Cremophor EL-based nanoemulsion enhances transcellular permeation of emodin through glucuronidation reduction in UGT1A1-overexpressing MDCKII cells

International Journal of Pharmaceutics

Volumn 501, Issue 1-2, 2016, Pages 190-198

  Zhang, Tianpeng ^a   Dong, Dong ^b   Lu, Danyi ^a   Wang, Shuai ^a   Wu, Baojian ^a  

^a JINAN UNIVERSITY   (China)

^b MEDICAL COLLEGE OF JINAN UNIVERSITY   (China)

Author keywords

Cremophor EL; Emodin; Glucuronidation; MDCK cells; Nanoemulsions; UGT

Indexed keywords

CREMOPHOR; DIETHYLENE GLYCOL MONOETHYL ETHER; DODECYL SULFATE SODIUM; EMODIN; GLUCURONOSYLTRANSFERASE 1A1; LENTIVIRUS VECTOR; MEDIUM CHAIN TRIACYLGLYCEROL; OLEIC ACID; EMULSION; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; GLYCEROL; NANOMATERIAL; UGT1A1 ENZYME;

ANIMAL CELL; ARTICLE; BASOLATERAL MEMBRANE; CELL METABOLISM; CELL PERMEABILIZATION; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG EXCRETION; DRUG FORMULATION; DRUG GLUCURONIDATION; DRUG RELEASE; DRUG STABILITY; EXCIPIENT COMPATIBILITY; GENETIC TRANSFECTION; IN VITRO STUDY; MDCK CELL LINE; MORPHOLOGY; NANOEMULSION; NANOFORMULATION; NONHUMAN; PARTICLE SIZE; PRIORITY JOURNAL; PROTEIN EXPRESSION; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; DOG; DRUG EFFECTS; EMULSION; ENDOCYTOSIS; GENETICS; METABOLISM;

ANIMALS; DOGS; DRUG LIBERATION; EMODIN; EMULSIONS; ENDOCYTOSIS; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; GLYCEROL; MADIN DARBY CANINE KIDNEY CELLS; NANOSTRUCTURES;

EID: 84957882488     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2016.01.067     Document Type: Article

References (36)

