Nanoparticles based on oleate alginate ester as curcumin delivery system

Current Drug Delivery

Volumn 12, Issue 5, 2015, Pages 613-627

  Raja, Mazhar Ali ^a   Liu, Chenguang ^a   Huang, Zhenhua ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

Author keywords

Alginate; Cell uptake studies; Curcumin; Cytotoxicity; Methyl oleate; Nanoparticles; Self assembled

Indexed keywords

ALGINIC ACID; CURCUMIN; NANOCARRIER; NANOCONJUGATE; OLEATE ALGINATE ESTER; OLEIC ACID; PYRENE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DRUG CARRIER; ESTER; GLUCURONIC ACID; HEXURONIC ACID; NANOPARTICLE;

ARTICLE; CELL VIABILITY; CHEMISTRY; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; CYTOTOXICITY ASSAY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG DIFFUSION; DRUG SOLUBILITY; DRUG STABILITY; FLUOROMETRY; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; MCF 7 CELL LINE; MORPHOLOGY; NANOENCAPSULATION; PARTICLE SIZE; PHYSICAL CHEMISTRY; PHYSICAL PARAMETERS; POLYDISPERSITY INDEX; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SURFACE CHARGE; SUSTAINED DRUG RELEASE; SYNTHESIS; TRANSESTERIFICATION; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL; CELL SURVIVAL; CHEMICAL STRUCTURE; DRUG EFFECTS; DRUG RELEASE; MCF-7 CELL LINE; SOLUBILITY; SURFACE PROPERTY;

ALGINATES; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; CURCUMIN; DRUG CARRIERS; DRUG LIBERATION; DRUG STABILITY; ESTERS; GLUCURONIC ACID; HEXURONIC ACIDS; HUMANS; MCF-7 CELLS; MOLECULAR STRUCTURE; NANOPARTICLES; OLEIC ACID; PARTICLE SIZE; SOLUBILITY; SURFACE PROPERTIES;

EID: 84947908593     PISSN: 15672018     EISSN: 18755704     Source Type: Journal    
DOI: 10.2174/1567201812666150511095029     Document Type: Article

References (64)

