The potential of immobilized artificial membrane chromatography to predict human oral absorption

European Journal of Pharmaceutical Sciences

Volumn 81, Issue , 2016, Pages 82-93

  Tsopelas, Fotios ^a,b   Vallianatou, Theodosia ^a   Tsantili Kakoulidou, Anna ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

Electrostatic interactions; Human oral absorption; IAM.PC.DD2; Immobilized artificial membrane chromatography; MDCK; Octanol water partitioning

Indexed keywords

ACETYLSALICYLIC ACID; ALLOPURINOL; AMOXICILLIN; ANION; CEFTRIAXONE; CHLORAMPHENICOL; CIMETIDINE; CINOXACIN; HYDROCORTISONE; ISOXICAM; LEVOFLOXACIN; LORNOXICAM; MELOXICAM; METHYLPREDNISOLONE; METOCLOPRAMIDE; MINOXIDIL; NADOLOL; NALIDIXIC ACID; NIFLUMIC ACID; OCTANOL; OMEPRAZOLE; PHOSPHATE; PIPEMIDIC ACID; PIPERACILLIN; SALICYLIC ACID; SULPIRIDE; UNINDEXED DRUG; VANCOMYCIN; WARFARIN; WATER; ARTIFICIAL MEMBRANE; DRUG;

ACIDITY; ANIMAL CELL; ARTICLE; ARTIFICIAL MEMBRANE; CHROMATOGRAPHY BY STATIONARY PHASE; DRUG ABSORPTION; ELECTRIC POTENTIAL; GASTROINTESTINAL ABSORPTION; HYDROGEN BOND; IMMOBILIZED ARTIFICIAL MEMBRANE CHROMATOGRAPHY; LIPOPHILICITY; MATHEMATICAL MODEL; MATHEMATICAL PARAMETERS; MDCK CELL LINE; MEMBRANE PERMEABILITY; MOLECULAR WEIGHT; NONHUMAN; PARTITION COEFFICIENT; PH; PREDICTIVE VALUE; PRIORITY JOURNAL; STATIC ELECTRICITY; ANIMAL; BIOLOGICAL MODEL; CHEMISTRY; CHROMATOGRAPHY; DEVICES; DOG; HUMAN; INTESTINE ABSORPTION; METABOLISM; NONLINEAR SYSTEM; PERMEABILITY; PROCEDURES;

1-OCTANOL; ANIMALS; CHROMATOGRAPHY; DOGS; HUMANS; HYDROGEN-ION CONCENTRATION; INTESTINAL ABSORPTION; MADIN DARBY CANINE KIDNEY CELLS; MEMBRANES, ARTIFICIAL; MODELS, BIOLOGICAL; MOLECULAR WEIGHT; NONLINEAR DYNAMICS; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; STATIC ELECTRICITY; WATER;

EID: 84945231560     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2015.09.020     Document Type: Article

References (47)

