Curcumin nanoformulations: A review of pharmaceutical properties and preclinical studies and clinical data related to cancer treatment

Biomaterials - Tập 35 Số 10 - Trang 3365-3383 - 2014
Ornchuma Naksuriya1,2, Siriporn Okonogi1, Raymond M. Schiffelers3, Wim E. Hennink2
1Department of Pharmaceutical Sciences, Faculty of Pharmacy, Chiang Mai University, Suthep Rd, Mueang, Chiang Mai 50200, Thailand
2Department of Pharmaceutics, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, Universiteitsweg 99, Utrecht 3805 TB, The Netherlands
3Department of Clinical Chemistry and Hematology, University Medical Center Utrecht, Utrecht, The Netherlands

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Tài liệu tham khảo

Vogel, 1815, Curcumin-biological and medicinal properties, J Pharmacol, 2

Milobedeska, 1910, Structure of curcumin, Ber Dtsch Chem Ges, 43, 2163

Lampe, 1913, Studien über curcumin, Ber Dtsch Chem Ges, 46, 2235, 10.1002/cber.191304602149

Sandur, 2007, Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism, Carcinogenesis, 28, 1765, 10.1093/carcin/bgm123

Liu, 2006, Effect of three different curcumin pigments on the proliferation of vascular smooth muscle cells by ox-LDL and the expression of LDL-R, Zhongguo Zhong Yao Za Zhi, 31, 500

Kim, 2001, Curcuminoids from Curcuma longa L. (Zingiberaceae) that protect PC12 rat pheochromocytoma and normal human umbilical vein endothelial cells from βA (1-42) insult, Neurosci Lett, 303, 57, 10.1016/S0304-3940(01)01677-9

Nishiyama, 2005, Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice, J Agric Food Chem, 53, 959, 10.1021/jf0483873

Kiuchi, 1993, Nematocidal activity of turmeric: synergistic action of curcuminoids, Chem Pharm Bull, 41, 1640, 10.1248/cpb.41.1640

Sharma, 2005, Curcumin: the story so far, Eur J Cancer, 41, 1955, 10.1016/j.ejca.2005.05.009

Asai, 2001, Dietary curcuminoids prevent high-fat diet–induced lipid accumulation in rat liver and epididymal adipose tissue, J Nutr, 131, 2932

Aggarwal, 2010, Targeting inflammation-induced obesity and metabolic diseases by curcumin and other nutraceuticals, Annu Rev Nutr, 30, 173, 10.1146/annurev.nutr.012809.104755

Olszanecki, 2005, Effect of curcumin on atherosclerosis in apoE/LDLR-double knockout mice, J Physiol Pharmacol, 56, 627

Shin, 2011, Longterm curcumin administration protects against atherosclerosis via hepatic regulation of lipoprotein cholesterol metabolism, Mol Nutr Food Res, 55, 1829, 10.1002/mnfr.201100440

Shah, 1999, Inhibitory effect of curcumin, a food spice from turmeric, on platelet-activating factor and arachidonic acid-mediated platelet aggregation through inhibition of thromboxane formation and Ca2+ signaling, Biochem Pharmacol, 58, 1167, 10.1016/S0006-2952(99)00206-3

Aggarwal, 2003, Anticancer potential of curcumin: preclinical and clinical studies, Anticancer Res, 23, 363

Jagetia, 2007, “Spicing up” of the immune system by curcumin, J Clin Immunol, 27, 19, 10.1007/s10875-006-9066-7

Aggarwal, 2006, Curcumin: the Indian solid gold, Adv Exp Med Biol, 595, 1

Goel, 2008, Curcumin as ‘‘curecumin’’: from kitchen to clinic, Biochem Pharmacol, 75, 787, 10.1016/j.bcp.2007.08.016

Aggarwal, 2009, Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases, Int J Biochem Cell Biol, 41, 40, 10.1016/j.biocel.2008.06.010

Duvoix, 2005, Chemopreventive and therapeutic effects of curcumin, Cancer Lett, 223, 181, 10.1016/j.canlet.2004.09.041

Anand, 2008, Curcumin and cancer: an “old-age” disease with an “age-old” solution, Cancer Lett, 267, 133, 10.1016/j.canlet.2008.03.025

Bar-Sela, 2010, Curcumin as an anti-cancer agent: review of the gap between basic and clinical applications, Curr Med Chem, 17, 190, 10.2174/092986710790149738

Ravindran, 2009, Curcumin and cancer cells: how many ways can curry kill tumor cells selectively?, AAPS J, 11, 495, 10.1208/s12248-009-9128-x

Maheshwari, 2006, Multiple biological activities of curcumin: a short review, Life Sci, 78, 2081, 10.1016/j.lfs.2005.12.007

Shishodia, 2007, Role of curcumin in cancer therapy, Curr Prob Cancer, 31, 243, 10.1016/j.currproblcancer.2007.04.001

Aggarwal, 2006, From traditional Ayurvedic medicine to modern medicine: identification of therapeutic targets for suppression of inflammation and cancer, Expert Opin Ther Targets, 10, 87, 10.1517/14728222.10.1.87

