Anti-tumor activity and safety evaluation of fisetin-loaded methoxy poly(ethylene glycol)-poly(ε-caprolactone) nanoparticles

Journal of Biomedical Nanotechnology

Volumn 10, Issue 4, 2014, Pages 580-591

  Yang, Qian ^a,b   Liao, Jinfeng ^a   Deng, Xin ^c   Liang, Jian ^c   Long, Chaofeng ^d   Xie, Chengshi ^d   Chen, Xiaoxin ^d   Zhang, Lan ^d   Sun, Jinxin ^d   Peng, Jinrong ^a   Chu, Bingyang ^a   Guo, Gang ^a   Luo, Feng ^a   Qian, ZhiYong ^a  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU MEDICAL COLLEGE   (China)

^c GUANGXI UNIVERSITY OF CHINESE MEDICINE   (China)

^d Guangdong Zhongsheng Pharmacy   (China)

Author keywords

Anti cancer drugs; Bioflavonoid; Fisetin; Nanoparticles; Tumor

Indexed keywords

ANTI-TUMOR ACTIVITIES; ANTICANCER ACTIVITIES; ANTICANCER DRUG; BIOFLAVONOID; FISETIN; INTRAVENOUS INJECTIONS; METHOXYPOLYETHYLENE GLYCOL; PARENTERAL ADMINISTRATION;

BIOCOMPATIBILITY; CHEMOTHERAPY; DISEASES; EMULSIFICATION; NANOPARTICLES; SOLUBILITY; TUMORS;

POLYETHYLENE GLYCOLS;

FISETIN; MACROGOL; METHOXY POLY(ETHYLENE GLYCOL); NANOPARTICLE; POLYCAPROLACTONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOCOMPATIBILITY; CANCER CHEMOTHERAPY; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG SAFETY; DRUG STRUCTURE; EMULSION; HEMOLYSIS; IN VITRO STUDY; IN VIVO STUDY; LEWIS CARCINOMA; LIVER TOXICITY; MALE; MOUSE; NANOENCAPSULATION; NONHUMAN; PARTICLE SIZE; RAT; SUSTAINED DRUG RELEASE; TECHNOLOGY;

ABSORPTION; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DIFFUSION; FLAVONOIDS; INJECTIONS, INTRAVENOUS; MALE; MICE; MICE, INBRED C57BL; NANOCAPSULES; NEOPLASMS, EXPERIMENTAL; PARTICLE SIZE; POLYESTERS; POLYETHYLENE GLYCOLS; RATS; RATS, SPRAGUE-DAWLEY; TREATMENT OUTCOME;

EID: 84896781552     PISSN: 15507033     EISSN: 15507041     Source Type: Journal    
DOI: 10.1166/jbn.2014.1746     Document Type: Article

References (52)

