Enhanced solubility and targeted delivery of curcumin by lipopeptide micelles

Journal of Biomaterials Science, Polymer Edition

Volumn 26, Issue 6, 2015, Pages 369-383

  Liang, Ju ^a   Wu, Wenlan ^a   Lai, Danyu ^a   Li, Junbo ^a   Fang, Cailin ^a  

^a HENAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

curcumin; lipopeptide; micelles; self assembly; targeted delivery

Indexed keywords

CYTOLOGY; PEPTIDES; SELF ASSEMBLY; SOLUBILITY; SYNTHESIS (CHEMICAL); TUMORS;

CLINICAL APPLICATION; CURCUMIN; LASER CONFOCAL SCANNING MICROSCOPES; LIPOPEPTIDES; PHOSPHATE BUFFER SALINES; SOLID PHASE PEPTIDE SYNTHESIS; TARGETED DELIVERY; TUMOR TARGETED DELIVERY;

MICELLES;

ARGINYLGLYCYLASPARTIC ACID; CURCUMIN; INTEGRIN; LAURIC ACID; LIPOPEPTIDE; PHOSPHATE BUFFERED SALINE; ANTINEOPLASTIC AGENT; DRUG CARRIER; MICELLE; WATER;

ANIMAL CELL; ARTICLE; CANCER CELL LINE; CELL TRANSPORT; CELL VIABILITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; DRUG TARGETING; HUMAN; HUMAN CELL; MICELLE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; SOLID PHASE SYNTHESIS; ANIMAL; CELL SURVIVAL; CHEMICAL PHENOMENA; CHEMISTRY; CHLOROCEBUS AETHIOPS; COS 1 CELL LINE; DRUG EFFECTS; HELA CELL LINE; HEPG2 CELL LINE; METABOLISM; SOLUBILITY;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; COS CELLS; CURCUMIN; DRUG CARRIERS; HELA CELLS; HEP G2 CELLS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INTEGRINS; LIPOPEPTIDES; MICELLES; SOLUBILITY; WATER;

EID: 84923842167     PISSN: 09205063     EISSN: 15685624     Source Type: Journal    
DOI: 10.1080/09205063.2015.1012034     Document Type: Article

References (52)

