A head-to-head multi-parametric high content analysis of a series of medium chain fatty acid intestinal permeation enhancers in Caco-2 cells

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 88, Issue 3, 2014, Pages 830-839

  Brayden, David J ^a   Gleeson, John ^a   Walsh, Edwin G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Caco 2 monolayers; Cytotoxicity assays; High content analysis; Medium chain fatty acids; Oral peptide delivery; Sodium caprate

Indexed keywords

CARBON; MANNITOL; MEDIUM CHAIN FATTY ACID; PENETRATION ENHANCING AGENT; SURFACTANT; FATTY ACID;

ANIMAL CELL; ARTICLE; CALCIUM CELL LEVEL; CELL GROWTH; CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; CONTENT ANALYSIS; CYTOTOXICITY; CYTOTOXICITY ASSAY; EC50; ELECTRIC RESISTANCE; FLUIDIZATION; HUMAN; HUMAN CELL; HYDROPHOBICITY; MONOLAYER CULTURE; NONHUMAN; PHYSICAL CHEMISTRY; CACO 2 CELL LINE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; INTESTINE ABSORPTION; METABOLISM; PERMEABILITY; PHYSIOLOGY;

CACO-2 CELLS; DOSE-RESPONSE RELATIONSHIP, DRUG; FATTY ACIDS; HUMANS; INTESTINAL ABSORPTION; PERMEABILITY;

EID: 84912528709     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2014.10.008     Document Type: Article

References (37)

