Oligoalanine-modified Pluronic-F127 nanocarriers for the delivery of curcumin with enhanced entrapment efficiency

References

• Ruby AJ, Kuttan G, Dinesh Babu KD, Rajasekharan KN, Kuttan R. Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett. 1995;94:79–83.10.1016/0304-3835(95)03827-J
   PubMed Web of Science ®Google Scholar
• Sharma OP. Antioxidant activity of curcumin and related compounds. Biochem. Pharmacol. 1976;25:1811–1812.10.1016/0006-2952(76)90421-4
   PubMed Web of Science ®Google Scholar
• Srimal RC, Dhawan BN. Pharmacology of diferuloyl methane (curcumin), a non-steroidal anti-inflammatory agent. J. Pharm. Pharmacol. 1973;25:447–452.10.1111/jphp.1973.25.issue-6
   PubMed Web of Science ®Google Scholar
• Mohanty C, Das M, Sahoo SK. Emerging role of nanocarriers to increase the solubility and bioavailability of curcumin. Expert Opin. Drug Delivery. 2012;9:1347–1364.10.1517/17425247.2012.724676
   PubMed Web of Science ®Google Scholar
• Gou M, Men K, Shi H, Xiang M, Zhang J, Song J, Long J, Wan Y, Luo F, Zhao X, Qian Z. Curcumin-loaded biodegradable polymeric micelles for colon cancer therapy in vitro and in vivo. Nanoscale. 2011;3:1558–1567.10.1039/c0nr00758g
   PubMed Web of Science ®Google Scholar
• Mohanty C, Acharya S, Mohanty AK, Dilnawaz F, Sahoo SK. Curcumin-encapsulated MePEG/PCL diblock copolymeric micelles: a novel controlled delivery vehicle for cancer therapy. Nanomedicine. 2010;5:433–449.10.2217/nnm.10.9
   PubMed Web of Science ®Google Scholar
• Huang J, Wang K. Novel micelle formulation of curcumin for enhancing antitumor activity and inhibiting colorectal cancer stem cells. Int. J. Nanomed. 2012;7:4487–4497.10.2147/IJN
   PubMedGoogle Scholar
• Allen C, Maysinger D, Eisenberg A. Nano-engineering block copolymer aggregates for drug delivery. Colloids Surf., B. 1999;16:3–27.10.1016/S0927-7765(99)00058-2
   Web of Science ®Google Scholar
• He C, Kim SW, Lee DS. In situ gelling stimuli-sensitive block copolymer hydrogels for drug delivery. J. Controlled Release. 2008;127:189–207.10.1016/j.jconrel.2008.01.005
   PubMed Web of Science ®Google Scholar
• Rangel-Yagui CO, Pessoa A Jr, Tavares LC. Micellar solubilization of drugs. J. Pharm. Pharm. Sci. 2005;8:147–165.
   PubMed Web of Science ®Google Scholar
• Tang Y, Liu SY, Armes SP, Billingham NC. Solubilization and controlled release of a hydrophobic drug using novel micelle-forming ABC triblock copolymers. Biomacromolecules. 2003;4:1636–1645.10.1021/bm030026t
   PubMed Web of Science ®Google Scholar
• Basak R, Bandyopadhyay R. Encapsulation of hydrophobic drugs in Pluronic F127 micelles: effects of drug hydrophobicity, solution temperature, and pH. Langmuir. 2013;29:4350–4356.10.1021/la304836e
   PubMed Web of Science ®Google Scholar
• Kim Y, Dalhaimer P, Christian DA, Discher DE. Polymeric worm micelles as nano-carriers for drug delivery. Nanotechnology. 2005;16:S484–S491.10.1088/0957-4484/16/7/024
   PubMedGoogle Scholar
• Natarajan JV, Darwitan A, Barathi VA, Ang M, Htoon HM, Boey F, Tam KC, Wong TT, Venkatraman SS. Sustained drug release in nanomedicine: a long-acting nanocarrier-based formulation for glaucoma. ACS Nano. 2014;8:419–429.10.1021/nn4046024
   PubMed Web of Science ®Google Scholar
• Li Y, Xu X, Shen Y, Qian C, Lu F, Guo S. Preparation and evaluation of copolymeric micelles with high paclitaxel contents and sustained drug release. Colloids Surf., A. 2013;429:12–18.10.1016/j.colsurfa.2013.03.043
   Web of Science ®Google Scholar
• Wang Y, Li Y, Zhang L, Fang X. Pharmacokinetics and biodistribution of paclitaxel-loaded Pluronic P105 polymeric micelles. Arch. Pharmacal Res. 2008;31:530–538.10.1007/s12272-001-1189-2
   PubMed Web of Science ®Google Scholar
• Han M, Diao YY, Fu YH, Hu YL, Jiang HL, Tsutsumi Y, Wei QC, Chen DW, Gao J-Q. Doxorubicin-loaded PEG-PCL copolymer micelles enhance cytotoxicity and intracellular accumulation of doxorubicin in adriamycin-resistant tumor cells. Int. J. Nanomed. 2011;6:1955–1962.
