Nanoemulsions of cancer chemopreventive agent benzyl isothiocyanate display enhanced solubility, dissolution, and permeability

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 23, 2011, Pages 12396-12404

  Qhattal, Hussaini Syed Sha ^a   Wang, Shu ^b   Salihima, Tri ^a   Srivastava, Sanjay K ^a   Liu, Xinli ^a  

^a TEXAS TECH UNIVERSITY HEALTH SCIENCES CENTER   (United States)

^b TEXAS TECH UNIVERSITY   (United States)

Author keywords

Benzyl isothiocyanate; Caco 2 permeability; chemoprevention; dissolution; nanoemulsion; self nanoemulsifying drug delivery system

Indexed keywords

BENZYL ISOTHIOCYANATE; CACO-2 PERMEABILITY; CHEMOPREVENTION; NANOEMULSION; SELF-NANOEMULSIFYING DRUG DELIVERY SYSTEM;

BIOCHEMISTRY; CELLS; DISEASES; DRUG DELIVERY; HOMOGENIZATION METHOD; MONOLAYERS; POLYDISPERSITY; SOLUBILITY;

DISSOLUTION;

ANTINEOPLASTIC AGENT; BENZYL ISOTHIOCYANATE; ISOTHIOCYANIC ACID DERIVATIVE;

ARTICLE; CELL STRAIN CACO 2; CHEMISTRY; COLLOID; EMULSION; HUMAN; NANOTECHNOLOGY; PERMEABILITY; SOLUBILITY; TUMOR CELL LINE;

ANTICARCINOGENIC AGENTS; CACO-2 CELLS; CELL LINE, TUMOR; COLLOIDS; EMULSIONS; HUMANS; ISOTHIOCYANATES; NANOTECHNOLOGY; PERMEABILITY; SOLUBILITY;

EID: 83055165760     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf202612b     Document Type: Article

References (58)