1. H. Zhou, J. Zhang, A. Li, Z. Wang, and X. Lou, Dihydroartemisinin improves the efficiency of chemotherapeutics in lung carcinomas in vivo and inhibits murine Lewis lung carcinoma cell line growth in vitro. Cancer Chem. Pharmacol. 66, 21 (2010).
2. A. Petrovski, B. Sudha, and J. McCall, Parallel Problem Solving from Nature - PPSN VIII, edited by X. Yao, Springer, Berlin, Heidelberg (2004). Vol. 3242, pp.633-641.
3. N. Khan, F. Afaq, and H. Mukhtar, Cancer chemoprevention through dietary antioxidants: Progress and promise. Antioxid Redox Signal 10, 475 (2008).
4. W. V. Berghe, Epigenetic impact of dietary polyphenols in cancer chemoprevention: Lifelong remodelling of our epigenomes. Pharmacol. Res. 65, 565 (2012).
5. E. Middleton, C. Kandaswami, and T. C. Theoharides, The Effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52, 673 (2000).
6. W. Ren, Z. Qiao, H. Wang, L. Zhu, and L. Zhang, Flavonoids: Promising anticancer agents. Med. Res. Rev. 23, 519 (2003).
7. Y. Arai, S. Watanabe, M. Kimira, K. Shimoi, R. Mochizuki, and N. Kinae, Dietary intakes of flavonols, flavones and isoflavones by japanese women and the inverse correlation between quercetin intake and plasma ldl cholesterol concentration. J. Nutr. 130, 2243 (2000).
8. O. L. Woodman and E. C. Chan, Vascular and anti-oxidant actions of flavonols and flavones. Clin. Exp. Pharmacol. Physio. 31, 786 (2004).
9. H. H. Park, S. Lee, J. M. Oh, M. S. Lee, K. H. Yoon, B. H. Park, J.W. Kim, H. Song, and S. H. Kim, Anti-inflammatory activity of fisetin in human mast cells (HMC-1). Pharmacolo. Res. 55, 31 (2007).
10. T. Fotsis, M. S. Pepper, E. Aktas, S. Breit, S. Rasku, H. Adlercreutz, K. Wähälä, R. Montesano, and L. Schweigerer, Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Cancer Res. 57, 2916 (1997).
11. T. A. Bhat, D. Nambiar, A. Pal, R. Agarwal, and R. P. Singh, Fisetin inhibits various attributes of angiogenesis in vitro and in vivo - implications for angioprevention. Carcinogenesis 33, 385 (2012).
12. W. R. Lee, S. C. Shen, H. Y. Lin, W. C. Hou, L. L. Yang, and Y. C. Chen, Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease. Biochem. Pharmacol. 63, 225 (2002).
13. 2 and Wnt/EGFR/NF-κB-signaling pathways. Carcinogenesis 30, 300 (2009).
14. E. Szliszka, K. J. Helewski, E. Mizgala, and W. Krol, The dietary flavonol fisetin enhances the apoptosis-inducing potential of TRAIL in prostate cancer cells. Int. J. Oncol. 39, 771 (2011).
15. H. Lu, D. J. Chang, B. Baratte, L. Meijer, and U. Schulze-Gahmen, Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin. J. Med. Chem. 48, 737 (2005).
16. B. Sung, M. K. Pandey, and B. B. Aggarwal, Fisetin, an inhibitor of cyclin-dependent kinase 6, down-regulates nuclear factor-κB-regulated cell proliferation, antiapoptotic and metastatic gene products through the suppression of TAK-1 and receptor-interacting protein-regulated IκBα kinase activation. Mol. Pharmacol. 71, 1703 (2007).
17. A. Olaharski, S. Mondrala, and D. Eastmond, Chromosomal malsegregation and micronucleus induction in vitro by the DNA topoisomerase II inhibitor fisetin. Mutat. Res. 582, 79 (2005).
18. J. Jankun, S. H. Selman, J. Aniola, and E. Skrzypczak-Jankun, Nutraceutical inhibitors of urokinase: Potential applications in prostate cancer prevention and treatment. Oncol. Rep. 16, 341 (2006).
19. Y. Suh, F. Afaq, N. Khan, J. J. Johnson, F. H. Khusro, and H. Mukhtar, Fisetin induces autophagic cell death through suppression of mTOR signaling pathway in prostate cancer cells. Carcinogenesis 31, 1424 (2010).