Kamat, 2007, Curcumin potentiates the apoptotic effects of chemotherapeutic agents and cytokines through down-regulation of nuclear factor-κB and nuclear factor-κB–regulated gene products in IFN-α–sensitive and IFN-α–resistant human bladder cancer cells, Mol Cancer Ther, 6, 1022, 10.1158/1535-7163.MCT-06-0545

Cheng, 2001, Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions, Anticancer Res, 21, 2895

Sharma, 2004, Phase I clinical trial of oral curcumin biomarkers of systemic activity and compliance, Clin Cancer Res, 10, 6847, 10.1158/1078-0432.CCR-04-0744

Hatcher, 2008, Curcumin: from ancient medicine to current clinical trials, Cell Mol Life Sci, 65, 1631, 10.1007/s00018-008-7452-4

Balaji, 2010, Toxicity prediction of compounds from turmeric (Curcuma longa L), Food Chem Toxicol, 48, 2951, 10.1016/j.fct.2010.07.032

Fujisawa, 2004, Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds, Anticancer Res, 24, 563

Kurien, 2007, Improving the solubility and pharmacological efficacy of curcumin by heat treatment, Assay Drug Dev Techn, 5, 567, 10.1089/adt.2007.064

Tønnesen, 2002, Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability, Int J Pharm, 244, 127, 10.1016/S0378-5173(02)00323-X

Wang, 1997, Stability of curcumin in buffer solutions and characterization of its degradation products, J Pharm Biomed, 15, 1867, 10.1016/S0731-7085(96)02024-9

Anand, 2007, Bioavailability of curcumin: problems and promises, Mol Pharmcol, 4, 807, 10.1021/mp700113r

Yang, 2007, Oral bioavailability of curcumin in rat and the herbal analysis from Curcuma longa by LC-MS/MS, J Chromatogr B, 853, 183, 10.1016/j.jchromb.2007.03.010

Shoba, 2007, Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers, Planta Med, 64, 353, 10.1055/s-2006-957450

Torchilin, 2009, Multifunctional and stimuli-sensitive pharmaceutical nanocarriers, Eur J Pharm Biopharm, 7, 431, 10.1016/j.ejpb.2008.09.026

Ruenraroengsak, 2010, Nanosystem drug targeting: facing up to complex realities, J Control Release, 141, 265, 10.1016/j.jconrel.2009.10.032

Sultana, 2013, Nanoparticles-mediated drug delivery approaches for cancer targeting: a review, J Drug Target, 21, 107, 10.3109/1061186X.2012.712130

Lammers, 2011, Theranostic nanomedicine, Accounts Chem Res, 44, 1029, 10.1021/ar200019c

Duncan, 2012, Endocytosis and intracellular trafficking as gateways for nanomedicine delivery: opportunities and challenges, Mol Pharm, 9, 2380, 10.1021/mp300293n

Devadasu, 2013, Can controversial nanotechnology promise drug delivery?, Chem Rev, 113, 1686, 10.1021/cr300047q

Maeda, 2000, Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review, J Control Release, 65, 271, 10.1016/S0168-3659(99)00248-5

Maeda, 2001, The enhanced permeability and retention (EPR) effect in tumor vasculature: the key role of tumor-selective macromolecular drug targeting, Adv Enzyme Regul, 41, 189, 10.1016/S0065-2571(00)00013-3

Fang, 2011, The EPR effect: unique features of tumor blood vessels for drug delivery, factors involved, and limitations and augmentation of the effect, Adv Drug Deliv Rev, 63, 136, 10.1016/j.addr.2010.04.009

Torchilin, 2011, Tumor delivery of macromolecular drugs based on the EPR effect, Adv Drug Deliv Rev, 63, 131, 10.1016/j.addr.2010.03.011

Hrkach, 2012, Preclinical development and clinical translation of a PSMA-targeted docetaxel nanoparticle with a differentiated pharmacological profile, Sci Transl Med, 4, 1, 10.1126/scitranslmed.3003651

Svenson, 2012, Clinical translation of nanomedicines, Curr Opin Solid St M, 16, 287, 10.1016/j.cossms.2012.10.001

Tong, 2012, Polymeric nanomedicines based on poly(lactide) and poly(lactide-co-glycolide), Curr Opin Solid St M, 16, 323, 10.1016/j.cossms.2013.01.001

Duncan, 2011, Nanomedicine (s) under the microscope, Mol Pharm, 8, 2101, 10.1021/mp200394t

Torchilin, 2005, Recent advances with liposomes as pharmaceutical carriers, Nat Rev Drug Discov, 4, 145, 10.1038/nrd1632

Torchilin, 2009, Multifunctional and stimuli-sensitive pharmaceutical nanocarriers, Eur J Pharm Biopharm, 71, 431, 10.1016/j.ejpb.2008.09.026

Barenholz, 2012, Doxil—the first FDA-approved nano-drug: lessons learned, J Control Release, 160, 117, 10.1016/j.jconrel.2012.03.020

Malam, 2009, Liposomes and nanoparticles: nanosized vehicles for drug delivery in cancer, Trends Pharmacol Sci, 30, 592, 10.1016/j.tips.2009.08.004

Karewicz, 2011, Interaction of curcumin with lipid monolayers and liposomal bilayers, Colloid Surf B, 88, 231, 10.1016/j.colsurfb.2011.06.037