   PubMed Web of Science ®Google Scholar
• Chakraborty H, Banerjee R, Sarkar M. Incorporation of NSAIDs in micelles: implication of structural switchover in drug–membrane interaction. Biophys. Chem. 2003;104:315–325.10.1016/S0301-4622(02)00389-7
   PubMed Web of Science ®Google Scholar
• Batrakova EV, Li S, Brynskikh AM, Sharma AK, Li Y, Boska M, Gong N, Mosley RL, Alakhov VY, Gendelman HE, Kabanov AV. Effects of Pluronic and doxorubicin on drug uptake, cellular metabolism, apoptosis and tumor inhibition in animal models of MDR cancers. J. Controlled Release. 2010;143:290–301.10.1016/j.jconrel.2010.01.004
   PubMed Web of Science ®Google Scholar
• Ugarenko M, Chan C-K, Nudelman A, Rephaeli A, Cutts SM, Phillips DR. Development of Pluronic micelle-encapsulated doxorubicin and formaldehyde-releasing prodrugs for localized anticancer chemotherapy. Oncol. Res. 2009;17:283–299.10.3727/096504009787721212
   PubMed Web of Science ®Google Scholar
• Foster B, Cosgrove T, Hammouda B. Pluronic triblock copolymer systems and their interactions with ibuprofen. Langmuir. 2009;25:6760–6766.10.1021/la900298m
   PubMed Web of Science ®Google Scholar
• Wan D-H, Zheng O, Zhou Y, Wu L-Y. Solubilization of ibuprofen in Pluronic block copolymer F127 micelles. Acta Phys. Chim. Sin. 2010;26:3243–3248.
   Web of Science ®Google Scholar
• Park KM, Bae JW, Joung YK, Shin JW, Park KD. Nanoaggregate of thermosensitive chitosan-Pluronic for sustained release of hydrophobic drug. Colloids Surf., B. 2008;63:1–6.10.1016/j.colsurfb.2007.10.024
   PubMed Web of Science ®Google Scholar
• Huang K, Lee BP, Ingram DR, Messersmith PB. Synthesis and characterization of self-assembling block copolymers containing bioadhesive end groups. Biomacromolecules. 2002;3:397–406.10.1021/bm015650p
   PubMed Web of Science ®Google Scholar
• Park SY, Lee Y, Bae KH, Ahn C-H, Park TG. Temperature/pH-sensitive hydrogels prepared from Pluronic copolymers end-capped with carboxylic acid groups via an oligolactide spacer. Macromol. Rapid Commun. 2007;28:1172–1176.10.1002/(ISSN)1521-3927
   Google Scholar
• Jung YK, Park MH, Moon HJ, Shinde UP, Jeong B. Changes in nanoassembly of oligocaprolactone end-capped Pluronic F127 and the abnormal hydrophobicity trend of phase transition. Macromolecules. 2013;46:4215–4222.10.1021/ma400268r
   Web of Science ®Google Scholar
• Liu R, He B, Li D, Lai Y, Chang J, Tang JZ, Gu Z. Effects of pH-sensitive chain length on release of doxorubicin from mPEG-b-PH-b-PLLA nanoparticles. Int. J. Nanomed. 2012;7:4433–4446.
   PubMed Web of Science ®Google Scholar
• Habraken GJM, Peeters M, Dietz CHJT, Koning CE, Heise A. How controlled and versatile is N-carboxy anhydride (NCA) polymerization at 0 °C? Effect of temperature on homo-, block- and graft (co)polymerization. Polym. Chem. 2010;1:514–524.10.1039/b9py00337a
   Web of Science ®Google Scholar
• Zhang X, Jackson JK, Burt HM. Determination of surfactant critical micelle concentration by a novel fluorescence depolarization technique. J. Biochem. Biophys. Methods. 1996;31:145–150.10.1016/0165-022X(95)00032-M
   PubMedGoogle Scholar
• Mahou R, Wandrey C. Versatile route to synthesize heterobifunctional poly(ethylene glycol) of variable functionality for subsequent pegylation. Polymers. 2012;4:561–589.10.3390/polym4010561
   Web of Science ®Google Scholar
• Kajjari PB, Manjeshwar LS, Aminabhavi TM. Novel blend microspheres of poly(3-hydroxybutyrate) and Pluronic F68/127 for controlled release of 6-mercaptopurine. J. Appl. Polym. Sci. 2014:131.
