Abstract
Curcumin, as a naturally occurring polyphenol, has been extensively used as anticancer and antioxidant agent due to its ability to protect cells from oxidative damage. However, its poor solubility and low bioavailability have limited its application. To increase the solubility and effectiveness of curcumin, a new multi-drug delivery system is developed based on curcumin-loaded cyclodextrin-conjugated gallic acid. For this purpose, β-cyclodextrin was grafted by gallic acid, and then, a 2:1 inclusion complex of cyclodextrin and curcumin was prepared. The mean particle size of the curcumin-loaded β-CD-g-GA was about 100 nm by DLS. All observations using FT-IR, NMR, UV–Vis and FE-SEM confirmed successful preparation of the CUR@β-CD-graft-gallic acid. In addition, antioxidant activity and release behavior of the curcumin-loaded β-CD-graft-GA was investigated. The IC50 value for CUR@β-CD-g-GA was estimated (0.4909 µg/mL) based on their inhibition percent–concentration curves using DPPH assay. Also, the total released amount of curcumin within 48 h in pH 7.4 and 5.4 was 41% and 91%, respectively. Because the designed multi-drug delivery system is convenient to prepare, possesses appropriate antioxidant activity and pH-sensitive release behavior and most importantly composed of fully green and safe materials, it may represent an attractive new potent multi-drug delivery system.
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References
Ren J, Li Q, Dong F, Feng Y, Guo Z (2013) Phenolic antioxidants-functionalized quaternized chitosan: synthesis and antioxidant properties. Int J Biol Macromol 53:77–81. https://doi.org/10.1016/j.ijbiomac.2012.11.011
Zhang M, Song CC, Su S, Du FS, Li ZC (2018) ROS-activated ratiometric fluorescent polymeric nanoparticles for self-reporting drug delivery. ACS Appl Mater Interfaces 10(9):7798–7810. https://doi.org/10.1021/acsami.7b18438
Singh A, Kureel AK, Dutta PK, Kumar S, Rai AK (2018) Curcumin loaded chitin-glucan quercetin conjugate: synthesis, characterization, antioxidant, in vitro release study, and anticancer activity. Int J Biol Macromol 110:234–244. https://doi.org/10.1016/j.ijbiomac.2017.11.002
Singh A, Dutta PK, Kumar H, Kureel AK, Rai AK (2018) Synthesis of chitin-glucan-aldehyde-quercetin conjugate and evaluation of anticancer and antioxidant activities. Carbohydr Polym 193:99–107. https://doi.org/10.1016/j.carbpol.2018.03.092
Wróblewska-Krepsztul J, Rydzkowski T, Borowski G, Szczypiński M, Klepka T, Thakur VK (2018) Recent progress in biodegradable polymers and nanocomposite-based packaging materials for sustainable environment. Int J Polym Anal Charact 23(4):383–395. https://doi.org/10.1080/1023666X.2018.1455382
Gao Y, Jiang F, Zhang L et al (2016) Enzymatic synthesis of polyguaiacol and its thermal antioxidant behavior in polypropylene. Polym Bull 73:1343. https://doi.org/10.1007/s00289-015-1551-9
Coscia MG, Bhardwaj J, Singh N, Santonicola MG, Richardson R, Thakur VK, Rahatekar S (2018) Manufacturing & characterization of regenerated cellulose/curcumin based sustainable composites fibers spun from environmentally benign solvents. Ind Crop Prod 111:536–543. https://doi.org/10.1016/j.indcrop.2017.09.041
Pandele AM, Neacsu P, Cimpean A, Staras AI, Miculescu F, Iordache A, Thakur VK, Toader OD (2018) Cellulose acetate membranes functionalized with resveratrol by covalent immobilization for improved osseointegration. Appl Surf Sci 438:2–13. https://doi.org/10.1016/j.apsusc.2017.11.102
Lim LM, Wong JJL, Wang D, Cheow WS, Hadinoto K (2018) Amorphous ternary nanoparticle complex of curcumin-chitosan-hypromellose exhibiting built-in solubility enhancement and physical stability of curcumin. Colloids Surf B 167:483–491. https://doi.org/10.1016/j.colsurfb.2018.04.049