1. Ferrari M. Cancer nanotechnology: opportunities and challenges. Nat. Rev. Cancer. 2005;5:161-171
2. Wang B, Chung S, Wu YY, Henning SM, Vadgama JV. Increased chemopreventive effect by combining arctigenin, green tea polyphenol and curcumin in prostate and breast cancer cells. RSC Adv. 2014;4:35242-35250
3. Aggarwal BB, Kumar A, Bharti AC. Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res. 2003;23:363-398
4. Siwak DR, Shishodia S, Aggarwal BB, Kurzrock R. Curcumin-induced antiproliferative and proapoptotic effects in melanoma cells are associated with suppression of IB kinase and nuclear factorB activity and are independent of the B-Raf/mitogen-activated/extracellular signal-regulated protein kinase pathway and the Akt pathway. Cancer. 2005;104:879-890
5. Gururaj AE, Belakavadi M, Venkatesh DA, Marmé D, Salimath BP. Molecular mechanisms of anti-angiogenic effect of curcumin. Biochem. Biophys. Res. Commun. 2002;297: 934-942
6. Belakavadi M, Salimath BP. 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
7. Ravindran J, Subbaraju GV, Ramani MV, Sung B, Aggarwal BB. Bisdemethylcurcumin and structurally related hispolon analogues of curcumin exhibit enhanced prooxidant, antiproliferative and anti-inflammatory activities in vitro. Biochem. Pharmacol. 2010;79: 1658-1666
8. Banerjee S, Zhang Y, Ali S, Bhuiyan M, Wang Z, Chiao PJ. Molecular evidence for increased antitumor activity of gemcitabine by genistein in vitro and in vivo using an orthotopic model of pancreatic cancer. Cancer Res. 2005;65:9064-9072
9. Aggarwal BB, Shishodia S, Takada Y. Curcumin suppresses the paclitaxel-induced nuclear factor-B pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice. Clin Cancer Res. 2005;11:7490-7498
10. Notarbartolo M, Poma P, Perri D, Dusonchet L, Cervello M, D'Alessandro N. 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. 2005;224:53-65
11. Lev-Ari S, Strier L, Kazanov D, Madar-Shapiro L, Dvory-Sobol H, Pinchuk I, Marian B, Lichtenberg D, Arber N. Celecoxib and curcumin synergistically inhibit the growth of colorectal cancer cells. Clin. Cancer Res. 2005;11:6738-6744
12. Sen S, Sharma H, Singh N. Curcumin enhances Vinorelbine mediated apoptosis in NSCLC cells by the mitochondrial pathway. Biochem. Biophys. Res. Commun. 2005;331: 1245-1252
13. Aggarwal BB, 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
14. Cheng AL, Hsu CH, Lin JK, Hsu MM, Ho YF, Shen TS, Ko JY, Lin JT, Lin BR, Ming-Shiang W, Yu HS, Jee SH, Chen GS, Chen TM, Chen CA, Lai MK, Pu YS, Pan MH, Wang YJ, Tsai CC, Hsieh CY. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 2001;21:2895-2900
15. Lao CD, Ruffin MT, Normolle D, Heath DD, Murray SI, Bailey JM, Boggs ME, Crowell J, Rock CL, Brenner DE. Dose escalation of a curcuminoid formulation. BMC Complement. Altern. Med. 2006;6:10
16. Somasundaram S, Edmund NA, Moore DT, Small GW, Shi YY, Orlowski RZ. Dietary curcumin inhibits chemotherapy-induced apoptosis in models of human breast cancer. Cancer Res. 2002;62:3868-3875
17. Fryer RA, Galustian C, Dalgelish AG. Recent advances and developments in treatment strategies against pancreatic cancer. Curr Clin Pharmacol. 2009;4:102-112
18. Harada T, Pham DT, Leung MHM, Ngo HT, Lincoln SF, Easton CJ, Kee TW. Cooperative binding and stabilization of the medicinal pigment curcumin by diamide linked-cyclodextrin dimers: a spectroscopic characterization. J. Phys. Chem. B. 2011;115:1268-1274
19. Leung MH, Kee TW. Effective stabilization of curcumin by association to plasma proteins: human serum albumin and fibrinogen. Langmuir. 2009;25:5773-5777
20. Mohanty C, Sahoo SK. The in vitro stability and in vivo pharmacokinetics of curcumin prepared as an aqueous nanoparticulate formulation. Biomaterials. 2010;31:6597-6611
21. Shaikh J, Ankola DD, Beniwal V, Singh D, Kumar MN. 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
22. Bisht S, Feldmann G, Soni S, Ravi R, Karikar C, Maitra A. Polymeric nanoparticleencapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy. J. Nanobiotechnol. 2007;5:3
23. Bansal SS, Goel M, Aqil F, Vadhanam MV, Gupta RC. Advanced drug delivery systems of curcumin for cancer chemoprevention. Cancer Prev. Res. (Phila). 2011;4:1158-1171
24. Sou K. Curcumin towards nanomedicine. Recent Pat. Nanomed. 2012;2:133-145
25. Dutta AK, Ikiki E. Novel drug delivery systems to improve bioavailability of curcumin. J. Bioequiv. Availab. 2013;6:1-9
26. Peng S, Hung WL, Peng YS, Chu IM. Oligoalanine-modified Pluronic-F127 nanocarriers for the delivery of curcumin with enhanced entrapment efficiency. J. Biomater. Sci., Polym. Ed. 2014;25:1225-1239
