Intestinal Permeability of β-Lapachone and Its Cyclodextrin Complexes and Physical Mixtures

European Journal of Drug Metabolism and Pharmacokinetics

Volumn 41, Issue 6, 2016, Pages 795-806

  Mangas Sanjuan, Victor ^a,b   Gutiérrez Nieto, Jorge ^b   Echezarreta López, Magdalena ^c   González Álvarez, Isabel ^a   González Álvarez, Marta ^a   Casabó, Vicente Germán ^a   Bermejo, Marival ^a   Landin, Mariana ^c  

^a MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LAPACHONE; CYCLODEXTRIN; SODIUM AZIDE; ABC TRANSPORTER SUBFAMILY B; ABCB1 PROTEIN, HUMAN; ANTINEOPLASTIC AGENT; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; BETA-LAPACHONE; EXCIPIENT; NAPHTHOQUINONE; RECOMBINANT PROTEIN; SBE7-BETA-CYCLODEXTRIN;

ARTICLE; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STRUCTURE; IN VITRO STUDY; INTESTINE MUCOSA PERMEABILITY; NONHUMAN; ANIMAL; CELL MEMBRANE PERMEABILITY; CHEMISTRY; COMPARATIVE STUDY; DOG; DRUG FORMULATION; DRUG RELEASE; GENETICS; IMPEDANCE; INTESTINE ABSORPTION; INTESTINE MUCOSA; MDCK CELL LINE; METABOLISM; METHYLATION; PERFUSION; SMALL INTESTINE; SOLUBILITY; WISTAR RAT;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ATP BINDING CASSETTE TRANSPORTER, SUB-FAMILY B; BETA-CYCLODEXTRINS; CELL MEMBRANE PERMEABILITY; DOGS; DRUG COMPOUNDING; DRUG LIBERATION; ELECTRIC IMPEDANCE; EXCIPIENTS; INTESTINAL ABSORPTION; INTESTINAL MUCOSA; INTESTINE, SMALL; MADIN DARBY CANINE KIDNEY CELLS; METHYLATION; NAPHTHOQUINONES; PERFUSION; RATS, WISTAR; RECOMBINANT PROTEINS; SOLUBILITY;

EID: 84948170048     PISSN: 03787966     EISSN: 21070180     Source Type: Journal    
DOI: 10.1007/s13318-015-0310-5     Document Type: Article

References (53)

