Curcumin loaded pH-sensitive hybrid lipid/block copolymer nanosized drug delivery systems

European Journal of Pharmaceutical Sciences

Volumn 78, Issue , 2015, Pages 67-78

  Jelezova, Ivelina ^a   Drakalska, Elena ^a   Momekova, Denitsa ^a   Shalimova, Natalia ^a   Momekov, Georgi ^a   Konstantinov, Spiro ^a   Rangelov, Stanislav ^b   Pispas, Stergios ^c  

^a MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

^b INSTITUTE OF POLYMERS   (Bulgaria)

^c THEORETICAL AND PHYSICAL CHEMISTRY INSTITUTE   (Greece)

Author keywords

Apoptosis; Curcumin; Inclusion complex; pH sensitive hybrid liposomes; Poly(isoprene b acrylic acid); Polyoxyethylated tert buthylcalix 4 arenes

Indexed keywords

CALCEIN; CASPASE 8; CASPASE 9; CHOLESTEROL; CISPLATIN; COPOLYMER; CURCUMIN; DIPALMITOYLPHOSPHATIDYLCHOLINE; DOXORUBICIN; DRUG CARRIER; LIPOSOME; POLY(ISOPRENE BETA ACRYLIC ACID); POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROCASPASE 9; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CALIXARENE; MACROGOL DERIVATIVE; NANOMATERIAL; PARA-TERT-BUTYLCALIX(4)ARENE;

APOPTOSIS; AQUEOUS SOLUTION; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG RELEASE; DRUG SOLUBILITY; HL 60 CELL LINE; IN VITRO STUDY; LIGHT SCATTERING; PH; PHOSPHOLIPID MEMBRANE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; ZETA POTENTIAL; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HUMAN;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CALIXARENES; CELL SURVIVAL; CHOLESTEROL; CURCUMIN; DRUG DELIVERY SYSTEMS; HL-60 CELLS; HUMANS; HYDROGEN-ION CONCENTRATION; LIPOSOMES; NANOSTRUCTURES; POLYETHYLENE GLYCOLS;

EID: 84936970983     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2015.07.005     Document Type: Article

References (68)