1. F. Barbato, G. Di Martino, L. Grumetto, and M.I. La Rotonda Prediction of drug-membrane interactions by IAM-HPLC: effects of different phospholipid stationary phases on the partition of bases Eur. J. Pharm. Sci. 22 2004 261 269
2. F. Barbato, G. Di Martino, L. Grumetto, and M.I. La Rotonda Can protonated β-blockers interact with biomembranes stronger than neutral isolipophilic compounds? A chromatographic study on three different phospholipid stationary phases (IAM-HPLC) Eur. J. Pharm. Sci. 25 2005 379 386
3. L.L. Brunton, J.S. Lazo, and K.L. Parker Goodman & Gilman's the pharmacological basis of therapeutics 11th edition 2006 McGraw-Hill USA
4. M. Chrysanthakopoulos, F. Tsopelas, and A. Tsantili-Kakoulidou Biomimetic chromatography, a useful tool in the drug discovery process E. Grushka, N. Grinberg, Advances in Chromatography 51 2014 CRC Press Taylor & Francis Group, New York 91 125
5. E. Deconinck, T. Hancock, D. Coomans, D.L. Massart, and Y. Vander Heyden Classification of drugs in absorption classes using the classification and regression trees (CART) methodology J. Pharm. Biomed. Anal. 39 2005 91 103
6. Drug Information System Pharma professional systems http://druginfosys.com (assessed in May 2015)
7. K.M. Giacomini, S.M. Huang, D.J. Tweedie, L.Z. Benet, K.L.R. Brouwer, X. Chu, A. Dahlin, R. Evers, V. Fischer, K.M. Hillgren, K.A. Hoffmaster, T. Ishikawa, D. Keppler, R.B. Kim, C.A. Lee, M. Niemi, J.W. Polli, Y. Sugiyama, P.W. Swaan, J.A. Ware, S.H. Wright, S. Wah Yee, M.J. Zamek-Gliszczynski, and L. Zhang Membrane transporters in drug development Nat. Rev. Drug Discov. 9 2010 215 236
8. C. Giaginis, and A. Tsantili-Kakoulidou Alternative measures of lipophilicity: from octanol-water partitioning to IAM retention J. Pharm. Sci. 97 2008 2984 3004
9. L. Grumetto, G. Russo, and F. Barbato Relationships between human intestinal absorption and polar interactions drug/ phospholipids estimated by IAM-HPLC Int. J. Pharm. 489 2015 186 194
10. E. Klosinska-Szmurlo, M. Grudzien, K. Betlejewska-Kielak, F. Plucinski, J. Biernacka, and A. Pawel Mazurek Physicochemical properties of lomefloxacin, levofloxacin and moxifloxacin relevant to the biopharmaceutics classification system Acta Chim. Slov. 61 2014 827 834
11. I. Kola, and J. Landis Can the pharmaceutical industry reduce attrition rates? Nat. Rev. Drug Discov. 3 2004 711 715
12. J. Kotecha, S. Shah, I. Rathod, and G. Subbaiah Relationship between immobilized artificial membrane chromatographic retention and human oral absorption of structurally diverse drugs Int. J. Pharm. 44 2007 127 135
13. J. Kotecha, S. Shah, I. Rathod, and G. Subbaiah Prediction of oral absorption in humans by experimental immobilized artificial membrane chromatography indices and physicochemical descriptors Int. J. Pharm. 360 2008 96 106
14. C.A. Larregieu, and L.Z. Benet Drug discovery and regulatory considerations for improving in silico and in vitro predictions that use Caco-2 as a surrogate for human intestinal permeability measurements AAPS J. 15 2013 483 497
15. V. Law, C. Knox, Y. Djoumbou, T. Jewison, A.C. Guo, Y. Liu, A. Maciejewski, D. Arndt, M. Wilson, V. Neveu, A. Tang, G. Gabriel, C. Ly, S. Adamjee, Z.T. Dame, B. Han, Y. Zhou, and D.S. Wishart DrugBank 4.0: shedding new light on drug metabolism Nucleic Acids Res. 42 2014 D1091 D1097
16. X. Liu, P. Fan, M. Chen, H. Hefesha, G.K.E. Scriba, D. Gabel, and A. Fahr Drug-Membrane interaction on immobilized liposome chromatography compared to immobilized artificial membrane (IAM), liposome/water, and octan-1-ol/water systems Helv. Chim. Acta 93 2010 203 211
