Interaction with Mixed Micelles in the Intestine Attenuates the Permeation Enhancing Potential of Alkyl-Maltosides

Molecular Pharmaceutics

Volumn 12, Issue 7, 2015, Pages 2245-2253

  Gradauer, Kerstin ^a,b   Nishiumi, Ayano ^a   Unrinin, Kota ^a   Higashino, Haruki ^a   Kataoka, Makoto ^a   Pedersen, Betty L ^b   Buckley, Stephen T ^b   Yamashita, Shinji ^a  

^a SETSUNAN UNIVERSITY   (Japan)

^b NOVO NORDISK A S   (Denmark)

Author keywords

biorelevant media; Caco 2; in vitro in vivo correlation (IVIVC); intestinal absorption; maltoside; permeation enhancement

Indexed keywords

ALKYL GROUP; BUFFER; LIPID; MONOMER; PENETRATION ENHANCING AGENT; SURFACTANT; TAUROCHOLIC ACID; MALTOSE; MICELLE; PHOSPHATIDYLCHOLINE; TETRADECYL MALTOSIDE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOAVAILABILITY; CACO 2 CELL LINE; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INTESTINE LOOP; INTESTINE MUCOSA PERMEABILITY; MICELLE; MONOLAYER CULTURE; NONHUMAN; PRIORITY JOURNAL; RAT; SMALL INTESTINE; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; DRUG EFFECTS; INTESTINE; INTESTINE ABSORPTION; MALE; METABOLISM; PERMEABILITY; SPRAGUE DAWLEY RAT;

ANIMALS; BIOLOGICAL AVAILABILITY; CACO-2 CELLS; HUMANS; INTESTINAL ABSORPTION; INTESTINES; LECITHINS; MALE; MALTOSE; MICELLES; PERMEABILITY; RATS; RATS, SPRAGUE-DAWLEY; SURFACE-ACTIVE AGENTS; TAUROCHOLIC ACID;

EID: 84936763232     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500776a     Document Type: Article

References (31)

