ANTIOXIDANT EFFECT OF CATECHIN LOADED POLYMERIC NANOPARTICLE

Year 2016, Volume: 34 Issue: 3, 453 - 465, 01.09.2016

Burcu Tuncer Banu Mansuroğlu Serap Derman

Abstract

Flavonoids are polyphenols compounds a structural class of mainly natural and a products of secondary metabolism of plants. Flavonoids, which can be found in herbs and trees, act as natural chemopreventives and anticancer agents [1]. As natural products, they have major importance for human life and also have a widespread effect such as antioxidant, antinflammatory, anticarcinogen, antidiabetic [2, 3]. However, bioavailability of this polyphenolic antioxidant have limited because of their high water solubility [4], low absorption, permeability, stability, slow dissolution rate, and light-induced decomposition over time in the physiological medium. In recent years, various methods have been tried to overcome the limitations of flavonoids, including its incorporation into micels and nanoparticles.

Keywords

Nanoparticle , catechin , antioxidant activity , polymeric nanoparticle

References

• [1] Papademetrio, D.L., et al., The catechin flavonoid reduces proliferation and induces apoptosis of murine lymphoma cells LB02 through modulation of antiapoptotic proteins. Revista Brasileira de Farmacognosia, 2013. 23(3): p. 455-463.
• [2] Middleton, E., C. Kandaswami, and T.C. Theoharides, The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacological reviews, 2000. 52(4): p. 673-751.
• [3] Sporn, M.B. and N. Suh, Chemoprevention: an essential approach to controlling cancer. Nature Reviews Cancer, 2002. 2(7): p. 537-543.
• [4] Aditya, N., et al., Co-delivery of hydrophobic curcumin and hydrophilic catechin by a water-in-oil-in-water double emulsion. Food chemistry, 2015. 173: p. 7-13.
• [5] Srivastava, A.K., et al., Synthesis of PLGA nanoparticles of tea polyphenols and their strong in vivo protective effect against chemically induced DNA damage. International journal of nanomedicine, 2013. 8: p. 1451.
• [6] Bhardwaj, P. and D. Khanna, Green tea catechins: defensive role in cardiovascular disorders. Chinese journal of natural medicines, 2013. 11(4): p. 345-353.
• [7] Zanwar, A., et al., Antioxidant role of catechin in health and disease. Polyphenols in Human Health and Disease; Watson, RR, Preedy, VR, Eds, 2014: p. 267-271.
• [8] Velayutham, P., A. Babu, and D. Liu, Green tea catechins and cardiovascular health: an update. Current medicinal chemistry, 2008. 15(18): p. 1840.
• [9] Dufresne, C.J. and E.R. Farnworth, A review of latest research findings on the health promotion properties of tea. The Journal of nutritional biochemistry, 2001. 12(7): p. 404-421.
• [10] How, C.W., et al., Effects of a synthetic antitumoral catechin and its tyrosinase-processed product on the structural properties of phosphatidylcholine membranes. Biochimica et Biophysica Acta (BBA)-Biomembranes, 2014. 1838(5): p. 1215-1224.
• [11] Cabrera, C., R. Artacho, and R. Giménez, Beneficial effects of green tea—a review. Journal of the American College of Nutrition, 2006. 25(2): p. 79-99.
• [12] Crespy, V. and G. Williamson, A review of the health effects of green tea catechins in in vivo animal models. The Journal of nutrition, 2004. 134(12): p. 3431S-3440S.
• [13] Cabrera, C., R. Giménez, and M.C. López, Determination of tea components with antioxidant activity. Journal of agricultural and food chemistry, 2003. 51(15): p. 4427-4435.
• [14] Horžić, D., et al., The composition of polyphenols and methylxanthines in teas and herbal infusions. Food chemistry, 2009. 115(2): p. 441-448.