1. P.J. O'Brien Discovery Toxicology Screening: Predictive, In Vitro Cytotoxicity, Hit and Lead Profiling 2010 Wiley-VCH Verlag GmbH & Co. KGaA London
2. P.J. O'Brien High Content Analysis of Sublethal Cytotoxicity in Human HepG2 Hepatocytes for Assessing Potential and Mechanism for Chemical- and Drug-induced Human Toxicity. High Content Screening 2007 John Wiley & Sons Inc. New York pp. 293-316
3. P.J. O'Brien, W. Irwin, D. Diaz, E. Howard-Cofield, C.M. Krejsa, M.R. Slaughter, B. Gao, N. Kaludercic, A. Angeline, P. Bernardi, P. Brain, and C. Hougham High concordance of drug-induced human hepatotoxicity with in vitro cytotoxicity measured in a novel cell-based model using high content screening Arch. Toxicol. 80 2006 580 604
4. L.B. Rawlinson, P.J. O'Brien, and D. J Brayden High content analysis of cytotoxic effects of pDMAEMA on human intestinal epithelial and monocyte cultures J. Control. Release 146 2010 84 92
5. A. Sturmer, N. Mehta, J. Giacchi, T. Cagatay, R. Tavakkol, S. Mitta, L. Fitzpatrick, J. Wald, J. Trang, and W. Stern Pharmacokinetics of oral recombinant human parathyroid hormone [rhPTH(1-31)NH2] in postmenopausal women with osteoporosis Clin. Pharmacokinet. 52 2013 995 1004
6. M.A. Karsdal, K. Henriksen, A.C. Bay-Jensen, B. Molloy, M. Arnold, M.R. John, I. Byrjalsen, M. Azria, B.J. Riis, P. Qvist, and C. Christiansen Lessons learned from the development of oral calcitonin: the first tablet formulation of a protein in phase III clinical trials J. Clin. Pharmacol. 51 2011 460 471
7. B.J. Aungst Absorption enhancers: applications and advances AAPS J. 14 2012 10 18
8. S. Maher, T.W. Leonard, J. Jacobsen, and D.J. Brayden Safety and efficacy of sodium caprate in promoting oral drug absorption: from in vitro to the clinic Adv. Drug Deliv. Rev. 61 2009 1427 1449
9. E.G. Walsh, B.E. Adamczyk, K.B. Chalasani, S. Maher, E.B. O'Toole, J.S. Fox, T.W. Leonard, and D.J. Brayden Oral delivery of macromolecules: rationale underpinning Gastrointestinal Permeation Enhancement Technology (GIPET) Ther. Deliv. 2 2011 1595 1610
10. S. Tuvia, J. Atsmon, S.L. Teichman, S. Katz, P. Salama, D. Pelled, I. Landau, I. Karmeli, M. Bidlingmaier, C.J. Strasburger, D.L. Kleinberg, S. Melmed, and R. Mamluk Oral octreotide absorption in human subjects: comparable pharmacokinetics to parenteral octreotide and effective growth hormone suppression J. Clin. Endocrinol. Metab. 97 2012 2362 2369
11. M. Kondoh, T. Yoshida, H. Kakutani, and K. Yagi Targeting tight junction proteins-significance for drug development Drug Discov. Today 13 2008 180 186
12. E.S. Swenson, W.B. Milisen, and W. Curatolo Intestinal permeability enhancement: efficacy, acute local toxicity, and reversibility Pharm. Res. 11 1994 1132 1142
13. T. Lindmark, Y. Kimura, and P. Artursson Absorption enhancement through intracellular regulation of tight junction permeability by medium chain fatty acids in Caco-2 cells J. Pharmacol. Exp. Ther. 284 1998 362 369
14. T. Lindmark, T. Nikkilä, and P. Artursson Mechanisms of absorption enhancement by medium chain fatty acids in intestinal epithelial Caco-2 cell monolayers J. Pharmacol. Exp. Ther. 275 1995 958 964
15. S.M. Krug, M. Amasheh, I. Dittmann, I. Christoffel, M. Fromm, and S. Amasheh Sodium caprate as an enhancer of macromolecule permeation across tricellular tight junctions of intestinal cells Biomaterials 34 2013 275 282
16. I. Dittmann, M. Amasheh, S.M. Krug, A.G. Markov, M. Fromm, and S. Amasheh Laurate permeates the paracellular pathway for small molecules in the intestinal epithelial cell model HT-29/B6 via opening the tight junctions by reversible relocation of claudin-5 Pharm. Res. 2014 Mar 15. [Epub ahead of print] PMID: 24633418
17. S. Hickey, S.A. Hagan, E. Kudryashov, and V. Buckin Analysis of phase diagram and microstructural transitions in an ethyl oleate/water/Tween 80/Span 20 microemulsion system using high-resolution ultrasonic spectroscopy Int. J. Pharm. 388 2010 213 222
18. I. Hubatsch, E.G. Ragnarsson, and P. Artursson Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers Nat. Protoc. 2 2007 2111 2119
19. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
20. E.K. Anderberg, T. Lindmark, and P. Artursson Sodium caprate elicits dilatations in human intestinal tight junctions and enhances drug absorption by the paracellular route Pharm. Res. 10 1993 857 864
21. Y. Kimura, Y. Hosoda, M. Shima, S. Adachi, and R. Matsuno Physico-chemical properties of fatty acids for assessing the threshold concentration to enhance the absorption of a hydrophilic substance Biosci. Biotechnol. Biochem. 62 1998 443 447
22. K. Whitehead, N. Karr, and N.S. Mitragotri Safe and effective permeation enhancers for oral drug delivery Pharm. Res. 25 2008 2008 1782 1788
23. M. Tomita, M. Shiga, M. Hayashi, and S. Awazu Enhancement of colonic drug absorption by the paracellular permeation route Pharm. Res. 5 1988 341 346
24. M. Sakai, T. Imai, H. Ohtake, H. Azuma, and M. Otagiri Effects of absorption enhancers on the transport of model compounds in Caco-2 cell monolayers: assessment by confocal laser scanning microscopy J. Pharm. Sci. 86 1997 779 785
25. R. Smith, and C. Tanford Hydrophobicity of long chain n-alkyl carboxylic acids, as measured by their distribution between heptane and aqueous solutions PNAS (USA) 70 1973 289 293
26. J.R. Kanicky, A.F. Poniatowski, N.R. Mehta, and D.O. Shah Cooperativity among molecules at interfaces in relation to various technological processes: effect of chain length on the pKa of fatty acid salt solutions Langmuir 16 1999 172 177
27. J.R. Kanicky, and D.O. Shah Effect of pre-micellar aggregation on the pKa of fatty acid soap solutions Langmuir 19 2003 2034 2038
28. A.T. Florence, and D. Atwood FASTtrack: Physical Pharmacy, Surfactants second ed. 2012 Pharmaceutical Press London (Chapter 4)
29. Y. Kimura, Y. Hosoda, M. Shima, S. Adachi, and R. Matsuno Physico-chemical properties of fatty acids for assessing the threshold concentration to enhance the absorption of a hydrophilic substance Biosci. Biotechnol. Biochem. 62 1998 443 447
30. W. Stremmel, J. Pohl, A. Ring, and T. Herrmann A new concept of cellular uptake and intracellular trafficking of long-chain fatty acids Lipids 36 2001 981 989
31. A.A. Papamandjaris, D.E. Macdougall, and P.J.J. Jones Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications Life Sci. 62 1998 1998 1203 1215
32. Y. Kirichok, G. Krapivinsky, and D.E. Clapham The mitochondrial calcium uniporter is a highly selective ion channel Nature 427 2004 360 364
33. C. Cerella, M. Diederich, and L. Ghibelli The dual role of calcium as messenger and stressor in cell damage, death, and survival Int. J. Cell Biol. 10 2010 546163 10.1155/2010/546163 (Epub 2010 Mar 15)
34. Y. Tsujimoto, and S. Shimizu Role of the mitochondrial membrane permeability transition in cell death Apoptosis 12 2007 835 840
35. B.F. Trump, and I.K. Berezesky Calcium-mediated cell injury and cell death FASEB J. 9 1995 219 228
36. L. Feighery, S. Cochrane, T. Quinn, A. Baird, D. O'Toole, S.-E Owens, D. O'Donoghue, R. Mrsny, and D. Brayden Myosin light chain kinase inhibition: correction of increased intestinal epithelial permeability in vitro Pharm. Res. 25 2008 1377 1386
37. D.J. Brayden, and E. Walsh Efficacious intestinal permeation enhancement induced by the sodium salt of 10-undecylenic acid, a medium chain fatty acid derivative AAPS J. 16 2014 1064 1076