Karewicz, 2013, Curcumin-containing liposomes stabilized by thin layers of chitosan derivatives, Colloid Surf B, 109, 307, 10.1016/j.colsurfb.2013.03.059

Re, 2011, Functionalization of liposomes with ApoE-derived peptides at different density affects cellular uptake and drug transport across a blood-brain barrier model, Nanomed Nanotechnol, 7, 551, 10.1016/j.nano.2011.05.004

Lin, 2012, A lipo-PEG-PEI complex for encapsulating curcumin that enhances its antitumor effects on curcumin-sensitive and curcumin-resistance cells, Nanomed Nanotechnol, 8, 318, 10.1016/j.nano.2011.06.011

Li, 2011, Silica-coated flexible liposomes as a nanohybrid delivery system for enhanced oral bioavailability of curcumin, Int J Nanomed, 7, 5995

Lazar, 2013, Curcumin-conjugated nanoliposomes with high affinity for Aβ deposits: possible applications to Alzheimer disease, Nanomed-Nanotechnol, 9, 712, 10.1016/j.nano.2012.11.004

Aditya, 2012, Curcuminoids-loaded liposomes in combination with arteether protects against Plasmodium berghei infection in mice, Exp Parasitol, 131, 292, 10.1016/j.exppara.2012.04.010

Rogers, 2012, Amelioration of renal ischaemia–reperfusion injury by liposomal delivery of curcumin to renal tubular epithelial and antigen-presenting cells, Br J Pharmacol, 166, 194, 10.1111/j.1476-5381.2011.01590.x

Sun, 2012, Advances in nanotechnology-based delivery systems for curcumin, Nanomedicine UK, 7, 1085, 10.2217/nnm.12.80

Danhier, 2012, PLGA-based nanoparticles: an overview of biomedical applications, J Control Release, 161, 505, 10.1016/j.jconrel.2012.01.043

Fredenberg, 2011, The mechanisms of drug release in poly (lactic-co-glycolic acid)-based drug delivery systems—a review, Int J Pharm, 415, 34, 10.1016/j.ijpharm.2011.05.049

Chaisri, 2011, Enhanced gentamicin loading and release of PLGA and PLHMGA microspheres by varying the formulation parameters, Colloids Surf B, 84, 508, 10.1016/j.colsurfb.2011.02.006

Jain, 2000, The manufacturing techniques of various drug loaded biodegradable poly (lactide-co-glycolide)(PLGA) devices, Biomaterials, 21, 2475, 10.1016/S0142-9612(00)00115-0

Acharya, 2011, PLGA nanoparticles containing various anticancer agents and tumour delivery by EPR effect, Adv Drug Deliv Rev, 63, 170, 10.1016/j.addr.2010.10.008

Shive, 1997, Biodegradation and biocompatibility of PLA and PLGA microspheres, Adv Drug Deliv Rev, 28, 5, 10.1016/S0169-409X(97)00048-3

Ford Versypt, 2013, Mathematical modeling of drug delivery from autocatalytically degradable PLGA microspheres—a review, J Control Release, 165, 29, 10.1016/j.jconrel.2012.10.015

Shaikh, 2009, 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, 37, 223, 10.1016/j.ejps.2009.02.019

Yallapu, 2010, Fabrication of curcumin encapsulated PLGA nanoparticles for improved therapeutic effects in metastatic cancer cells, J Colloid Interface Sci, 351, 19, 10.1016/j.jcis.2010.05.022

Doane, 2012, Nanoparticle ζ–potentials, Accounts Chem Res, 45, 317, 10.1021/ar200113c

Ghosh, 2012, Nanocapsulated curcumin: oral chemopreventive formulation against diethylnitrosamine induced hepatocellular carcinoma in rat, Chem Biol Interact, 195, 206, 10.1016/j.cbi.2011.12.004

Anand, 2010, Design of curcumin-loaded PLGA nanoparticles formulation with enhanced cellular uptake, and increased bioactivity in vitro and superior bioavailability in vivo, Biochem Pharmacol, 79, 330, 10.1016/j.bcp.2009.09.003

Khalil, 2013, Pharmacokinetics of curcumin-loaded PLGA and PLGA-PEG blend nanoparticles after oral administration in rats, Colloid Surf B, 101, 353, 10.1016/j.colsurfb.2012.06.024

Bisht, 2007, Polymeric nanoparticle-encapsulated curcumin (“nanocurcumin”): a novel strategy for human cancer therapy, J Nanobiotechnology, 5, 1

Liu, 2012, Preparation and characterization of cationic curcumin nanoparticles for improvement of cellular uptake, Carbohyd Polym, 90, 16, 10.1016/j.carbpol.2012.04.036

Rejinold, 2011, Biocompatible, biodegradable and thermo-sensitive chitosan-g-poly (N-isopropylacrylamide) nanocarrier for curcumin drug delivery, Int J Biol Macromol, 49, 161, 10.1016/j.ijbiomac.2011.04.008

Dimitrov, 2007, Thermosensitive water-soluble copolymers with doubly responsive reversibly interacting entities, Prog Polym Sci, 32, 1275, 10.1016/j.progpolymsci.2007.07.001