• [15] Goodin, M., et al., Estrogen receptor-mediated actions of polyphenolic catechins in vivo and in vitro. Toxicological Sciences, 2002. 69(2): p. 354-361.
• [16] Zaveri, N.T., Green tea and its polyphenolic catechins: medicinal uses in cancer and noncancer applications. Life sciences, 2006. 78(18): p. 2073-2080.
• [17] Chiu, F.-L. and J.-K. Lin, HPLC analysis of naturally occurring methylated catechins, 3''-and 4''-methyl-epigallocatechin gallate, in various fresh tea leaves and commercial teas and their potent inhibitory effects on inducible nitric oxide synthase in macrophages. Journal of agricultural and food chemistry, 2005. 53(18): p. 7035-7042.
• [18] Chou, C.W., et al., (−)‐Epigallocatechin gallate, the most active polyphenolic catechin in green tea, presynaptically facilitates Ca2+‐dependent glutamate release via activation of protein kinase C in rat cerebral cortex. Synapse, 2007. 61(11): p. 889-902.
• [19] Mukhtar, H., S.K. Katiyar, and R. Agarwal, Green tea and skin--anticarcinogenic effects. Journal of investigative dermatology, 1994. 102(1): p. 3-7.
• [20] Mukhtar, H., et al., Tea components: antimutagenic and anticarcinogenic effects. Preventive Medicine, 1992. 21(3): p. 351-360.
• [21] Higdon, J.V. and B. Frei, Tea catechins and polyphenols: health effects, metabolism, and antioxidant functions. 2003.
• [22] Matsuzaki, T. and Y. Hara, Antioxidative activity of tea leaf catechins. Journal of the Agricultural Chemical Society of Japan (Japan), 1985.
• [23] Ruch, R.J., S.-j. Cheng, and J.E. Klaunig, Prevention of cytotoxicity and inhibition of intercellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis, 1989. 10(6): p. 1003-1008.
• [24] Cao, J., et al., Chemopreventive effects of green and black tea on pulmonary and hepatic carcinogenesis. Toxicological Sciences, 1996. 29(2): p. 244-250.
• [25] El-Beshbishy, H.A., Hepatoprotective effect of green tea (Camellia sinensis) extract against tamoxifen-induced liver injury in rats. BMB Reports, 2005. 38(5): p. 563-570.
• [26] Raj, P.V., et al., Protective role of catechin on d-galactosamine induced hepatotoxicity through a p53 dependent pathway. Indian Journal of Clinical Biochemistry, 2010. 25(4): p. 349-356.
• [27] Yang, B., et al., Relationship of electrochemical oxidation of catechins on their antioxidant activity in microsomal lipid peroxidation. Chemical and pharmaceutical bulletin, 2001. 49(6): p. 747-751.
• [28] Nanjo, F., et al., Scavenging effects of tea catechins and their derivatives on 1, 1-diphenyl-2-picrylhydrazyl radical. Free Radical Biology and Medicine, 1996. 21(6): p. 895-902.
• [29] Nash, K.M. and S. Ahmed, Nanomedicine in the ROS-mediated pathophysiology: Applications and clinical advances. Nanomedicine: Nanotechnology, Biology and Medicine, 2015. 11(8): p. 2033-2040.
• [30] Embuscado, M.E., Spices and herbs: natural sources of antioxidants–a mini review. Journal of Functional Foods, 2015. 18: p. 811-819.
• [31] Frei, B. and J.V. Higdon, Antioxidant activity of tea polyphenols in vivo: evidence from animal studies. The Journal of nutrition, 2003. 133(10): p. 3275S-3284S.
• [32] Fang, J.-Y., et al., Effect of liposome encapsulation of tea catechins on their accumulation in basal cell carcinomas. Journal of dermatological science, 2006. 42(2): p. 101-109.
• [33] Paquay, J.B., et al., Protection against nitric oxide toxicity by tea. Journal of Agricultural and Food Chemistry, 2000. 48(11): p. 5768-5772.
