Naringenin-loaded nanoparticles improve the physicochemical properties and the hepatoprotective effects of naringenin in orally-administered rats with CCl4-induced acute liver failure

Pharmaceutical Research

Volumn 26, Issue 4, 2009, Pages 893-902

  Yen, Feng Lin ^a   Wu, Tzu Hui ^a   Lin, Liang Tzung ^b   Cham, Thau Ming ^a   Lin, Chun Ching ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b DALHOUSIE UNIVERSITY   (Canada)

Author keywords

Antiapoptotic; Antioxidant; Naringenin loaded nanoparticles; Oral administration; Physicochemical characterization

Indexed keywords

ALANINE AMINOTRANSFERASE; ASPARTATE AMINOTRANSFERASE; CARBON TETRACHLORIDE; CASPASE 3; CASPASE 8; CASPASE 9; CATALASE; EUDRAGIT; GLUTATHIONE PEROXIDASE; MALONALDEHYDE; NANOPARTICLE; NARINGENIN; POLYVINYL ALCOHOL; SUPEROXIDE DISMUTASE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; ENZYME ACTIVITY; INFRARED SPECTROSCOPY; LIPID PEROXIDATION; LIVER FAILURE; LIVER FUNCTION; LIVER PROTECTION; LIVER TOXICITY; MALE; NONHUMAN; PARTICLE SIZE; PHYSICAL CHEMISTRY; PRECIPITATION; PRIORITY JOURNAL; RAT; X RAY POWDER DIFFRACTION;

EID: 61449086284     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-008-9791-0     Document Type: Article

References (63)

