β-lactam functionalized poly(isoprene-b-ethylene oxide) amphiphilic block copolymer micelles as a new nanocarrier system for curcumin

Current Nanoscience

Volumn 6, Issue 3, 2010, Pages 277-284

  Gardikis, Konstantinos ^a   Dimas, Konstantinos ^b   Georgopoulos, Aristidis ^a   Kaditi, Eleni ^c   Pispas, Stergios ^c   Demetzos, Costas ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b BIOMEDICAL RESEARCH FOUNDATION   (Greece)

^c THEORETICAL AND PHYSICAL CHEMISTRY INSTITUTE   (Greece)

Author keywords

Block copolymer micelles; Colorectal cancer cell lines; Curcumin; Cytotoxic activity

Indexed keywords

AMPHIPHILIC BLOCK COPOLYMERS; ANTICANCER EFFECTS; BIOLOGICAL ACTIVITIES; BLOCK COPOLYMER MICELLES; CELLULAR UPTAKE; COLORECTAL CANCER CELL; CURCUMIN; CYTOTOXIC ACTIVITIES; ENCAPSULATION EFFICIENCY; ETHYLENE OXIDES; FUNCTIONALIZED; IN-VITRO; LOADING CAPACITIES; NANOCARRIERS; NATURAL COMPOUNDS; POST-POLYMERIZATION FUNCTIONALIZATION; SYNTHETIC BLOCKS; WATER SOLUBILITIES;

ANIONIC POLYMERIZATION; BIOCHEMISTRY; BLOCK COPOLYMERS; CELL CULTURE; CELLS; COPOLYMERIZATION; ENCAPSULATION; ETHYLENE; FUNCTIONAL POLYMERS; PLASTIC PRODUCTS; STRESS ANALYSIS;

MICELLES;

AMPHOPHILE; BETA LACTAM; COPOLYMER; CURCUMIN; NANOCARRIER; POLY(ISOPRENE B ETHYLENE OXIDE); UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; COLORECTAL CANCER; CYTOTOXICITY; DRUG RELEASE; ENCAPSULATION; IC 50; LIPOPHILICITY; MICELLE; PHYSICAL CHEMISTRY; POLYMERIZATION; PRIORITY JOURNAL;

EID: 77953978600     PISSN: 15734137     EISSN: None     Source Type: Journal    
DOI: 10.2174/157341310791171090     Document Type: Article

References (34)