1. T. Alaikov, S.M. Konstantinov, T. Tzanova, K. Dinev, M. Topashka-Ancheva, and M.R. Berger Antineoplastic and anticlastogenic properties of curcumin Ann. N.Y. Acad. Sci. 1095 2007 355 370
2. Y. Alvarado, and F.J. Giles Ras as a therapeutic target in hematologic malignancies Exp. Opin. Emerg. Drugs 12 2007 271 284
3. R.J. Anto, A. Mukhopadhyay, K. Denning, and B.B. Aggarwal Curcumin (diferuloylmethane) induces apoptosis through activation of caspase-8, BID cleavage and cytochrome c release: its suppression by ectopic expression of Bcl-2 and Bcl-xl Carcinogenesis 23 2002 143 150
4. N. Apiratikul, T. Penglong, K. Suksen, S. Svasti, A. Chairoungdua, and B. Yingyongnarongkula In vitro delivery of curcumin with cholesterol-based cationic liposomes Bioorg. Khim. 39 2013 497 503
5. 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. (Phila.) 4 2011 1158 1171
6. J. Barry, M. Fritz, J.R. Brender, P.E. Smith, D.K. Lee, and A. Ramamoorthy Determining the effects of lipophilic drugs on membrane structure by solid-state NMR spectroscopy: the case of the antioxidant curcumin J. Am. Chem. Soc. 131 2009 4490 4498
7. S. Barui, S. Saha, G. Mondal, S. Haseena, and A. Chaudhuri Simultaneous delivery of doxorubicin and curcumin encapsulated in liposomes of pegylated RGDK-lipopeptide to tumor vasculature Biomaterials 35 2014 1643 1656
8. K. Berginc, S. Suljakovic, N. Skalko-Basnet, and A. Kristl Mucoadhesive liposomes as new formulation for vaginal delivery of curcumin Eur. J. Pharm. Biopharm. 2014 10.1016/j.ejpb.2014.02.006 pii: S0939-6411(14)00051-4
9. J.A. Bush, K.J. Cheung Jr., and G. Li Curcumin induces apoptosis in human melanoma cells through a Fas receptor/caspase-8 pathway independent of p53 Exp. Cell Res. 271 2001 305 314
10. Z. Chang, J. Xing, and X. Yu Curcumin induces osteosarcoma MG63 cells apoptosis via ROS/Cyto-C/Caspase-3 pathway Tumour Biol. 35 2014 753 758
11. H. Chen, J. Wu, M. Sun, C. Guo, A. Yu, F. Cao, L. Zhao, Q. Tan, and G. Zhai N-trimethyl chitosan chloride-coated liposomes for the oral delivery of curcumin J. Liposome Res. 22 2012 100 109
12. Chen, P., Li, J., Jiang, H.G., Lan, T., Chen, Y.C., 2014. Curcumin reverses cisplatin resistance in cisplatin-resistant lung caner cells by inhibiting FA/BRCA pathway. Tumour Biol.
13. A.L. Cheng, C.H. Hsu, J.K. Lin, M.M. Hsu, Y.F. Ho, T.S. Shen, J.Y. Ko, J.T. Lin, B.R. Lin, W. Ming-Shiang, H.S. Yu, S.H. Jee, G.S. Chen, T.M. Chen, C.A. Chen, M.K. Lai, Y.S. Pu, M.H. Pan, Y.J. Wang, C.C. Tsai, and C.Y. Hsieh Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions Anticancer Res. 21 2001 2895 2900
14. C.J. Chu, J. Dijkstra, M.Z. Lai, K. Hong, and F.C. Szoka Efficiency of cytoplasmic delivery by pH-sensitive liposomes to cells in culture Pharm. Res. 7 1990 824 834
15. S.S. Dhule, P. Penfornis, T. Frazier, R. Walker, J. Feldman, G. Tan, J. He, A. Alb, V. John, and R. Pochampally Curcumin-loaded gamma-cyclodextrin liposomal nanoparticles as delivery vehicles for osteosarcoma Nanomedicine 8 2012 440 451
16. E. Drakalska, D. Momekova, Y. Manolova, D. Budurova, G. Momekov, M. Genova, L. Antonov, N. Lambov, and S. Rangelov Hybrid liposomal PEGylated calix[4]arene systems as drug delivery platforms for curcumin Int. J. Pharm. 472 2014 165 174
17. R. Feng, Z. Song, and G. Zhai Preparation and in vivo pharmacokinetics of curcumin-loaded PCL-PEG-PCL triblock copolymeric nanoparticles Int. J. Nanomed. 7 2012 4089 4098
18. S. Ganta, and M. Amiji Coadministration of Paclitaxel and curcumin in nanoemulsion formulations to overcome multidrug resistance in tumor cells Mol. Pharm. 6 2009 928 939
