In vitro and in vivo evaluations of the performance of an indirubin derivative, formulated in four different self-emulsifying drug delivery systems

Journal of Pharmacy and Pharmacology

Volumn 66, Issue 11, 2014, Pages 1567-1575

  Heshmati, Nasim ^a   Cheng, Xinlai ^a   Dapat, Else ^b   Sassene, Philip ^d   Eisenbrand, Gerhard ^c   Fricker, Gert ^a   Müllertz, Anette ^d  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY OF THE PHILIPPINES MANILA   (Philippines)

^c France   (Germany)

^d UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

bioavailability; E804; in vitro lipolysis; Indirubin; Self emulsifying drug delivery systems (SEDDS)

Indexed keywords

ALCOHOL; CALCIUM CHLORIDE; DIACYLGLYCEROL DERIVATIVE; INDIRUBIN 3' OXIME 2,3 DIHYDROXYPROPYL ETHER; MACROGOL 400; OCTANOIN; PECEOL; POLYSORBATE 20; POLYSORBATE 80; SODIUM HYDROXIDE; SOLUTOL HS 15; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; ACYLGLYCEROL; DRUG CARRIER; EMULSION; INDIRUBIN; INDOLE DERIVATIVE; MICELLE; SURFACTANT; WATER;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM COMPARISON; DRUG FORMULATION; DRUG SCREENING; DRUG SOLUBILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; LIPOLYSIS; MALE; MASS SPECTROMETRY; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PH; PRECIPITATION; RAT; SELF EMULSIFYING DRUG DELIVERY SYSTEM; TIME TO MAXIMUM PLASMA CONCENTRATION; ANIMAL; BIOAVAILABILITY; BLOOD; CHEMISTRY; COMPARATIVE STUDY; EMULSION; MEDICINAL CHEMISTRY; MICELLE; ORAL DRUG ADMINISTRATION; PHARMACOKINETICS; SOLUBILITY; WISTAR RAT;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; EMULSIONS; GLYCERIDES; INDOLES; LIPOLYSIS; MALE; MICELLES; RATS, WISTAR; SOLUBILITY; SURFACE-ACTIVE AGENTS; WATER;

EID: 84915798208     PISSN: 00223573     EISSN: 20427158     Source Type: Journal    
DOI: 10.1111/jphp.12286     Document Type: Article

References (41)