1. Goel, A.; Kunnumakkara, A.B.; Aggarwal, B.B. Curcumin as "Curecumin": from kitchen to clinic. Biochem. Pharmacol., 2008, 75,787-809.
2. Aggarwal, B.B.; Harikumar, K.B. Potential therapeutic effects of curcumin the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. Int. J. Biochem. Cell Biol., 2009, 41, 40-59.
3. Lin, M.S.; Lee, Y.H.; Chiu W.T.; Hung, K.S. Curcumin provides neuroprotection after spinal cord injury. J. Surgical Res., 2011, 16, 280-289.
4. Aggarwal, B.B.; Kumar, A.; Bharti, A.C. Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res., 2003, 23, 363-398.
5. Aggarwal, B.B; Sung, B. Pharmacological basis for the role of curcumin in chronic diseases: An age-old spice with modern targets. Trends Pharmacol. Sci., 2009, 30, 85-94.
6. Mythri, R.B.; Harish, G.; Dubey, S.K.; Misra, K.; Bharath, M.M.S. Glutamoyl diester of the dietary polyphenol curcumin offers improved protection against peroxynitrite-mediated nitrosative stress and damage of brain mitochondria in vitro: Implications for Parkinson's disease. Mol. Cell. Biochem., 2011, 347, 135-143.
7. Belakavadi, M.; Salimath, B.P. Mechanism of inhibition of ascites tumor growth in mice by curcumin is mediated by NF-kB and caspase activated Dnase. Mol. Cell. Biochem., 2005, 273, 57-67.
8. Aggarwal, B.B.; Shishodia, S.; Takada, Y.; Banerjee, S.; Newman, R.A.; Bueso-Ramos, C.E.; Price, J.E. Curcumin suppresses the paclitaxel-induced nuclear Factor-kappa B pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice. Clin. Cancer Res., 2005, 11, 7490-7498.
9. Glienke, W.; Maute. L.; Wicht, J.; Bergmann, L. Curcumin inhibits constitutive STAT3 phosphorylation in human pancreatic cancer cell lines and down regulation of survivin/BIRC5 gene expression. Cancer Investig., 2009, 28, 166-171.
10. Lin, S.S.; Lai, K.C.; Hsu, S.C.; Yang, J.S.; Kuo, C.L.; Lin, J.P. Curcumin inhibits the migration and invasion of human A549 lung cancer cells through the inhibition of matrix metalloproteinase-2 and-9 and vascular endothelial growth factor (VEGF). Cancer Lett., 2009, 285, 127-133.
11. Jutooru, I.; Chadalapaka, G.; Lei, P.; Safe, S. Inhibition of NFκB and pancreatic cancer cell and tumor growth by curcumin is dependent on specificity protein down-regulation. J. Biol. Chem., 2010, 285, 25332-25344.
12. Yu, L.L.; Wu, J.G.; Dai, N.; Yu, H.G.; Si, J.M. Curcumin reverses chemo resistance of human gastric cancer cells by down regulating the NF-k - transcription factor. Oncol. Rep., 2011, 26, 197-203.
13. Bhattacharyya, S.; Mandal, D.; Saha, B.; Sen, G.S.; Das. T.; Sa, G. Curcumin prevents tumor-induced apoptosis through Stat-5amediated Bcl-2 induction. J. Biol. Chem., 2007, 282, 15954-15964.
14. Kurup, V.P.; Barrios, C.S.; Raju, R. Immune response modulation by curcumin in a latex allergy model. Clin. Mol. Allergy, 2007, 5, 1-12.
15. Kurien, B.T.; Singh, A.; Matsumoto, H.; Scofield, R.H. Improving the solubility and pharmacological efficacy of curcumin by heat treatment. Assay Drug Dev. Technol., 2007, 5, 567-576.
16. Yang, K.Y.; Lin, L.C.; Tseng, T.Y.; Wang, S.C.; Tsai, T.H. Oral bioavailability of curcumin in rat and the herbal analysis from Curcuma longa by LC-MS/MS. J. Chromatogr. B., 2007, 853, 183-189.
17. Bisht, S.; Feldmann, G.; Soni, S.; Ravi, R.; Karikar, C.; Maitra, A. Polymeric nanoparticle-encapsulated curcumin “ nanocurcumin& rdquo; a novel strategy for human cancer therapy. J. Nanobiotech., 2007, 5, 3-21.
18. Muller, R.H.; Keck, C.M. Challenges and solutions for the delivery of Biotech drugs - a review of drug nanocrystal technology and lipid nanoparticles. J. Biotech., 2004, 113, 151-155.
19. Rajasekar, A.; Devasena,T. Facile Synthesis of Curcumin Nanocrystals and Validation of Its Antioxidant Activity Against Circulatory Toxicity in Wistar Rats. J. Nanosci. Nanotechnol., 2015, 15, 4119-4125
20. Tiyaboonchai, W.; Tungpradit, W.; Plianbangchang, P. Formulation and characterization of curcuminoids loaded solid lipid nanoparticles. Int. J. Pharm., 2007, 337, 299-306.
21. Kumar, V.; Lewis, S.A.; Mutalik, S.; Shenoy D.B.; Udupa, N. Biodegradable microspheres of curcumin for the treatment of inflammation. Indian J. Phys. Pharmacol., 2002, 46, 209-217.
22. Sou, K.; Inenaga, S.; Takeoka, S.; Tsuchida, E. Loading of curcumin into macrophages using lipid-based nanoparticles. Int. J. Pharm., 2008, 352, 287-293
