Curcumin solid dispersion based on three model acrylic polymers
formulation and release properties
DOI:
https://doi.org/10.1590/s2175-97902022e18946Keywords:
Control release, Curcumin, Solid dispersion, In vitro digestion, Eudragit polymerAbstract
To investigate structure-property relationship of polymer-based curcumin solid dispersion (SD), three acrylic polymers were used to formulate curcumin SD by solvent evaporation method. Curcumin Eudragit EPO SD (cur@EPO), curcumin Eudragit RS PO SD (cur@RSPO) and curcumin Eudragit RL PO SD (cur@RLPO) showed deep red, golden orange and reddish orange color, respectively. Cur@RSPO entrapped 15.42 wt% of curcumin followed by cur@RL PO and cur@EPO. FTIR spectra indicated that in cur@EPO, curcumin may transfer hydrogen to the dimethylaminoethyl methacrylate group and thus change its color to red. In contrast, curcumin may form hydrogen bonding with Eudragit RS PO and Eudragit RL. Curcumin exists in amorphous state in three SDs as proved by differential scanning calorimetry and X-Ray diffraction measurement. In vitro digestion presented that lower pH value in simulated gastric fluid (SGF) stimulates the curcumin release from cur@EPO while permeability influences the release profile in other two SDs. When in simulated intestinal fluid (SIF), first order release model governs the release behaviors of all three SDs which showed sustained release pattern. Our results are helpful to elucidate how structure of polymer may impact on the major properties of curcumin contained SD and will be promising to broaden its therapeutic applications.
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Abbaspour MR, Sadeghi F, Garekani HA. Preparation and characterization of ibuprofen pellets based on Eudragit RS PO and RL PO or their combination. Int J Pharm. 2005;303(1-2):88-94.
Apu AS, Pathan AH, Shrestha D, Kibria G, Jalil RU. Investigation of In vitro Release Kinetics of Carbamazepine from Eudragit (R) RS PO and RL PO Matrix Tablets. Trop J Pharm Res. 2009;8(2):145-152.
Boyanapalli SSS, Huang Y, Su Z, Cheng D, Zhang C, Guo Y, et al. Pharmacokinetics and Pharmacodynamics of Curcumin in regulating anti-inflammatory and epigenetic gene expression. Biopharm Drug Dispos. 2018;39(6):289-297.
Breitenbach J. Melt extrusion: from process to drug delivery technology. Eur J Pharm Biopharm. 2002;54(2):107-117.
Changdeo JS, Vinod M, Shankar KB, Rajaram CA. Physicochemical characterization and solubility enhancement studies of allopurinol solid dispersions. Braz J Pharm Sci. 2011;47(3):513-523.
Crotts G, Sheth A, Twist J, Ghebre-Sellassie I. Development of an enteric coating formulation and process for tablets primarily composed of a highly water-soluble, organic acid. Eur J Pharm Biopharm . 2001;51(1):71-76.
Deck LM, Hunsaker LA, Vander Jagt TA, Whalen LJ, Royer RE, Vander Jagt DL. Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin. Eur J Med Chem. 2018;143:854-865.
Desai S, Simonelli A, Higuchi W. Investigation of factors influencing release of solid drug dispersed in inert matrices. J Pharm Sci. 1965;54(10):1459-1464.
Esmaili M, Ghaffari SM, Moosavi-Movahedi Z, Atri MS, Sharifizadeh A, Farhadi M, et al. Beta casein-micelle as a nano vehicle for solubility enhancement of curcumin; food industry application. LWT-Food Sci Technol. 2011;44(10):2166-2172.
Gallardo D, Skalsky B, Kleinebudde P. Controlled release solid dosage forms using combinations of (meth)acrylate copolymers. Pharm Dev Technol. 2008;13(5):413-423.
Gangwar RK, Tomar GB, Dhumale VA, Zinjarde S, Sharma RB, Datar S. Curcumin conjugated silica nanoparticles for improving bioavailability and its anticancer applications. J Agr Food Chem. 2013;61(40):9632-9637.
Hasan M, Belhaj N, Benachour H, Barberi-Heyob M, Kahn CJF, Jabbari E, et al. Liposome encapsulation of curcumin: Physico-chemical characterizations and effects on MCF7 cancer cell proliferation. Int J Pharm. 2014;461(1-2):519-528.
Heger M, van Golen RF, Broekgaarden M, Michel MC. The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer. Pharmacol Rev. 2014;66(1):222-307.
Higuchi T. Mechanism of Sustained-Action Medication - Theoretical analysis of rate of release of solid drugs dispersed in solid matrices. J Pharm Sci . 1963;52(12):1145-1149.
Jiang Y, Li FF, Luan YX, Cao WT, Ji XQ, Zhao LX et al. Formation of drug/surfactant catanionic vesicles and their application in sustained drug release. Int J Pharm . 2012;436(1-2):806-814.
Kakran M, Sahoo NG, Tan IL, Li L. Preparation of nanoparticles of poorly water-soluble antioxidant curcumin by antisolvent precipitation methods. J Nanopart Res. 2012;14(3):757-768.
Kharat M, Zhang G, McClements DJ. Stability of curcumin in oil-in-water emulsions: Impact of emulsifier type and concentration on chemical degradation. Food Res Int. 2018;111:178-186.
Kim BK, Hwang SJ, Park JB, Park HJ. Preparation and characterization of drug-loaded polymethacrylate microspheres by an emulsion solvent evaporation method. J Microencapsul. 2002;19(6):811-822.