Raveendran R, Mullen KM, Wellard RM, Sharma CP, Hoogenboom R, Dargaville TR (2017) Poly (2-oxazoline) block copolymer nanoparticles for curcumin loading and delivery to cancer cells. Eur Polym J 93:682–694. https://doi.org/10.1016/j.eurpolymj.2017.02.043
Rui L, Xie M, Hu B, Zhou L, Yin D, Zeng X (2017) A comparative study on chitosan/gelatin composite films with conjugated or incorporated gallic acid. Carbohydr Polym 173:473–481. https://doi.org/10.1016/j.carbpol.2017.05.072
Munin A, Edwards-Lévy F (2011) Encapsulation of natural polyphenolic compounds; a review. Pharmaceutics 3(4):793–829. https://doi.org/10.3390/pharmaceutics3040793
Yang TS, Liu TT, Lin IH (2017) Functionalities of chitosan conjugated with stearic acid and gallic acid and application of the modified chitosan in stabilizing labile aroma compounds in an oil-in-water emulsion. Food Chem 228:541–549. https://doi.org/10.1016/j.foodchem.2017.02.035
Liu J, Wang X, Yong H, Kan J, Zhang N, Jin C (2018) Preparation, characterization, digestibility and antioxidant activity of quercetin grafted Cynanchum auriculatum starch. Int J Biol Macromol 114:130–136. https://doi.org/10.1016/j.ijbiomac.2018.03.101
Sattari S, Tehrani AD, Adeli M, Azarbani F (2018) Development of new nanostructure based on poly (aspartic acid)-g-amylose for targeted curcumin delivery using helical inclusion complex. J Mol Liq 258:18–26. https://doi.org/10.1016/j.molliq.2018.02.116
Park HH, Ko SC, Oh GW, Jang YM, Kim YM, Park WS, Jung WK (2018) Characterization and biological activity of PVA hydrogel containing chitooligosaccharides conjugated with gallic acid. Carbohydr Polym. https://doi.org/10.1016/j.carbpol.2018.06.070
Esfanjani AF, Jafari SM (2016) Biopolymer nano-particles and natural nano-carriers for nano-encapsulation of phenolic compounds. Colloids Surf B 146:532–543. https://doi.org/10.1016/j.colsurfb.2016.06.053
Chanphai P, Tajmir-Riahi HA (2017) Probing the binding of resveratrol, genistein and curcumin with chitosan nanoparticles. J Mol Liq 243:108–114. https://doi.org/10.1016/j.molliq.2017.08.024
Thakur S, Sharma B, Verma A, Chaudhary J, Tamulevicius S, Thakur VK (2018) Recent progress in sodium alginate based sustainable hydrogels for environmental applications. J Clean Prod 198:143–159. https://doi.org/10.1016/j.jclepro.2018.06.259
Miculescu F, Maidaniuc A, Voicu SI, Thakur VK, Stan GE, Ciocan LT (2017) Progress in hydroxyapatite–starch based sustainable biomaterials for biomedical bone substitution applications. ACS Sustain Chem Eng 5(10):8491–8512. https://doi.org/10.1021/acssuschemeng.7b02314
Aytac Z, Uyar T (2016) Antioxidant activity and photostability of α-tocopherol/β-cyclodextrin inclusion complex encapsulated electrospun polycaprolactone nanofibers. Eur Polym J 79:140–149. https://doi.org/10.1016/j.eurpolymj.2016.04.029
Kamimura JA, Santos EH, Hill LE, Gomes CL (2014) Antimicrobial and antioxidant activities of carvacrol microencapsulated in hydroxypropyl-beta-cyclodextrin. LWT-Food Sci Technol 57(2):701–709. https://doi.org/10.1016/j.lwt.2014.02.014
Zhang L, Man S, Qiu H, Liu Z, Zhang M, Ma L, Gao W (2016) Curcumin-cyclodextrin complexes enhanced the anti-cancer effects of curcumin. Environ Toxicol Pharmacol 48:31–38. https://doi.org/10.1016/j.etap.2016.09.021
Shlar I, Droby S, Choudhary R, Rodov V (2017) The mode of antimicrobial action of curcumin depends on the delivery system: monolithic nanoparticles vs. supramolecular inclusion complex. RSC Adv 7(67):42559–42569. https://doi.org/10.1039/C7RA07303H
Olga G, Styliani C, Ioannis RG (2015) Coencapsulation of ferulic and gallic acid in hp-b-cyclodextrin. Food Chem 185:33–40. https://doi.org/10.1016/j.foodchem.2015.03.058
Cheng JG, Tian BR, Huang Q, Ge HR, Wang ZZ (2018) Resveratrol functionalized carboxymethyl-β-Cyclodextrin: synthesis, characterization, and photostability. J Chem 1:2–8. https://doi.org/10.1155/2018/6789076