23. Dhule, S.S; Penfornis, P.; Frazier, T.; Walker. R.; Feldman, J.; Tan. G. Curcumin-loaded γ-cyclodextrin liposomal nanoparticles as delivery vehicles for osteosarcoma. Nanomedicine, 2012, 8, 440-451.
24. Vemula, P.K.; Li, J.; John, G. Enzyme catalysis: Tool to make and break amygdalin hydrogelators from renewable resources: A delivery model for hydrophobic drugs J. Am. Chem. Soc., 2006, 128, 8932-8938.
25. Li, L.; Ahmed, B.; Mehta, K.; Kurzrock, R. Liposomal curcumin with and without oxaliplatin: Effects on cell growth, apoptosis, and angiogenesis in colorectal cancer. Mol. Cancer Ther., 2007, 6, 127-1282.
26. Wang, D.; Veena, M.S.; Stevenson, K.; Tang, C.; Ho, B.; Suh, J.D. Liposome encapsulated curcumin suppresses growth of head and neck squamous cell carcinoma in vitro and in xenografts through the inhibition of nuclear factor κB by an AKT independent pathway. Clin. Cancer Res., 2008, 14, 6228-6236.
27. Peer, D.; Karp, J.M.; Hong, S.; Farokhzad, O.C.; Margalit, R.; Langer, R. Nanocarriers as an emerging platform for cancer therapy. Nat. Nanotech., 2007, 2, 751-760.
28. Acharya, S.; Sahoo, S.K. PLGA nanoparticles containing various anticancer agents and tumor delivery by EPR effect. Adv. Drug Deliv. Rev., 2011, 63, 170-183
29. Mohanty, C.; Sahoo, S.K. The in vitro stability and in vivo pharmacokinetics of curcumin prepared as an aqueous nanoparticulate formulation. Biomaterials, 2010, 31, 6597-6611.
30. Shaikh, J.; Ankola, D.D.; Beniwal, V.; Singh. D.; Ravi Kumar, M.N.V. Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur. J. Pharm. Sci., 2009, 37, 223-230.
31. Liu, J.; Lihua, L.; Chuantong, L.; Dafeng, Z.; Siqian, W.; Zhennan, D.; Weiwei, L.; Haihong, X.; Bai, Q.; Jianfeng. M. Preparation and characterization of curcumin nanoparticles for improvement of cellular uptake. Carbohydr. Polym., 2012, 90, 16-22.
32. Yallapu, M.M.; Khan, S.; Maher, D.M.; Ebeling, M.C.; Sundram, V.; Chauhan, N.; Ganju, A.; Balakrishna, S.; Gupta, B.K.; Zafar, N.; Jaggi, M.; Chauhan, S.C. Anti cancer activity of curcumin loaded nanoparticles in prostate cancer. Biomaterials, 2014, 35, 8635-8648.
33. Zhou, N.; Zan, X.; Wang, Z.; Wu, H.; Yin, D.; Liao, C.; Wan Y. Galactosylated chitosan-polycaprolactone nanoparticles for hepatocyte-targeted delivery of curcumin. Carbohydr. Polym., 2013, 94, 420-429.
34. Lee, K.Y.; Mooney, D.J. Alginate: properties and biomedical applications. Prog. Polym. Sci., 2012, 37, 106-126.
35. Pillay, V.; Fassihi, R. in vitro release modulation from cross linked pellets for site-specific drug delivery to the gastrointestinal tract I. Comparison of pH-responsive drug release and associated kinetics. J. Control. Release, 1999, 59, 229-242.
36. Pillay V.; Fassihi, R. in vitro release modulation from cross linked pellets for site-specific drug delivery to the gastrointestinal tract II. Physicochemical characterization of calcium-alginate, calciumpectinate and calcium-alginate-pectinate pellets. J. Control. Release, 1999, 59, 243-256.
37. Joshi, A.; Solanki, S.; Chaudhari, R.; Bahadur, D.; Aslam, M.; Srivastava, R. Multifunctional alginate microspheres for biosensing, drug delivery and magnetic resonance imaging. Acta Biomater., 2011, 7, 3955-3963.
38. Mobus, K.; Siepmann, J.; Bodmeir, R. Zinc-alginate microparticles for controlled pulmonary delivery of proteins prepared by spraydrying. Eur. J. Pharm. Biopharm., 2012, 81, 121-130.
39. Nograles, N.; Abdullah, S.; Shamsudin, M.N.; Bella, N.; Rosli, R. Formation and characterization of pDNA loaded alginate microspheres for oral administration in mice. J. Biosci. Bioeng., 2012, 113, 133-140.
40. Taha, M.O.; Nasser, W.; Ardakani, A.; Alkhatib, H.S. Sodium lauryl sulfate impedes drug release from zinc-cross linked alginate beads: switching from enteric coating release into biphasic profile. Int. J. Pharm., 2008, 350, 291-300.
41. Nokhodchi, A; Tailor, A. In situ cross linking of sodium alginate with calcium and aluminum ions to sustain the release of theophylline from polymeric matrices. FARMACO., 2004, 59, 999-1004.
42. Pelletier, S.; Hubert, P.; Lapicque, F.; Payan, E.; Dellacherie, E. Amphiphilic derivatives of sodium alginate and hyaluronate: synthesis and physico-chemical properties of aqueous dilute solutions. Carbohydr. Polym., 2000, 43, 343-349.
