Preparation of curcumin self-micelle solid dispersion with enhanced bioavailability and cytotoxic activity by mechanochemistry

References

• Anand P, Nair HB, Sung B, et al. (2010). Design of curcumin-loaded PLGA nanoparticles formulation with enhanced cellular uptake, and increased bioactivity in vitro and superior bioavailability in vivo. Biochem Pharmacol 79:330–8.
   PubMed Web of Science ®Google Scholar
• Bisht S, Feldmann G, Soni S, et al. (2007). Polymeric nanoparticle-encapsulated curcumin (“nanocurcumin”): a novel strategy for human cancer therapy. J Nanobiotechnol 5:1–18.
   PubMedGoogle Scholar
• Braga D, Maini L, Grepioni F. (2013). ChemInform abstract: mechanochemical preparation of CO-crystals. ChemInform 44. doi:10.1002/chin.201343272
   Google Scholar
• Chistyachenko YS, Dushkin AV, Polyakov NE, et al. (2015). Polysaccharide arabinogalactan from larch Larix sibirica as carrier for molecules of salicylic and acetylsalicylic acid: preparation, physicochemical and pharmacological study. Drug Deliv 22:400–7.
   PubMed Web of Science ®Google Scholar
• Deese AJ, Dratz EA, Hymel L, Fleischer S. (1982). Proton NMR T1, T2, and T1 rho relaxation studies of native and reconstituted sarcoplasmic reticulum and phospholipid vesicles. Biophys J 37:207–16.
   PubMed Web of Science ®Google Scholar
• Descamps M, Willart JF. (2016). Perspectives on the amorphisation/milling relationship in pharmaceutical materials. Adv Drug Deliv Rev 100:51–66.
   PubMed Web of Science ®Google Scholar
• Dushkin AV, Tolstikova TG. (2012). Complexes of polysaccharides and glycyrrhizic acid with drug molecules – mechanochemical synthesis and pharmacological activity. Complex world of polysaccharides. Croatia: InTech, 573–602.
   Google Scholar
• Fang J, Lu J, Holmgren A. (2005). Thioredoxin reductase is irreversibly modified by curcumin: a novel molecular mechanism for its anticancer activity. J Biol Chem 280:25284–90.
   PubMed Web of Science ®Google Scholar
• Gao X, Kuo J, Jiang H, et al. (2001). Immunomodulatory activity of curcumin: suppression of lymphocyte proliferation, development of cell-mediated cytotoxicity, and cytokine production in vitro. Biochem Pharmacol 62:1299–308.
   PubMed Web of Science ®Google Scholar
• Gong C, Deng S, Wu Q, et al. (2013). Improving antiangiogenesis and anti-tumor activity of curcumin by biodegradable polymeric micelles. Biomaterials 34:1413–32.
   PubMed Web of Science ®Google Scholar
• Hagl S, Kocher A, Schiborr C, et al. (2015). Curcumin micelles improve mitochondrial function in neuronal PC12 cells and brains of NMRI mice – impact on bioavailability. Neurochem Int 89:234–42.
   PubMed Web of Science ®Google Scholar
• Hazra MK, Roy S, Bagchi B. (2014). Hydrophobic hydration driven self-assembly of curcumin in water: similarities to nucleation and growth under large metastability, and an analysis of water dynamics at heterogeneous surfaces. J Chem Phys 141:18C501.
   PubMed Web of Science ®Google Scholar
• Higuchi TA, Connors KA. (1965). Phase-solubility techniques. In: Reilley CN, ed. Advances in analytical chemistry and instrumentation, vol. 4. NY, USA: Wiley, 117–212.
   Google Scholar
• Kansy M, Senner F, Gubernator K. (1998). Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes. J Med Chem 41:1007–10.
   PubMed Web of Science ®Google Scholar
• Kocher A, Schiborr C, Behnam D, Frank J. (2015). The oral bioavailability of curcuminoids in healthy humans is markedly enhanced by micellar solubilisation but not further improved by simultaneous ingestion of sesamin, ferulic acid, naringenin and xanthohumol. J Funct Foods 14:183–91.