Schmaljohann, 2006, Thermo-and pH-responsive polymers in drug delivery, Adv Drug Deliv Rev, 58, 1655, 10.1016/j.addr.2006.09.020

Anitha, 2011, Preparation, characterization, in vitro drug release and biological studies of curcumin loaded dextran sulphate-chitosan nanoparticles, Carbohyd Polym, 84, 1158, 10.1016/j.carbpol.2011.01.005

Kataoka, 2001, Block copolymer micelles for drug delivery: design, characterization and biological significance, Adv Drug Deliv Rev, 47, 113, 10.1016/S0169-409X(00)00124-1

Gaucher, 2005, Block copolymer micelles: preparation, characterization and application in drug delivery, J Control Release, 109, 169, 10.1016/j.jconrel.2005.09.034

Gaucher, 2010, Polymeric micelles for oral drug delivery, Eur J Pharm Biopharm, 76, 147, 10.1016/j.ejpb.2010.06.007

Oerlemans, 2010, Polymeric micelles in anticancer therapy: targeting, imaging and triggered release, Pharm Res, 27, 2569, 10.1007/s11095-010-0233-4

Talelli, 2012, Polymeric micelles for cancer therapy: 3 C's to enhance efficacy, Curr Opin Solid St M, 16, 302, 10.1016/j.cossms.2012.10.003

Matsumura, 2009, Preclinical and clinical studies of anticancer agent-incorporating polymer micelles, Cancer Sci, 100, 572, 10.1111/j.1349-7006.2009.01103.x

Deng, 2012, Biodegradable polymeric micelles for targeted and controlled anticancer drug delivery: promises, progress and prospects, Nano Today, 7, 467, 10.1016/j.nantod.2012.08.005

Lu, 2013, Polymeric micelles and alternative nanonized delivery vehicles for poorly soluble drugs, Int J Pharm, 453, 198, 10.1016/j.ijpharm.2012.08.042

Song, 2011, Polymeric micelles for parenteral delivery of curcumin: preparation, characterization and in vitro evaluation, Colloid Surf A, 390, 25, 10.1016/j.colsurfa.2011.08.031

Song, 2011, Curcumin-loaded PLGA–PEG–PLGA triblock copolymeric micelles: preparation, pharmacokinetics and distribution in vivo, J Colloid Interface Sci, 354, 116, 10.1016/j.jcis.2010.10.024

Zhao, 2012, Curcumin loaded mixed micelles composed of pluronic P123 and F68: preparation, optimization and in vitro characterization, Colloid Surf B, 97, 101, 10.1016/j.colsurfb.2012.04.017

Samanta, 2013, Interaction of curcumin with PEO-PPO-PEO triblock copolymers: a molecular dynamics study, J Phys Chem B, 117, 3250, 10.1021/jp309476u

Gong, 2013, Improving antiangiogenesis and anti-tumor activity of curcumin by biodegradable polymeric micelles, Biomaterials, 34, 1413, 10.1016/j.biomaterials.2012.10.068

Ma, 2008, Micelles of poly(ethylene oxide)-b-poly(Ɛ-caprolactone) as vehicles for the solubilization, stabilization, and controlled delivery of curcumin, J Biomed Mater Res A, 86, 300, 10.1002/jbm.a.31584

Parvathy, 2010, Curcumin–amino acid conjugates: synthesis, antioxidant and antimutagenic attributes, Food Chem, 120, 523, 10.1016/j.foodchem.2009.10.047

Manju, 2011, Conjugation of curcumin onto hyaluronic acid enhances its aqueous solubility and stability, J Colloid Interface Sci, 359, 318, 10.1016/j.jcis.2011.03.071

Tang, 2010, Amphiphilic curcumin conjugate-forming nanoparticles as anticancer prodrug and drug carriers: in vitro and in vivo effects, Nanomedicine, 5, 855, 10.2217/nnm.10.67

Yang, 2012, Biodegradable polymer-curcumin conjugate micelles enhance the loading and delivery of low-potency curcumin, Pharm Res, 29, 3512, 10.1007/s11095-012-0848-8

Wichitnithad, 2011, Effects of different carboxylic ester spacers on chemical stability, release characteristics, and anticancer activity of mono-PEGylated curcumin conjugates, J Pharm Sci, 100, 5206, 10.1002/jps.22716

Esmaili, 2011, Beta casein-micelle as a nano vehicle for solubility enhancement of curcumin; food industry application, LWT Food Sci Technol, 44, 2166, 10.1016/j.lwt.2011.05.023

Kratz, 2008, Albumin as a drug carrier: design of prodrugs, drug conjugates and nanoparticles, J Control Release, 132, 171, 10.1016/j.jconrel.2008.05.010

Elzoghby, 2012, Albumin-based nanoparticles as potential controlled release drug delivery systems, J Control Release, 157, 168, 10.1016/j.jconrel.2011.07.031

Kim, 2011, Preparation and characterization of water-soluble albumin-bound curcumin nanoparticles with improved antitumor activity, Int J Pharm, 403, 285, 10.1016/j.ijpharm.2010.10.041

Kragh-Hansen, 2001, Detergents as probes of hydrophobic binding cavities in serum albumin and other water-soluble proteins, Biophys J, 80, 2898, 10.1016/S0006-3495(01)76255-8