Nazir S, Soetikno JS, Ho AL (2018) Antioxidant properties of polyphenol glycoside catalyzed by transglycosylation reaction of cyclodextrin glucanotransferase derived from Trichoderma viride. J Food Biochem. https://doi.org/10.1111/jfbc.12499
Vieira AC, Serra AC, Veiga FJ, Gonsalves AMDAR, Basit AW, Murdan S (2016) Diclofenac-β-cyclodextrin for colonic drug targeting: in vivo performance in rats. Int J Pharm 500(1–2):366–370. https://doi.org/10.1016/j.ijpharm.2016.01.024
Chu HM, Zhang RX, Huang Q, Bai CC, Wang ZZ (2017) Chemical conjugation with cyclodextrins as a versatile tool for drug delivery. J Inclusion Phenom Macrocyclic Chem 89(1–2):29–38. https://doi.org/10.1007/s10847-017-0743-3
Mujeeb Rahman P, Abdul Mujeeb VM, Muraleedharan K (2017) Chitosan–green tea extract powder composite pouches for extending the shelf life of raw meat. Polym Bull 74:3399. https://doi.org/10.1007/s00289-016-1901-2
Mangolim CS, Moriwaki C, Nogueira AC, Sato F, Baesso ML, Neto AM, Matioli G (2014) Curcumin-β-cyclodextrin inclusion complex: stability, solubility, characterisation by FT-IR, FT-Raman, X-ray diffraction and photoacoustic spectroscopy, and food application. Food Chem 153:361–370. https://doi.org/10.1016/j.foodchem.2013.12.067
Chatterjee NS, Panda SK, Navitha M, Asha KK, Anandan R, Mathew S (2015) Vanillic acid and coumaric acid grafted chitosan derivatives: improved grafting ratio and potential application in functional food. J Food Sci Technol 52(11):7153–7162. https://doi.org/10.1007/s13197-015-1874-4
Cho YS, Kim SK, Ahn CB, Je JY (2011) Preparation, characterization, and antioxidant properties of gallic acid-grafted-chitosans. Carbohydr Polym 83(4):1617–1622. https://doi.org/10.1016/j.carbpol.2010.10.019
Xie M, Hu B, Wang Y, Zeng X (2014) Grafting of gallic acid onto chitosan enhances antioxidant activities and alters rheological properties of the copolymer. J Agric Food Chem 62(37):9128–9136. https://doi.org/10.1021/jf503207s
Criado P, Fraschini C, Salmieri S, Becher D, Safrany A, Lacroix M (2016) Free radical grafting of gallic acid (GA) on cellulose nanocrystals (CNCS) and evaluation of antioxidant reinforced gellan gum films. Radiat Phys Chem 118:61–69. https://doi.org/10.1016/j.radphyschem.2015.05.030
Hu L, Kong D, Hu Q, Gao N, Pang S (2015) Evaluation of high-performance curcumin nanocrystals for pulmonary drug delivery both in vitro and in vivo. Nanoscale Res Lett 10(1):381
Sbora RALUCA, Budura EA, Niţulescu GM, Balaci T, Lupuleasa D (2015) Preparation and characterization of inclusion complexes of prazosin hydrochloride with β-cyclodextrin and hydroxypropyl-β-cyclodextrin. J Pharm Biomed Anal 63(4):548–555. https://doi.org/10.1186/s11671-015-1085-y
Wu A, Shen X, He Y (2006) Investigation on γ-cyclodextrin nanotube induced by N, N′-diphenylbenzidine molecule. J Colloid Interface Sci 297(2):525–533. https://doi.org/10.1016/j.jcis.2005.11.014
Tang B, Ma L, Wang HY, Zhang GY (2002) Study on the supramolecular interaction of curcumin and β-cyclodextrin by spectrophotometry and its analytical application. J Agric Food Chem 50(6):1355–1361. https://doi.org/10.1021/jf0111965
Zhu G, Xiao Z, Zhu G (2017) Preparation, characterization and the release kinetics of mentha-8-thiol-3-one-β-cyclodextrin inclusion complex. Polym Bull 74:2263. https://doi.org/10.1007/s00289-016-1835-8
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The authors wish to gratefully acknowledge the support of Lorestan University. This research did not receive any specific grant from funding agencies in the public, commercial or not-for-profit sectors.
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Omrani, Z., Dadkhah Tehrani, A. New cyclodextrin-based supramolecular nanocapsule for codelivery of curcumin and gallic acid. Polym. Bull. 77, 2003–2019 (2020). https://doi.org/10.1007/s00289-019-02845-5
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DOI: https://doi.org/10.1007/s00289-019-02845-5