• [34] Haenen, G. and A. Bast, Nitric oxide radical scavenging of flavonoids. Methods in enzymology, 1999. 301: p. 490.
• [35] Haenen, G.R., et al., Peroxynitrite scavenging by flavonoids. Biochemical and biophysical research communications, 1997. 236(3): p. 591-593.
• [36] Agarwal, R., et al., Protection against ultraviolet B radiation‐induced effects in the skin of SKH‐1 hairless mice by a polyphenolic fraction isolated from green tea. Photochemistry and photobiology, 1993. 58(5): p. 695-700.
• [37] Park, H.J., et al., Green tea extract attenuates hepatic steatosis by decreasing adipose lipogenesis and enhancing hepatic antioxidant defenses in ob/ob mice. The Journal of nutritional biochemistry, 2011. 22(4): p. 393-400.
• [38] Bruno, R., J.A. Bomser, and M.G. Ferruzzi. Antioxidant Capacity of Green Tea (Camellia sinensis). in Elsevier Inc. 2014.
• [39] Morris, J.D., et al., Selenium-or quercetin-induced retardation of DNA synthesis in primary prostate cells occurs in the presence of a concomitant reduction in androgen-receptor activity. Cancer letters, 2006. 239(1): p. 111-122.
• [40] Renold, W., et al., An investigation of the tea aroma. Part I. New volatile black tea constituents. Helvetica Chimica Acta, 1974. 57(5): p. 1301-1308.
• [41] Chaudhuri, T., et al., Phytochemical investigation of the roots of Camellia sinensis L.(O. Kuntze). Journal of the Indian Chemical Society, 1997. 74(2).
• [42] Sabu, M., K. Smitha, and R. Kuttan, Anti-diabetic activity of green tea polyphenols and their role in reducing oxidative stress in experimental diabetes. Journal of ethnopharmacology, 2002. 83(1): p. 109-116.
• [43] Riso, P., et al., Effect of green tea extract on DNA repair and oxidative damage due to H 2 O 2 in Jurkat T cells. Nutrition Research, 2002. 22(10): p. 1143-1150.
• [44] Geetha, T., et al., Delineation of antimutagenic activity of catechin, epicatechin and green tea extract. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 2004. 556(1): p. 65- 74.
• [45] Finger, A., U.H. Engelhardt, and V. Wray, Flavonol triglycosides containing galactose in tea. Phytochemistry, 1991. 30(6): p. 2057-2060.
• [46] Mikaberidze, K. and I. Moniava, Umbelliferone from tea leaves. Chemistry of Natural Compounds, 1974. 10(1): p. 81-81.
• [47] Sandhir, R., et al., Nano-antioxidants: An emerging strategy for intervention against neurodegenerative conditions. Neurochemistry international, 2015. 89: p. 209-226.
• [48] Aditya, N., et al., Curcumin and catechin co-loaded water-in-oil-in-water emulsion and its beverage application. Journal of Functional Foods, 2015. 15: p. 35-43.
• [49] Tolochko, N., History of nanotechnology. Nanoscience and nanotechnologies. Encyclopaedia of Life Support Systems (EOLSS), Developed under the auspices of the UNESCO, Eolss Publishers, Oxford. http:// www. eolss. net, 2009.
• [50] Dangi, R. and S. Shakya, Preparation, optimization and characterization of PLGA nanoparticle. International Journal of Pharmacy & Life Sciences, 2013. 4(7).
• [51] Li, Z., et al., A review: Using nanoparticles to enhance absorption and bioavailability of phenolic phytochemicals. Food Hydrocolloids, 2015. 43: p. 153-164.
• [52] Gao, S. and M. Hu, Bioavailability challenges associated with development of anti-cancer phenolics. Mini reviews in medicinal chemistry, 2010. 10(6): p. 550.
• [53] Gentile, P., et al., An overview of poly (lactic-co-glycolic) acid (PLGA)-based biomaterials for bone tissue engineering. International journal of molecular sciences, 2014. 15(3): p. 3640-3659.