   Web of Science ®Google Scholar
• Kornievskaya VS, Kruppa AI, Polyakov NE, Leshina TV. (2007). Effect of glycyrrhizic acid on lappaconitine phototransformation. J Phys Chem B 111:11447.
   PubMed Web of Science ®Google Scholar
• Kumari P, Muddineti OS, Rompicharla SV, et al. (2017). Cholesterol-conjugated poly(d, l-lactide)-based micelles as a nanocarrier system for effective delivery of curcumin in cancer therapy. Drug Deliv 24:209–23.
   PubMed Web of Science ®Google Scholar
• Li L, Ahmed B, Mehta K, Kurzrock R. (2007). Liposomal curcumin with and without oxaliplatin: effects on cell growth, apoptosis, and angiogenesis in colorectal cancer. Mol Cancer Ther 6:1276–82.
   PubMed Web of Science ®Google Scholar
• Li L, Braiteh FS, Kurzrock R. (2005). Liposome-encapsulated curcumin: in vitro and in vivo effects on proliferation, apoptosis, signaling, and angiogenesis. Cancer 104:1322–31.
   PubMed Web of Science ®Google Scholar
• Madane RG, Mahajan HS. (2016). Curcumin-loaded nanostructured lipid carriers (NLCs) for nasal administration: design, characterization, and in vivo study. Drug Deliv 23:1326–34.
   PubMed Web of Science ®Google Scholar
• Maiti K, Mukherjee K, Gantait A, et al. (2007). Curcumin-phospholipid complex: preparation, therapeutic evaluation and pharmacokinetic study in rats. Int J Pharm 330:155–63.
   PubMed Web of Science ®Google Scholar
• Manolova Y, Deneva V, Antonov L, et al. (2014). The effect of the water on the curcumin tautomerism: a quantitative approach. Spectrochim Acta A Mol Biomol Spectrosc 132:815.
   PubMed Web of Science ®Google Scholar
• Mccallum MM. (2013). High-throughput approaches for the assessment of factors influencing bioavailability of small molecules in pre-clinical drug development [PhD thesis]. The University of Wisconsin – Milwaukee.
   Google Scholar
• Mishra S, Palanivelu K. (2008). The effect of curcumin (turmeric) on Alzheimer's disease: an overview. Ann Indian Acad Neurol 11:13–9.
   PubMed Web of Science ®Google Scholar
• Moghadamtousi SZ, Kadir HA, Hassandarvish P, et al. (2014). A review on antibacterial, antiviral, and antifungal activity of curcumin. Biomed Res Int 2014:186864.
   PubMed Web of Science ®Google Scholar
• Mosmann T. (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55.
   PubMed Web of Science ®Google Scholar
• Motterlini R, Foresti R, Bassi R, Green CJ. (2000). Curcumin, an antioxidant and anti-inflammatory agent, induces heme oxygenase-1 and protects endothelial cells against oxidative stress. Free Radic Biol Med 28:1303–12.
   PubMed Web of Science ®Google Scholar
• Paradkar A, Ambike AA, Jadhav BK, Mahadik KR. (2004). Characterization of curcumin-PVP solid dispersion obtained by spray drying. Int J Pharm 271:281–6.
   PubMed Web of Science ®Google Scholar
• Phan QT, Mai HL, Le TTH, et al. (2016). Characteristics and cytotoxicity of folate-modified curcumin-loaded PLA-PEG micellar nano systems with various PLA:PEG ratios. Int J Pharm 507:32–40.
   PubMed Web of Science ®Google Scholar
• Piper JT, Singhal SS, Salameh MS, et al. (1998). Mechanisms of anticarcinogenic properties of curcumin: the effect of curcumin on glutathione linked detoxification enzymes in rat liver. Int J Biochem Cell Biol 30:445–56.
   PubMed Web of Science ®Google Scholar
• Polyakov NE, Khan VK, Taraban MB, Leshina TV. (2008). Complex of calcium receptor blocker nifedipine with glycyrrhizic acid. J Phys Chem B 112:4435–40.
