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

Journal of Pharmaceutical and Biomedical Analysis

Volumn 75, Issue , 2013, Pages 165-172

  Grumetto, Lucia ^a   Carpentiero, Carmen ^a   Di Vaio, Paola ^a   Frecentese, Francesco ^a   Barbato, Francesco ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

BBB permeation; IAM HPLC; Lipophilicity; Membrane partition; Phospholipids

Indexed keywords

ACETYLSALICYLIC ACID; CAFFEINE; CHOLINE; DIAZEPAM; FLUMAZENIL; IBUPROFEN; INDOMETACIN; MEMBRANE PHOSPHOLIPID; OCTANOL; OXAZEPAM; PARACETAMOL; PHENAZONE; PHENYLBUTAZONE; PHENYTOIN; PROGESTERONE; SALICYLIC ACID; THEOBROMINE; THEOPHYLLINE; THIOPENTAL; TOLUENE; WATER;

ARTICLE; ARTIFICIAL MEMBRANE; BINDING AFFINITY; BLOOD BRAIN BARRIER; CHEMICAL BOND; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG PENETRATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; IMMOBILIZED ARTIFICIAL MEMBRANE; LIPOPHILICITY; MEMBRANE PERMEABILITY; MEMBRANE TRANSPORT; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PARTITION COEFFICIENT; PH; PRIORITY JOURNAL; STATIC ELECTRICITY; SURFACE CHARGE;

ANIMALS; BLOOD-BRAIN BARRIER; CELL MEMBRANE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG EVALUATION, PRECLINICAL; DRUGS, INVESTIGATIONAL; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MEMBRANES, ARTIFICIAL; MODELS, BIOLOGICAL; PERMEABILITY; PHOSPHOLIPIDS;

EID: 84871758744     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.11.034     Document Type: Article

References (21)

1. Krämer S.D., Abbott N.J., Begley D.J. Biological models to study blood-brain barrier permeation. Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical and Computational Strategies 2001, 127-153. Wiley-VHCA, Zurich. B. Testa, H. van de Waterbeemd, G. Folkers, R.H. Guy (Eds.).
2. Abbott N.J., Patabendige A.A., Dolmen D.E., Yusof S.R., Begley D.J. Structure and function in the blood-brain barrier. Neurobiol. Dis. 2010, 37:13-25.
3. van Bree J.B., de Beer A.G., Danhof M., Breiner D.D. Drug transport across the blood-brain barrier. I: anatomical and physiological aspects. Pharm. Weekbl. Sci. 1992, 14:305-310.
4. Leo A.J., Hansch C., Elkins D. Partition coefficients and their use. Chem. Rev. 1971, 71:525-616.
5. Amato M., Barbato F., Morrica P., Quaglia F., La Rotonda M.I. Interactions between amines and phospholipids: a chromatographic study on immobilized artificial membrane (IAM) stationary phases at various pH values. Helv. Chim. Acta 2000, 83:2836-2847.
6. Barbato F., La Rotonda M.I., Quaglia F. Chromatographic indices determined on an immobilized artificial membrane (IAM) column as descriptors of lipophilic and polar interactions of 4-phenyldihydropyridine calcium-channel blockers with biomembranes. Eur. J. Med. Chem. 1996, 31:311-318.
7. 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, 14:1699-1705.
8. Barbato F., di Martino G., Grumetto L., La Rotonda M.I. Prediction of drug-membrane interactions by IAM-HPLC: effects of different phospholipid stationary phases on the partition of bases. Eur. J. Pharm. Sci. 2004, 22:261-269.
9. Barbato F., di Martino G., Grumetto L., La Rotonda M.I. Can protonated beta-blockers interact with biomembranes stronger than neutral isolipophilic compounds? A chromatographic study on three different phospholipids stationary phases (IAM-HPLC). Eur. J. Pharm. Sci. 2005, 25:379-386.
10. Barbato F., Cirocco V., Grumetto L., La Rotonda M.I. Comparison between immobilized artificial membrane (IAM) HPLC data and lipophilicity in n-octanol for quinolone antibacterial agents. Eur. J. Pharm. Sci. 2007, 31:288-297.
11. Austin R.P., Davis A.M., Manners C.N. Partitioning of ionizing molecules between aqueous buffers and phospholipid vesicles. J. Pharm. Sci. 1995, 84:1180-1183.
12. Barbato F., La Rotonda M.I., Quaglia F. Interactions of nonsteroidal antiinflammatory drugs with phospholipids: comparison between octanol/buffer coefficients and chromatographic indexes on immobilized artificial membranes. J. Pharm. Sci. 1997, 86:225-229.
13. Avdeef A., Box K.J., Comer J.E.A., Hibbert C., Tam K.Y. pH-Metric logP 10. Determination of liposomal membrane-water partition coefficients of ionizable drugs. Pharm. Res. 1998, 15:209-215.
14. Barbato F. The use of immobilised artificial membrane (IAM) chromatography for determination of lipophilicity. Curr. Comput. Aided Drug Des. 2006, 2:341-352.
15. Taillardat-Bertschinger A., Carrupt P.-A., Barbato F., Testa B. Immobilized artificial membrane HPLC in drug research. J. Med. Chem. 2003, 46:655-665.
16. 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, 45:685-692.
17. Taillardat-Bertschinger A., Barbato F., Quercia M.T., Carrupt P.A., Reist M., La Rotonda M.I., Testa B. Structural properties governing retention mechanisms on immobilized artificial membrane (IAM) HPLC columns. Helv. Chim. Acta 2002, 85:519-532.
18. Platts J.A., Abraham M.H., Zhao Y.H., Hersey A., Ijaz L., Butina D. Correlation and prediction of a large blood-brain distribution data set - an LFER study. Eur. J. Med. Chem. 2001, 36:719-730.
19. w, versus liquid-liquid partition coefficients as a model of the hydrophobicity of phenylureas, S-triazines and phenoxycarbonic acid derivatives. J. Chromatogr. 1983, 261:329-343.
20. Pehourcq F., Matoga M., Bannwarth B. Diffusion of arylpropionate non-steroidal anti-inflammatory drugs into the cerebrospinal fluid: a quantitative structure-activity relationship approach. Fundam. Clin. Pharmacol. 2004, 18:65-70.
21. Mälkiä A., Murtomäki L., Urtti A., Kontturi K. Drug permeation in biomembranes: in vitro and in silico prediction and influence of physicochemical properties. Eur. J. Pharm. Sci. 2004, 23:13-47.