1. Weingart, S. N.; Brown, E.; Bach, P. B.; Eng, K.; Johnson, S. A.; Kuzel, T. M.; Langbaum, T. S.; Leedy, R. D.; Muller, R. J.; Newcomer, L. N.; O'Brien, S.; Reinke, D.; Rubino, M.; Saltz, L.; Walters, R. S. NCCN Task Force Report: Oral Chemotherapy J. Natl. Compr. Cancer Netw. 2008, 6 (Suppl. 3) S1-S14
2. Shahani, K.; Swaminathan, S. K.; Freeman, D.; Blum, A.; Ma, L.; Panyam, J. Injectable sustained release microparticles of curcumin: a new concept for cancer chemoprevention Cancer Res. 2010, 70 (11) 4443-4452
3. Ru, Q.; Yu, H.; Huang, Q. Encapsulation of epigallocatechin-3-gallate (EGCG) using oil-in-water (O/W) submicrometer emulsions stabilized by iota-carrageenan and beta-lactoglobulin J. Agric. Food Chem. 2010, 58 (19) 10373-10381
4. Rocha, S.; Generalov, R.; Pereira Mdo, C.; Peres, I.; Juzenas, P.; Coelho, M. A. Epigallocatechin gallate-loaded polysaccharide nanoparticles for prostate cancer chemoprevention Nanomedicine (London) 2011, 6 (1) 79-87
5. Le Marchand, L.; Yoshizawa, C. N.; Kolonel, L. N.; Hankin, J. H.; Goodman, M. T. Vegetable consumption and lung cancer risk: a population-based case-control study in Hawaii J. Natl. Cancer Inst. 1989, 81 (15) 1158-1164
6. Verhoeven, D. T.; Goldbohm, R. A.; van Poppel, G.; Verhagen, H.; van den Brandt, P. A. Epidemiological studies on brassica vegetables and cancer risk Cancer Epidemiol. Biomarkers Prev. 1996, 5 (9) 733-748
7. Vermeulen, M.; van den Berg, R.; Freidig, A. P.; van Bladeren, P. J.; Vaes, W. H. Association between consumption of cruciferous vegetables and condiments and excretion in urine of isothiocyanate mercapturic acids J. Agric. Food Chem. 2006, 54 (15) 5350-5358
8. Wattenberg, L. W. Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds J. Natl. Cancer Inst. 1977, 58 (2) 395-398
9. Zhang, Y.; Talalay, P. Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms Cancer Res. 1994, 54 (7 Suppl.) 1976s-1981s
10. Conaway, C. C.; Yang, Y. M.; Chung, F. L. Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans Curr. Drug Metab. 2002, 3 (3) 233-255
11. Hecht, S. S., Chemoprevention by Isothiocyanates; Humana Press: Totowa, NJ, 2004; Vol. 1, pp 21-35.
12. Sahu, R. P.; Zhang, R.; Batra, S.; Shi, Y.; Srivastava, S. K. Benzyl isothiocyanate-mediated generation of reactive oxygen species causes cell cycle arrest and induces apoptosis via activation of MAPK in human pancreatic cancer cells Carcinogenesis 2009, 30 (10) 1744-1753
13. Sahu, R. P.; Srivastava, S. K. The role of STAT-3 in the induction of apoptosis in pancreatic cancer cells by benzyl isothiocyanate J. Natl. Cancer Inst. 2009, 101 (3) 176-193
14. Batra, S.; Sahu, R. P.; Kandala, P. K.; Srivastava, S. K. Benzyl isothiocyanate-mediated inhibition of histone deacetylase leads to NF-κB turnoff in human pancreatic carcinoma cells Mol. Cancer Ther. 2010, 9 (6) 1596-1608
15. Mennicke, W. H.; Gorler, K.; Krumbiegel, G.; Lorenz, D.; Rittmann, N. Studies on the metabolism and excretion of benzyl isothiocyanate in man Xenobiotica 1988, 18 (4) 441-447
16. Rao, J.; McClements, D. J. Formation of flavor oil microemulsions, nanoemulsions and emulsions: influence of composition and preparation method J. Agric. Food Chem. 2011, 59 (9) 5026-5035
17. McClements, D. J.; Rao, J. Food-grade nanoemulsions: formulation, fabrication, properties, performance, biological fate, and potential toxicity Crit. Rev. Food Sci. Nutr. 2011, 51 (4) 285-330
18. Anton, N.; Vandamme, T. F. Nano-emulsions and micro-emulsions: clarifications of the critical differences Pharm. Res. 2011, 28 (5) 978-985
19. Forgiarini, A.; Esquena, J.; González, C.; Solans, C. Formation of nano-emulsions by low-energy emulsification methods at constant temperature Langmuir 2001, 17 (7) 2076-2083
20. Rajpoot, P.; Pathak, K.; Bali, V. Therapeutic applications of nanoemulsion based drug delivery systems: a review of patents in last two decades Recent Pat. Drug Deliv. Formul. 2011, 5 (2) 163-172
21. Porter, C. J.; Charman, W. N. Lipid-based formulations for oral administration: opportunities for bioavailability enhancement and lipoprotein targeting of lipophilic drugs J. Recept. Signal. Transduct. Res. 2001, 21 (2-3) 215-257
22. Azeem, A.; Rizwan, M.; Ahmad, F. J.; Iqbal, Z.; Khar, R. K.; Aqil, M.; Talegaonkar, S. Nanoemulsion components screening and selection: a technical note AAPS PharmSciTech 2009, 10 (1) 69-76
23. Shafiq-un-Nabi, S.; Shakeel, F.; Talegaonkar, S.; Ali, J.; Baboota, S.; Ahuja, A.; Khar, R. K.; Ali, M. Formulation development and optimization using nanoemulsion technique: a technical note. AAPS PharmSciTech 2007, 8 (2), article 28.
24. Thakkar, H.; Nangesh, J.; Parmar, M.; Patel, D. Formulation and characterization of lipid-based drug delivery system of raloxifene-microemulsion and self-microemulsifying drug delivery system J. Pharm. Bioallied Sci. 2011, 3 (3) 442-448
25. Ganta, S.; Amiji, M. Coadministration of Paclitaxel and curcumin in nanoemulsion formulations to overcome multidrug resistance in tumor cells Mol. Pharmaceutics 2009, 6 (3) 928-939
26. Vyas, T. K.; Shahiwala, A.; Amiji, M. M. Improved oral bioavailability and brain transport of Saquinavir upon administration in novel nanoemulsion formulations Int. J. Pharm. 2008, 347 (1-2) 93-101
27. Shakeel, F.; Ramadan, W.; Ahmed, M. A. Investigation of true nanoemulsions for transdermal potential of indomethacin: characterization, rheological characteristics, and ex vivo skin permeation studies J. Drug Target. 2009, 17 (6) 435-441