1. U. Agrawal, R. Sharma, M. Gupta, and S.P. Vyas Is nanotechnology a boon for oral drug delivery? Drug Discov. Today 19 10 2014 1530 1546
2. L.Z. Benet The role of BCS (biopharmaceutics classification system) and BDDCS (biopharmaceutics drug disposition classification system) in drug development J. Pharm. Sci. 102 1 2013 34 42
3. A. Bernkop-Schnürch Nanocarrier systems for oral drug delivery: Do we really need them? Eur. J. Pharm. Sci. 49 2 2013 272 277
4. R.C. Bravo Gonzalez, J. Huwyler, F. Boess, I. Walter, and B. Bittner In vitro investigation on the impact of the surface-active excipients Cremophor EL, Tween 80 and Solutol HS 15 on the metabolism of midazolam Biopharm. Drug Dispos. 25 2004 37 49
5. D. Chen, Y. Xiong, L. Wang, B. Lv, and Y. Lin Characteristics of emodin on modulating the contractility of jejunal smooth muscle Can. J. Physiol. Pharmacol. 90 4 2012 455 462
6. S.C. Chien, Y.C. Wu, Z.W. Chen, and W.C. Yang Naturally occurring anthraquinones: chemistry and therapeutic potential in autoimmune diabetes Evid. Based Complement. Alternat. Med. 2015 2015 357357
7. A. Cornish-Bowden A simple graphical method for determining the inhibition constants of mixed, uncompetitive and noncompetitive inhibitors Biochem. J. 137 1 1974 143 144
8. S.S. D'Souza, and P.P. DeLuca Development of a dialysis in vitro release method for biodegradable microspheres AAPS PharmSciTech 6 2 2005 E323 E328
9. X. Di, X. Wang, X. Di, and Y. Liu Effect of piperine on the bioavailability and pharmacokinetics of emodin in rats J. Pharm. Biomed. Anal. 115 2015 144 149
10. S. Hsua, and J. Chung Anticancer potential of emodin BioMedicine 2 3 2012 108 116
11. J.W. Liang, S.L. Hsiu, P.P. Wu, and P.D. Chao Emodin pharmacokinetics in rabbits Planta Med. 61 5 1995 406 408
12. Y. Liu, and M. Hu Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model Drug Metab. Dispos. 30 4 2002 370 377
13. W. Liu, L. Tang, L. Ye, Z. Cai, B. Xia, J. Zhang, M. Hu, and Z. Liu Species and gender differences affect the metabolism of emodin via glucuronidation AAPS J. 12 3 2010 424 436
14. Y. Liu, L. Huang, and F. Liu Paclitaxel nanocrystals for overcoming multidrug resistance in cancer Mol. Pharm. 7 3 2010 863 869
15. W. Liu, Q. Feng, Y. Li, L. Ye, M. Hu, and Z. Liu Coupling of UDP-glucuronosyltransferases and multidrug resistance-associated proteins is responsible for the intestinal disposition and poor bioavailability of emodin Toxicol. Appl. Pharmacol. 265 3 2012 316 324
16. B. Liu, B. Yuan, L. Zhang, W. Mu, and C. Wang ROS/p38/p53/Puma signaling pathway is involved in emodin-induced apoptosis of human colorectal cancer cells Int. J. Clin. Exp. Med. 8 9 2015 15413 15422
17. J. Ma, H. Lu, S. Wang, B. Chen, Z. Liu, X. Ke, T. Liu, and J. Fu The anthraquinone derivative emodin inhibits angiogenesis and metastasis through downregulating Runx2 activity in breast cancer Int. J. Oncol. 46 4 2015 1619 1628
18. K.S. Pang, H.J. Maeng, and J. Fan Interplay of transporters and enzymes in drug and metabolite processing Mol. Pharm. 6 6 2009 1734 1755
19. K. Pathak, and S. Raghuvanshi Oral bioavailability: Issues and solutions via nanoformulations Clin. Pharmacokinet. 54 4 2015 325 357
20. E. Quan, H. Wang, D. Dong, X. Zhang, and B. Wu Characterization of chrysin glucuronidation in UGT1A1-overexpressing HeLa cells: Elucidating the transporters responsible for efflux of glucuronide Drug Metab. Dispos. 43 4 2015 433 443
21. A. Rowland, J.O. Miners, and P.I. Mackenzie The UDP-glucuronosyltransferases: Their role in drug metabolism and detoxification Int. J. Biochem. Cell Biol. 45 6 2013 1121 1132
22. C.S. Shia, Y.C. Hou, S.Y. Tsai, P.H. Huieh, Y.L. Leu, and P.D. Chao Differences in pharmacokinetics and ex vivo antioxidant activity following intravenous and oral administrations of emodin to rats J. Pharm. Sci. 99 4 2010 2185 2195
23. D. Singh, M.S.M. Rawat, A. Semalty, and M. Semalty Emodin-phospholipid complex: A potential of herbal drug in the novel drug delivery system J. Therm. Anal Calorim. 108 2012 289 298
24. P. Song, J.H. Kim, J. Ghim, J.H. Yoon, A. Lee, Y. Kwon, H. Hyun, H.Y. Moon, H.S. Choi, P.O. Berggren, P.G. Suh, and S.H. Ryu Emodin regulates glucose utilization by activating AMP-activated protein kinase J. Biol. Chem. 288 8 2013 5732 5742
25. G. Srinivas, S. Babykutty, P.P. Sathiadevan, and P. Srinivas Molecular mechanism of emodin action: Transition from laxative ingredient to an antitumor agent Med. Res. Rev. 27 2007 591 608
26. J.B. Tagne, S. Kakumanu, and R.J. Nicolosi Nanoemulsion preparations of the anticancer drug dacarbazine significantly increase its efficacy in a xenograft mouse melanoma model Mol. Pharm. 5 6 2008 1055 1063
27. S. Takeda, Y. Kitajima, Y. Ishii, Y. Nishimura, P.I. Mackenzie, K. Oguri, and H. Yamada Inhibition of UDP-glucuronosyltransferase 2b7-catalyzed morphine glucuronidation by ketoconazole: Dual mechanisms involving a novel noncompetitive mode Drug Metab. Dispos. 34 8 2006 1277 1282
28. M.V. Varma, I. Gardner, S.J. Steyn, P. Nkansah, C.J. Rotter, C. Whitney-Pickett, H. Zhang, L. Di, M. Cram, K.S. Fenner, and A.F. El-Kattan pH-Dependent solubility and permeability criteria for provisional biopharmaceutics classification (BCS and BDDCS) in early drug discovery Mol. Pharm. 9 5 2012 1199 1212
29. W.T. Wei, S.Z. Lin, D.L. Liu, and Z.H. Wang The distinct mechanisms of the antitumor activity of emodin in different types of cancer (review) Oncol. Rep. 30 6 2013 2555 2562
30. B. Wu, K. Kulkarni, S. Basu, S. Zhang, and M. Hu First-pass metabolism via UDP-glucuronosyltransferase: A barrier to oral bioavailability of phenolics J. Pharm. Sci. 100 9 2011 3655 3681
31. W. Wu, N. Hu, Q. Zhang, Y. Li, P. Li, R. Yan, and Y. Wang In vitro glucuronidation of five rhubarb anthraquinones by intestinal and liver microsomes from humans and rats Chem. Biol. Interact. 219 2014 18 27
32. H. Zhang, C.P. Hollis, Q. Zhang, and T. Li Preparation and antitumor study of camptothecin nanocrystals Int. J. Pharm. 415 1-2 2011 293 300
33. L. Zhang, S. Wang, M. Zhang, and J. Sun Nanocarriers for oral drug delivery J. Drug Target. 21 6 2013 515 527
34. X. Zhang, D. Dong, H. Wang, Z. Ma, Y. Wang, and B. Wu Stable knock-down of efflux transporters leads to reduced glucuronidation in UGT1A1-overexpressing HeLa cells: The evidence for glucuronidation-transport interplay Mol. Pharm. 12 4 2015 1268 1278
35. Y.F. Zheng, C.F. Liu, W.F. Lai, Q. Xiang, Z.F. Li, H. Wang, and N. Lin The laxative effect of emodin is attributable to increased aquaporin 3 expression in the colon of mice and HT-29 cells Fitoterapia 96 2014 25 32
36. J. Zhou, M. Zhou, F.F. Yang, C.Y. Liu, R.L. Pan, Q. Chang, X.M. Liu, and Y.H. Liao Involvement of the inhibition of intestinal glucuronidation in enhancing the oral bioavailability of resveratrol by labrasol containing nanoemulsions Mol. Pharm. 12 4 2015 1084 1095