Preparation, characterization, and release kinetics of chitosan-coated nanoliposomes encapsulating curcumin in simulated environments

Molecules

Volumn 24, Issue 10, 2019, Pages

  Hasan, Mahmoud ^a   Elkhoury, Kamil ^a   Kahn, Cyril J F ^a   Arab Tehrany, Elmira ^a   Linder, Michel ^a  

^a UNIVERSITÉ DE LORRAINE   (France)

Author keywords

Chitosan; Curcumin; Gastrointestinal environment; Nanoliposomes; Release kinetics

Indexed keywords

CHITOSAN; CURCUMIN; FATTY ACID; LIPOSOME; NANOPARTICLE;

ANIMAL; CHEMISTRY; DRUG RELEASE; KINETICS; SALMONINE;

ANIMALS; CHITOSAN; CURCUMIN; DRUG LIBERATION; FATTY ACIDS; KINETICS; LIPOSOMES; NANOPARTICLES; SALMON;

EID: 85066288947     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules24102023     Document Type: Article

References (79)

1. Alisi, I. O.; Uzairu, A.; Abechi, S. E.; Idris, S. O. Evaluation of the antioxidant properties of curcumin derivatives by genetic function algorithm. J. Adv. Res. 2018, 12, 47-54. [CrossRef] [PubMed]
2. Dhir, A. Curcumin in epilepsy disorders: Curcumin and Epilepsy. Phytother. Res. 2018, 32, 1865-1875. [CrossRef]
3. Babu, A.; Mohammed, S.; Harikumar, K. B. Antioxidant Properties of Curcumin: Impact on Neurological Disorders. In Curcumin for Neurological and Psychiatric Disorders; Elsevier: Thiruvananthapuram, India, 2019; pp. 155-167, ISBN 978-0-12-815461-8.
4. Barchitta, M.; Maugeri, A.; Favara, G.; Magnano San Lio, R.; Evola, G.; Agodi, A.; Basile, G. Nutrition and Wound Healing: An Overview Focusing on the Beneficial effects of Curcumin. IJMS 2019, 20, 1119. [CrossRef]
5. Akbik, D.; Ghadiri, M.; Chrzanowski, W.; Rohanizadeh, R. Curcumin as A wound healing agent. Life Sci. 2014, 116, 1-7. [CrossRef]
6. Tomeh, M.; Hadianamrei, R.; Zhao, X. A Review of Curcumin and Its Derivatives as Anticancer Agents. IJMS 2019, 20, 1033. [CrossRef]
7. Suhito, I. R.; Lee, W.; Baek, S.; Lee, D.; Min, J.; Kim, T.-H. Rapid and sensitive electrochemical detection of anticancer effects of curcumin on human glioblastoma cells. Sens. Actuators B Chem. 2019, 288, 527-534. [CrossRef]
8. Hasan, M.; Belhaj, N.; Benachour, H.; Barberi-Heyob, M.; Kahn, C. J. F.; Jabbari, E.; Linder, M.; Arab-Tehrany, E. Liposome encapsulation of curcumin: Physico-chemical characterizations and effects on MCF7 cancer cell proliferation. Int. J. Pharm. 2014, 461, 519-528. [CrossRef]
9. Panahi, Y.; Fazlolahzadeh, O.; Atkin, S. L.; Majeed, M.; Butler, A. E.; Johnston, T. P.; Sahebkar, A. Evidence of curcumin and curcumin analogue effects in skin diseases: A narrative review. J. Cell. Physiol. 2019, 234, 1165-1178. [CrossRef]
10. Gómez-Estaca, J.; Balaguer, M. P.; López-Carballo, G.; Gavara, R.; Hernández-Muñoz, P. Improving antioxidant and antimicrobial properties of curcumin by means of encapsulation in gelatin through electrohydrodynamic atomization. Food Hydrocoll. 2017, 70, 313-320. [CrossRef]