28. Stenberg, P.; Norinder, U.; Luthman, K.; Artursson, P. Experimental and computational screening models for the prediction of intestinal drug absorption J. Med. Chem. 2001, 44 (12) 1927-1937
29. Youdim, K. A.; Avdeef, A.; Abbott, N. J. In vitro trans-monolayer permeability calculations: often forgotten assumptions Drug Discov. Today 2003, 8 (21) 997-1003
30. Liebes, L.; Conaway, C. C.; Hochster, H.; Mendoza, S.; Hecht, S. S.; Crowell, J.; Chung, F. L. High-performance liquid chromatography-based determination of total isothiocyanate levels in human plasma: application to studies with 2-phenethyl isothiocyanate Anal. Biochem. 2001, 291 (2) 279-289
31. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 1990, 82 (13) 1107-1112
32. Waitzberg, D. L.; Torrinhas, R. S.; Jacintho, T. M. New parenteral lipid emulsions for clinical use JPEN 2006, 30 (4) 351-367
33. Krohn, K.; Koletzko, B. Parenteral lipid emulsions in paediatrics Curr. Opin. Clin. Nutr. Metab. Care 2006, 9 (3) 319-323
34. Hippalgaonkar, K.; Majumdar, S.; Kansara, V. Injectable lipid emulsions - advancements, opportunities and challenges AAPS PharmSciTech 2010, 11 (4) 1526-1540
35. Dahan, A.; Hoffman, A. Rationalizing the selection of oral lipid based drug delivery systems by an in vitro dynamic lipolysis model for improved oral bioavailability of poorly water soluble drugs J. Controlled Release 2008, 129 (1) 1-10
36. Caughey, G. E.; Mantzioris, E.; Gibson, R. A.; Cleland, L. G.; James, M. J. The effect on human tumor necrosis factor alpha and interleukin 1 beta production of diets enriched in n-3 fatty acids from vegetable oil or fish oil Am. J. Clin. Nutr. 1996, 63 (1) 116-122
37. Dwivedi, C.; Natarajan, K.; Matthees, D. P. Chemopreventive effects of dietary flaxseed oil on colon tumor development Nutr, Cancer 2005, 51 (1) 52-58
38. Rose, D. P.; Connolly, J. M. Omega-3 fatty acids as cancer chemopreventive agents Pharmacol. Ther. 1999, 83 (3) 217-244
39. Williams, D.; Verghese, M.; Walker, L. T.; Boateng, J.; Shackelford, L.; Chawan, C. B. Flax seed oil and flax seed meal reduce the formation of aberrant crypt foci (ACF) in azoxymethane-induced colon cancer in Fisher 344 male rats Food Chem. Toxicol. 2007, 45 (1) 153-159
40. Zhao, Y.; Wang, C.; Chow, A. H.; Ren, K.; Gong, T.; Zhang, Z.; Zheng, Y. Self-nanoemulsifying drug delivery system (SNEDDS) for oral delivery of Zedoary essential oil: formulation and bioavailability studies Int. J. Pharm. 2010, 383 (1-2) 170-177
41. Craig, D. Q. M.; Barker, S. A.; Banning, D.; Booth, S. W. An investigation into the mechanisms of self-emulsification using particle size analysis and low frequency dielectric spectroscopy Int. J. Pharm. 1995, 114 (1) 103-110
42. Kawakami, K.; Yoshikawa, T.; Moroto, Y.; Kanaoka, E.; Takahashi, K.; Nishihara, Y.; Masuda, K. Microemulsion formulation for enhanced absorption of poorly soluble drugs. I. Prescription design J. Controlled Release 2002, 81 (1-2) 65-74
43. Bali, V.; Ali, M.; Ali, J. Nanocarrier for the enhanced bioavailability of a cardiovascular agent: in vitro, pharmacodynamic, pharmacokinetic and stability assessment Int. J. Pharm. 2011, 403 (1-2) 46-56
44. Kumar, M.; Pathak, K.; Misra, A. Formulation and characterization of nanoemulsion-based drug delivery system of risperidone Drug Dev. Ind. Pharm. 2009, 35 (4) 387-395
45. Tiwari, S. B.; Amiji, M. M. Improved oral delivery of paclitaxel following administration in nanoemulsion formulations J. Nanosci. Nanotechnol. 2006, 6 (9-10) 3215-3221
46. Wooster, T. J.; Golding, M.; Sanguansri, P. Impact of oil type on nanoemulsion formation and Ostwald ripening stability Langmuir 2008, 24 (22) 12758-12765
47. Desai, A.; Vyas, T.; Amiji, M. Cytotoxicity and apoptosis enhancement in brain tumor cells upon coadministration of paclitaxel and ceramide in nanoemulsion formulations J. Pharm. Sci. 2008, 97 (7) 2745-2756
48. Amidon, G. L.; Lennernas, H.; Shah, V. P.; Crison, J. R. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 1995, 12 (3) 413-420
49. Lawrence, M. J.; Rees, G. D. Microemulsion-based media as novel drug delivery systems Adv. Drug Deliv. Rev. 2000, 45 (1) 89-121
50. Balimane, P. V.; Han, Y. H.; Chong, S. Current industrial practices of assessing permeability and P-glycoprotein interaction AAPS J. 2006, 8 (1) E1-E13
51. Hubatsch, I.; Ragnarsson, E. G.; Artursson, P. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers Nat. Protoc. 2007, 2 (9) 2111-2119
52. Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells Biochem. Biophys. Res. Commun. 1991, 175 (3) 880-885
53. Artursson, P.; Palm, K.; Luthman, K. Caco-2 monolayers in experimental and theoretical predictions of drug transport Adv. Drug Deliv. Rev. 2001, 46 (1-3) 27-43
54. 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 (1-2) 221-232
55. 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 (9) 2051-2061
56. 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 (10) 1674-1680
57. Armand, M.; Pasquier, B.; Andre, M.; Borel, P.; Senft, M.; Peyrot, J.; Salducci, J.; Portugal, H.; Jaussan, V.; Lairon, D. Digestion and absorption of 2 fat emulsions with different droplet sizes in the human digestive tract Am. J. Clin. Nutr. 1999, 70 (6) 1096-1106
58. Singh, H.; Ye, A.; Horne, D. Structuring food emulsions in the gastrointestinal tract to modify lipid digestion Prog. Lipid Res. 2009, 48 (2) 92-100