Leung, 2009, Effective stabilization of curcumin by association to plasma proteins: human serum albumin and fibrinogen, Langmuir, 25, 5773, 10.1021/la804215v

Loftsson, 2007, Cyclodextrins and their pharmaceutical applications, Int J Pharm, 329, 1, 10.1016/j.ijpharm.2006.10.044

Loftsson, 2002, Self-association and cyclodextrin solubilization of drugs, J Pharm Sci, 91, 2307, 10.1002/jps.10226

Yadav, 2010, Cyclodextrin-complexed curcumin exhibits anti-inflammatory and antiproliferative activities superior to those of curcumin through higher cellular uptake, Biochem Pharmacol, 80, 1021, 10.1016/j.bcp.2010.06.022

Yallapu, 2010, β-Cyclodextrin-curcumin self-assembly enhances curcumin delivery in prostate cancer cells, Colloid Surf B, 79, 113, 10.1016/j.colsurfb.2010.03.039

Yallapu, 2010, Poly (β-cyclodextrin)/curcumin self-assembly: a novel approach to improve curcumin delivery and its therapeutic efficacy in prostate cancer cells, Macromol Biosci, 10, 1141, 10.1002/mabi.201000084

Ford, 1986, The current status of solid dispersions, Pharm Acta Helv, 61, 69

Alam, 2012, Solid dispersions: a strategy for poorly aqueous soluble drugs and technology updates, Expert Opin Drug Del, 9, 1419, 10.1517/17425247.2012.732064

Okonogi, 1999, Physicochemical properties of ursodeoxycholic acid dispersed in controlled pore glass, J Colloid Interface Sci, 216, 276, 10.1006/jcis.1999.6331

Okonogi, 2006, Dissolution improvement of high drug-loaded solid dispersion, AAPS Pharmscitech, 7, 148, 10.1208/pt070252

Janssens, 2009, Review: physical chemistry of solid dispersions, J Pharm Pharmacol, 61, 1571, 10.1211/jpp.61.12.0001

Giri, 2012, A novel and alternative approach to controlled release drug delivery system based on solid dispersion technique, B-FOPCU, 50, 147

Hegge, 2013, Solid dispersions for preparation of phototoxic supersaturated solutions for antimicrobial photodynamic therapy (aPDT): studies on curcumin and curcuminoides L, Eur J Pharm Biopharm, 83, 95, 10.1016/j.ejpb.2012.09.011

Seo, 2012, Preparation and pharmacokinetic evaluation of curcumin solid dispersion using Solutol®HS15 as a carrier, Int J Pharm, 424, 18, 10.1016/j.ijpharm.2011.12.051

Mohanty, 2010, The in vitro stability and in vivo pharmacokinetics of curcumin prepared as an aqueous nanoparticulate formulation, Biomaterials, 31, 6597, 10.1016/j.biomaterials.2010.04.062

Anuchapreeda, 2012, Preparation of lipid nanoemulsions incorporating curcumin for cancer therapy, J Nanotechnol, 41, 1

Zanotto-Filho, 2013, Curcumin-loaded lipid-core nanocapsules as a strategy to improve pharmacological efficacy of curcumin in glioma treatment, Eur J Pharm Biopharm, 83, 156, 10.1016/j.ejpb.2012.10.019

Sahay, 2010, Endocytosis of nanomedicines, J Control Release, 145, 182, 10.1016/j.jconrel.2010.01.036

Nichols, 2012, Odyssey of a cancer nanoparticle: from injection site to site of action, Nano Today, 7, 606, 10.1016/j.nantod.2012.10.010

Dhule, 2012, Curcumin-loaded γ-cyclodextrin liposomal nanoparticles as delivery vehicles for osteosarcoma, Nanomed Nanotechnol, 8, 440, 10.1016/j.nano.2011.07.011

Daleke, 1990, Endocytosis of liposomes by macrophages: binding, acidification and leakage of liposomes monitored by a new fluorescence assay, BBA Biomembranes, 1024, 352, 10.1016/0005-2736(90)90365-U

Raveendran, 2013, In vitro cytotoxicity and cellular uptake of curcumin-loaded pluronic/polycaprolactone micelles in colorectal adenocarcinoma cells, J Biomater Appl, 27, 811, 10.1177/0885328211427473

Park, 2012, Amphiphilic peptide carrier for the combined delivery of curcumin and plasmid DNA into the lungs, Biomaterials, 33, 6542, 10.1016/j.biomaterials.2012.05.046

Yallapu, 2013, Plasma proteins interaction with curcumin nanoparticles: implications in cancer therapeutics, Curr Drug Metab, 14, 504, 10.2174/1389200211314040012

Zhang, 2010, Curcumin promotes apoptosis in A549/DDP multidrug-resistant human lung adenocarcinoma cells through an miRNA signaling pathway, Biochem Biophys Res Commun, 399, 1, 10.1016/j.bbrc.2010.07.013

Duan, 2012, Reversion of multidrug resistance by co-encapsulation of doxorubicin and curcumin in chitosan/poly (butyl cyanoacrylate) nanoparticles, Int J Pharm, 426, 193, 10.1016/j.ijpharm.2012.01.020

