Ertl, P.; Palyulin, V. A.; Radchenko, E. V.; Zefirov, N. S.; Makarenko, A. S.; Tanchuk, V. Y.; Prokopenko, V. V. Virtual Computational Chemistry Laboratory - Design and Description J. Comput.-Aided Mol. Des. 2005, 19 (6) 453-463 10.1007/s10822-005-8694-y
28. Avdeef, A.; Barrett, D. A.; Shaw, P. N.; Knaggs, R. D.; Davis, S. S. Octanol-, Chloroform-, and Propylene Glycol Dipelargonat-Water Partitioning of Morphine-6-Glucuronide and Other Related Opiates J. Med. Chem. 1996, 39 (22) 4377-4381 10.1021/jm960073m
29. Grumetto, L.; Russo, G.; Barbato, F. Polar Interactions Drug/phospholipids Estimated by IAM-HPLC vs Cultured Cell Line Passage Data: Their Relationships and Comparison of Their Effectiveness in Predicting Drug Human Intestinal Absorption Int. J. Pharm. 2016, 500 (1-2) 275-290 10.1016/j.ijpharm.2016.01.019
30. Grumetto, L.; Russo, G.; Barbato, F. Relationships between Human Intestinal Absorption and Polar Interactions Drug/phospholipids Estimated by IAM-HPLC Int. J. Pharm. 2015, 489 (1-2) 186-194 10.1016/j.ijpharm.2015.04.062
31. Barbato, F.; Grumetto, L.; Carpentiero, C.; Rocco, A.; Fanali, S. Capillary Electrochromatography as a New Tool to Assess Drug Affinity for Membrane Phospholipids J. Pharm. Biomed. Anal. 2011, 54 (5) 893-899 10.1016/j.jpba.2010.11.037
32. Tsopelas, F.; Malaki, N.; Vallianatou, T.; Chrysanthakopoulos, M.; Vrakas, D.; Ochsenkuhn-Petropoulou, M.; Tsantili-Kakoulidou, A. Insight into the Retention Mechanism on Immobilized Artificial Membrane Chromatography Using Two Stationary Phases J. Chromatogr. A 2015, 1396, 25-33 10.1016/j.chroma.2015.03.060