Curcumin-loaded guanidine functionalized PEGylated I3ad mesoporous silica nanoparticles KIT-6: Practical strategy for the breast cancer therapy

European Journal of Medicinal Chemistry

Volumn 83, Issue , 2014, Pages 646-654

  Ma'Mani, Leila ^a   Nikzad, Safoora ^b   Kheiri Manjili, Hamidreza ^b   Al Musawi, Sharafaldin ^b   Saeedi, Mina ^a   Askarlou, Sonia ^c   Foroumadi, Alireza ^a   Shafiee, Abbas ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

^c SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Breast cancer; Curcumin; Drug delivery system; Guanidine functionalized PEGylated mesoporous silica nanoparticles; I3ad mesoporous silica nanoparticle KIT 6; pH sensitive

Indexed keywords

CURCUMIN; GUANIDINE; KIT 6; MACROGOL; NANOPARTICLE; SILICON DIOXIDE; UNCLASSIFIED DRUG; PEGYLATED I3AD MESOPOROUS SILICA NANOPARTICLE KIT 6; POLYMER; SILICA NANOPARTICLE; DRUG CARRIER; MACROGOL DERIVATIVE;

ADSORPTION; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST ADENOCARCINOMA; BREAST CANCER; BREAST EPITHELIUM; CANCER CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; HUMAN; HUMAN CELL; PARTICLE SIZE; PH; SCANNING ELECTRON MICROSCOPY; SUSTAINED DRUG RELEASE; THERMOGRAVIMETRY; X RAY POWDER DIFFRACTION; ANIMAL CELL; APOPTOSIS; BREAST CANCER CELL LINE; DRUG LOADING CAPACITY; DRUG SYNTHESIS; DYNAMIC LIGHT SCATTERING; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; HYDROGEN BOND; INTERNALIZATION; ISOELECTRIC POINT; LIGHT SCATTERING; N2 ADSORPTION DESORPTION ANALYSIS; NONHUMAN; PHARMACOLOGICAL PARAMETERS; PORE SIZE; PORE VOLUME; SURFACE CHARGE; SURFACE PROPERTY; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL; ANIMAL; BREAST NEOPLASMS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECTS; MCF 7 CELL LINE; METABOLISM; MOUSE; PATHOLOGY; POROSITY; TRANSPORT AT THE CELLULAR LEVEL;

ANIMALS; APOPTOSIS; BIOLOGICAL TRANSPORT; BREAST NEOPLASMS; CURCUMIN; DRUG CARRIERS; GUANIDINE; HUMANS; MCF-7 CELLS; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NANOPARTICLES; POLYETHYLENE GLYCOLS; POROSITY; SILICON DIOXIDE;

EID: 84903958725     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.069     Document Type: Article

References (51)