20. N. Khan, F. Afaq, F. H. Khusro, V. Mustafa Adhami, Y. Suh, and H. Mukhtar, Dual inhibition of phosphatidylinositol 3-kinase/Akt and mammalian target of rapamycin signaling in human nonsmall cell lung cancer cells by a dietary flavonoid fisetin. Int. J. Cancer 130, 1695 (2012).
21. R. Tripathi, T. Samadder, S. Gupta, A. Surolia, and C. Shaha, Anti-cancer activity of a combination of cisplatin and fisetin in embryonal carcinoma cells and xenograft tumors. Mol. Cancer Ther. 10, 255 (2011).
22. Y. Touil, J. Seguin, D. Scherman, and G. Chabot, Improved antiangiogenic and antitumour activity of the combination of the natural flavonoid fisetin and cyclophosphamide in Lewis lung carcinoma-bearing mice. Cancer Chemother. Pharmacol. 68, 445 (2011).
23. M. López-Lázaro, E. Willmore, and C. A. Austin, The dietary flavonoids myricetin and fisetin act as dual inhibitors of DNA topoisomerases I and II in cells. Mutat. Res. 696, 41 (2010).
24. Y. S. Touil, N. Auzeil, F. Boulinguez, H. Saighi, A. Regazzetti, D. Scherman, and G. G. Chabot, Fisetin disposition and metabolism in mice: Identification of geraldol as an active metabolite. Biochem. Pharmacol. 82, 1731 (2011).
25. I. Brigger, C. Dubernet, and P. Couvreur, Nanoparticles in cancer therapy and diagnosis. Adv. Drug Deliv. Rev. 64, Supplement, 24 (2012).
26. R. Duncan, Polymer conjugates for tumour targeting and intracytoplasmic delivery. The EPR effect as a common gateway? Pharm. Sci. Technolo. Today 2, 441 (1999).
27. H. Maeda, K. Greish, and J. Fang, in Polymer Therapeutics II, edited by R. Satchi-Fainaro and R. Duncan, Springer, Berlin, Heidelberg (2006), Vol. 193, pp.1-65.
28. H. Maeda, Tumor-selective delivery of macromolecular drugs via the EPR effect: Background and future prospects. Bioconjug. Chem. 21, 797 (2010).
29. R. Gref, Y. Minamitake, M. T. Peracchia, V. Trubetskoy, V. Torchilin, and R. Langer, Biodegradable long-circulating polymeric nanospheres. Science 263, 1600 (1994).
30. N. Kamaly, Z. Xiao, P. M. Valencia, A. F. Radovic-Moreno, and O. C. Farokhzad, Targeted polymeric therapeutic nanoparticles: Design, development and clinical translation. Chem. Soc. Rev. 41, 2971 (2012).
31. S. Zhou, X. Deng, and H.Yang, Biodegradable poly(ε-caprolactone)- poly(ethylene glycol) block copolymers: Characterization and their use as drug carriers for a controlled delivery system. Biomaterials 24, 3563 (2003).
32. X. Wei, C. Gong, S. Shi, S. Fu, K. Men, S. Zeng, X. Zheng, M. Gou, L. Chen, L. Qiu, and Z. Qian, Self-assembled honokiol-loaded micelles based on poly(ε-caprolactone)-poly(ethylene glycol)- poly(ε-caprolactone) copolymer. Int. J. Pharm. 369, 170 (2009).
33. N. Rapoport, Physical stimuli-responsive polymeric micelles for anti-cancer drug delivery. Prog. Polym. Sci. 32, 962 (2007).
34. A. Kumari, S. K. Yadav, and S. C. Yadav, Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf. B: Biointerfaces 75, 1 (2010).
35. E. M. Pridgen, R. Langer, and O. C. Farokhzad, Biodegradable, polymeric nanoparticle delivery systems for cancer therapy. Nanomedicine (London, England) 2, 669 (2007).
36. R. Gref, M. Lück, P. Quellec, M. Marchand, E. Dellacherie, S. Harnisch, T. Blunk, and R. H. Müller, 'Stealth' corona-core nanoparticles surface modified by polyethylene glycol (PEG): Influences of the corona (PEG chain length and surface density) and of the core composition on phagocytic uptake and plasma protein adsorption. Colloids Surf. B: Biointerfaces 18, 301 (2000).