1. Cunha-Filho MS, Dacunha-Marinho B, Torres-Labandeira JJ, Martinez-Pacheco R, Landin M. Characterization of beta-lapachone and methylated beta-cyclodextrin solid-state systems. AAPS PharmSciTech. 2007;8(3):E60.
2. Ough M, Lewis A, Bey EA, Gao J, Ritchie JM, Bornmann W, et al. Efficacy of beta-lapachone in pancreatic cancer treatment: exploiting the novel, therapeutic target NQO1. Cancer Biol Ther. 2005;4(1):95–102.
3. Gomez-Castellanos JRPJ, Heinrich M. Red Lapacho (Tabebuia impetiginosa)—a global ethnopharmacological commodity? J Ethnopharmacol. 2009;121(1):1–13.
4. Reinicke KE, Bey EA, Bentle MS, Pink JJ, Ingalls ST, Hoppel CL, et al. Development of beta-lapachone prodrugs for therapy against human cancer cells with elevated NAD(P)H:quinone oxidoreductase 1 levels. Clin Cancer Res. 2005;11(8):3055–64.
5. Wuerzberger SM, Pink JJ, Planchon SM, Byers KL, Bornmann WG, Boothman DA. Induction of apoptosis in MCF-7:WS8 breast cancer cells by beta-lapachone. Cancer Res. 1998;58(9):1876–85.
6. Jang SB, Kim D, Kim SY, Park C, Jeong JH, Kuh HJ, et al. Impact of micellar vehicles on in situ intestinal absorption properties of beta-lapachone in rats. Korean J Physiol Pharmacol. 2013;17(1):9–13.
7. Nasongkla N, Wiedmann AF, Bruening A, Beman M, Ray D, Bornmann WG, et al. Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes. Pharm Res. 2003;20(10):1626–33.
8. Tewari A, Raman JD, Chang P, Rao S, Divine G, Menon M. Long-term survival probability in men with clinically localized prostate cancer treated either conservatively or with definitive treatment (radiotherapy or radical prostatectomy). Urology. 2006;68(6):1268–74.
9. Cunha-Filho MS, Martinez-Pacheco R, Landin M. Dissolution rate enhancement of the novel antitumoral beta-lapachone by solvent change precipitation of microparticles. Eur J Pharm Biopharm. 2008;69(3):871–7.
10. Wang F, Blanco E, Ai H, Boothman DA, Gao J. Modulating beta-lapachone release from polymer millirods through cyclodextrin complexation. J Pharm Sci. 2006;95(10):2309–19.
11. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem Rev. 1998;98(5):1743–54.
12. Gamsiz ED, Miller L, Thombre AG, Ahmed I, Carrier RL. Modeling the influence of cyclodextrins on oral absorption of low solubility drugs: II. Experimental validation. Biotechnol Bioeng. 2009;105(2):421–30.
13. Irie T, Uekama K. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J Pharm Sci. 1997;86(2):147–62.
14. Li P, Zhao L, Yalkowsky SH. Combined effect of cosolvent and cyclodextrin on solubilization of nonpolar drugs. J Pharm Sci. 1999;88(11):1107–11.
15. Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci. 1996;85(10):1017–25.
16. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci. 1996;85(11):1142–69.
17. Rao VM, Stella VJ. When can cyclodextrins be considered for solubilization purposes? J Pharm Sci. 2003;92(5):927–32.
18. Stella VJ, Rajewski RA. Cyclodextrins: their future in drug formulation and delivery. Pharm Res. 1997;14(5):556–67.
19. Carrier RL, Miller LA, Ahmed I. The utility of cyclodextrins for enhancing oral bioavailability. JCR. 2007;123(2):78–99.
20. Khan KA, Rhodes CT. Effect of compaction pressure on the dissolution efficiency of some direct compression systems. Pharm Acta Helv. 1972;47(10):594–607.
21. Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins: basic science and product development. J Pharm Pharmacol. 2010;62(11):1607–21.
22. Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes. J Pharm Pharmacol. 2011;63(9):1119–35.
23. Loftsson T, Magnusdottir A, Masson M, Sigurjonsdottir JF. Self-association and cyclodextrin solubilization of drugs. J Pharm Sci. 2002;91(11):2307–16.
24. Loftsson T, Duchene D. Cyclodextrins and their pharmaceutical applications. Int J Pharm. 2007;329(1–2):1–11.
25. Dahan A, Miller JM, Hoffman A, Amidon GE, Amidon GL. The solubility–permeability interplay in using cyclodextrins as pharmaceutical solubilizers: mechanistic modeling and application to progesterone. J Pharm Sci. 2010;99(6):2739–49.
26. Lozoya-Agullo I, Zur M, Wolk O, Beig A, Gonzalez-Alvarez I, Gonzalez-Alvarez M, et al. In-situ intestinal rat perfusions for human Fabs prediction and BCS permeability class determination: investigation of the single-pass vs. the Doluisio experimental approaches. Int J Pharm. 2015;480(1–2):1–7.
27. Merino V, Freixas J, del Val Bermejo M, Garrigues TM, Moreno J, Pla-Delfina JM. Biophysical models as an approach to study passive absorption in drug development: 6-fluoroquinolones. J Pharm Sci. 1995;84(6):777–82.
28. Sanchez-Castano G, Ruiz-Garcia A, Banon N, Bermejo M, Merino V, Freixas J, et al. Intrinsic absolute bioavailability prediction in rats based on in situ absorption rate constants and/or in vitro partition coefficients: 6-fluoroquinolones. J Pharm Sci. 2000;89(11):1395–403.
29. Cunha-Filho MS, Martinez-Pacheco R, Landin M. Fast dissolving beta-lapachone particles and tablets: an approach using surface adsorption technique. Drug Dev Ind Pharm. 2012;38(7):866–71.