19. Y. Gao, Z. Li, M. Sun, H. Li, C. Guo, J. Cui, A. Li, F. Cao, Y. Xi, H. Lou, and G. Zhai Preparation, characterization, pharmacokinetics, and tissue distribution of curcumin nanosuspension with TPGS as stabilizer Drug Dev. Ind. Pharm. 36 2010 1225 1234
20. G. Garcea, D.P. Berry, D.J. Jones, R. Singh, A.R. Dennison, P.B. Farmer, R.A. Sharma, W.P. Steward, and A.J. Gescher Consumption of the putative chemopreventive agent curcumin by cancer patients: assessment of curcumin levels in the colorectum and their pharmacodynamic consequences Cancer Epidemiol. Biomark. Prev. 14 2005 120 125
21. G. Garcea, D.J. Jones, R. Singh, A.R. Dennison, P.B. Farmer, R.A. Sharma, W.P. Steward, A.J. Gescher, and D.P. Berry Detection of curcumin and its metabolites in hepatic tissue and portal blood of patients following oral administration Br. J. Cancer 90 2004 1011 1015
22. M.H. Gelb, L. Brunsveld, C.A. Hrycyna, S. Michaelis, F. Tamanoi, W.C. Van Voorhis, and H. Waldmann Therapeutic intervention based on protein prenylation and associated modifications Nat. Chem. Biol. 2 2006 518 528
23. R. Gogada, M. Amadori, H. Zhang, A. Jones, A. Verone, J. Pitarresi, S. Jandhyam, V. Prabhu, J.D. Black, and D. Chandra Curcumin induces Apaf-1-dependent, p21-mediated caspase activation and apoptosis Cell Cycle 10 2011 4128 4137
24. S.L. Gosangari, and K.L. Watkin Effect of preparation techniques on the properties of curcumin liposomes: characterization of size, release and cytotoxicity on a squamous oral carcinoma cell line Pharm. Dev. Technol. 17 2012 103 109
25. V.S. Gota, G.B. Maru, T.G. Soni, T.R. Gandhi, N. Kochar, and M.G. Agarwal Safety and pharmacokinetics of a solid lipid curcumin particle formulation in osteosarcoma patients and healthy volunteers J. Agric. Food. Chem. 58 2010 2095 2099
26. A.L. Hilchie, S.J. Furlong, K. Sutton, A. Richardson, M.R. Robichaud, C.A. Giacomantonio, N.D. Ridgway, and D.W. Hoskin Curcumin-induced apoptosis in PC3 prostate carcinoma cells is caspase-independent and involves cellular ceramide accumulation and damage to mitochondria Nutr. Cancer 62 2010 379 389
27. W.C. Hung, F.Y. Chen, C.C. Lee, Y. Sun, M.T. Lee, and H.W. Huang Membrane-thinning effect of curcumin Biophys. J. 94 2008 4331 4338
28. Y. Ilieva, K. Kaloyanov, D. Yosifov, B. Robev, I. Zhelezova, M. Genova, A. Mihova, G. Balatzenko, M.M. Zaharieva, M.R. Berger, and S.M. Konstantinov Antineoplastic potential of curcumin (cooperative study in Bulgaria and Germany) Phytochem. Rev. 13 2014 459 469
29. A. Karewicz, D. Bielska, A. Loboda, B. Gzyl-Malcher, J. Bednar, A. Jozkowicz, J. Dulak, and M. Nowakowska Curcumin-containing liposomes stabilized by thin layers of chitosan derivatives Colloids Surf. B Biointerfaces 109 2013 307 316
30. N.M. Khalil, T.C. do Nascimento, D.M. Casa, L.F. Dalmolin, A.C. de Mattos, I. Hoss, M.A. Romano, and R.M. Mainardes Pharmacokinetics of curcumin-loaded PLGA and PLGA-PEG blend nanoparticles after oral administration in rats Colloids Surf. B Biointerfaces 101 2013 353 360
31. S.M. Konstantinov, H. Eibl, and M.R. Berger BCR-ABL influences the antileukaemic efficacy of alkylphosphocholines Br. J. Haematol. 107 1999 365 380
32. C.L. Kuo, S.Y. Wu, S.W. Ip, P.P. Wu, C.S. Yu, J.S. Yang, P.Y. Chen, S.H. Wu, and J.G. Chung Apoptotic death in curcumin-treated NPC-TW 076 human nasopharyngeal carcinoma cells is mediated through the ROS, mitochondrial depolarization and caspase-3-dependent signaling responses Int. J. Oncol. 39 2011 319 328
33. Kurzrock, R., Li, L., Mehta, K., Aggarwal, B.B., 2004. Liposomal Curcumin for Treatment of Cancer. WO2004080396.
34. C. Li, Y. Zhang, T. Su, L. Feng, Y. Long, and Z. Chen Silica-coated flexible liposomes as a nanohybrid delivery system for enhanced oral bioavailability of curcumin Int. J. Nanomed. 7 2012 5995 6002