1. K. Tanikawa T. Torimura 2006 Studies on oxidative stress in liver diseases: important future trends in liver research Med. Mol. Morphol. 39 22
2. L. Cesaratto C. Vascotto S. Calligaris G. Tell 2004 The importance of redox state in liver damage Ann. Hepatol. 3 86
3. D. J. Tuma 2002 Role of malondialdehyde-acetaldehyde adducts in liver injury Free. Radic. Biol. Med. 32 303
4. R. Q. Gill R. K. Sterling 2001 Acute liver failure J. Clin. Gastroenterol. 33 191
5. S. R. Naik V. S. Panda 2007 Antioxidant and hepatoprotective effects of Ginkgo biloba phytosomes in carbon tetrachloride-induced liver injury in rodents Liver. Int. 27 393
6. 4-induced oxidative damage in rats Food. Chem. Toxicol. 45 888
7. Z. M. Wu T. Wen Y. F. Tan Y. Liu F. Ren H. Wu 2007 Effects of salvianolic acid A on oxidative stress and liver injury induced by carbon tetrachloride in rats Basic. Clin. Pharmacol. Toxicol. 100 115
8. L. W. Weber M. Boll A. Stampfl 2003 Hepatotoxicity and mechanism of action of haloalkanes: carbon tetrachloride as a toxicological model Crit. Rev. Toxicol. 33 105
9. G. Poli 1993 Liver damage due to free radicals Br. Med. Bull. 49 604
10. S. Basu 2003 Carbon tetrachloride-induced lipid peroxidation: eicosanoid formation and their regulation by antioxidant nutrients Toxicology 189 113
11. P. Y. Chiu M. H. Tang D. H. Mak M. K. Poon K. M. Ko 2003 Hepatoprotective mechanism of schisandrin B: role of mitochondrial glutathione antioxidant status and heat shock proteins Free. Radic. Biol. Med. 35 368
12. U. Singh S. Devaraj I. Jialal 2005 Vitamin E, oxidative stress, and inflammation Annu. Rev. Nutr. 25 151
13. P. G. Pietta 2000 Flavonoids as antioxidants J. Nat. Prod. 63 1035
14. T. Ozben 2007 Oxidative stress and apoptosis: impact on cancer therapy J. Pharm. Sci. 96 2181
15. H. Schulze-Bergkamen M. Schuchmann B. Fleischer P. R. Galle 2006 The role of apoptosis versus oncotic necrosis in liver injury: facts or faith? J. Hepatol. 44 984
16. C. Garcia-Ruiz J. C. Fernández-Checa 2007 Redox regulation of hepatocyte apoptosis J. Gastroenterol. Hepatol. 22 Suppl 1 S38
17. A. Dembinski Z. Warzecha S.J. Konturek P. Ceranowicz M. Dembinski W. W. Pawlik B. Kusnierz-Cabala J.W. Naskalski 2004 Extract of grapefruit-seed reduces acute pancreatitis induced by ischemia/reperfusion in rats: possible implication of tissue antioxidants J. Physiol. Pharmacol. 55 811
18. G. Le Gall M. S. DuPont F. A. Mellon A. L. Davis G. J. Collins M. E. Verhoeyen I. J. Colquhoun 2003 Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits J. Agric. Food. Chem. 51 2438
19. H. Wang M. G. Nair G. M. Strasburg A. M. Booren J. I. Gray 1999 Antioxidant polyphenols from tart cherries (Prunus cerasus) J. Agric. Food. Chem. 47 840
20. I. Erlund E. Meririnne G. Alfthan A. Aro 2001 Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice J. Nutr. 131 235
21. T. Stark S. Bareuther T. Hofmann 2005 Sensory-guided decomposition of roasted cocoa nibs (Theobroma cacao) and structure determination of taste-active polyphenols J. Agric. Food. Chem. 53 5407
22. S. C. Shen C. H. Ko S. W. Tseng S. H. Tsai Y. C. Chen 2004 Structurally related antitumor effects of flavanones in vitro and in vivo: involvement of caspase 3 activation, p21 gene expression, and reactive oxygen species production Toxicol. Appl. Pharmacol. 197 84
23. H. J. Heo D. O. Kim S. C. Shin M. J. Kim B. G. Kim D. H. Shin 2004 Effect of antioxidant flavanone, naringenin, from Citrus junoson neuroprotection J. Agric. Food. Chem. 52 1520
24. S. Kanno A. Tomizawa T. Hiura Y. Osanai A. Shouji M. Ujibe T. Ohtake K. Kimura M. Ishikawa 2005 Inhibitory effects of naringenin on tumor growth in human cancer cell lines and sarcoma S-180-implanted mice Biol. Pharm. Bull. 28 527
25. S. Hirai Y. I. Kim T. Goto M. S. Kang M. Yoshimura A. Obata R. Yu T. Kawada 2007 Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages Life. Sci. 81 1272
26. M. H. Lee S. Yoon J. O. Moon 2004 The flavonoid naringenin inhibits dimethylnitrosamine-induced liver damage in rats Biol. Pharm. Bull. 27 72
27. S. L. Hsiu T. Y. Huang Y. C. Hou D. H. Chin P. D. Chao 2002 Comparison of metabolic pharmacokinetics of naringin and naringenin in rabbits Life. Sci. 70 1481
28. D. V. Ratnam D. D. Ankola V. Bhardwaj D. K. Sahana M. N. Kumar 2006 Role of antioxidants in prophylaxis and therapy: A pharmaceutical perspective J. Control. Release. 113 189
29. J. Dai T. Nagai X. Wang T. Zhang M. Meng Q. Zhang 2004 pH-sensitive nanoparticles for improving the oral bioavailability of cyclosporine A Int. J. Pharm. 280 229
30. J. Y. Jung S. D. Yoo S. H. Lee K. H. Kim D. S. Yoon K. H. Lee 1999 Enhanced solubility and dissolution rate of itraconazole by a solid dispersion technique Int. J. Pharm. 187 209
31. S. L. Wang S. Y. Lin T. F. Chen W. T. Cheng 2004 Eudragit E accelerated the diketopiperazine formation of enalapril maleate determined by thermal FTIR microspectroscopic technique Pharm. Res. 21 2127
32. T. H. Wu F. L. Yen L. T. Lin T. R. Tsai C. C. Lin T. M. Cham 2008 Preparation, physicochemical characterization, and antioxidant effects of quercetin nanoparticles Int. J. Pharm. 346 160
33. U. Bilati E. Allémann E. Doelker 2005 Nanoprecipitation versus emulsion-based techniques for the encapsulation of proteins into biodegradable nanoparticles and process-related stability issues AAPS. PharmSciTech. 6 E594
