Development and characterization of co-loaded curcumin/triazole-halloysite systems and evaluation of their potential anticancer activity

International Journal of Pharmaceutics

Volumn 475, Issue 1, 2014, Pages 613-623

  Riela, Serena ^a   Massaro, Marina ^a   Colletti, Carmelo G ^a   Bommarito, Alessandra ^a   Giordano, Carla ^a   Milioto, Stefana ^a   Noto, Renato ^a   Poma, Paola ^a   Lazzara, Giuseppe ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

Curcumin; Drug carrier; Halloysite nanotubes; In vitro anticancer activity; Triazolium salts

Indexed keywords

ALUMINUM SILICATE; ANTINEOPLASTIC AGENT; ASCORBIC ACID; CLAY; CURCUMIN; DRUG ADMINISTRATION; DRUG CARRIER; NANOTUBE; NITROGEN; ORGANIC SOLVENT; PHARMACOLOGY; TRIAZOLE DERIVATIVE;

ADSORPTION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CALIBRATION; CANCER CELL LINE; CELL GROWTH ASSAY; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL REACTION; CHEMISTRY; COLORIMETRY; CONTROLLED STUDY; CYTOTOXICITY; DISPERSION; DRUG INCOMPATIBILITY; DRUG RELEASE; HUMAN; HUMAN CELL; IN VITRO STUDY; INTERNALIZATION; LIGHT SCATTERING; MICROPLATE READER; MOLECULAR WEIGHT; MTT ASSAY; PAPILLARY THYROID CARCINOMA CELL; PHARMACEUTICS; REFRACTION INDEX; ROOM TEMPERATURE; SCANNING ELECTRON MICROSCOPY; SOLUBILITY; THERMOGRAVIMETRY; THYROID CARCINOMA; TUMOR CELL LINE; ULTRASOUND; ULTRAVIOLET SPECTROSCOPY; VOLATILIZATION;

ADMINISTRATION AND DOSAGE; ALUMINUM SILICATES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CHEMISTRY; CURCUMIN; DRUG CARRIERS; DRUG INCOMPATIBILITY; DRUG LIBERATION; HUMANS; MICROSCOPY, ELECTRON, SCANNING; NANOTUBES; PHARMACOLOGY; TECHNOLOGY, PHARMACEUTICAL; THERMOGRAVIMETRY; TRIAZOLES;

EID: 84908120565     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2014.09.019     Document Type: Article

References (58)