35. P.M. Li, Y.L. Li, B. Liu, W.J. Wang, Y.Z. Wang, and Z. Li Curcumin inhibits MHCC97H liver cancer cells by activating ROS/TLR-4/caspase signaling pathway Asian Pac. J. Cancer Prev. 15 2014 2329 2334
36. S. Li, Z. Liu, F. Zhu, X. Fan, X. Wu, H. Zhao, and L. Jiang Curcumin lowers erlotinib resistance in non-small cell lung carcinoma cells with mutated EGF receptor Oncol. Res. 21 2013 137 144
37. Y. Li, J.L. Revalde, G. Reid, and J.W. Paxton Modulatory effects of curcumin on multi-drug resistance-associated protein 5 in pancreatic cancer cells Cancer Chemother. Pharmacol. 68 2011 603 610
38. Y.F. Liao, H.C. Hung, T.C. Hour, P.C. Hsu, M.C. Kao, G.J. Tsay, and G.Y. Liu Curcumin induces apoptosis through an ornithine decarboxylase-dependent pathway in human promyelocytic leukemia HL-60 cells Life Sci. 82 2008 367 375
39. H.F. Lu, K.C. Lai, S.C. Hsu, H.J. Lin, M.D. Yang, Y.L. Chen, M.J. Fan, J.S. Yang, P.Y. Cheng, C.L. Kuo, and J.G. Chung Curcumin induces apoptosis through FAS and FADD, in caspase-3-dependent and -independent pathways in the N18 mouse-rat hybrid retina ganglion cells Oncol. Rep. 22 2009 97 104
40. A.H. Matloob, S. Mourtas, P. Klepetsanis, and S.G. Antimisiaris Increasing the stability of curcumin in serum with liposomes or hybrid drug-in-cyclodextrin-in-liposome systems: a comparative study Int. J. Pharm. 476 2014 108 115
41. R. Misra, and S.K. Sahoo Coformulation of doxorubicin and curcumin in poly(d,l-lactide-co-glycolide) nanoparticles suppresses the development of multidrug resistance in K562 cells Mol. Pharm. 8 2011 852 866
42. D. Momekova, D. Budurova, E. Drakalska, S. Shenkov, G. Momekov, B. Trzebicka, N. Lambov, E. Tashev, and S. Rangelov Aggregation behavior and in vitro biocompatibility study of octopus-shaped macromolecules based on tert-butylcalix[4]arenes Int. J. Pharm. 436 2012 410 417
43. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
44. M. Pandelidou, K. Dimas, A. Georgopoulos, S. Hatziantoniou, and C. Demetzos Preparation and characterization of lyophilised egg PC liposomes incorporating curcumin and evaluation of its activity against colorectal cancer cell lines J. Nanosci. Nanotechnol. 11 2011 1259 1266
45. K. Piwocka, A. Bielak-Mijewska, and E. Sikora Curcumin induces caspase-3-independent apoptosis in human multidrug-resistant cells Ann. N.Y. Acad. Sci. 973 2002 250 254
46. K. Piwocka, E. Jaruga, J. Skierski, I. Gradzka, and E. Sikora Effect of glutathione depletion on caspase-3 independent apoptosis pathway induced by curcumin in Jurkat cells Free Radic. Biol. Med. 31 2001 670 678
47. K.I. Priyadarsini Photophysics, photochemistry and photobiology of curcumin: studies from organic solutions, bio-mimetics and living cells J. Photochem. Photobiol. C: Photochem. Rev. 10 2009 81 95
48. S. Rahman, S. Cao, K.J. Steadman, M. Wei, and H.S. Parekh Native and beta-cyclodextrin-enclosed curcumin: entrapment within liposomes and their in vitro cytotoxicity in lung and colon cancer Drug Deliv. 19 2012 346 353
49. D.K. Rao, H. Liu, S.V. Ambudkar, and M. Mayer A combination of curcumin with either gramicidin or ouabain selectively kills cells that express the multidrug resistance-linked ABCG2 transporter J. Biol. Chem. 289 2014 31397 31410
50. M. Roy, and S. Mukherjee Reversal of resistance towards cisplatin by curcumin in cervical cancer cells Asian Pac. J. Cancer Prev. 15 2014 1403 1410
51. A.J. Schroit, J. Madsen, and R. Nayar Liposome-cell interactions: in vitro discrimination of uptake mechanism and in vivo targeting strategies to mononuclear phagocytes Chem. Phys. Lipids 40 1986 373 393