Korsmeyer RW, Gurny R, Doelker E, Buri P, Peppas NA. Mechanisms of Solute Release from Porous Hydrophilic Polymers. Int J Pharm . 1983;15(1):25-35.
Li B, Konecke S, Wegiel LA, Taylor LS, Edgar KJ. Both solubility and chemical stability of curcumin are enhanced by solid dispersion in cellulose derivative matrices. Carbohyd Polym. 2013;98(1):1108-1116.
Li J, Lee IW, Shin GH, Chen X, Park HJ. Curcumin-Eudragit® E PO solid dispersion: A simple and potent method to solve the problems of curcumin. Eur J Pharm Biopharm . 2015a;94:322-332.
Li J, Shin GH, Chen X, Park HJ. Modified Curcumin with Hyaluronic Acid: Combination of Pro-drug and Nano- micelle Strategy to Address the Curcumin Challenge. Food Res Int . 2015b;69:202-208.
Liu HJ, Wang P, Zhang XY, Shen F, Gogos CG. Effects of extrusion process parameters on the dissolution behavior of indomethacin in Eudragit (R) E PO solid dispersions. Int J Pharm . 2010;383(1-2):161-169.
Menjoge AR, Kulkarni MG. Mechanistic investigations of phase behavior in Eudragit (R) blends. Int J Pharm . 2007;343(1-2):106-121.
Najib N, Suleiman MS. The Kinetics of Drug Release from Ethylcellulose Solid Dispersions. Drug Dev Ind Pharm. 1985;11(12):2169-2181.
Paradkar A, Ambike AA, Jadhav BK, Mahadik KR. Characterization of curcumin-PVP solid dispersion obtained by spray drying. Int J Pharm . 2004;271(1-2):281-286.
Paramera EI, Konteles SJ, Karathanos VT. Stability and release properties of curcumin encapsulated in Saccharomyces cerevisiae, beta-cyclodextrin and modified starch. Food Chem. 2011;125(3):913-922.
Pawar YB, Shete G, Popat D, Bansal AK. Phase behavior and oral bioavailability of amorphous Curcumin. Eur J Pharm Sci . 2012;47(1):56-64.
Pourreza N, Golmohammadi H. Application of curcumin nanoparticles in a lab-on-paper device as a simple and green pH probe. Talanta. 2015;131:136-141.
Sahoo J, Murthy PN, Biswal S, Ghosh M. Formulation of Sustained-Release Dosage Form of Verapamil Hydrochloride by Solid Dispersion Technique Using Eudragit RLPO or KollidonA (R) SR. Aaps Pharmscitech. 2009;10(1):27-33.
Sanmukhani J, Anovadiya A, Tripathi CB. Evaluation of antidepressant like activity of curcumin and its combination with fluoxetine and imipramine: an acute and chronic study. ACTA Pol Pharm. 2011;68:769-775.
Sanphui P, Goud NR, Khandavilli UB, Bhanoth S, Nangia A. New polymorphs of curcumin. Chem Commun. 2011;47: 5013-5015.
Soleimani H, Amini A, Taheri S, Sajadi E, Shafikhani S, Schuger LA, et al. The effect of combined photobiomodulation and curcumin on skin wound healing in type I diabetes in rats. J Photoch Photobio B. 2018;181:23-30.
Sun DD, Lee PI. Probing the mechanisms of drug release from amorphous solid dispersions in medium-soluble and medium- insoluble carriers. J Control Release. 2015;211:85-93.
Tønnesen HH, Karlsen J. Studies on curcumin and curcuminoids. Zeitschrift für Lebensmittel-Untersuchung und Forschung. 1985;180(5):402-404.
Takka S, Rajbhandari S, Sakr A. Effect of anionic polymers on the release of propranolol hydrochloride from matrix tablets. Eur J Pharm Biopharm . 2001;52(1):75-82.
Tang B, Ma L, Wang HY, Zhang Y. Study on the supramolecular interaction of curcumin and β-cyclodextrin by spectrophotometry and its analytical application. J Agr Food Chem. 2002;50(6):1355-1361.
Thorat AA, Dalvi SV. Solid-state phase transformations and storage stability of curcumin polymorphs. Cryst Growth Des. 2015;15:1757-1770.
Tonnesen HH, Masson M, Loftsson T. Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability. Int J Pharm . 2002;244(1-2):127-135.
Ueda H, Wakabayashi S, Kikuchi J, Ida Y, Kadota K, Tozuka Y. Anomalous role change of tertiary amino and ester groups as hydrogen acceptors in eudragit e based solid dispersion depending on the concentration of Naproxen. Mol Pharmaceutics. 2015;12(4):1050-1061.
Varshosaz J, Faghihian H, Rastgoo K. Preparation and characterization of metoprolol controlled-release solid dispersions. Drug Deliv. 2006;13(4):295-302.
Wegiel LA, Zhao YH, Mauer LJ, Edgar KJ, Taylor LS. Curcumin amorphous solid dispersions: the influence of intra and intermolecular bonding on physical stability. Pharm Dev Technol . 2014;19(8):976-986.
Wu CB, McGinity JW. Influence of methylparaben as a solid-state plasticizer on the physicochemical properties of Eudragit (R) RS PO hot-melt extrudates. Eur J Pharm Biopharm . 2003;56(1):95-100.
Zhang F, Koh GY, Jeansonne DP, Hollingsworth J, Russo PS, Vicente G, et al. A novel solubility-enhanced curcumin formulation showing stability and maintenance of anticancer activity. J Pharm Sci . 2011;100(7):2778-2789.
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