1. E. Abdullayev, R.R. Price, D. Shchukin, and Y.M. Lvov Halloysite tubes as nanocontainers for anticorrosion coating with benzotriazole Appl. Mater. Interfaces 1 2009 1437 1443
2. S. Aggarwal, H. Ichikawa, Y. Takada, S.K. Sandur, S. Shishodia, and B.B. Aggarwal Curcumin downregulates expression of cell proliferation: antiapoptotic and metastatic gene products through suppression of IκBa kinase and AKT activation Mol. Pharmacol. 69 2008 195 206
3. I.A. Al-Masoudi, Y.A. Al-Soud, N.J. Al-Salihi, and N.A. Al-Masoudi 1,2,4-Triazoles: synthetic approaches and pharmacological importance Chem. Heterocycl. Compd. 42 2006 1377 1403
4. P. Anand, A.B. Kunnumakkara, R.A. Newman, and B.B. Aggarwal Bioavailability of curcumin: problems and promises Mol. Pharm. 4 2007 807 818
5. G.B. Bagihalli, P.G. Avaji, S.A. Patil, and P.S. Badami Eur. J. Med. Chem. 43 2008 2639 2649
6. T.F. Bates, F.A. Hildebrand, and A. Swineford Morphology and structure of endellite and halloysite Am. Mineral. 35 1950 463 484
7. M. Bernabé-Pineda, M.T. Ramìrez-Silva, M. Romero-Romo, E. Gonzàlez-Vergara, and A. Rojas-Hernàndez Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition Spectrochim. Acta A: Mol. Biomol. Spectrosc. 60 2004 1091 1097
8. G. Cavallaro, G. Lazzara, and S. Milioto Dispersions of nanoclays of different shapes into aqueous and solid biopolymeric matrices: extended physicochemical study Langmuir 27 2011 1158 1167
9. G. Cavallaro, G. Lazzara, and S. Milioto Exploitong the colloidal stability and solubilization ability of clay nanotubes/ionic surfactant hybrid nanomaterials J. Phys. Chem. C 116 2012 21932 21938
10. H.-W. Chen, J.-Y. Lee, J.-Y. Huang, C.-C. Wang, W.-J. Chen, S.-F. Su, C.-W. Huang, C.-C. Ho, J.J.W. Chen, M.-F. Tsai, S.-L. Yu, and P.-C. Yang Curcumin inhibits lung cancer cell invasion and metastasis through the tumor suppressor HLJ1 Cancer Res. 68 2008 7428 7438
11. H. Choi, Y.S. Chun, S.W. Kim, M.S. Kim, and J.W. Park Curcumin inhibits hypoxia-inducible factor-1 by degrading aryl hydrocarbon receptor nuclear translocator: a mechanism of tumor growth inhibition Mol. Pharmacol. 70 2006 1664 1671
12. S. Dash, P.N. Murthy, L. Nath, and P. Chowdury Kinetic modelling on drug release from controlled drug delivery systems Acta Pol. Pharm.-Drug Res. 67 2010 217 223
13. M. Du, B. Guo, and D. Jia Newly emerging applications of halloysite nanotubes: a review Polym. Int. 59 2010 574 582
14. M. Du, B. Guo, and D. Jia Thermal stability and flame retardant effects of halloysite nanotubes on poly(propylene) Eur. Polym. J. 42 2006 1362 1369
15. J. Duan, Y. Zhang, S. Han, Y. Chen, B. Li, A. Liao, W. Chen, X. Deng, J. Zhao, and B. Huang Synthesis and in vitro/in vivo anti-cancer evaluation of curcumin-loaded chitosan/poly(butyl cyanoacrylate) nanoparticles Int. J. Pharm. 400 2010 211 220
16. S.S. Feng Nanoparticles of biodegradable polymers for new-concept chemotherapy Expert Rev. Med. Devices 1 2004 115 125
17. M.G. Finn, and V.V. Fokin Click chemistry: function follows form Chem. Soc. Rev. 39 2010 1231 1232
18. S. Ganta, and M. Amiji Co-administration of paclitaxel and curcumin in nanoemulsion formulations to overcome multidrug resistance in tumor cells Mol. Pharm. 6 2009 928 939
19. H. Guo-Qiang, H. Li-Li, X. Song-Qiang, and H. Wen-Long Design: synthesis and antitumor activity of asymmetric bis(s-triazole Schiff-base)s bearing functionalized side-chain Chin. J. Chem. 26 2008 1145 1149
20. S. Horiuchi, T. Hanada, M. Ebisawa, Y. Matsuda, M. Kobayashi, and A. Takahara Contamination-free transmission electron microscopy for high-resolution carbon elemental mapping of polymers ACS Nano 3 2009 1297 1304