   PubMed Web of Science ®Google Scholar
• Polyakov NE, Kispert LD. (2015). Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery. Carbohydr Polym 128:207–19.
   PubMed Web of Science ®Google Scholar
• Polyakov NE. (2011). Glycyrrhizic acid as a novel drug delivery vector: synergy of drug transport and efficacy. TOPROCJ 2:64–72.
   Google Scholar
• Poole CPJ. (1971). Relaxation in magnetic resonance. New York (NY): Academic Press.
   Google Scholar
• Priyadarsini KI. (2014). The chemistry of curcumin: from extraction to therapeutic agent. Molecules 19:20091–112.
   PubMed Web of Science ®Google Scholar
• Selyutina OY, Apanasenko IE, Kim AV, et al. (2016b). Spectroscopic and molecular dynamics characterization of glycyrrhizin membrane-modifying activity. Colloids Surf B Biointerfaces 147:459–66.
   PubMed Web of Science ®Google Scholar
• Selyutina OY, Polyakov NE, Korneev DV, Zaitsev BN. (2016a). Influence of glycyrrhizin on permeability and elasticity of cell membrane: perspectives for drugs delivery. Drug Deliv 23:848–55.
   Web of Science ®Google Scholar
• Seo SW, Han HK, Chun MK, Choi HK. (2012). Preparation and pharmacokinetic evaluation of curcumin solid dispersion using Solutol® HS15 as a carrier. Int J Pharm 424:18–25.
   PubMed Web of Science ®Google Scholar
• Srivastava RM, Singh S, Dubey SK, et al. (2011). Immunomodulatory and therapeutic activity of curcumin. Int Immunopharmacol 11:331–41.
   PubMed Web of Science ®Google Scholar
• Su X, Wu L, Hu M, et al. (2017). Glycyrrhizic acid: a promising carrier material for anticancer therapy. Biomed Pharmacother = Biomed Pharmacother 95:670.
   PubMed Web of Science ®Google Scholar
• Taki M, Tagami T, Fukushige K, Ozeki T. (2016). Fabrication of nanocomposite particles using a two-solution mixing-type spray nozzle for use in an inhaled curcumin formulation. Int J Pharm 511:104–10.
   PubMed Web of Science ®Google Scholar
• Tsai YM, Chien CF, Lin LC, Tsai TH. (2011). Curcumin and its nano-formulation: the kinetics of tissue distribution and blood–brain barrier penetration. Int J Pharm 416:331–8.
   PubMed Web of Science ®Google Scholar
• Varalakshmi C, Ali AM, Pardhasaradhi BVV, et al. (2008). Immunomodulatory effects of curcumin: in-vivo. Int Immunopharmacol 8:688–700.
   PubMed Web of Science ®Google Scholar
• Vasconcelos T, Marques S, Das NJ, Sarmento B. (2016). Amorphous solid dispersions: rational selection of a manufacturing process. Adv Drug Deliv Rev 100:85–101.
   PubMed Web of Science ®Google Scholar
• Veber DF, Johnson SR, Cheng HY, et al. (2002). Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 45:2615–23.
   PubMed Web of Science ®Google Scholar
• Wan K, Sun L, Hu X, et al. (2016). Novel nanoemulsion based lipid nanosystems for favorable in vitro and in vivo characteristics of curcumin. Int J Pharm 504:80–8.
   PubMed Web of Science ®Google Scholar
• Wang GW. (2013). Mechanochemical organic synthesis. Chem Soc Rev 42:7668–700.
   PubMed Web of Science ®Google Scholar
• Yoncheva K, Kamenova K, Perperieva T, et al. (2015). Cationic triblock copolymer micelles enhance antioxidant activity, intracellular uptake and cytotoxicity of curcumin. Int J Pharm 490:298–307.
   PubMed Web of Science ®Google Scholar
• Yu JB, Zhang Y, Jiang ZJ, Su WK. (2016). Mechanically induced Fe(III) catalysis at room temperature: solvent-free cross-dehydrogenative coupling of 3-benzylic Indoles with methylenes/indoles. J Org Chem 81:11514.
   PubMed Web of Science ®Google Scholar