Structure-activity relationships for enhancement of paracellular permeability by 2-alkoxy-3-alkylamidopropylphosphocholines across Caco-2 cell monolayers

Journal of Pharmaceutical Sciences

Volumn 88, Issue 11, 1999, Pages 1169-1174

  Liu, Dong Zhou ^a,b   Morris Natschke, Susan L ^a   Kucera, Louis S ^c   Ishaq, Khalid S ^a   Thakker, Dhiren R ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b PFIZER INC   (United States)

^c WAKE FOREST SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MANNITOL; PHOSPHOLIPID DERIVATIVE; PHOSPHORYLCHOLINE;

ARTICLE; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG PENETRATION; DRUG POTENCY; ELECTRIC RESISTANCE; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

EID: 0032742302     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js9900957     Document Type: Article

References (28)

1. Van Hoogdalem, E. J., De Boer, A. G., Breimer, D. D. Intestinal drug absorption enhancement: an overview. Pharmacol. Ther. 1989, 44, 407-443.
2. Lutz, K. L.; Siahaan, T. J. Molecular structure of the apical junction complex and its contribution to the paracellular barrier. J. Pharm. Sci. 1997, 86, 977-984.
3. Lee, V. H. L.; Yamamoto, A.; Kompella, U. B. Mucosal penetration enhancers for facilitation of peptide and protein drug absorption. Crit. Rev. Ther. Drug Carrier Syst. 1991, 8 (2), 91-192.
4. LeCluyse, E. L.; Sutton, S. C. In vitro models for selection of development candidates. Permeability studies to define mechanisms of absorption enhancement. Adv. Drug Delivery Rev. 1997, 23, 163-183.
5. Swenson, E. C.; Curatolo, W. J. Intestinal permeability enhancement for proteins, peptides and other polar drugs: Mechanisms and potential toxicity. Adv. Drug Delivery Rev. 1992, 8 (1), 39-92.
6. Van Hoogdalem, E. J.; Wackwitz, A. T. E.; De Boer, A. G.; Breimer, D. D. Topical effects of absorption enhancing agents on the rectal mucosa of rats in vivo. J. Pharm. Sci. 1990, 79 (10), 866-70.
7. Weltzien, H. U. Cytolytic and membrane-perturbing properties of lysophosphatidylcholine. Biochim. Biophys. Acta 1979, 559, 259-287.
8. Drejer, K.; Vaag, A.; Bech, K.; Hansen, P.; Sørensen, A. R.; Mygind, N. Intranasal administration of insulin with phospholipids as absorption enhancer: pharmacokinetics in normal subjects. Diabetic Med. 1992, 9, 335-340.
9. Jacobs, M. A.; Schreuder, R. H.; Jap-A-Joe, K.; Nauta, J. J.; Andersen, P. M.; Heine, R. J. The pharmacodynamics and activity of intranasally administered insulin in healthy male volunteers. Diabetes 1993, 42, 1649-1655.
10. Fisher, A. N.; Farraj, N. F.; O'Hagan, D. T.; Jabbal-Gill, I.; Johnsen, B. R.; Davis, S. S.; Ilium, L. Effect of L-α-lysophosphatidylcholine on the nasal absorption of human growth hormone in three animal species. Int. J. Pharm. 1991, 74, 147-156.
11. Brondsted, H.; Nielsen, H. M.; Hovgaard, L. Drug delivery studies in Caco-2 monolayers. III. Intestinal transport of various vasopressin analogues in the presence of lysophosphatidylcholine. Intl. J. Pharm. 1995, 114, 115-157.
12. Hovgaard, L.; Bronsted, H.; Nielsen, H. M. Drug delivery studies in Caco-2 monolayers. II. Absorption enhancer effects of lysophosphatidylcholine. Int. J. Pharm. 1995, 114, 141-149.
13. Schulze, C.; Smales, C.; Rubin, L. L.; Staddon, J. M. Lyspphosphatidic acid increases tight junction permeability in cultured brain endothelial cells. J. Neurochem. 1997, 68, 991-1000.
14. Liu, D.-Z.; LeCluyse, E. L.; Thakker, D. R. Dodecylphosphocholine-mediated enhancement of paracellular permeability and cytotoxicity in Caco-2 cell monolayers. J. Pharm. Sci. 1999, 88, 1161-1168.
15. Hochman, J. H.; Fix, J.; LeCluyse, E. L. In vitro and in vivo analysis of the mechanism of absorption enhancement by palmitoyl carnitine. J. Pharmacol. Exp. Ther. 1994, 269 (2), 813-822.
16. Shimazaki, T.; Tomita, M.; Sadahiro, S.; Hayashi, M.; Awazu, S. Absorption-enhancing effects of sodium caprate and palmitoyl carnitine in rat and human colons. Dig. Dis. Sci. 1998, 43, 641-645.
17. Knipp, G. T.; Ho, N. F.; Barsuhn, C. L.; Borchardt, R. T. Paracellular diffusion in Caco-2 cell monolayers: effect of perturbation on the transport of hydrophilic compounds that vary in charge and size. J. Pharm. Sci. 1997, 86 (10), 1105-10.
18. Anderberg, E. K.; Lindmark, T.; Artursson, P. Sodium caprate elicits dilatations in human intestinal tight junctions and enhances drug absorption by paracellular route. Pharm. Res. 1993, 10, 857-864.
19. Tomita, M.; Hayashi, M.; Awazu, S. Absorption-enhancing mechanism of EDTA, caprate and decanoylcarnitine in Caco-2 cells. J. Pharm. Sci. 1996, 85 (6), 608-611.
20. Lindmark, T.; Kimura, Y.; Artursson, P. Absorption enhancement through intracellular regulation of tight junction permeability by medium chain fatty acids in Caco-2 cells. J. Pharmacol. Exp. Ther. 1998, 284, 362-369.
21. Gan, L.-S.; Thakker, D. R. Applications of the Caco-2 model in the design and development of orally active drugs: Elucidation of biological and physical barriers posed by the intestinal epithelium. Adv. Drug Delivery Rev. 1997, 23, 80-100.
22. Liu, D. Z.; Morris-Natschke, S. L. Ishaq, K. S.; Thakker, D. R. Structural requirements for synthetic phospholipids that modulate tight junction permeability across Caco-2 cells. PharmSci 1998, 1 (1), S-453.
23. Liu, D. Z.; Thakker, D. R. Modulation of Caco-2 cell tight junctions by dodecanoylphosphorylcholine (DPC). Pharm. Res. 1997, 14, S-23.
24. Meyer, K. L.; Marasco, C. J.; Morris-Natschke, S. L.; Ishaq, K, S.; Piantadosi, C.; Kucera, L. S. In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents. J. Med. Chem. 1991, 34 (4), 1377-83.
25. Surles, J. R.; Morris-Natschke, S.; Marx, M. H.; Piantadosi, C. Multigram synthesis of 1-alkylamido phospholipids. Lipids 1993, 28 (1), 55-57.
26. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
27. Andenberg, E. K.; Artursson, P. Epithelial transport of drugs in cell culture: VIII. Effects of the pharmaceutical surfactant sodium dodecyl sulfate on cell membrane and tight junctional permeability in human intestinal epithelial (caco-2) cells. J. Pharm. Sci. 1993, 82, 392-398.
28. Artursson, P.; Magnusson, C. Epithelial transport of drugs in cell culture. II. Effect of extracellular calcium concentration on the paracellular transport of drugs of different lipophilicities across monolayers of intestinal epithelial (Caco-2) cells. J. Pharm. Sci. 1990, 79, 595-600.