17. F. Lombardo, M.Y. Shalaeva, K.A. Tupper, F. Gao, and M.H. Abraham ElogPoct: a tool for lipophilicity determination in drug discovery J. Med. Chem. 43 2000 2922 2928
18. P. Matsson, G. Englund, G. Ahlin, C.A.S. Bergstrom, U. Norinder, and P. Artursson A global drug inhibition pattern for the human ATP-binding cassette transporter breast cancer resistance protein (ABCG2) J. Pharmacol. Exp. Ther. 323 2007 19 30
19. P. Matsson, J.M. Pedersen, U. Norinder, C.A.S. Bergstrom, and P. Artursson Identification of novel specific and general inhibitors of the three major human ATP-binding cassette transporters P-gp, BCRP and MRP2 among registered drugs Pharm. Res. 26 2009 1816 1831
20. A. Okyar, C. Dressler, A. Hanafy, G. Baktir, B. Lemmer, and H. Spahn-Langguth Circadian variations in exsorptive transport: in situ intestinal perfusion data and in vivo relevance Chronobiol. Int. 29 2002 443 453
21. S. Ong, H. Liu, X. Qiu, G. Bhat, and C. Pidgeon Membrane partition coefficients chromatographically measured using immobilized artificial membrane surfaces Anal. Chem. 67 1995 755 762
22. S. Ong, H. Liu, and C. Pidgeon Immobilized-artificial-membrane chromatography: measurements of membrane partition coefficient and predicting drug membrane permeability J. Chromatogr. A 728 1996 113 128
23. Prescription drug information, interactions and news for professionals and consumers www.drugs.com (assessed in September 2014)
24. A. Reichel, and D.J. Begley Potential of immobilized artificial membranes for predicting drug penetration across the blood-brain barrier Pharm. Res. 15 1998 1270 1274
25. D.P. Reynolds, K. Lanevskij, P. Japertas, R. Didziapetris, and A. Petrauskas Ionization-specific analysis of human intestinal absorption J. Pharm. Sci. 98 2009 4039 4054
26. F.G.M. Russell Transporters: importance in drug absorption, distribution and removal K.S. Pang, A.D. Rodrigues, R.M. Peter, Enzyme- and Transporter-Based Drug-Drug Interactions: Progress and Future Challenges 2010 Springer Heidelberg 27 49
27. B.S. Shin, C.H. Yoon, J.P. Balthasar, B.Y. Choi, S.H. Hong, H.J. Kim, J.B. Lee, S.W. Hwang, and S.D. Yoo Prediction of drug bioavailability in humans using immobilized artificial membrane phosphatidylcholine column chromatography and in vitro hepatic metabolic clearance Biomed. Chromatogr. 23 2009 764 769
28. E. Sjogren, B. Abrahamsson, P. Augustijns, D. Becker, M.B. Bolger, M. Brewster, J. Brouwers, T. Flanagan, M. Harwood, C. Heinen, R. Holm, H.P. Juretschke, M. Kubbinga, A. Lindahl, V. Lukacova, U. Munster, S. Neuhoff, M.A. Nguyen, A.V. Peer, C. Reppas, A.R. Hodjegan, C. Tannergren, W. Weitschies, C. Wilson, P. Zane, H. Lennernas, and P. Langguth In vivo methods for drug absorption - comparative physiologies, model selection, correlations with in vivo methods (IVIVC), and applications for formulation/ API/ excipient characterization including food effects Eur. J. Pharm. Sci. 57 2014 99 151
29. G. Stein, and G. Wilkinson Seminars in general adult psychiatry 2nd edition 2007 Royal College of Psychiatrists UK
30. V. Stepanic, D. Ziher, V. Gabelica-Markovic, D. Jelic, S. Nunhuck, K. Valko, and S. Kostrun Physicochemical profile of macrolides and their comparison with small molecules Eur. J. Med. Chem. 47 2012 462 472
31. K. Sugano, N. Takata, M. Machida, K. Saitoh, and K. Terada Prediction of passive intestinal absorption using bio-mimetic artificial membrane permeation assay and the paracellular pathway model Int. J. Pharm. 241 2002 241 251