21. R. Huisgen 1,3-Dipolar cycloadditions. Past and future Angew. Chem. Int. Ed. Engl. 2 1963 565 598
22. J.Y. Jin, L.X. Zhang, A.J. Zhang, X.X. Lei, and J.H. Zhu Synthesis and biological activity of some novel derivatives of 4-amino-3-(d-galactopentitol-1-yl)-5-mercapto-1,2,4-triazole Molecules 12 2007 1596 1605
23. Karl, A., Buder, W., 1983. US Patent 4401598.
24. T.H. Kim, H.H. Jiang, Y.S. Youn, C.W. Park, K.K. Tak, S. Lee, H. Kim, S. Jon, X. Chen, and K.C. Lee Preparation and characterization of water soluble albumin-bound curcumin nanoparticles Int. J. Pharm. 403 2011 285 291
25. R.W. Korsmeyer, R. Gurny, E. Doelker, P. Buri, and N.A. Peppas Mechanisms of solute release from porous hydrophilic polymers Int. J. Pharm. 15 1983 25 35
26. B.T. Kurien, A. Singh, H. Matsumoto, and R.H. Scofield Improving the solubility and pharmacological efficacy of curcumin by heat treatment Assay Drug Dev. Technol. 5 2007 567 576
27. X. Lai, M. Agarwal, Y.M. Lvov, C. Pachpande, K. Varahramyan, and F.A. Witzmann Proteomic profiling of halloysite clay nanotube exposure in intestinal cell co-culture J. Appl. Toxicol. 33 2013 1316 1329
28. C. Li, J. Liu, X. Qu, B. Guo, and Z. Yang Polymer-modified halloysite composite nanotubes J. Appl. Polym. Sci. 110 2008 3638 3643
29. Y.G. Lin, A.B. Kunnumakkara, A. Nair, W.M. Merritt, L.Y. Han, G.N. Armaiz-Pena, A.A. Kamat, W.A. Spannuth, D.M. Gershenson, S.K. Lutgendorf, B.B. Aggarwal, and A.K. Sood Curcumin inhibits tumor growth and angiogenesis in ovarian carcinoma by targeting the nuclear factor-κB pathway Clin. Cancer Res. 13 2007 3423 3430
30. Y. Lvov, R.R. Price, B. Gaber, and I. Ichinose Thin film nanofabrication via layer-by-layer adsorption of tubule halloysite spherical silica, proteins and polycations Colloid Surf. A-Physicochem. Eng. Asp. 198 2002 375 382
31. R. Matsuno, H. Otsuka, and A. Takahara Polystyrene-grafted titanium oxide nanoparticles prepared through surface-initiated nitroxide-mediated radical polymerization and their application to polymer hybrid thin films Soft Matter 2 2006 415 421
32. W. Ma, H. Otsuka, and A. Takahara Poly(methyl methacrylate) grafted imogolite nanotubes prepared through surface-initiated ARGET ATRP Chem. Commun. 47 2011 5813 5815
33. W. Ma, W.O. Yah, H. Otsuka, and A. Takahara Application of imogolite clay nanotubes in organic-inorganic nanohybrid materials J. Mater. Chem. 22 2012 11887 11892
34. J. Madejova, and P. Komadel Baseline studies of the clay mineral society source clays: infrared methods Clay Clay Miner. 49 2001 410 432
35. M. Massaro, S. Riela, G. Cavallaro, M. Gruttadauria, S. Milioto, R. Noto, and G. Lazzara Eco-friendly functionalization of natural halloysite clay nanotube with ionic liquids by microwave irradiation for Suzuki coupling reaction J. Organomet. Chem. 749 2014 410 417
36. M. Massaro, S. Riela, G. Lazzara, M. Gruttadauria, S. Milioto, and R. Noto Green conditions for the Suzuki reaction using microwave irradiation and a new HNT supported ionic liquid-like phase (HNT-SILLP) catalyst Appl. Organomet. Chem. 28 2014 234 238
37. R. Matsuno, K. Yamamoto, H. Otsuka, and A. Takahara Polystirene-grafted magnetite nanoparticles prepared through surface-initiated nitroxyl-mediated radical polymerization Chem. Mater. 15 2003 3 5
38. M. Meldal, and C.W. Tornoe Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 108 2008 2952
39. R. Noël, X. Song, R. Jiang, M.J. Chalmers, P.R. Griffin, and T.M. Kamenecka Efficient methodology for the synthesis of 3-amino-1,2,4-triazoles J. Org. Chem. 74 2009 7595 7597