11. Krausz, A. E.; Adler, B. L.; Cabral, V.; Navati, M.; Doerner, J.; Charafeddine, R. A.; Chandra, D.; Liang, H.; Gunther, L.; Clendaniel, A.; et al. Curcumin-encapsulated nanoparticles as innovative antimicrobial and wound healing agent. Nanomed. Nanotechnol. Biol. Med. 2015, 11, 195-206. [CrossRef] [PubMed]
12. Fadus, M. C.; Lau, C.; Bikhchandani, J.; Lynch, H. T. Curcumin: An age-old anti-inflammatory and anti-neoplastic agent. J. Tradit. Complement. Med. 2017, 7, 339-346. [CrossRef]
13. Chin, K.-Y. The spice for joint inflammation: anti-inflammatory role of curcumin in treating osteoarthritis. DDDT 2016, 10, 3029-3042. [CrossRef]
14. Edwards, R. L.; Luis, P. B.; Varuzza, P. V.; Joseph, A. I.; Presley, S. H.; Chaturvedi, R.; Schneider, C. The anti-inflammatory activity of curcumin is mediated by its oxidative metabolites. J. Biol. Chem. 2017, 292, 21243-21252. [CrossRef]
15. Song, W.; Su, X.; Gregory, D.; Li, W.; Cai, Z.; Zhao, X. Magnetic Alginate/Chitosan Nanoparticles for Targeted Delivery of Curcumin into Human Breast Cancer Cells. Nanomaterials 2018, 8, 907. [CrossRef]
16. Shoba, G.; Joy, D.; Joseph, T.; Majeed, M.; Rajendran, R.; Srinivas, P. Influence of Piperine on the Pharmacokinetics of Curcumin in Animals and Human Volunteers. Planta Med. 1998, 64, 353-356. [CrossRef]
17. Zhang, J.; Tang, Q.; Xu, X.; Li, N. Development and evaluation of A novel phytosome-loaded chitosan microsphere system for curcumin delivery. Int. J. Pharm. 2013, 448, 168-174. [CrossRef] [PubMed]
18. Sari, T. P.; Mann, B.; Kumar, R.; Singh, R. R. B.; Sharma, R.; Bhardwaj, M.; Athira, S. Preparation and characterization of nanoemulsion encapsulating curcumin. Food Hydrocoll. 2015, 43, 540-546. [CrossRef]
19. Montalbán, M.; Coburn, J.; Lozano-Pérez, A.; Cenis, J.; Víllora, G.; Kaplan, D. Production of Curcumin-Loaded Silk Fibroin Nanoparticles for Cancer Therapy. Nanomaterials 2018, 8, 126. [CrossRef] [PubMed]
20. Song, W.; Muthana, M.; Mukherjee, J.; Falconer, R. J.; Biggs, C. A.; Zhao, X. Magnetic-Silk Core-Shell Nanoparticles as Potential Carriers for Targeted Delivery of Curcumin into Human Breast Cancer Cells. Acs Biomater. Sci. Eng. 2017, 3, 1027-1038. [CrossRef]
21. Wang, T.; Ma, X.; Lei, Y.; Luo, Y. Solid lipid nanoparticles coated with cross-linked polymeric double layer for oral delivery of curcumin. Colloids Surf. B Biointerfaces 2016, 148, 1-11. [CrossRef]
22. Hajj Ali, H.; Michaux, F.; Bouelet Ntsama, I. S.; Durand, P.; Jasniewski, J.; Linder, M. Shea butter solid nanoparticles for curcumin encapsulation: Influence of nanoparticles size on drug loading: Control of shea butter SLN size for curcumin encapsulation. Eur. J. Lipid Sci. Technol. 2016, 118, 1168-1178. [CrossRef]
23. Bhandari, R.; Gupta, P.; Dziubla, T.; Hilt, J. Z. Single step synthesis, characterization and applications of curcumin functionalized iron oxide magnetic nanoparticles. Mater. Sci. Eng. C 2016, 67, 59-64. [CrossRef] [PubMed]
24. Minnelli, C.; Moretti, P.; Fulgenzi, G.; Mariani, P.; Laudadio, E.; Armeni, T.; Galeazzi, R.; Mobbili, G. A Poloxamer-407 modified liposome encapsulating epigallocatechin-3-gallate in the presence of magnesium: Characterization and protective effect against oxidative damage. Int. J. Pharm. 2018, 552, 225-234. [CrossRef]