Zhongfa, 2012, Enhancement of curcumin oral absorption and pharmacokinetics of curcuminoids and curcumin metabolites in mice, Cancer Chemother Pharmacol, 69, 679, 10.1007/s00280-011-1749-y

Tobio, 2000, The role of PEG on the stability in digestive fluids and in vivo fate of PEG-PLA nanoparticles following oral administration, Colloid Surf B, 18, 315, 10.1016/S0927-7765(99)00157-5

Plapied, 2011, Fate of polymeric nanocarriers for oral drug delivery, Curr Opin Colloid, 16, 228, 10.1016/j.cocis.2010.12.005

Ghahremankhani, 2008, PLGA-PEG-PLGA tri-block copolymers as in situ gel-forming peptide delivery system: effect of formulation properties on peptide release, Pharm Dev Technol, 13, 49, 10.1080/10837450701702842

Thorne, 2006, In vivo diffusion analysis with quantum dots and dextrans predicts the width of brain extracellular space, Proc Natl Acad Sci U S A, 103, 5567, 10.1073/pnas.0509425103

Serrano, 2006, Protein-lipid interactions and surface activity in the pulmonary surfactant system, Chem Phys Lipids, 141, 105, 10.1016/j.chemphyslip.2006.02.017

Gao, 2010, Preparation, characterization, pharmacokinetics, and tissue distribution of curcumin nanosuspension with TPGS as stabilizer, Drug Dev Ind Pharm, 36, 1225, 10.3109/03639041003695139

Zou, 2013, Polymeric curcumin nanoparticle pharmacokinetics and metabolism in bile duct cannulated rats, Mol Pharm, 10, 1977, 10.1021/mp4000019

Alexis, 2008, Factors affecting the clearance and biodistribution of polymeric nanoparticles, Mol Pharm, 5, 505, 10.1021/mp800051m

Torchilin, 1995, Which polymers can make nanoparticulate drug carriers long-circulating?, Adv Drug Deliv Rev, 16, 141, 10.1016/0169-409X(95)00022-Y

Torchilin, 2007, Targeted pharmaceutical nanocarriers for cancer therapy and imaging, AAPS J, 9, 128, 10.1208/aapsj0902015

Woodle, 1993, Surface-modified liposomes: assessment and characterization for increased stability and prolonged blood circulation, Chem Phys Lipids, 64, 249, 10.1016/0009-3084(93)90069-F

Li, 2010, Stealth nanoparticles: high density but sheddable PEG is a key for tumor targeting, J Control Release, 145, 178, 10.1016/j.jconrel.2010.03.016

Romberg, 2008, Sheddable coatings for long-circulating nanoparticles, Pharm Res, 25, 55, 10.1007/s11095-007-9348-7

Khandare, 2012, Multifunctional dendritic polymers in nanomedicine: opportunities and challenges, Chem Soc Rev, 41, 2824, 10.1039/C1CS15242D

Babaei, 2012, Dendrosomal curcumin significantly suppresses cancer cell proliferation in vitro and in vivo, Int Immunopharmacol, 12, 226, 10.1016/j.intimp.2011.11.015

Murphy, 2012, Reproductive effects of a pegylated curcumin, Reprod Toxicol, 34, 120, 10.1016/j.reprotox.2012.04.005

Cheng, 2012, Highly stabilized curcumin nanoparticles tested in an in vitro blood–brain barrier model and in Alzheimer's disease Tg2576 Mice, AAPS J, 15, 324, 10.1208/s12248-012-9444-4

Cutrin, 2013, Curcumin/Gd loaded apoferritin: a novel “theranostic” agent to prevent hepatocellular damage in toxic induced acute hepatitis, Mol Pharm, 10, 2079, 10.1021/mp3006177

Li, 2012, In vivo evaluation of curcumin nanoformulation loaded methoxy poly (ethylene glycol)-graft-chitosan composite film for wound healing application, Carbohyd Polym, 88, 84, 10.1016/j.carbpol.2011.11.068

Gong, 2013, A biodegradable hydrogel system containing curcumin encapsulated in micelles for cutaneous wound healing, Biomaterials, 34, 6377, 10.1016/j.biomaterials.2013.05.005

Chereddy, 2013, Combined effect of PLGA and curcumin on wound healing activity, J Control Release, 171, 208, 10.1016/j.jconrel.2013.07.015

Kakkar, 2013, Curcumin loaded solid lipid nanoparticles: an efficient formulation approach for cerebral ischemic reperfusion injury in rats, Eur J Pharm Biopharm, 85, 339, 10.1016/j.ejpb.2013.02.005

Wang, 2012, Enhanced bioavailability and efficiency of curcumin for the treatment of asthma by its formulation in solid lipid nanoparticles, Int J Nanomed, 7, 3667, 10.2147/IJN.S30428

Akhtar, 2012, Oral delivery of curcumin bound to chitosan nanoparticles cured Plasmodium yoelii infected mice, Biotechnol Adv, 30, 310, 10.1016/j.biotechadv.2011.05.009

Sunagawa, 2012, A novel drug delivery system of oral curcumin markedly improves efficacy of treatment for heart failure after myocardial infarction in rats, Biol Pharm Bull, 35, 139, 10.1248/bpb.35.139