40. M. Notarbartolo, P. Poma, D. Perri, L. Dusonchet, M. Cervello, and N. D'Alessandro Antitumor effects of curcumin alone or in combination with cisplatin or doxorubicin, on human hepatic cancer cells. Analysis of their possible relationship to changes in NF-kB activation levels and in IAP gene expression Cancer Lett. 224 2005 53 65
41. N. Pokhodylo, O. Shyyka, and V. Matiychuck Synthesis of 1,2,3-triazole derivatives and evaluation of their anticancer activity Sci. Pharm. 81 2013 663 676
42. R.R. Price, B.B. Gaber, and Y.M. Lvov In-vitro release characteristics of tetracycline HCl, khellin and nicotinamide adenine dineculeotide from halloysite: a cylindrical mineral J. Microencapsul. 18 2001 713 722
43. Z. Rezaei, S. Khabnadideh, K. Pakshir, Z. Hossaini, F. Amiri, and E. Assadpour Design synthesis, and antifungal activity of triazole and benzotriazole derivatives Eur. J. Med. Chem. 44 2009 3064 3067
44. L. Shargel, and A. Yu Applied Biopharmaceutics and Pharmacokinetics 2012 McGraw Hill New York
45. D.B. Shenoy, and M.M. Amiji Poly(ethylene oxide)-modified poly(varepsilon-caprolactone) nanoparticles for targeted delivery of tamoxifen in breast cancer Int. J. Pharm. 293 2005 261 270
46. K. Singh, D.P. Singh, M.S. Barwa, P. Tyagi, and Y. Mirza Antibacterial Co(II), Ni(II), Cu(II) and Zn(II) complexes of Schiff bases derived from fluorobenzaldehyde and triazoles J. Enzyme Inhib. Med. Chem. 21 2006 557 562
47. H. Tang, C.J. Murphy, B. Zhang, Y. Shen, M. Sui, E.A. Van Kirk, X. Feng, and W.J. Murdoch Amphiphilic curcumin conjugate-forming nanoparticles as anticancer prodrug and drug carriers: in vitro and in vivo effects Nanomedicine 5 2010 855 865
48. Y. Terayama, M. Kikuchi, M. Kobayashi, and A. Takahara Well-defined poly(sulfobetaine) brushes prepared by surface-initiated ATRP using a fluoroalcohol and ionic liquids as the solvents Macromolecules 44 2010 104 111
49. J.W. Thompson, J.W. Kaiser, and J.W. Jorgenson Viscosity measurements of methanol-water and acetonitrile-water mixtures at pressures up to 3500 using a novel capillary time-of-flight viscometer J. Chromatogr. A 1134 2006 201 209
50. I.K. Tonle, E. Ngameni, D. Njopwouo, C. Carteret, and A. Walcarius Functionalization of natural smectite-type clays by grafting with organosilane: physico-chemical characterization and application to mercury(II) uptake Phys. Chem. Chem. Phys. 5 2003 4951 4961
51. E.F. Vansant, P. Van Der Voort, and K.C. Vrancken Characterization and Chemical Modification of the Silica Surface 93 1995 Elsevier New York
52. N.G. Veerabadran, R.R. Price, and Y.M. Lvov Clay nanotubes for encapsulation and sustained release of drugs Nano 2 2007 115 120
53. V. Vergaro, E. Abdullayev, Y.M. Lvov, A. Zeitoun, R. Cingolani, R. Rinaldi, and S. Leporatti Cytocompatibility and uptake of halloysite clay nanotubes Biomacromolecules 11 2010 820 826
54. L.-P. Wang, Y.-P. Wang, X.-W. Pei, and B. Peng Synthesis of poly(methyl methacrylate)-b-poly(N-isopropylacrylamide) (PMMA-b-PNIPAM) amphiphilic diblock copolymer brushes on halloysite substrate via reverse ATRP React. Funct. Polym. 68 2008 649 655
55. L. Wang, X. Xu, Y. Zhang, Y. Zhang, Y. Zhu, J. Shi, Y. Sun, and Q. Huang Encapsulation of curcumin within poly(amidoamine) dendrimers for delivery to cancer cells J. Mater. Sci. Mater. Med. 24 2013 2137 2144
56. L.D. White, and C.P. Tripp An infrared study of the amine-catalyzed reaction of methoxymethylsilanes with silica J. Colloid Interface Sci. 227 2000 237 243
57. P. Yuan, P.D. Southon, Z. Liu, M.E.R. Green, J.M. Hook, S.J. Antill, and C.J. Kepert Functionalization of halloysite clay nanotubes by grafting with γ-aminopropyltriethoxysilane J. Phys. Chem. C 112 2008 15742 15751
58. S. Zhang, J. Li, G. Lykotrafitis, G. Bao, and S. Suresh Size-dependent endocytosis of nanoparticles Adv. Mater. 21 2009 419 424