52. R.A. Sharma, S.A. Euden, S.L. Platton, D.N. Cooke, A. Shafayat, H.R. Hewitt, T.H. Marczylo, B. Morgan, D. Hemingway, S.M. Plummer, M. Pirmohamed, A.J. Gescher, and W.P. Steward Phase I clinical trial of oral curcumin: biomarkers of systemic activity and compliance Clin. Cancer Res. 10 2004 6847 6854
53. A. Shehzad, F. Wahid, and Y.S. Lee Curcumin in cancer chemoprevention: molecular targets, pharmacokinetics, bioavailability, and clinical trials Arch. Pharm. (Weinheim) 343 2010 489 499
54. E. Sikora, A. Bielak-Zmijewska, A. Magalska, K. Piwocka, G. Mosieniak, M. Kalinowska, P. Widlak, I.A. Cymerman, and J.M. Bujnicki Curcumin induces caspase-3-dependent apoptotic pathway but inhibits DNA fragmentation factor 40/caspase-activated DNase endonuclease in human Jurkat cells Mol. Cancer Ther. 5 2006 927 934
55. N. Singh, A. Shrivastav, and R.K. Sharma Curcumin induces caspase and calpain-dependent apoptosis in HT29 human colon cancer cells Mol. Med. Rep. 2 2009 627 631
56. S. Singh, and A. Khar Biological effects of curcumin and its role in cancer chemoprevention and therapy Anticancer Agents Med. Chem. 6 2006 259 270
57. K. Sou Curcumin towards nanomedicine Rec. Pat. Nanomed. 2 2012 133 145
58. K. Sou, S. Inenaga, S. Takeoka, and E. Tsuchida Loading of curcumin into macrophages using lipid-based nanoparticles Int. J. Pharm. 352 2008 287 293
59. C.N. Sreekanth, S.V. Bava, E. Sreekumar, and R.J. Anto Molecular evidences for the chemosensitizing efficacy of liposomal curcumin in paclitaxel chemotherapy in mouse models of cervical cancer Oncogene 30 2011 3139 3152
60. S. Sreenivasan, S. Ravichandran, U. Vetrivel, and S. Krishnakumar In vitro and in silico studies on inhibitory effects of curcumin on multi drug resistance associated protein (MRP1) in retinoblastoma cells Bioinformation 8 2012 13 19
61. T.W. Tan, H.R. Tsai, H.F. Lu, H.L. Lin, M.F. Tsou, Y.T. Lin, H.Y. Tsai, Y.F. Chen, and J.G. Chung Curcumin-induced cell cycle arrest and apoptosis in human acute promyelocytic leukemia HL-60 cells via MMP changes and caspase-3 activation Anticancer Res. 26 2006 4361 4371
62. J.C. Tang, H.S. Shi, L.Q. Wan, Y.S. Wang, and Y.Q. Wei Enhanced antitumor effect of curcumin liposomes with local hyperthermia in the LL/2 model Asian Pac. J. Cancer Prev. 14 2013 2307 2310
63. F. Thayyullathil, S. Chathoth, A. Hago, M. Patel, and S. Galadari Rapid reactive oxygen species (ROS) generation induced by curcumin leads to caspase-dependent and - independent apoptosis in L929 cells Free Radic. Biol. Med. 45 2008 1403 1412
64. Y.J. Wang, M.H. Pan, A.L. Cheng, L.I. Lin, Y.S. Ho, C.Y. Hsieh, and J.K. Lin Stability of curcumin in buffer solutions and characterization of its degradation products J. Pharm. Biomed. Anal. 15 1997 1867 1876
65. Q. Wu, Y. Chen, and X.G. Li Effect of curcumin on caspase 8- and caspase 9-induced apoptosis of lymphoma Raji cell Zhongguo Shi Yan Xue Ye Xue Za Zhi 13 2005 624 627
66. S.H. Wu, L.W. Hang, J.S. Yang, H.Y. Chen, H.Y. Lin, J.H. Chiang, C.C. Lu, J.L. Yang, T.Y. Lai, Y.C. Ko, and J.G. Chung Curcumin induces apoptosis in human non-small cell lung cancer NCI-H460 cells through ER stress and caspase cascade- and mitochondria-dependent pathways Anticancer Res. 30 2010 2125 2133
67. M.X. Ye, Y.L. Zhao, Y. Li, Q. Miao, Z.K. Li, X.L. Ren, L.Q. Song, H. Yin, and J. Zhang Curcumin reverses cis-platin resistance and promotes human lung adenocarcinoma A549/DDP cell apoptosis through HIF-1alpha and caspase-3 mechanisms Phytomedicine 19 2012 779 787
68. L. Zhongfa, M. Chiu, J. Wang, W. Chen, W. Yen, P. Fan-Havard, L.D. Yee, and K.K. Chan Enhancement of curcumin oral absorption and pharmacokinetics of curcuminoids and curcumin metabolites in mice Cancer Chemother. Pharmacol. 69 2012 679 689