1. R.K. Maheshwari, A.K. Singh, J. Gaddipati, and R.C. Srimal Multiple biological activities of curcumin: a short review Life Sci. 78 2006 2081 2087
2. H.P. Ammon, and M.A. Wahl Pharmacology of Curcuma longa Planta Med. 57 1991 1 7
3. S.C. Gupta, S. Patchva, W. Koh, and B.B. Aggarwal Discovery of curcumin, a component of golden spice, and its miraculous biological activities Clin. Exp. Pharmacol. Physiol. 39 2012 283 299
4. T. Ak, and İ. Gülçin Antioxidant and radical scavenging properties of curcumin Chem. Biol. Interact. 174 2008 27 37
5. O.P. Sharma Antioxidant activity of curcumin and related compounds Biochem. Pharmacol. 25 1976 1811 1812
6. P. Verderio, P. Bonetti, M. Colombo, L. Pandolfi, and D. Prosperi Intracellular drug release from curcumin-loaded PLGA nanoparticles induces G2/M block in breast cancer cells Biomacromolecules 14 2013 672 682
7. S. Bhattacharyya, D. Mandal, G.S. Sen, S. Pal, S. Banerjee, L. Lahiry, J.H. Finke, C.S. Tannebaum, T. Das, and G. Sa Tumor-induced oxidative stress perturbs nuclear factor-κB activity-augmenting tumor necrosis factor-α-mediated T-cell death: Protection by curcumin Cancer Res. 67 2007 362 370 (Pubitemid 46142796)
8. S.K. Sandur, M.K. Pandey, B. Sung, K.S. Ahn, A. Murakami, G. Sethi, P. Limtrakul, V. Madmaev, and B.B. Aggarwal Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism Carcinogenesis 28 2007 1765 1773 (Pubitemid 47289040)
9. R. De, P. Kundu, S. Swarnakar, T. Ramamurthy, A. Chowdhury, G.B. Nair, and A.K. Mukhopadhyay Antimicrobial activity of curcumin against helicobacter pylori isolates from India and during infections in mice Antimicrob. Agents Chemother. 53 2009 1592 1597
10. S.-H. Mun, D.-K. Joung, Y.-S. Kim, O.-H. Kang, S.-B. Kim, Y.-S. Seo, Y.-C. Kim, D.-S. Lee, D.-W. Shin, K.-T. Kweon, and D.-Y. Kwon Synergistic antibacterial effect of curcumin against methicillin-resistant Staphylococcus aureus Phytomedicine 20 2013 714 718
11. C.V.B. Martins, D.L. da Silva, A.T.M. Neres, T.F.F. Magalhães, and G.A. Watanabe Curcumin as a promising antifungal of clinical interest J. Antimicrob. Chemother. 63 2009 337 339
12. O.A.K. Khalil, O.M.M. de Faria Oliveira, J.C.R. Vellosa, A.U. de Quadros, L.M. Dalposso, T.K. Karam, R.M. Mainardes, and N.M. Khalil Curcumin antifungal and antioxidant activities are increased in the presence of ascorbic acid Food Chem. 133 2012 1001 1005
13. V. Ravindranath, and N. Chandrasekhara Absorption and tissue distribution of curcumin in rats Toxicology 16 1980 259 265 (Pubitemid 10056763)
14. V. Ravindranath, and N. Chandrasekhara In vitro studies on the intestinal absorption of curcumin in rats Toxicology 20 1981 251 257 (Pubitemid 11117911)
15. V. Ravindranath, and N. Chandrasekhara Metabolism of curcumin-studies with [3H]curcumin Toxicology 22 1981 337 344
16. S.S. Bansal, M. Goel, F. Aqil, M.V. Vadhanam, and R.C. Gupta Advanced drug delivery systems of curcumin for cancer chemoprevention Cancer Prev. Res. 4 2011 1158 1171
17. A.K. Renfrew, N.S. Bryce, and T.W. Hambley Delivery and release of curcumin by a hypoxia-activated cobalt chaperone: a XANES and FLIM study Chem. Sci. 4 2013 3731 3739
18. B.B. Aggarwal, C. Sundaram, N. Malani, and H. Ichikawa Curcumin: the Indian solid gold Adv. Exp. Med. Biol. 595 2007 1 75
19. B.B. Aggarwal, A. Kumar, and A.C. Bharti Anticancer potential of curcumin: preclinical and clinical studies Anticancer Res. 23 2003 363 398 (Pubitemid 36361976)