• [54] McCarron, P.A., R.F. Donnelly, and W. Marouf, Celecoxib-loaded poly (D, L-lactide-co-glycolide) nanoparticles prepared using a novel and controllable combination of diffusion and emulsification steps as part of the salting-out procedure. Journal of microencapsulation, 2006. 23(5): p. 480-498.
• [55] Reis, C.P., et al., Nanoencapsulation I. Methods for preparation of drug-loaded polymeric nanoparticles. Nanomedicine: Nanotechnology, Biology and Medicine, 2006. 2(1): p. 8-21.
• [56] Rao, J.P. and K.E. Geckeler, Polymer nanoparticles: preparation techniques and size-control parameters. Progress in Polymer Science, 2011. 36(7): p. 887-913.
• [57] Nagavarma, B., et al., Different techniques for preparation of polymeric nanoparticles—a review. Asian J. Pharm. Clin. Res, 2012. 5(3): p. 16-23.
• [58] Nordström, P., Formation of polymeric nanoparticles encapsulating and releasing a new hydrophobic cancer drug. 2011.
• [59] Bennet, D. and S. Kim, Polymer Nanoparticles for Smart Drug Delivery. 2014.
• [60] Ramazani, F., et al., Strategies for encapsulation of small hydrophilic and amphiphilic drugs in PLGA microspheres: State-of-the-art and challenges. International Journal of Pharmaceutics, 2016. 499(1): p. 358-367.
• [61] Kulhari, H., et al., Peptide conjugated polymeric nanoparticles as a carrier for targeted delivery of docetaxel. Colloids and Surfaces B: Biointerfaces, 2014. 117: p. 166-173.
• [62] Mohanraj, V. and Y. Chen, Nanoparticles-a review. Tropical Journal of Pharmaceutical Research, 2007. 5(1): p. 561-573.
• [63] Mali, A.D. and R.S. Bathe, UPDATED REVIEW ON NANOPARTICLES AS DRUG DELIVERY SYSTEMS.
• [64] Hirsjärvi, S., Preparation and characterization of Poly (lactic acid) nanoparticles for pharmaceutical use. 2008.
• [65] Song, X., et al., Dual agents loaded PLGA nanoparticles: systematic study of particle size and drug entrapment efficiency. European journal of pharmaceutics and biopharmaceutics, 2008. 69(2): p. 445- 453.
• [66] Koppel, D.E., Analysis of macromolecular polydispersity in intensity correlation spectroscopy: the method of cumulants. The Journal of Chemical Physics, 1972. 57(11): p. 4814-4820.
• [67] Bououdina, M., Handbook of Research on Nanoscience, Nanotechnology, and Advanced Materials. 2014: IGI Global.
• [68] Varma, J.R., et al., Formulation and characterization of pyrazinamide polymeric nanoparticles for pulmonary tuberculosis: Efficiency for alveolar macrophage targeting. Indian journal of pharmaceutical sciences, 2015. 77(3): p. 258.
• [69] Xu, R., C. Wu, and H. Xu, Particle size and zeta potential of carbon black in liquid media. Carbon, 2007. 45(14): p. 2806-2809.
• [70] He, C., et al., Effects of particle size and surface charge on cellular uptake and biodistribution of polymeric nanoparticles. Biomaterials, 2010. 31(13): p. 3657-3666.
• [71] Delgado, Á.V., et al., Measurement and interpretation of electrokinetic phenomena. Journal of colloid and interface science, 2007. 309(2): p. 194-224.
• [72] Xu, R. and G. Smart, Electrophoretic Mobility Study of Dodecyltrimethylammonium Bromide in Aqueous Solution and Adsorption on Microspheres1. Langmuir, 1996. 12(17): p. 4125-4133.