1. Humberstone AJ, Charman WN. Lipid-based vehicles for the oral delivery of poorly water soluble drugs. Adv Drug Deliv Rev 1997; 25: 103-128
2. Porter CJ, Charman WN. In vitro assessment of oral lipid based formulations. Adv Drug Deliv Rev 2001; 50(Suppl. 1): S127-S147
3. Fatouros DG et al. In vitro-in vivo correlations of self-emulsifying drug delivery systems combining the dynamic lipolysis model and neurofuzzy networks. Eur J Pharm Biopharm 2008; 69: 887-898
4. Larsen A et al. Lipid-based formulations for danazol containing a digestible surfactant, Labrafil M2125CS: in vivo bioavailability and dynamic in vitro lipolysis. Pharm Res 2008; 25: 2769-2777
5. Cuine JF et al. Evaluation of the impact of surfactant digestion on the bioavailability of danazol after oral administration of lipidic selfemulsifying formulations to dogs. J Pharm Sci 2008; 97: 995-1012
6. Sek L et al. Examination of the impact of a range of Pluronic surfactants on the in-vitro solubilisation behaviour and oral bioavailability of lipidic formulations of atovaquone. J Pharm Pharmacol 2006; 58: 809-820
7. Dahan A, Hoffman A. The effect of different lipid based formulations on the oral absorption of lipophilic drugs: the ability of in vitro lipolysis and consecutive ex vivo intestinal permeability data to predict in vivo bioavailability in rats. Eur J Pharm Biopharm 2007; 67: 96-105
8. Zangenberg NH et al. A dynamic in vitro lipolysis model. I. Controlling the rate of lipolysis by continuous addition of calcium. Eur J Pharm Sci 2001; 14: 115-122
9. Zangenberg NH et al. A dynamic in vitro lipolysis model. II: evaluation of the model. Eur J Pharm Sci 2001; 14: 237-244
10. Fatouros DG, Müllertz A. In vitro lipid digestion models in design of drug delivery systems for enhancing oral bioavailability. Expert Opin Drug Metab Toxicol 2008; 4: 65-76
11. Porter CJ et al. Lipids and lipid-based formulations: optimizing the oral delivery of lipophilic drugs. Nat Rev Drug Discov 2007; 6: 231-248
12. Damiens E et al. Anti-mitotic properties of indirubin-3'-monoxime, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest. Oncogene 2001; 20: 3786-3797
13. Hoessel R et al. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nat Cell Biol 1999; 1: 60-67
14. Marko D et al. Inhibition of cyclindependent kinase 1 (CDK1) by indirubin derivatives in human tumour cells. Br J Cancer 2001; 84: 283-289
15. Eisenbrand G et al. Molecular mechanisms of indirubin and its derivatives: novel anticancer molecules with their origin in traditional Chinese phytomedicine. J Cancer Res Clin Oncol 2004; 130: 627-635
16. Perabo FG et al. Indirubin-3'-monoxime, a CDK inhibitor induces growth inhibition and apoptosisindependent up-regulation of survivin in transitional cell cancer. Anticancer Res 2006; 26: 2129-2135
17. Nam S et al. Indirubin derivatives inhibit Stat3 signaling and induce apoptosis in human cancer cells. Proc Natl Acad Sci U S A 2005; 102: 5998-6003
18. Nam S et al. Indirubin derivatives induce apoptosis of chronic myelogenous leukemia cells involving inhibition of Stat5 signaling. Mol Oncol 2012; 6: 276-283
19. Cheng X. Synthesis and In Vitro Metabolism of Indirubinen with Improved Water Solubility, and Increased Metabolic Stability. Kaiserslautern, Germany: Department of Chemistry, University of Kaiserslautern, 2009
20. Heshmati N et al. Physicochemical characterization and in vitro permeation of an indirubin derivative. Eur J Pharm Sci 2013; 50: 467-475
21. Heshmati N et al. Enhancement of oral bioavailability of E804 by selfnanoemulsifying drug delivery system (SNEDDS) in rats. J Pharm Sci 2013; 102: 3792-3799
22. Sassene PJ et al. Precipitation of a poorly soluble model drug during in vitro lipolysis: characterization and dissolution of the precipitate. J Pharm Sci 2010; 99: 4982-4991
23. Gargouri Y et al. Gastric lipases: b iochemical and physiological studies. Biochim Biophys Acta 1989; 1006: 255-271
24. Carriere F et al. Secretion and contribution to lipolysis of gastric and pancreatic lipases during a test meal in humans. Gastroenterology 1993; 105: 876-888
25. Dressman JB et al. Upper gastrointestinal (GI) pH in young, healthy men and women. Pharm Res 1990; 7: 756-761
26. Larsen AT et al. In vitro lipolysis models as a tool for the characterization of oral lipid and surfactant based drug delivery systems. Int J Pharm 2011; 417: 245-255
27. Singh AK et al. Oral bioavailability enhancement of exemestane from selfmicroemulsifying drug delivery system (SMEDDS). AAPS PharmSciTech 2009; 10: 906-916
28. MacGregor K. Influence of lipolysis of drug absorption from the gastrointestinal tract. Adv Drug Deliv Rev 1997; 25: 33-46
29. Scow RO et al. Lipolysis and lipid movement in a membrane model. Action of lipoprotein lipase. J Biol Chem 1979; 254: 6456-6463
30. Brockerhoff H. Substrate specificity of pancreatic lipase. Biochim Biophys Acta 1968; 159: 296-303
31. Müllertz A et al. New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs. J Pharm Pharmacol 2010; 62: 1622-1636
32. Dahan A, Hoffman A. Use of a dynamic in vitro lipolysis model to rationalize oral formulation development for poor water soluble drugs: correlation with in vivo data and the relationship to intra-enterocyte processes in rats. Pharm Res 2006; 23: 2165-2174
33. Reymond JP, Sucker H. In vitro model for ciclosporin intestinal absorption in lipid vehicles. Pharm Res 1988; 5: 673-676
34. Porter CJ et al. Susceptibility to lipasemediated digestion reduces the oral bioavailability of danazol after administration as a medium-chain lipid-based microemulsion formulation. Pharm Res 2004; 21: 1405-1412
35. Porter CJ et al. Use of in vitro lipid digestion data to explain the in vivo performance of triglyceride-based oral lipid formulations of poorly watersoluble drugs: studies with halofantrine. J Pharm Sci 2004; 93: 1110-1121
36. Kaukonen AM et al. Drug solubilization behavior during in vitro digestion of simple triglyceride lipid solution formulations. Pharm Res 2004; 21: 245-253
37. Grove M et al. Bioavailability of seocalcitol I: relating solubility in biorelevant media with oral bioavailability in rats-effect of medium and long chain triglycerides. J Pharm Sci 2005; 94: 1830-1838
38. Grove M et al. Bioavailability of seocalcitol II: development and characterisation of selfmicroemulsifying drug delivery systems (SMEDDS) for oral administration containing medium and long chain triglycerides. Eur J Pharm Sci 2006; 28: 233-242
39. Mistry R, Sheth NA. Review: self emulsifying drug delivery system. Int J Pharm Pharm Sci 2011; 3: 23-28
40. Marten B et al. Medium-chain triglycerides. Int Dairy J 2006; 16: 1374-1382
41. Thomas N et al. In vitro and in vivo performance of novel supersaturated self-nanoemulsifying drug delivery systems (super-SNEDDS). J Control Release 2012; 160: 25-32