43. Yang, L.; Zhang, B.; Wen, L.; Liang, Q.; Zhang, L.M. Amphiphilic cholesteryl grafted sodium alginate derivative: synthesis and self assembly in aqueous solution. Carbohydr. Polym., 2007, 68, 218-225.
44. Colinet, I.; Dulong, V.; Hamaide, T.; Le Cerf, D.; Picton, L. New amphiphilic modified Polysaccharides with original solution behavior in salt media. Carbohydr. Polym., 2009, 75, 454-462.
45. Colinet, I.; Dulong, V.; Mocanu, G.; Picton, L.; Le Cerf, D. New amphiphilic and pH-sensitive hydrogel for controlled release of a model poorly water-soluble drug. Eur. J. Pharm. Biopharm., 2009, 73, 345-350.
46. Aburto, J.; Alric, I.; Borredon, E.; Cedex, T. Preparation of long chain esters of starch using fatty acid chlorides in the absence of an organic solvent. Starch/Staerke., 1999, 51, 132-135.
47. Shigemasa, Y.; Matsuura, H.; Sashiwa, H.; Saimoto, H. Evaluation of different absorbance ratios from infrared spectroscopy for ana lyzing the degree of deacetylation in Chitin. Intl. J. Biol. Macromol., 1996, 18, 237-242.
48. Sashiwa, H.; Shigemasa, Y. Chemical modification of chitin and chitosan 2: preparation and water soluble property of N-acylated or N-alkylated partially deacetylated chitins. Carbohydr. Polym., 1999, 39, 127-138.
49. Liu, C.G.; Desai, K.G.; Chen, X.G.; Park, H.J. Linolenic acidmodified chitosan for formation of self-assembled nanoparticles, J. Agric. Food Chem., 2005, 53, 437-441.
50. Amiji, M.M. Pyrene florescence study of chitosan self-association in aqueous solution. Carbohydr. Polym., 1995, 26, 211-213.
51. Lee, H.; Lee, K.; Park, T.G. Hyaluronic acid-paclitaxel conjugate micelles synthesis, characterization and antitumor activity. Bioconj. Chem., 2008, 19, 1319-1325.
52. Magny, I.B.; Iliopolous, R.; Zana, R.; Audebert, R. Mixed micelles formed by cationic surfactants and anionic hydrophobically modified polyelectrolytes. Langmuir, 1994, 10, 3180-3187.
53. kalyanasundaram, K.; Thomas, J.K. Raman spectroscopy of uncomplexed valinomycin. 2. Nonpolar and polar solution. J. Am. Chem. Soc., 1977, 99, 2039-2040.
54. Gessner, A.; Waicza, R.; Lieske, A.; Paulke, B.R.; Mader, K.; Muller, R.H. Nanoparticles with decreasing surface hydrophobicities: Influence on plasma protein adsorption. Int. J. Pharm., 2000, 196, 245-249.
55. Sun, J.; Chao, B.; Chan, H.M.; Sun, S.; Zhang, Q.; Zheng,Y. Curcumin-loaded solid lipid nanoparticles have Prolonged in vitro antitumor activity, cellular uptake, and improved in vivo bioavailability. Colloids Surf. B: Biointerfaces, 2013, 111, 376-375.
56. Ghosh, D.; Choudhury, S.T.; Ghosh, S; Mandal, A.K.; Sarkar, S.; Ghosh, A.; Saha, K.D. Nanocapsulated curcumin: oral chemopreventive formulation against diethylnitrosamine induced hepatocellular carcinoma in rat. Chem. Biol. Interact., 2012, 195, 206-214.
57. Anand, P.; Kunnumakkara, A.B.; Newman, R.A.; Aggarwal, B.B. Bioavailability of curcumin: problems and promises. Mol. Pharmacol., 2007, 4, 807-818.
58. Anitha, A.; Deepagan, V.G.; Divya Rani, V.V.; Menon, D.; Nair, S.V.; Jayakumar, R. Preparation, characterization, in vitro drug release and biological studies of curcumin loaded dextran sulphate chitosan nanoparticles. Carbohydr. Polym., 2011, 84, 1158-1164
59. Yu, H.L.; Huang, Q.R. Enhanced in vitro anti-cancer activity of curcumin encapsulated in hydrophobically modified starch. Food Chem., 2010, 119, 669-674.
60. Letchford, k.; Liggins, R.; Burt, H. Solubilization of hydrophobic drugs by methoxy poly (ethylene glycol)-block-polycaprolactone diblock copolymer micelles: theoretical and experimental data and correlations. J. Pharm. Sci., 2007, 97, 1179-1190.
61. Dey, S.; Sreenivasan, K. Conjugation of curcumin onto alginate enhances aqueous solubility and stability of curcumin. Carbohydr. Polym., 2014, 99, 499-507.
62. Liu, L.; Li, C.; Li, X.; Yuan, Z.; An, Y.; He, B. J. Biodegradable polylactide/poly(ethylene glycol)/polylactide triblock copolymer micelles as anticancer drug carriers. J. Appl. Polym. Sci., 2001, 80, 1976-1982.
63. Ruan, G.; Feng, S.S. Preparation and characterization of poly (lactic acid)-poly (ethylene glycol)-poly (lactic acid) (PLA-PEG-PLA) microspheres for controlled release of paclitaxel. Biomaterials 2003, 24, 5037-5044.
64. Muller, R.H.; Mader, K.; Gohla, S. Solid lipid nanoparticles (SLN) for controlled drug delivery-a review of the state of the art. Eur. J. Pharm. Biopharm., 2000, 50, 161-177.