20. F. Tang, L. Li, and D. Chen Mesoporous silica nanoparticles: synthesis, biocompatibility and drug delivery Adv. Mater. 24 2012 1504 1534
21. I.I. Slowing, B.G. Trewyn, S. Giri, and V.S.-Y. Lin Mesoporous silica nanoparticles for drug delivery and biosensing applications Adv. Funct. Mater. 17 2007 1225 1236 (Pubitemid 46847636)
22. T. Yanagisawa, T. Shimizu, K. Kuroda, and C. Kato The preparation of alkyltrimethylammonium-kanemite complexes and their conversion to microporous materials Bull. Chem. Soc. Jpn. 63 1990 988 992 (Pubitemid 20314864)
23. J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.-W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCullen, J.B. Higgins, and J.L. Schlenkert A new family of mesoporous molecular sieves prepared with liquid crystal templates J. Am. Chem. Soc. 114 1992 10834 10843
24. C.-H. Lee, S.-H. Cheng, Y.-J. Wang, Y.-C. Chen, N.-T. Chen, J. Souris, C.-T. Chen, C.-Y. Mou, C.-S. Yang, and L.-W. Lo Near-infrared mesoporous silica nanoparticles for optical imaging: characterization and in vivo biodistribution Adv. Funct. Mater. 19 2009 215 222
25. I.I. Slowing, C.-W. Wu, J.L. Vivero-Escoto, and V.S.-Y. Lin Mesoporous silica nanoparticles for reducing hemolytic activity towards mammalian red blood cells Small 5 2009 57 62
26. K.M.L. Taylor, J.S. Kim, W.J. Rieter, H. An, W. Lin, and W. Lin Mesoporous silica nanospheres as highly efficient MRI contrast agents J. Am. Chem. Soc. 130 2008 2154 2155 (Pubitemid 351287981)
27. S.-H. Wu, Y.-S. Lin, Y. Hung, Y.-H. Chou, Y.-H. Hsu, C. Chang, and C.-Y. Mou Multifunctional mesoporous silica nanoparticles for intracellular labeling and animal magnetic resonance imaging studies ChemBioChem 9 2008 53 57
28. Y. Cho, R. Shi, R.B. Borgens, and A. Ivanisevic Functionalized mesoporous silica nanoparticle-based drug delivery system to rescue acrolein-mediated cell death Nanomedicine 3 2009 507 519
29. S.-H. Kim, J.-H. Park, and C.-Y. Lee Surface-functionalized mesoporous silica nanoparticles as sorbents for BTEX J. Porous Mater. 20 2013 1087 1093
30. X. Liu, B. Tian, C. Yu, F. Gao, S. Xie, B. Tu, R. Che, L.-M. Peng, and D. Zhao Room-temperature synthesis in acidic media of large-pore three-dimensional bicontinuous mesoporous silica with Ia3d symmetry Angew. Chem. Int. Ed. 41 2002 3876 3878 (Pubitemid 35278026)
31. F. Kleitz, S.H. Choi, and R. Ryoo Cubic Ia3d large mesoporous silica: synthesis and replication to platinum nanowires, carbon nanorods and carbon nanotubes Chem. Commun. 2003 2136 2137 (Pubitemid 37076083)
32. Y.-T. Chan, H.-P. Lin, C.-Y. Mou, and S.-T. Liu Ia3d cubic mesoporous silicas using EO17MA23 diblock copolymers made from ATRP Chem. Commun. 2002 2878 2879 (Pubitemid 35375725)
33. A. Vinu, N. Gokulakrishnan, V.V. Balasubramanian, S. Alam, M.P. Kapoor, K. Ariga, and T. Mori Three-dimensional ultralarge-pore Ia3d mesoporous silica with various pore diameters and their application in biomolecule immobilization Chem. Eur. J. 14 2008 11529 11538
34. H. Kouchakzadeh, S.A. Shojaosadati, A. Maqhsoudi, and E.V. Farahani Optimization of PEGylation conditions for BSA nanoparticles using response surface methodology AAPS PharmSciTech 11 2010 1206 1211
35. E.K.U. Larsen, T. Nielsen, T. Wittenborn, H. Birkedal, T. Vorup-Jensen, M.H. Jakobsen, L. Ostergaard, M.R. Horsman, F. Besenbacher, K.A. Howard, and J. Kjems Size-dependent accumulation of pegylated silane-coated magnetic iron oxide nanoparticles in murine tumors ACS Nano 3 2009 1947 1951