25. Daraee, H.; Etemadi, A.; Kouhi, M.; Alimirzalu, S.; Akbarzadeh, A. Application of liposomes in medicine and drug delivery. Artif. Cells Nanomed. Biotechnol. 2016, 44, 381-391. [CrossRef]
26. Bozzuto, G.; Molinari, A. Liposomes as nanomedical devices. IJN 2015, 10, 975. [CrossRef] [PubMed]
27. Zhang, W.; Wang, G.; Falconer, J. R.; Baguley, B. C.; Shaw, J. P.; Liu, J.; Xu, H.; See, E.; Sun, J.; Aa, J.; et al. Strategies to Maximize Liposomal Drug Loading for A PoorlyWater-soluble Anticancer Drug. Pharm. Res. 2015, 32, 1451-1461. [CrossRef] [PubMed]
28. Nogueira, E.; Gomes, A. C.; Preto, A.; Cavaco-Paulo, A. Design of liposomal formulations for cell targeting. Colloids Surf. B Biointerfaces 2015, 136, 514-526. [CrossRef]
29. Shin, G. H.; Chung, S. K.; Kim, J. T.; Joung, H. J.; Park, H. J. Preparation of Chitosan-Coated Nanoliposomes for Improving the Mucoadhesive Property of Curcumin Using the Ethanol Injection Method. J. Agric. Food Chem. 2013, 61, 11119-11126. [CrossRef]
30. Ahmadi Ashtiani, H. R.; Bishe, P.; Lashgari, N.-A.; Nilforoushzadeh, M. A.; Zare, S. Liposomes in Cosmetics. J. Ski. Stem Cell 2016, 3, e65815. [CrossRef]
31. Emami, S.; Azadmard-Damirchi, S.; Peighambardoust, S. H.; Valizadeh, H.; Hesari, J. Liposomes as carrier vehicles for functional compounds in food sector. J. Exp. Nanosci. 2016, 11, 737-759. [CrossRef]
32. Zylberberg, C.; Matosevic, S. Pharmaceutical liposomal drug delivery: A review of new delivery systems and A look at the regulatory landscape. Drug Deliv. 2016, 23, 3319-3329. [CrossRef]
33. Ma, Y.-H.; Yang, J.; Li, B.; Jiang, Y.-W.; Lu, X.; Chen, Z. Biodegradable and injectable polymer-liposome hydrogel: A promising cell carrier. Polym. Chem. 2016, 7, 2037-2044. [CrossRef]
34. Kadri, R.; Ben Messaoud, G.; Tamayol, A.; Aliakbarian, B.; Zhang, H. Y.; Hasan, M.; Sánchez-González, L.; Arab-Tehrany, E. Preparation and characterization of nanofunctionalized alginate/methacrylated gelatin hybrid hydrogels. Rsc Adv. 2016, 6, 27879-27884. [CrossRef]
35. Lin, C.-C.; Lin, H.-Y.; Chen, H.-C.; Yu, M.-W.; Lee, M.-H. Stability and characterisation of phospholipid-based curcumin-encapsulated microemulsions. Food Chem. 2009, 116, 923-928. [CrossRef]
36. Calder, P. C.; Yaqoob, P. Understanding omega-3 polyunsaturated fatty acids. Postgrad. Med. 2009, 121, 148-157. [CrossRef]
37. Van der Meerena, G.; Tlusty, M.; Metzlerc, A.; Van der Meerend, T. effects of dietary DHA and EPA on neurogenesis, growth, and survival of juvenile American lobster, Homarus americanus. N. Z. J. Mar. Freshw. Res. 2009, 43, 225-232. [CrossRef]
38. Belhaj, N.; Arab-Tehrany, E.; Linder, M. Oxidative kinetics of salmon oil in bulk and in nanoemulsion stabilized by marine lecithin. Process Biochem. 2010, 45, 187-195. [CrossRef]