34. Z. Zili S. Sfar H. Fessi 2005 Preparation and characterization of poly-epsilon-caprolactone nanoparticles containing griseofulvin Int. J. Pharm. 294 261
35. P. Muriel M. Mourelle 1992 Characterization of membrane fraction lipid composition and function of cirrhotic rat liver. Role of S-adenosyl-L-methionine J. Hepatol. 14 16
36. H. Ohkawa N. Ohishi K. Yagi 1979 Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction Anal. Biochem. 95 351
37. H. Aebi 1984 Catalase in vitro Methods Enzymol. 105 121
38. O. H. Lowry N. J Rosebrough A. L. Farr R. J. Randall 1951 Protein measurement with the Folin phenol reagent J. Biol. Chem. 193 265
39. J. Xing D. Zhang T. Tan 2007 Studies on the oridonin-loaded poly(D,L-lactic acid) nanoparticles in vitro and in vivo Int. J. Biol. Macromol. 40 153
40. T. Y. Lee H. H. Chang M. Y. Wu H. C. Lin 2007 Yin-Chen-Hao-Tang ameliorates obstruction-induced hepatic apoptosis in rats J. Pharm. Pharmacol. 59 583
41. T. Y. Lee H. H. Chang G. J. Wang J. H. Chiu Y. Y. Yang H. C. Lin 2006 Water-soluble extract of Salvia miltiorrhiza ameliorates carbon tetrachloride-mediated hepatic apoptosis in rats J. Pharm. Pharmacol. 58 659
42. Y. Chen J. Liu X. Yang X. Zhao H. Xu 2005 Oleanolic acid nanosuspensions: preparation, in-vitro characterization and enhanced hepatoprotective effect J. Pharm. Pharmacol. 57 259
43. S. K. Sahoo J. Panyam S. Prabha V. Labhasetwar 2002 Residual polyvinyl alcohol associated with poly (D,L-lactide-co-glycolide) nanoparticles affects their physical properties and cellular uptake J. Control. Release. 82 105
44. Y. N. Konan-Kouakou R. Boch R. Gurny E. Allémann 2005 In vitro and in vivo activities of verteporfin-loaded nanoparticles J. Control. Release. 103 83
45. P. P Shah R. C. Mashru Y. M. Rane A. Thakkar 2008 Design and optimization of mefloquine hydrochloride microparticles for bitter taste masking AAPS. PharmSciTech. 9 377
46. D. R. Koop 1992 Oxidative and reductive metabolism by cytochrome P450 2E1 FASEB. J. 6 724
47. C. Y. Wang F. L. Ma J. T. Liu J. W. Tian F. H. Fu 2007 Protective effect of salvianic acid A on acute liver injury induced by carbon tetrachloride in rats Biol. Pharm. Bull. 30 44
48. M. A. Mansour 2000 Protective effects of thymoquinone and desferrioxamine against hepatotoxicity of carbon tetrachloride in mice Life. Sci. 66 2583
49. F. Sun E. Hamagawa C. Tsutsui Y. Ono Y. Ogiri S. Kojo 2001 Evaluation of oxidative stress during apoptosis and necrosis caused by carbon tetrachloride in rat liver Biochim. Biophys. Acta. 1535 186
50. H. Ikeda Y. Kume K. Tejima T. Tomiya T. Nishikawa N. Watanabe N. Ohtomo M. Arai C. Arai M. Omata K. Fujiwara Y. Yatomi 2007 Rho-kinase inhibitor prevents hepatocyte damage in acute liver injury induced by carbon tetrachloride in rats Am. J. Physiol. Gastrointest. Liver. Physiol. 293 G911
51. R. Rodrigo C. Guichard R. Charles 2007 Clinical pharmacology and therapeutic use of antioxidant vitamins Fundam. Clin. Pharmacol. 21 111
52. Y. Hu J. Xie Y. W. Tong C. H. Wang 2007 Effect of PEG conformation and particle size on the cellular uptake efficiency of nanoparticles with the HepG2 cells J. Control. Release. 118 7
53. H. F. Liang T. F. Yang C. T. Huang M. C. Chen H. W. Sung 2005 Preparation of nanoparticles composed of poly(gamma-glutamic acid)-poly(lactide) block copolymers and evaluation of their uptake by HepG2 cells J. Control. Release. 105 213
54. A. Salazar-Montes V. Delgado-Rizo J. Armenda'riz-Borunda 2000 Differential gene expression of pro-inflammatory and anti-inflammatory cytokines in acute and chronic liver injury Hepatol. Res. 16 181
55. A. Lamprecht N. Ubrich H. Yamamoto U. Schäfer H. Takeuchi P. Maincent Y. Kawashima C.M. Lehr 2001 Biodegradable nanoparticles for targeted drug delivery in treatment of inflammatory bowel disease J. Pharmacol. Exp. Ther. 299 775
56. M. Hashida S. Takemura M. Nishikawa Y. Takakura 1998 Targeted delivery of plasmid DNA complexed with galactosylated poly(L-lysine) J. Control. Release. 53 301
57. J. Shi K. Aisaki Y. Ikawa K. Wake 1998 Evidence of hepatocyte apoptosis in rat liver after the administration of carbon tetrachloride Am. J. Pathol. 153 515
58. B. Zhang J. Hirahashi X. Cullere T. N. Mayadas 2003 Elucidation of molecular events leading to neutrophil apoptosis following phagocytosis: cross-talk between caspase 8, reactive oxygen species, and MAPK/ERK activation J. Biol. Chem. 278 28443
59. N. Kaplowitz 2002 Biochemical and cellular mechanisms of toxic liver injury Semin. Liver. Dis. 22 137
60. M. L. Bajt S.L. Vonderfecht H. Jaeschke 2001 Differential protection with inhibitors of caspase-8 and caspase-3 in murine models of tumor necrosis factor and Fas receptor-mediated hepatocellular apoptosis Toxicol. Appl. Pharmacol. 175 243
61. S. M. Riordan R. Williams 2003 Mechanisms of hepatocyte injury, multiorgan failure, and prognostic criteria in acute liver failure Semin. Liver. Dis. 23 203
62. M. E. Guicciardi G. J. Gores 2005 Apoptosis: a mechanism of acute and chronic liver injury Gut. 54 1024
63. M. A. El-Mahdy Q. Zhu Q. E. Wang G. Wani S. Patnaik Q. Zhao E. S. Arafa B. Barakat S. N. Mir A. A. Wani 2007 Naringenin protects HaCaT human keratinocytes against UVB-induced apoptosis and enhances the removal of cyclobutane pyrimidine dimers from the genome Photochem. Photobiol. 84 2 307 316