Gupta, 2013, Therapeutic roles of curcumin: lessons learned from clinical trials, AAPS J, 15, 195, 10.1208/s12248-012-9432-8

Carroll, 2011, Phase IIa clinical trial of curcumin for the prevention of colorectal neoplasia, Cancer Prev Res, 4, 354, 10.1158/1940-6207.CAPR-10-0098

He, 2011, Upregulation of p53 expression in patients with colorectal cancer by administration of curcumin, Cancer Invest, 29, 208, 10.3109/07357907.2010.550592

Kanai, 2011, A phase I/II study of gemcitabine-based chemotherapy plus curcumin for patients with gemcitabine-resistant pancreatic cancer, Cancer Chemother Pharmacol, 68, 157, 10.1007/s00280-010-1470-2

Epelbaum, 2010, Curcumin and gemcitabine in patients with advanced pancreatic cancer, Nutr Cancer, 62, 1137, 10.1080/01635581.2010.513802

Bayet-Robert, 2010, Phase I dose escalation trial of docetaxel plus curcumin in patients with advanced and metastatic breast cancer, Cancer Biol Ther, 9, 8, 10.4161/cbt.9.1.10392

Golombick, 2009, The potential role of curcumin in patients with monoclonal gammopathy of undefined significance-its effect on paraproteinemia and the urinary N-telopeptide of type I collagen bone turnover marker, Clin Cancer Res, 15, 5917, 10.1158/1078-0432.CCR-08-2217

Lao, 2006, Dose escalation of a curcuminoid formulation, BMC Complement Altern Med, 6, 6, 10.1186/1472-6882-6-10

Vareed, 2008, Pharmacokinetics of curcumin conjugate metabolites in healthy human subjects, Cancer Epidem Biomar, 17, 1411, 10.1158/1055-9965.EPI-07-2693

Garcea, 2005, Consumption of the putative chemopreventive agent curcumin by cancer patients: assessment of curcumin levels in the colorectum and their pharmacodynamic consequences, Cancer Epidem Biomar, 14, 120, 10.1158/1055-9965.120.14.1

Gota, 2010, Safety and pharmacokinetics of a solid lipid curcumin particle formulation in osteosarcoma patients and healthy volunteers, J Agric Food Chem, 58, 2095, 10.1021/jf9024807

Sasaki, 2011, Innovative preparation of curcumin for improved oral bioavailability, Biol Pharm Bull, 34, 660, 10.1248/bpb.34.660

Kanai, 2012, Dose-escalation and pharmacokinetic study of nanoparticle curcumin, a potential anticancer agent with improved bioavailability, in healthy human volunteers, Cancer Chemother Pharm, 69, 65, 10.1007/s00280-011-1673-1

Kooijmans, 2012, Exosome mimetics: a novel class of drug delivery systems, Int J Nanomed, 7, 1525

Van Dommelen, 2012, Microvesicles and exosomes: opportunities for cell-derived membrane vesicles in drug delivery, J Control Release, 161, 635, 10.1016/j.jconrel.2011.11.021

Sun, 2010, A novel nanoparticle drug delivery system: the anti-inflammatory activity of curcumin is enhanced when encapsulated in exosomes, Mol Ther, 18, 1606, 10.1038/mt.2010.105

Shimatsu, 2012, Clinical application of “curcumin”, a multi-functional substance, J Anti-Aging Med, 9, 75

Khar, 2001, Induction of stress response renders human tumor cell lines resistant to curcumin-mediated apoptosis: role of reactive oxygen intermediates, Cell Stress Chaperones, 6, 368, 10.1379/1466-1268(2001)006<0368:IOSRRH>2.0.CO;2

Elattar, 2000, The inhibitory effect of curcumin, genistein, quercetin and cisplatin on the growth of oral cancer cells in vitro, Anticancer Res, 20, 1733

Liebmann, 1993, Cytotoxic studies of paclitaxel (Taxol) in human tumour cell lines, Br J Cancer, 68, 1104, 10.1038/bjc.1993.488

Limtrakul, 2007, Modulation of function of three ABC drug transporters, P-glycoprotein (ABCB1), mitoxantrone resistance protein (ABCG2) and multidrug resistance protein 1 (ABCC1) by tetrahydrocurcumin, a major metabolite of curcumin, Mol Cell Biochem, 296, 85, 10.1007/s11010-006-9302-8

Chearwae, 2006, Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1), Cancer Chemother Pharm, 57, 376, 10.1007/s00280-005-0052-1

Zhang, 2007, Curcumin synergistically augments bcr/abl phosphorothioate antisense oligonucleotides to inhibit growth of chronic myelogenous leukemia cells, Acta Pharmacol Sin, 28, 105, 10.1111/j.1745-7254.2007.00471.x

El-Sayed, 2011, Cardioprotective effects of Curcuma longa L. extracts against doxorubicin-induced cardiotoxicity in rats, J Med Plants Res, 5, 4049

Bava, 2005, Sensitization of taxol-induced apoptosis by curcumin involves down-regulation of nuclear factor-kappaB and the serine/threonine kinase Akt and is independent of tubulin polymerization, J Biol Chem, 280, 6301, 10.1074/jbc.M410647200