1. Swenson, E. S.; Curatolo, W. J. (C) Means to enhance penetration: (2) Intestinal permeability enhancement for proteins, peptides and other polar drugs: mechanisms and potential toxicity Adv. Drug Delivery Rev. 1992, 8, 39-92
2. Walsh, E. G.; Adamczyk, B. E.; Chalasani, K. B.; Maher, S.; O'Toole, E. B.; Fox, J. S.; Leonard, T. W.; Brayden, D. J. Oral delivery of macromolecules: rationale underpinning gastrointestinal permeation enhancement technology (GIPET) Ther. Delivery 2011, 2, 1595-1610
3. Aungst, B. J. Absorption enhancers: applications and advances AAPS J. 2012, 14, 10-18
4. Maher, S.; Brayden, D. J. Overcoming poor permeability: translating permeation enhancers for oral peptide delivery Drug Discovery Today: Technol. 2012, 9, 113-119
5. Ahsan, F.; Arnold, J. J.; Yang, T.; Meezan, E.; Schwiebert, E. M.; Pillion, D. J. Effects of the permeability enhancers, tetradecylmaltoside and dimethyl-beta-cyclodextrin, on insulin movement across human bronchial epithelial cells (16HBE14o-) Eur. J. Pharm. Sci. 2003, 20, 27-34
6. Yang, T.; Arnold, J. J.; Ahsan, F. Tetradecylmaltoside (TDM) enhances in vitro and in vivo intestinal absorption of enoxaparin, a low molecular weight heparin J. Drug Targeting 2005, 13, 29-38
7. Tirumalasetty, P. P.; Eley, J. G. Evaluation of dodecylmaltoside as a permeability enhancer for insulin using human carcinoma cells J. Pharm. Sci. 2005, 94, 246-255
8. Petersen, S. B.; Nolan, G.; Maher, S.; Rahbek, U. L.; Guldbrandt, M.; Brayden, D. J. Evaluation of alkylmaltosides as intestinal permeation enhancers: comparison between rat intestinal mucosal sheets and Caco-2 monolayers Eur. J. Pharm. Sci. 2012, 47, 701-712
9. Galia, E.; Nicolaides, E.; Horter, D.; Lobenberg, R.; Reppas, C.; Dressman, J. B. Evaluation of various dissolution media for predicting in vivo performance of class I and II drugs Pharm. Res. 1998, 15, 698-705
10. Ingels, F.; Beck, B.; Oth, M.; Augustijns, P. Effect of simulated intestinal fluid on drug permeability estimation across Caco-2 monolayers Int. J. Pharm. 2004, 274, 221-232
11. Kataoka, M.; Masaoka, Y.; Sakuma, S.; Yamashita, S. Effect of food intake on the oral absorption of poorly water-soluble drugs: in vitro assessment of drug dissolution and permeation assay system J. Pharm. Sci. 2006, 95, 2051-2061
12. Markopoulos, C.; Thoenen, F.; Preisig, D.; Symillides, M.; Vertzoni, M.; Parrott, N.; Reppas, C.; Imanidis, G. Biorelevant media for transport experiments in the Caco-2 model to evaluate drug absorption in the fasted and the fed state and their usefulness Eur. J. Pharm. Biopharm. 2014, 86, 438-448
13. Fossati, L.; Dechaume, R.; Hardillier, E.; Chevillon, D.; Prevost, C.; Bolze, S.; Maubon, N. Use of simulated intestinal fluid for Caco-2 permeability assay of lipophilic drugs Int. J. Pharm. 2008, 360, 148-155
14. Frank, K. J.; Westedt, U.; Rosenblatt, K. M.; Holig, P.; Rosenberg, J.; Magerlein, M.; Brandl, M.; Fricker, G. Impact of FaSSIF on the solubility and dissolution-/permeation rate of a poorly water-soluble compound Eur. J. Pharm. Sci. 2012, 47, 16-20
15. Tippin, T. K.; Thakker, D. R. Biorelevant refinement of the Caco-2 cell culture model to assess efficacy of paracellular permeability enhancers J. Pharm. Sci. 2008, 97, 1977-1992
16. Masahiro, M.; Yoko, K.; Kanji, T.; Shozo, M. Assessment of enhancing ability of medium-chain alkyl saccharides as new absorption enhancers in rat rectum Int. J. Pharm. 1992, 79, 159-169
17. Uchiyama, T.; Sugiyama, T.; Quan, Y. S.; Kotani, A.; Okada, N.; Fujita, T.; Muranishi, S.; Yamamoto, A. Enhanced permeability of insulin across the rat intestinal membrane by various absorption enhancers: their intestinal mucosal toxicity and absorption-enhancing mechanism of n -lauryl-beta- d -maltopyranoside J. Pharm. Pharmacol. 1999, 51, 1241-1250
18. Kataoka, M.; Masaoka, Y.; Yamazaki, Y.; Sakane, T.; Sezaki, H.; Yamashita, S. In vitro system to evaluate oral absorption of poorly water-soluble drugs: simultaneous analysis on dissolution and permeation of drugs Pharm. Res. 2003, 20, 1674-1680
19. Kataoka, M.; Itsubata, S.; Masaoka, Y.; Sakuma, S.; Yamashita, S. In vitro dissolution/permeation system to predict the oral absorption of poorly water-soluble drugs: effect of food and dose strength on it Biol. Pharm. Bull. 2011, 34, 401-407
20. Kataoka, M.; Sugano, K.; da Costa, M. C.; Wong, J. W.; Jones, K. L.; Masaoka, Y.; Sakuma, S.; Yamashita, S. Application of dissolution/permeation system for evaluation of formulation effect on oral absorption of poorly water-soluble drugs in drug development Pharm. Res. 2012, 29, 1485-1494
21. Holm, R.; Mullertz, A.; Mu, H. Bile salts and their importance for drug absorption Int. J. Pharm. 2013, 453, 44-55
22. Klein, S. The use of biorelevant dissolution media to forecast the in vivo performance of a drug AAPS J. 2010, 12, 397-406
23. Sugano, K. Biopharmaceutics Modeling and Simulations: Theory, Practice, Methods, and Applications, 1 st ed.; John Wiley Sons, Inc.: Hoboken, NJ, 2012.
24. Yano, K.; Masaoka, Y.; Kataoka, M.; Sakuma, S.; Yamashita, S. Mechanisms of membrane transport of poorly soluble drugs: role of micelles in oral absorption processes J. Pharm. Sci. 2010, 99, 1336-1345
25. Brayden, D. J.; Gleeson, J.; Walsh, E. G. A head-to-head multi-parametric high content analysis of a series of medium chain fatty acid intestinal permeation enhancers in Caco-2 cells Eur. J. Pharm. Biopharm. 2014, 88, 830-839
26. Deshmukh, D. D.; Nagilla, R.; Ravis, W. R.; Betageri, G. V. Effect of dodecylmaltoside (DDM) on uptake of BCS III compounds, tiludronate and cromolyn, in Caco-2 cells and rat intestine model Drug Delivery 2010, 17, 145-151
27. Yamamoto, A.; Okagawa, T.; Kotani, A.; Uchiyama, T.; Shimura, T.; Tabata, S.; Kondo, S.; Muranishi, S. Effects of different absorption enhancers on the permeation of ebiratide, an ACTH analogue, across intestinal membranes J. Pharm. Pharmacol. 1997, 49, 1057-1061
28. Sugibayashi, K.; Onuki, Y.; Takayama, K. Displacement of tight junction proteins from detergent-resistant membrane domains by treatment with sodium caprate Eur. J. Pharm. Sci. 2009, 36, 246-253
29. Pike, L. J. Rafts defined: a report on the Keystone Symposium on lipid rafts and cell function J. Lipid Res. 2006, 47, 1597-1598
30. Nusrat, A.; Parkos, C. A.; Verkade, P.; Foley, C. S.; Liang, T. W.; Innis-Whitehouse, W.; Eastburn, K. K.; Madara, J. L. Tight junctions are membrane microdomains J. Cell Sci. 2000, 113, 1771-1781
31. Lambert, D.; O'Neill, C. A.; Padfield, P. J. Depletion of Caco-2 cell cholesterol disrupts barrier function by altering the detergent solubility and distribution of specific tight-junction proteins Biochem. J. 2005, 387, 553-560