37. M. Gou, X. Zheng, K. Men, J. Zhang, L. Zheng, X. Wang, F. Luo, Y. Zhao, X. Zhao, Y. Wei, and Z. Qian, Poly(ε-caprolactone)/Poly(ethylene glycol)/Poly(ε-caprolactone) Nanoparticles: Preparation, Characterization, and Application in Doxorubicin Delivery. J. Phys. Chem. B 113, 12928 (2009).
38. M. Gou, Men, K., H. Shi, M. Xiang, J. Zhang, J. Song, J. Long, Y. Wan, F. Luo, X. Zhao, and Z. Qian, Curcumin-loaded biodegradable polymeric micelles for colon cancer therapy in vitro and in vivo. Nanoscale 3, 1558 (2011).
39. C. Wang, Y. Wang, Y. Wang, M. Fan, F. Luo, and Z. Qian, Characterization, pharmacokinetics and disposition of novel nanoscale preparations of paclitaxel. Int. J. Pharm. 414, 251 (2011).
40. C. Gong, S. Deng, Q. Wu, M. Xiang, X. Wei, L. Li, X. Gao, B. Wang, L. Sun, and Y. Chen, Improving antiangiogenesis and anti-tumor activity of curcumin by biodegradable polymeric micelles. Biomaterials 34, 1413 (2013).
41. M. Gou, X. Zheng, K. Men, J. Zhang, B. Wang, L. Lv, X. Wang, Y. Zhao, F. Luo, L. Chen, X. Zhao, Y. Wei, and Z. Qian, Self-Assembled hydrophobic honokiol loaded MPEG-PCL diblock copolymer micelles. Pharm. Res. 26, 2164 (2009).
42. J. Mursu, S. Voutilainen, T. Nurmi, T. P. Tuomainen, S. Kurl, and J. T. Salonen, Flavonoid intake and the risk of ischaemic stroke and CVD mortality in middle-aged Finnish men: The kuopio ischaemic heart disease risk factor study. Br. J. Nutr. 100, 890 (2008).
43. P. Lagiou, E. Samoli, A. Lagiou, A. Tzonou, A. Kalandidi, J. Peterson, J. Dwyer, and D. Trichopoulos, Intake of specific flavonoid classes and coronary heart disease[mdash]a case-control study in Greece. Eur. J. Clin. Nutr. 58, 1643 (2004).
44. L. Zhang, F. Gu, J. Chan, A. Wang, R. Langer, and O. Farokhzad, Nanoparticles in medicine: Therapeutic applications and developments. Clin. Pharmacol. Ther. 83, 761 (2007).
45. S. K. Hobbs, W. L. Monsky, F. Yuan, W. G. Roberts, L. Griffith, V. P. Torchilin, and R. K. Jain, Regulation of transport pathways in tumor vessels: Role of tumor type and microenvironment. Proc. Natl. Acad. Sci. USA 95, 4607 (1998).
46. F. Yuan, M. Dellian, D. Fukumura, M. Leunig, D. A. Berk, V. P. Torchilin, and R. K. Jain, Vascular permeability in a human tumor xenograft: Molecular size dependence and cutoff size. Cancer Res. 55, 3752 (1995).
47. M. Dellian, F. Yuan, V. Trubetskoy, V. Torchilin, and R. Jain, Vascular permeability in a human tumour xenograft: Molecular charge dependence. Br. J. Cancer 82, 1513 (2000).
48. N. Desai, Challenges in development of nanoparticle-based therapeutics. The AAPS journal 14, 282 (2012).
49. K. S. Soppimath, T. M. Aminabhavi, A. R. Kulkarni, and W. E. Rudzinski, Biodegradable polymeric nanoparticles as drug delivery devices. J. Control. Release 70, 1 (2001).
50. H. Rosen and T. Abribat, The rise and rise of drug delivery. Nat. Rev. Drug Discov. 4, 381 (2005).
51. N. Mignet, J. Seguin, M. Ramos Romano, L. Brullé, Y. S. Touil, D. Scherman, M. Bessodes, and G. G. Chabot, Development of a liposomal formulation of the natural flavonoid fisetin. Int. J. Pharm. 423, 69 (2012).
52. H. Ragelle, S. Crauste-Manciet, J. Seguin, D. Brossard, D. Scherman, P. Arnaud, and G. G. Chabot, Nanoemulsion formulation of fisetin improves bioavailability and antitumour activity in mice. Int. J. Pharm. 427, 452 (2012).