39. Gbogouri, G. A.; Linder, M.; Fanni, J.; Parmentier, M. Analysis of lipids extracted from salmon (Salmo salar) heads by commercial proteolytic enzymes. Eur. J. Lipid Sci. Technol. 2006, 108, 766-775. [CrossRef]
40. Kato, Y.; Hosokawa, T.; Hayakawa, E.; Ito, K. Influence of Liposomes on Tryptic Digestion of Insulin. Biol. Pharm. Bull. 1993, 16, 457-461. [CrossRef] [PubMed]
41. Iwanaga, K.; Ono, S.; Narioka, K.; Kakemi, M.; Morimoto, K.; Yamashita, S.; Namba, Y.; Oku, N. Application of surface coated liposomes for oral delivery of peptide: effects of coating the liposome's surface on the GI transit of insulin. J. Pharm. Sci. 1999, 88, 248-252. [CrossRef]
42. Manconi, M.; Manca, M. L.; Valenti, D.; Escribano, E.; Hillaireau, H.; Fadda, A. M.; Fattal, E. Chitosan and hyaluronan coated liposomes for pulmonary administration of curcumin. Int. J. Pharm. 2017, 525, 203-210.[CrossRef]
43. Manconi, M.; Nácher, A.; Merino, V.; Merino-Sanjuan, M.; Manca, M. L.; Mura, C.; Mura, S.; Fadda, A. M.; Diez-Sales, O. Improving Oral Bioavailability and Pharmacokinetics of Liposomal Metformin by Glycerolphosphate-Chitosan Microcomplexation. Aaps Pharmscitech 2013, 14, 485-496. [CrossRef]
44. Hasan, M.; Ben Messaoud, G.; Michaux, F.; Tamayol, A.; Kahn, C. J. F.; Belhaj, N.; Linder, M.; Arab-Tehrany, E. Chitosan-coated liposomes encapsulating curcumin: Study of lipid-polysaccharide interactions and nanovesicle behavior. Rsc Adv. 2016, 6, 45290-45304. [CrossRef]
45. Takeuchi, H.; Matsui, Y.; Yamamoto, H.; Kawashima, Y. Mucoadhesive properties of carbopol or chitosan-coated liposomes and their effectiveness in the oral administration of calcitonin to rats. J. Control. Release 2003, 86, 235-242. [CrossRef]
46. Henriksen, I.; Vagen, S. R.; Sande, S. A.; Smistad, G.; Karlsen, J. Interactions between liposomes and chitosan. effect of selected parameters on aggregation and leakage. Int. J. Pharm. 1997, 146, 193-203. [CrossRef]
47. Takeuchi, H.; Yamamoto, H.; Niwa, T.; Hino, T.; Kawashima, Y. Enteral absorption of insulin in rats from mucoadhesive chitosan-coated liposomes. Pharm. Res. 1996, 13, 896-901. [CrossRef]
48. Kotzé, A. F.; Henrik, L. L.; Thanou, M.; Verhoef, J. C.; de Boer, A. G.; Junginger, H. E. Chitosan and Chitosan Derivatives as Absorption Enhancers for Peptide Drugs Across Mucosal Epithelia. In Bioadhesive Drug Delivery Systems; Drugs and the Pharmaceutical Sciences; CRC Press, Marcel Dekker Inc.: New York, NY, USA, 1999; pp. 341-386.
49. Wajda, R.; Zirkel, J.; Schaffer, T. Increase of bioavailability of coenzyme Q(10) and vitamin E. J. Med. Food 2007, 10, 731-734. [CrossRef]
50. Manca, M. L.; Castangia, I.; Matricardi, P.; Lampis, S.; Fernàndez-Busquets, X.; Fadda, A. M.; Manconi, M. Molecular arrangements and interconnected bilayer formation induced by alcohol or polyalcohol in phospholipid vesicles. Colloids Surf. B Biointerfaces 2014, 117, 360-367. [CrossRef]
51. Zweers, M. L. T.; Grijpma, D. W.; Engbers, G. H. M.; Feijen, J. The preparation of monodisperse biodegradable polyester nanoparticles with A controlled size. J. Biomed. Mater. Res. 2003, 66B, 559-566. [CrossRef] [PubMed]