   PubMed Web of Science ®Google Scholar
• Xie W, Zhu W, Shen Z. Synthesis, isothermal crystallization and micellization of mPEG–PCL diblock copolymers catalyzed by yttrium complex. Polymer. 2007;48:6791–6798.10.1016/j.polymer.2007.09.021
   Web of Science ®Google Scholar
• Jia W, Gu Y, Gou M, Dai M, Li X, Kan B, Yang J, Song Q, Wei Y, Qian Z. Preparation of biodegradable polycaprolactone/poly (ethylene glycol)/polycaprolactone (PCEC) nanoparticles. Drug Delivery. 2008;15:409–416.10.1080/10717540802321727
   PubMed Web of Science ®Google Scholar
• Huang M-H, Li S, Hutmacher DW, Schantz J-T, Vacanti CA, Braud C, Vert M. Degradation and cell culture studies on block copolymers prepared by ring opening polymerization of e-caprolactone in the presence of poly(ethylene glycol). J. Biomed. Mater. Res. A. 2004;69A:417–427.10.1002/(ISSN)1097-4636
   Web of Science ®Google Scholar
• Shan Y, Qin Y, Chuan Y, Li H, Yuan M. The synthesis and characterization of hydroxyapatite-β-alanine modified by grafting polymerization of γ-benzyl-L-glutamate-N-carboxyanhydride. Molecules. 2013;18:13979–13991.10.3390/molecules181113979
   PubMed Web of Science ®Google Scholar
• Zhang Y, Zhao L, Chen M, Lang M. Synthesis and properties of Pluronic-based pentablock copolymers with pendant amino groups. Colloid Polym. Sci. 2013;291:1563–1571.10.1007/s00396-012-2889-2
   Web of Science ®Google Scholar
• Rathore O, Sogah DY. Self-assembly of β-sheets into nanostructures by poly(alanine) segments incorporated in multiblock copolymers inspired by spider silk. J. Am. Chem. Soc. 2001;123:5231–5239.10.1021/ja004030d
   PubMed Web of Science ®Google Scholar
• Song MJ, Lee DS, Ahn JH, Kim DJ, Kim SC. Thermosensitive sol-gel transition behaviors of poly(ethylene oxide)/aliphatic polyester/poly(ethylene oxide) aqueous solutions. J. Polym. Sci., Part A: Polym. Chem. 2004;42:772–784.10.1002/(ISSN)1099-0518
   Web of Science ®Google Scholar
• Ma J, Guo C, Tang Y, Liu H. 1H NMR spectroscopic investigations on the micellization and gelation of PEO−PPO−PEO block copolymers in aqueous solutions. Langmuir. 2007;23:9596–9605.10.1021/la701221f
   PubMed Web of Science ®Google Scholar
• Veeren A, Bhaw-Luximon A, Jhurry D. Polyvinylpyrrolidone–polycaprolactone block copolymer micelles as nanocarriers of anti-TB drugs. Eur. Polym. J. 2013;49:3034–3045.10.1016/j.eurpolymj.2013.06.020
   Web of Science ®Google Scholar
• Jeetah R, Bhaw-Luximon A, Jhurry D. New amphiphilic PEG-b-P(ester–ether) micelles as potential drug nanocarriers. J. Nanopart. Res. 2012;14:1–13.
   PubMed Web of Science ®Google Scholar
• Sezgin Z, Yuksel N, Baykara T. Preparation and characterization of polymeric micelles for solubilization of poorly soluble anticancer drugs. Eur. J. Pharm. Biopharm. 2006;64:261–268.10.1016/j.ejpb.2006.06.003
   PubMed Web of Science ®Google Scholar
• Nardo L, Paderno R, Andreoni A, Másson M, Haukvik T, Tønnesen HH. Role of H-bond formation in the photoreactivity of curcumin. Spectroscopy. 2008;22:187–198.10.1155/2008/928407
   Web of Science ®Google Scholar
• Ghosh R, Mondal JA, Palit DK. Ultrafast dynamics of the excited states of curcumin in solution. J. Phys. Chem. B. 2010;114:12129–12143.10.1021/jp1038249
   PubMed Web of Science ®Google Scholar
• Fu Y, Kao WJ. Drug release kinetics and transport mechanisms of non-degradable and degradable polymeric delivery systems. Expert Opin. Drug Delivery. 2010;7:429–444.10.1517/17425241003602259
   PubMed Web of Science ®Google Scholar
• Khoee S, Hassanzadeh S, Goliaie B. Effects of hydrophobic drug–polyesteric core interactions on drug loading and release properties of poly(ethylene glycol)–polyester–poly(ethylene glycol) triblock core–shell nanoparticles. Nanotechnology. 2007;18:175602.10.1088/0957-4484/18/17/175602
   Web of Science ®Google Scholar