1. Ammon, H. P.; Wahl, M. A. Pharmacology of Curcuma Longa. Planta Med., 1991, 57, 1-7.
2. Duvoix, A.; Blasius R.; Delhale, S.; Schnekenburger, M.; Morceau, F.; Henry, E.; Dicato, M.; Diedrich, M. Chemopreventive and therapeutic effects of curcumin. Cancer Lett., 2005, 223, 181-190.
3. Dorai, T.; Arragwal, B. B. Role of chemopreventive agents in cancer therapy. Cancer Lett., 2004, 215, 129-140.
4. Sharma, R. A.; Gescher, A. J.; Steward, W. P. Curcumin: the story so far. Eur. J. Cancer, 2005, 41, 1955-1968.
5. Bisht, S.; Feldman, G.; Soni, S.; Ravi, R.; Karikar, C.; Maitra, A. Polymeric nanoparticle-encapsulated curcumin (nanocurcumin): a novel strategy for human cancer therapy. J. Nanobiotechnol., 2007, 5, 3-8.
6. Goel, A.; Kunnumakkara, A. B.; Aggarwal, B. B. Curcumin as Curecumin: from kitchen to clinic. Biochem. Pharmacol., 2008, 75, 787-809.
7. Maheshwari, R.; Singh, A. K.; Gaddipati, J.; Srimal, R. C. Multiple biological activities of curcumin: A short review. Life Sci., 2006, 78, 2081-2087.
8. Allen, T.M. Liposomes. Opportunities in drug delivery. Drugs, 1997, 54, 8-14.
9. Jung, S.; Otberg, N.; Thiede, G.; Richter, H.; Sterry, W.; Panzer, S.; Lademann, J. Innovative liposomes as a Transfollicular drug delivery system: penetration into porcine hair follicles. J. Investig. Dermatol., 2006, 126, 1728-1732.
10. Sou, K.; Inenaga, S.; Takeoka, S.; Tsuchida, E. Loading of curcumin into macrophages using lipid-based nanoparticles. Int. J. Pharm., 2008, 20, 287-293.
11. Li, L.; Braiteh, F. S.; Kurzrock, R. Liposome-encapsulated curcumin: in vitro and in vivo effects on proliferation, apoptosis, signaling, and angiogenesis. Cancer, 2005, 104, 1322-1331.
12. Shi, W.; Dolai, S.; Rizk, S.; Hussain, A.; Tariq, H.; Averick, S.; L'Amoreaux, W.; El ldrissi, A.; Banerjee, P.; Raja, K. Synthesis of monofunctional curcumin derivatives, clicked curcumin dimer, and a PAMAM dendrimer curcumin conjugate for therapeutic applications. Org. Lett., 2007, 20, 5461-5464.
13. Lee, M. H.; Lin, H. Y.; Chen, H. C.; Thomas, J. L. Ultrasound mediates the release of curcumin from microemulsions. Langmuir, 2008, 4, 1707-1713.
14. Salmaso, S.; Bersani, S.; Semenzato, A.; Caliceti, P. New cyclodextrin bioconjugates for active tumour targeting. J. Drug Target., 2007, 15, 379-390.
15. Kumar, V.; Lewis, S. A.; Mutalik, S.; Shenoy, D. B.; Venkatesh, A.; Udupa, N. Biodegradable microspheres of curcumin for treatment of inflammation. Indian J. Physiol. Pharmacol., 2002, 46, 209-217.
16. Ma, Z.; Shayeganpour, A.; Brocks, D. R.; Lavasanifar, A.; Samuel, J. High-performance liquid chromatography analysis of curcumin in rat plasma: application to pharmacokinetics of polymeric micellar formulation of curcumin. Biomed. Chromatogr., 2007, 21, 546-552.
17. Ma, Z.; Haddadi, A.; Molavi, O.; Lavasanifar, A.; Lai, R.; Samuel, J. Mi-celles of poly(ethylene oxide)-b-poly(epsilon-caprolactone) as vehicles for the solubilization, stabilization, and controlled delivery of curcumin. J. Biomed. Mater. Res., 2008, 86, 300-310.
18. Sahu, A.; Bora, U.; Kasoju, N.; Goswmi, P. Synthesis of novel biodegradable and self-assembling methoxy poly(ethylene glycol)-palmitate nanocarrier for curcumin delivery to cancer cells. Acta Biomater., 2008, 4, 1752-1761.
19. 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.
20. Iwunze, M. O. Binding and distribution characteristics of curcumin solubilized in CTAB micelle. J. Mol. Liq., 2004, 111, 161-165.
21. Letchford, K.; Liggins, R.; Burt, H. Solubilization of hydrophobic drugs by methoxy poly(ethylene glycol)-block-polycaprolactone biblock copolymer micelles: theoretical and experimental data and correlations. J. Pharm. Sci., 2008, 97, 1179-1190.
22. Wang, F.; Wu, X.; Wang, F.; Liu, S.; Jia, Z.; Yang, J. The sensitive fluorimetric method for the determination of curcumin using the enhancement of mixed micelles. J. Fluoresc., 2006, 16, 53-59.
23. Tonnesen, H. H. Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Studies of curcumin and curcuminoids, XXVIII. Pharmazie, 2002, 57, 820-824.
24. Chignell, C. F.; Bilski, P.; Reszka, K. J.; Motten, A. G.; Sik, R. H.; Dahl, T. A. Spectral and photochemical properties of curcumin. Photochem. Photobiol., 1994, 59, 295-302.
25. Leung, M.H.M.; Colangelo, H.; Kee, T. W. Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis. Langmuir, 2008, 24, 5672-5675.
26. Holder, G.M.; Plummer, J.L.; Ryan, A.J. The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat. Xenobiotica, 1978, 8, 761-768.
27. Dimas, K.; Papadaki, M.; Tsimplouli, C.; Hatziantoniou, S.; Alevizopoulos, K.; Pantazis, P.; Demetzos, C. Labd-14-ene-8, 13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs. Biomed. Pharmacother., 2006, 60, 127-133.
28. Dimas, K.; Hatziantoniou, S.; Tseleni, S.; Khan, H.; Georgopoulos, A.; Alevizopoulos, K.; Wyche, J.H.; Pantazis, P.; Demetzos, C. Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. Apoptosis, 2007, 12, 685-694.
29. Dahl, T. A.; Bilski, P.; Reszka, K. J.; Chignell, C. F. Photocytotoxicity of curcumin. Photochem. Photobiol., 1994, 59, 290-294.
30. Ireson, C.; Orr, S.; Jones, D. J.; Verschcoyle, R.; Lim, C. K.; Luo, J. L.; Howells, L.; Plummer, S.; Jukes, R.; Eilliams, M.; Steward, W. P.; Gescher, A. Characterization of metabolites of the chemopreventive agents curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Cancer Res., 2001, 61, 1058-1064.
31. Harris, J.M. Poly(ethylene glycol) Chemistry, Biotechnical and Biomedical Applications, Plenum Press: New York, 1992.
32. Zhao, F.; Xie, D.; Zhang, G.; Pispas, S. Thermoresponsive complex amphiphilic block copolymer micelles investigated by laser light scattering. J. Phys. Chem., 2008, 112, 6358-6362.
33. Tamvakopoulos, C.; Dimas, K.; Sofianos, Z. D.; Hatziantoniou, S.; Han, Z.; Liu, Z. L.; Wyche, J.H.; Pantazis, P. Metabolism and anticancer activity of the curcumin analogue, dimethoxycurcumin. Clin. Cancer Res., 2007, 13, 1269-1277.
34. Chauhan, D. P. Chemotherapeutic potential of curcumin for colorectal cancer. Curr. Pharm. Des., 2002, 8, 1695-1706.