27. Huang L, Cai MT, Xie XX, Chen YW, Luo XL. Uptake enhancement of curcumin encapsulated into phosphatidylcholine-shielding micelles by cancer cells. J. Biomater. Sci., Polym. Ed. 2014;25:1407-1424
28. Soliman M, Miktoarm G. Star micelles containing curcumin reduce cell viability of sensitized glioblastoma. J. Nanomed. Biotherapeutic Discov. 2014;4:1-10
29. Soliman GM, Redon R, Sharma A, Mejía D, Maysinger D, Kakkar A. Miktoarm star polymer based multifunctional traceable nanocarriers for efficient delivery of poorly water soluble pharmacological agents. Macromol. Biosci. 2014;14:1312-1324
30. Yang C, Chen H, Zhao J, Pang X, Xi Y, Zhai G. Development of a folate-modified curcumin loaded micelle delivery system for cancer targeting. Colloids Surf., B. 2014;121: 206-213
31. Leung MH, Colangelo H, Kee TW. Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis. Langmuir. 2008;24:5672-5675
32. Sahu A, Kasoju N, Bora U. Fluorescence study of the curcumin casein micelle complexation and its application as a drug nanocarrier to cancer cells. Biomacromolecules. 2008;9:2905-2912
33. Wang ZF, Leung MHM, Kee TW, English DS. The role of charge in the surfactant-assisted stabilization of the natural product curcumin. Langmuir. 2010;26(8):5520-5526
34. Terech P, Weiss RG. Low molecular mass gelators of organic liquids and the properties of their gels. Chem. Rev. 1997;97:3133-3160
35. Lee KY, Mooney DJ. Hydrogels for tissue engineering. Chem. Rev. 2001;101:1869-1880
36. Zhang S. Fabrication of novel biomaterials through molecular self-assembly. Nat. Biotechnol. 2003;21:1171-1178
37. Estroff LA, Hamilton AD. Water gelation by small organic molecules. Chem. Rev. 2004;104:1201-1218
38. Xu XD, Chen JX, Cheng H, Zhang XZ, Zhuo RX. Controlled peptide coated nanostructures via the self-assembly of functional peptide building blocks. Polym. Chem. 2012;3:2479-2486
39. Chen JX, Wang HY, Li C, Han K, Zhang XZ, Zhuo RX. Construction of surfactant-like tetra-tail amphiphilic peptide with RGD ligand for encapsulation of porphyrin for photodynamic therapy. Biomaterials. 2011;32:1678-1684
40. Xu X-D, Chen CS, Lu B, Cheng SX, Zhang XZ, Zhuo RX. Coassembly of oppositely charged short peptides into well-defined supramolecular hydrogels. J. Phys. Chem. B. 2010;114:2365-2372
41. Mart RJ, Osborne RD, Stevens MM, Ulijn RV. Peptide-based stimuli-responsive biomaterials. Soft Matter. 2006;2:822-835
42. Xu XD, Lin BB, Feng J, Wang Y, Cheng SX, Zhang XZ, Zhuo RX. Biological glucose metabolism regulated peptide self-assembly as a simple visual biosensor for glucose detection. Macromol. Rapid Commun. 2012;33:426-431
43. Santoso S, Hwang W, Hartman H, Zhang S. Self-assembly of surfactant-like peptides with variable glycine tails to form nanotubes and nanovesicles. Nano Lett. 2002;2:687-691
44. von Maltzahn G, Vauthey S, Santoso S, Zhang SG. Positively charged surfactant-like peptides self-assemble into nanostructures. Langmuir. 2003;19:4332-4337
45. Liang J, Wu WL, Xu XD, Zhuo RX, Zhang XZ. pH responsive micelle self-assembled from a new amphiphilic peptide as anti-tumor drug carrier. Colloids Surf., B. 2014;114:398-403
46. Lim YB, Moon KS, Lee M. Stabilization of an Helix by-sheet-mediated self-assembly of a macrocyclic peptide. Angew. Chem. Int. Ed. 2009;48:1601-1605
47. Muraoka T, Cui H, Stupp SI. Quadruple helix formation of a photoresponsive peptide amphiphile and its light-triggered dissociation into single fibers. J. Am. Chem. Soc. 2008;130:2946-2947
48. Chen CS, Ji TJ, Xu XD, Zhang XZ, Zhuo RX. Nanofibers self-assembled from structural complementary borono-decapeptides. Macromol. Rapid Commun. 2010;31:1903-1908
49. Giancotti FG, Ruoslahti E. Integrin signaling. Science. 1999;285:1028-1033
50. Nejjari M, Hafdi Z, Gouysse G, Fiorentino M, Béatrix O, Dumortier J, Pourreyron C, Barozzi C, D'errico A, Grigioni WF, Scoazec JY. Expression, regulation, and function ofV integrins in hepatocellular carcinoma: an in vivo and in vitro study. Hepatology. 2002;36:418-426
51. Misra SK, Kondaiah P, Bhattacharya S, Boturyn D, Dumy P. Co-liposomes comprising a lipidated multivalent RGD-peptide and a cationic gemini cholesterol induce selective gene transfection inv3 andv5 integrin receptor-rich cancer cells. J. Mater. Chem. B. 2014;2:5758-5767
52. Li J, Tan H, Xong X, Xu Z, Shi C, Han X, Jiang H, Krissansen GW, Sun X. Antisense integrinV and3 gene therapy suppresses subcutaneously implanted hepatocellular carcinomas. Dig. Liver Dis. 2007;39:557-565.