52. Paolino, D.; Fresta, M.; Sinha, D.; Ferrari, M. Drug delivery systems. In Encyclopedia of Medical Devices and Instrumentation, 2nd ed.; Webester, J. G., Ed.; John Wiley & Sons, Inc.: New York, NY, USA, 2006; pp. 437-495.
53. Mady, M. M.; Darwish, M. M.; Khalil, S.; Khalil, W. M. Biophysical studies on chitosan-coated liposomes. Eur. Biophys. J. Biophys. Lett. 2009, 38, 1127-1133. [CrossRef] [PubMed]
54. Kuang, G.; Zhang, Z.; Liu, S.; Zhou, D.; Lu, X.; Jing, X.; Huang, Y. Biphasic drug release from electrospun polyblend nanofibers for optimized local cancer treatment. Biomater. Sci. 2018, 6, 324-331. [CrossRef]
55. Preetha, P.; Srinivasa, A.; Pushpalatha, P. Biphasicdrug delivery in controlled release formulations-A REVIEW. Int. J. Pharm. Technol. 2015, 6, 3046-3060.
56. Joraholmen, M. W.; Vanic, Z.; Tho, I.; Skalko-Basnet, N. Chitosan-coated liposomes for topical vaginal therapy: Assuring localized drug effect. Int. J. Pharm. 2014, 472, 94-101. [CrossRef]
57. Maherani, B.; Arab-Tehrany, E.; Kheirolomoom, A.; Geny, D.; Linder, M. Calcein release behavior from liposomal bilayer; influence of physicochemical/mechanical/structural properties of lipids. Biochimie 2013, 95, 2018-2033. [CrossRef]
58. Anal, A. K.; Singh, H. Recent advances in microencapsulation of probiotics for industrial applications and targeted delivery. Trends Food Sci. Technol. 2007, 18, 240-251. [CrossRef]
59. Vandenberg, G. W.; Drolet, C.; Scott, S. L.; de la Noue, J. Factors Affecting protein release from alginate-chitosan coacervate microcapsules during production and gastric/intestinal simulation. J. Control. Release 2001, 77, 297-307. [CrossRef]
60. Lee, J.-S.; Kim, H. W.; Chung, D.; Lee, H. G. Catechin-loaded calcium pectinate microparticles reinforced with liposome and hydroxypropylmethylcellulose: Optimization and in vivo antioxidant activity. Food Hydrocoll. 2009, 23, 2226-2233. [CrossRef]
61. Liu, M.; Ishida, Y.; Ebina, Y.; Sasaki, T.; Aida, T. Photolatently modulable hydrogels using unilamellar titania nanosheets as photocatalytic crosslinkers. Nat. Commun. 2013, 4, 2029. [CrossRef]
62. Liu, W.; Ye, A.; Liu, C.; Liu, W.; Singh, H. Structure and integrity of liposomes prepared from milk-or soybean-derived phospholipids during in vitro digestion. Food Res. Int. 2012, 48, 499-506. [CrossRef]
63. Gao, W. W.; Hu, C. M. J.; Fang, R. H.; Zhang, L. F. Liposome-like nanostructures for drug delivery. J. Mater. Chem. B 2013, 1, 6569-6585. [CrossRef] [PubMed]
64. Xing, H.; Tang, L.; Yang, X. J.; Hwang, K.; Wang, W. D.; Yin, Q.; Wong, N. Y.; Dobrucki, L. W.; Yasui, N.; Katzenellenbogen, J. A.; et al. Selective delivery of an anticancer drug with aptamer-functionalized liposomes to breast cancer cells in vitro and in vivo. J. Mater. Chem. B 2013, 1, 5288-5297. [CrossRef]
65. Sugihara, H.; Yamamoto, H.; Kawashima, Y.; Takeuchi, H. effectiveness of submicronized chitosan-coated liposomes in oral absorption of indomethacin. J. Liposome Res. 2012, 22, 72-79. [CrossRef]