• [73] Ware, B.R., & Haas, D. D., Electrophoretic light scattering, in Fast methods in physical biochemistry and cell biology, I.R. I. and S.a.S.M. Fernandez, Editors. 1983, Elsevier: New York. p. 173–220.
• [74] Xu, R., Progress in nanoparticles characterization: Sizing and zeta potential measurement. Particuology, 2008. 6(2): p. 112-115.
• [75] Javidparvar, A., B. Ramezanzadeh, and E. Ghasemi, Effects of surface morphology and treatment of iron oxide nanoparticles on the mechanical properties of an epoxy coating. Progress in Organic Coatings, 2016. 90: p. 10-20.
• [76] Chan, H.-K., What is the role of particle morphology in pharmaceutical powder aerosols? Expert opinion on drug delivery, 2008. 5(8): p. 909-914.
• [77] Todokoro, H. and M. Ezumi, Scanning electron microscope. 1999, Google Patents.
• [78] Yue, P.-F., et al., The study on the entrapment efficiency and in vitro release of puerarin submicron emulsion. Aaps Pharmscitech, 2009. 10(2): p. 376-383.
• [79] Bader, R.A. and D.A. Putnam, Engineering polymer systems for improved drug delivery. 2014: John Wiley & Sons.
• [80] Fonseca, C., S. Simoes, and R. Gaspar, Paclitaxel-loaded PLGA nanoparticles: preparation, physicochemical characterization and in vitro anti-tumoral activity. Journal of Controlled Release, 2002. 83(2): p. 273-286.
• [81] Peltonen, L., et al., Improved entrapment efficiency of hydrophilic drug substance during nanoprecipitation of poly (I) lactide nanoparticles. Aaps Pharmscitech, 2004. 5(1): p. 115-120.
• [82] Zhang, Z. and S.-S. Feng, The drug encapsulation efficiency, in vitro drug release, cellular uptake and cytotoxicity of paclitaxel-loaded poly (lactide)–tocopheryl polyethylene glycol succinate nanoparticles. Biomaterials, 2006. 27(21): p. 4025-4033.
• [83] Mudshinge, S.R., et al., Nanoparticles: emerging carriers for drug delivery. Saudi pharmaceutical journal, 2011. 19(3): p. 129-141.
• [84] Magenheim, B., M. Levy, and S. Benita, A new in vitro technique for the evaluation of drug release profile from colloidal carriers-ultrafiltration technique at low pressure. International journal of pharmaceutics, 1993. 94(1): p. 115-123.
• [85] Fang, Z. and B. Bhandari, Encapsulation of polyphenols–a review. Trends in Food Science & Technology, 2010. 21(10): p. 510-523.
• [86] Liu, J., et al., A modified double-emulsion method for the preparation of daunorubicin-loaded polymeric nanoparticle with enhanced in vitro anti-tumor activity. Biomedical Materials, 2010. 5(6): p. 065002.
• [87] Tice, T.R. and R.M. Gilley, Preparation of injectable controlled-release microcapsules by a solvent-evaporation process. Journal of Controlled Release, 1985. 2: p. 343-352.
• [88] Anand, P., et al., RETRACTED: Design of curcumin-loaded PLGA nanoparticles formulation with enhanced cellular uptake, and increased bioactivity in vitro and superior bioavailability in vivo. Biochemical pharmacology, 2010. 79(3): p. 330-338.
• [89] Lambert, G., E. Fattal, and P. Couvreur, Nanoparticulate systems for the delivery of antisense oligonucleotides. Advanced drug delivery reviews, 2001. 47(1): p. 99-112.
• [90] Quintanar-Guerrero, D., et al., Preparation techniques and mechanisms of formation of biodegradable nanoparticles from preformed polymers. Drug development and industrial pharmacy, 1998. 24(12): p. 1113-1128.
• [91] Jacobson, G.B., et al., Biodegradable nanoparticles with sustained release of functional siRNA in skin. Journal of pharmaceutical sciences, 2010. 99(10): p. 4261-4266.