36. J. Park, P.M. Fong, J. Lu, K.S. Russell, C.J. Booth, W.M. Saltzman, and T.M. Fahmy PEGylated PLGA nanoparticles for the improved delivery of doxorubicin Nanomedicine 5 2009 410 418
37. A.-C. Faure, S. Dufort, V. Josserand, P. Perriat, J.-L. Coll, S. Roux, and O. Tillement Control of the in vivo biodistribution of hybrid nanoparticles with different poly(ethylene glycol) coatings Small 5 2009 2565 2575
38. C.S. Fishburn The pharmacology of PEGylation: balancing PD with PK to generate novel therapeutics J. Pharm. Sci. 97 2008 4167 4183
39. U.I. Tromsdorf, O.T. Bruns, S.C. Salmen, U. Beisiegel, and H. Weller A highly effective, nontoxic T1 MR contrast agent based on ultrasmall PEGylated iron oxide nanoparticles Nano Lett. 9 2009 4434 4440
40. A.S. Karakoti, S. Singh, A. Kumar, M. Malinska, S.V.N.T. Kuchibhatla, K. Wozniak, W.T. Self, and S. Seal PEGylated nanoceria as radical scavenger with tunable redox chemistry J. Am. Chem. Soc. 131 2009 14144 14145
41. B. Thierry, L. Zimmer, S. McNiven, K. Finnie, C. Barbé, and H.J. Griesser Electrostatic self-assembly of PEG copolymers onto porous silica nanoparticles Langmuir 24 2008 8143 8150
42. J. Yang, J. Lee, J. Kang, K. Lee, J.-S. Suh, H.-G. Yoon, Y.-M. Huh, and S. Haam Hollow silica nanocontainers as drug delivery vehicles Langmuir 24 2008 3417 3421 (Pubitemid 351549185)
43. Q. He, J. Zhang, J. Shi, Z. Zhu, L. Zhang, W. Bu, L. Guo, and Y. Chen The effect of PEGylation of mesoporous silica nanoparticles on nonspecific binding of serum proteins and cellular responses Biomaterials 31 2010 1085 1092
44. C.L. Lay, H.Q. Liu, D. Wu, and Y. Liu Poly(ethylene glycol)-graft-hollow silica vesicles for drug delivery Chem. Eur. J. 16 2010 3001 3004
45. 2 nanoparticles via bioinspired silification for magnetic resonance imaging Adv. Funct. Mater. 20 2010 722 731
46. M. Falahati, A.A. Saboury, L. Ma'mani, A. Shafiee, and H.A. Rafieepour The effect of functionalization of mesoporous silica nanoparticles on the interaction and stability of confined enzyme Int. J. Biol. Macromol. 50 2012 1048 1054
47. T.W. Kim, F. Kleitz, B. Paul, and R. Ryoo MCM-48-like large mesoporous silicas with tailored pore structure: facile synthesis domain in a ternary triblock copolymer-butanol-water system J. Am. Chem. Soc. 127 2005 7601 7610 (Pubitemid 40746046)
48. M. Falahati, L. Ma'mani, A.A. Saboury, A. Shafiee, A. Foroumadi, and A.R. Badiei Aminopropyl-functionalized cubic Ia3d mesoporous silica nanoparticle as an efficient support for immobilization of superoxide dismutase Biochim. Biophys. Acta 1814 2011 1195 1202
49. Y.L. Choi, J. Jaworski, M.L. Seo, S.J. Lee, and J.H. Jung Controlled release using mesoporous silica nanoparticles functionalized with 18-crown-6 derivative J. Mater. Chem. 21 2011 7882 7885
50. F.Q. Hu, G.F. Ren, H. Yuan, Y.Z. Du, and S. Zeng Shell cross-linked stearic acid grafted chitosan oligosaccharide self-aggregated micelles for controlled release of paclitaxel Colloids Surf. B. Biointerfaces 50 2006 97 103 (Pubitemid 43946659)
51. K. Buch, T. Peters, T. Nawroth, M. Sänger, H. Schmidberger, and P. Langguth Determination of cell survival after irradiation via clonogenic assay versus multiple MTT assay-A comparative study Radiat. Oncol. 9 2012 71