66. Filipovic-Grcic, J.; Skalko-Basnet, N.; Jalsenjak, I. Mucoadhesive chitosan-coated liposomes: characteristics and stability. J. Microencapsul. 2001, 18, 3-12. [CrossRef]
67. Espinal-Ruiz, M.; Parada-Alfonso, F.; Restrepo-Sanchez, L. P.; Narvaez-Cuenca, C. E.; McClements, D. J. Impact of dietary fibers [methyl cellulose, chitosan, and pectin] on digestion of lipids under simulated gastrointestinal conditions. Food Funct. 2014, 5, 3083-3095. [CrossRef]
68. Rodriguez, M. S.; Albertengo, L. E. Interaction between chitosan and oil under stomach and duodenal digestive chemical conditions. Biosci. Biotechnol. Biochem. 2005, 69, 2057-2062. [CrossRef] [PubMed]
69. McConnell, E. L.; Murdan, S.; Basit, A. W. An investigation into the digestion of chitosan (noncrosslinked and crosslinked) by human colonic bacteria. J. Pharm. Sci. 2008, 97, 3820-3829. [CrossRef]
70. Shen, C. R.; Liu, C. L.; Lee, H. P.; Chen, J. K. The Identification and Characterization of Chitotriosidase Activity in Pancreatin from Porcine Pancreas. Molecules 2013, 18, 2978-2987. [CrossRef] [PubMed]
71. Zhang, H.; Alsarra, I. A.; Neau, S. H. An in vitro evaluation of A chitosan-containing multiparticulate system for macromolecule delivery to the colon. Int. J. Pharm. 2002, 239, 197-205. [CrossRef]
72. Kean, T.; Thanou, M. Biodegradation, biodistribution and toxicity of chitosan. Adv. Drug Deliv. Rev. 2010, 62, 3-11. [CrossRef]
73. Linder, M.; Matouba, E.; Fanni, J.; Parmentier, M. Enrichment of salmon oil with n-3 PUFA by lipolysis, filtration and enzymatic re-esterification. Eur. J. Lipid Sci. Technol. (Print) 2002, 104, 455-462. [CrossRef]
74. Ackman, R. G. Remarks on official methods employing boron trifluoride in the preparation of methyl esters of the fatty acids of fish oils. J. Am. Oil Chem. Soc. 1998, 75, 541-545. [CrossRef]
75. Hasan, M.; Latifi, S.; Kahn, C.; Tamayol, A.; Habibey, R.; Passeri, E.; Linder, M.; Arab-Tehrany, E. The Positive Role of Curcumin-Loaded Salmon Nanoliposomes on the Culture of Primary Cortical Neurons. Mar. Drugs 2018, 16, 218. [CrossRef] [PubMed]
76. Aditya, N. P.; Shim, M.; Lee, I.; Lee, Y.; Im, M. H.; Ko, S. Curcumin and Genistein Coloaded Nanostructured Lipid Carriers: in Vitro Digestion and Antiprostate Cancer Activity. J. Agric. Food Chem. 2013, 61, 1878-1883. [CrossRef]
77. Singh, H.; Sarkar, A. Behaviour of protein-stabilised emulsions under various physiological conditions. Adv. Colloid Interface Sci. 2010, 165, 47-57. [CrossRef]
78. Tikekar, R. V.; Pan, Y. J.; Nitin, N. Fate of curcumin encapsulated in silica nanoparticle stabilized Pickering emulsion during storage and simulated digestion. Food Res. Int. 2013, 51, 370-377. [CrossRef]
79. Sun, J. B.; Bi, C.; Chan, H. M.; Sun, S. P.; Zhang, Q. W.; Zheng, Y. Curcumin-loaded solid lipid nanoparticles have prolonged in vitro antitumour activity, cellular uptake and improved in vivo bioavailability. Colloids Surf. B-Biointerfaces 2013, 111, 367-375. [CrossRef]