Notarbartolo, 2005, 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, 224, 53, 10.1016/j.canlet.2004.10.051

Kunnumakkara, 2007, Curcumin potentiates antitumor activity of gemcitabine in an orthotopic model of pancreatic cancer through suppression of proliferation, angiogenesis, and inhibition of nuclear factor-κb–regulated gene products, Cancer Res, 67, 3853, 10.1158/0008-5472.CAN-06-4257

Lin, 2007, Curcumin inhibits tumor growth and angiogenesis in ovarian carcinoma by targeting the nuclear factor-κB pathway, Clin Cancer Res, 13, 3423, 10.1158/1078-0432.CCR-06-3072

Ganta, 2009, Coadministration of paclitaxel and curcumin in nanoemulsion formulations to overcome multidrug resistance in tumor cells, Mol Pharm, 6, 928, 10.1021/mp800240j

Misra, 2011, 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, 852, 10.1021/mp100455h

Boztas, 2013, Synergistic interaction of paclitaxel and curcumin with cyclodextrin polymer complexation in human cancer cells, Mol Pharm, 10, 2676, 10.1021/mp400101k

López-Lázaro, 2008, Anticancer and carcinogenic properties of curcumin: considerations for its clinical development as a cancer chemopreventive and chemotherapeutic agent, Mol Nutr Food Res, 52, S103

Wang, 2001, Stimulation of topoisomerase II-mediated DNA damage via a mechanism involving protein thiolation, Biochemistry, 40, 3316, 10.1021/bi002786j

Moos, 2004, Curcumin impairs tumor suppressor p53 function in colon cancer cells, Carcinogenesis, 25, 1611, 10.1093/carcin/bgh163

Utkhede, 1998, Effect of lipid dose on the redistribution and blood pool clearance kinetics of peg-modified technetium-labeled lipid vesicles, J Liposome Res, 8, 381, 10.3109/08982109809035541

Koide, 2008, Particle size-dependent triggering of accelerated blood clearance phenomenon, Int J Pharm, 362, 197, 10.1016/j.ijpharm.2008.06.004

Lu, 2007, Brain delivery property and accelerated blood clearance of cationic albumin conjugated pegylated nanoparticle, J Control Release, 118, 38, 10.1016/j.jconrel.2006.11.015

Ishihara, 2009, Accelerated blood clearance phenomenon upon repeated injection of PEG-modified PLA-nanoparticles, Pharm Res, 26, 2270, 10.1007/s11095-009-9943-x

Schellekens, 2013, The immunogenicity of polyethylene glycol: facts and fiction, Pharm Res, 30, 1729, 10.1007/s11095-013-1067-7

Ishida, 2007, PEGylated liposomes elicit an anti-PEG IgM response in a T cell-independent manner, J Control Release, 122, 349, 10.1016/j.jconrel.2007.05.015

Ishida, 2008, Accelerated blood clearance (ABC) phenomenon upon repeated injection of PEGylated liposomes, Int J Pharm, 354, 56, 10.1016/j.ijpharm.2007.11.005

Romberg, 2007, Pharmacokinetics of poly (hydroxyethyl-L-asparagine)-coated liposomes is superior over that of PEG-coated liposomes at low lipid dose and upon repeated administration, BBA-Biomembranes, 1768, 737, 10.1016/j.bbamem.2006.12.005

Immordino, 2006, Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential, Int J Nanomed, 1, 297

Shiraishi, 2013, Hydrophobic blocks of PEG-conjugates play a significant role in the accelerated blood clearance (ABC) phenomenon, J Control Release, 165, 183, 10.1016/j.jconrel.2012.11.016

Abu Lila, 2013, The accelerated blood clearance (ABC) phenomenon: clinical challenge and approaches to manage, J Control Release, 172, 38, 10.1016/j.jconrel.2013.07.026

Sou, 2008, Loading of curcumin into macrophages using lipid-based nanoparticles, Int J Pharm, 352, 287, 10.1016/j.ijpharm.2007.10.033

Sou, 2007, Selective uptake of surface-modified phospholipid vesicles by bone marrow macrophages in vivo, Biomaterials, 28, 2655, 10.1016/j.biomaterials.2007.01.041

Ahsan, 2002, Targeting to macrophages: role of physicochemical properties of particulate carriers-liposomes and microspheres-on the phagocytosis by macrophages, J Control Release, 79, 29, 10.1016/S0168-3659(01)00549-1

Huang, 2012, Targeted delivery of oligonucleotides into tumor-associated macrophages for cancer immunotherapy, J Control Release, 158, 286, 10.1016/j.jconrel.2011.11.013

Etzerodt, 2012, Efficient intracellular drug-targeting of macrophages using stealth liposomes directed to the hemoglobin scavenger receptor CD163, J Control Release, 160, 72, 10.1016/j.jconrel.2012.01.034

Altunbas, 2011, Encapsulation of curcumin in self-assembling peptide hydrogels as injectable drug delivery vehicles, Biomaterials, 32, 5906, 10.1016/j.biomaterials.2011.04.069

Shpaisman, 2012, One-step synthesis of biodegradable curcumin-derived hydrogels as potential soft tissue fillers after breast cancer surgery, Biomacromolecules, 13, 2279, 10.1021/bm300518e