32. A. Taillardat-Bertschinger, C.A.M. Martinet, P.A. Carrupt, M. Reist, G. Caron, R. Fruttero, and B. Testa Molecular factors influencing retention on immobilized artificial membranes (IAM) compared to partitioning in liposomes and n-octanol Pharm. Res. 19 2002 729 737
33. The Biopharmaceutics Classification System (BCS) Guidance http://www.fda.gov/AboutFDA/CentersOffices/OfficeofMedicalProductsandTobacco/CDER/ucm128219.htm (assessed in February 2015)
34. V.E. Thiel-Demby, J.E. Humphreys, L.A. St.J. Williams, H.M. Ellens, N. Shah, A.D. Ayrton, and J.W. Polli Biopharmaceutics classification system: validation and learnings of an in vitro permeability assay Mol. Pharm. 6 2008 11 18
35. R.S. Tsai, P.A. Carrupt, N. El Tayar, Y. Giroud, P. Andrade, B. Testa, F. Bree, and J.P. Tillement Physicochemical and structural properties of non-steroidal anti-inflammatory oxicams Helv. Chim. Acta 76 1993 842 854
36. A. Tsantili-Kakoulidou, I. Panderi, F. Csizmadia, and F. Darvas Prediction of distribution coefficient from structure. 2. Validation of prolog D, an expert system J. Pharm. Sci. 86 1997 1173 1179
37. F. Tsopelas, M. Ochsenkühn-Petropoulou, and A. Tsantili-Kakoulidou Void volume markers in reversed-phase and biomimetic liquid chromatography J. Chromatogr. A 1217 2010 2847 2854
38. F. Tsopelas, A. Tsantili-Kakoulidou, and M. Ochsenkühn-Petropoulou Exploring the elution mechanism of selenium species on liquid chromatography J. Sep. Sci. 34 2011 376 384
39. F. Tsopelas, M. Ochsenkühn-Petropoulou, and A. Tsantili-Kakoulidou Lipophilicity, biomimetic retention profile and antioxidant activity of selenium species Microchem. J. 110 2013 711 718
40. F. Tsopelas, N. Malaki, T. Vallianatou, M. Chrysanthakopoulos, D. Vrakas, M. Ochsenkühn-Petropoulou, and A. Tsantili-Kakoulidou Insight into the retention mechanism on immobilized artificial membrane chromatography using two stationary phases J. Chromatogr. A 1396 2015 25 33
41. a J. Pharmacol. Exp. Ther. 314 2005 391 399
42. K.L. Valko, S.B. Nunhuck, and A.P. Hill Estimating unbound volume of distribution and tissue binding by in vitro HPLC-based human serum albumin and immobilized artificial membrane-binding measurements J. Pharm. Sci. 100 2011 849 862
43. D. Vrakas, D. Hadjipavlou-Litina, and A. Tsantili-Kakoulidou Retention of substituted coumarins using immobilized artificial membrane (IAM) chromatography: a comparative study with n-octanol partitioning and reversed-phase HPLC and TLC J. Pharm. Biomed. Anal. 39 2005 908 913
44. D. Vrakas, C. Giaginis, and A. Tsantili-Kakoulidou Different retention behavior of structurally diverse basic and neutral drugs in immobilized artificial membrane and reversed-phase high performance liquid chromatography: comparison with octanol-water partitioning J. Chromatogr. A 1116 2006 158 164
45. D. Vrakas, C. Giaginis, and A. Tsantili-Kakoulidou Electrostatic interactions and ionization effect in immobilized artificial membrane retention. A comparative study with octanol-water partitioning J. Chromatogr. A 1187 2008 67 78
46. T.E. Yen, S. Agatonovic-Kustrin, A.M. Evans, R.L. Nation, and J. Ryand Prediction of drug absorption based on immobilized artificial membrane (IAM) chromatography separation and calculated molecular descriptors J. Pharm. Biomed. Anal. 38 2005 472 478
47. Y.H. Zhao, J. Le, M.H. Abraham, A. Hersey, P.J. Eddershaw, C.N. Luscombe, D. Boutina, G. Beck, B. Sherborne, I. Cooper, and J.A. Platts Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure - activity relationship (QSAR) with the Abraham descriptors J. Pharm. Sci. 90 2001 749 784