30. Costa P, Sousa Lobo JM. Modeling and comparison of dissolution profiles. Eur J Pharm Sci. 2001;13(2):123–33.
31. Doluisio JT, Billups NF, Dittert LW, Sugita ET, Swintosky JV. Drug absorption. I. An in situ rat gut technique yielding realistic absorption rates. J Pharm Sci. 1969;58(10):1196–200.
32. Gonzalez-Alvarez I, Fernandez-Teruel C, Casabo-Alos VG, Garrigues TM, Polli JE, Ruiz-Garcia A, et al. In situ kinetic modelling of intestinal efflux in rats: functional characterization of segmental differences and correlation with in vitro results. Biopharm Drug Dispos. 2007;28(5):229–39.
33. Fernandez-Teruel C, Gonzalez-Alvarez I, Casabo VG, Ruiz-Garcia A, Bermejo M. Kinetic modelling of the intestinal transport of sarafloxacin. Studies in situ in rat and in vitro in Caco-2 cells. J Drug Target. 2005;13(3):199–212.
34. Tsume Y, Mudie DM, Langguth P, Amidon GE, Amidon GL. The biopharmaceutics classification system: subclasses for in vivo predictive dissolution (IPD) methodology and IVIVC. Eur J Pharm Sci. 2014;57:152–63.
35. Irvine JD, Takahashi L, Lockhart K, Cheong J, Tolan JW, Selick HE, et al. MDCK (Madin–Darby canine kidney) cells: a tool for membrane permeability screening. J Pharm Sci. 1999;88(1):28–33.
36. Troutman MD, Thakker DR. Efflux ratio cannot assess P-glycoprotein-mediated attenuation of absorptive transport: asymmetric effect of P-glycoprotein on absorptive and secretory transport across Caco-2 cell monolayers. Pharm Res. 2003;20(8):1200–9.
37. Troutman MD, Thakker DR. Rhodamine 123 requires carrier-mediated influx for its activity as a P-glycoprotein substrate in Caco-2 cells. Pharm Res. 2003;20(8):1192–9.
38. Smith D, Artursson P, Avdeef A, Di L, Ecker GF, Faller B, et al. Passive lipoidal diffusion and carrier-mediated cell uptake are both important mechanisms of membrane permeation in drug disposition. Mol Pharm. 2014;11(6):1727–38.
39. Rodriguez-Ibanez M, Nalda-Molina R, Montalar-Montero M, Bermejo MV, Merino V, Garrigues TM. Transintestinal secretion of ciprofloxacin, grepafloxacin and sparfloxacin: in vitro and in situ inhibition studies. Eur J Pharm Biopharm. 2003;55(2):241–6.
40. Ming X, Knight BM, Thakker DR. Vectorial transport of fexofenadine across Caco-2 cells: involvement of apical uptake and basolateral efflux transporters. Mol Pharm. 2011;8(5):1677–86.
41. Ballatori N, Christian WV, Wheeler SG, Hammond CL. The heteromeric organic solute transporter, OSTalpha-OSTbeta/SLC51: a transporter for steroid-derived molecules. Mol Aspects Med. 2013;34(2–3):683–92.
42. Bermejo MV G-AI. How and where are drugs absorbed? In: Gad SC, editor. Preclinical development handbook: ADME and biopharmaceutical properties. New York: Wiley; 2008.
43. Kim I, Kim H, Ro J, Jo K, Karki S, Khadka P, et al. Preclinical pharmacokinetic evaluation of beta-lapachone: characteristics of oral bioavailability and first-pass metabolism in rats. Biomol Ther (Seoul). 2015;23(3):296–300.
44. Camenisch G, Folkers G, van de Waterbeemd H. Shapes of membrane permeability–lipophilicity curves: extension of theoretical models with an aqueous pore pathway. Eur J Pharm Sci. 1998;6(4):325–9.
45. Martin-Villodre A, Pla-Delfina JM, Moreno J, Perez-Buendia D, Miralles J, Collado EF, et al. Studies on the reliability of a bihyperbolic functional absorption model. I. Ring-substituted anilines. J Pharmacokinet Biopharm. 1986;14(6):615–33.
46. Salamat-Miller NJT. Current strategies used to enhance the paracellular transport of therapeutic polypeptides across the intestinal epithelium. Int J Pharm. 2005;294(1–2):201–16.
47. Fenyvesi F, Kiss T, Fenyvesi E, Szente L, Veszelka S, Deli MA, et al. Randomly methylated beta-cyclodextrin derivatives enhance taxol permeability through human intestinal epithelial Caco-2 cell monolayer. J Pharm Sci. 2011;100(11):4734–44.
48. Nakanishi K, Nadai T, Masada M, Miyajima K. Effect of cyclodextrins on biological membrane. II. Mechanism of enhancement on the intestinal absorption of non-absorbable drug by cyclodextrins. Chem Pharm Bull. 1992;40(5):1252–6.
49. Uekama K. Design and evaluation of cyclodextrin-based drug formulation. Chem Pharm Bull (Tokyo). 2004;52(8):900–15.
50. Lambert D, O’Neill CA, Padfield PJ. 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(Pt 2):553–60.
51. Beig A, Miller JM, Dahan A. Accounting for the solubility–permeability interplay in oral formulation development for poor water solubility drugs: the effect of PEG-400 on carbamazepine absorption. Eur J Pharm Biopharm. 2012;81(2):386–91.
52. Dahan A, Miller JM. The solubility–permeability interplay and its implications in formulation design and development for poorly soluble drugs. AAPS J. 2012;14(2):244–51.
53. Miller JM, Dahan A. Predicting the solubility–permeability interplay when using cyclodextrins in solubility-enabling formulations: model validation. Int J Pharm. 2012;430(1–2):388–91.