Chitosan-coated liposomes encapsulating curcumin: Study of lipid-polysaccharide interactions and nanovesicle behavior

Despite various spectacular therapeutic properties, curcumin has low bioavailability mainly due to its poor solubility in water. In this paper, we encapsulated curcumin by nanoliposomes prepared from salmon purified phospholipid and coated with chitosan. Various techniques were used in order to study the interactions among phospholipid, chitosan and curcumin. FTIR results showed both electrostatic and hydrophobic interactions as well as hydrogen bonding between chitosan and phospholipid, while hydrophobic forces and hydrogen bonding dominated the interactions between curcumin and phospholipid as well as between curcumin and chitosan. Shear viscosity measurements demonstrated a flow behavior change from Newtonian to shear thinning after liposome coating. The increase/decrease stress ramp showed that the addition of chitosan layer decreased significantly the hysteresis loop area (thixotropic behavior) and therefore increased significantly the liposomal dispersion stability. The viscoelastic properties investigated by small-amplitude oscillatory shear rheology demonstrated improvement of mechanical stability after chitosan addition. Small-angle X-ray scattering experiments revealed that the liposome membrane structure was not affected by the chitosan layer or the encapsulated curcumin.

[1]  M. Linder,et al.  Analysis of lipids extracted from salmon (Salmo salar) heads by commercial proteolytic enzymes , 2006 .

[2]  Paolo Colombo,et al.  Metallic colloid nanotechnology, applications in diagnosis and therapeutics. , 2005, Current pharmaceutical design.

[3]  R. Joseph,et al.  Water soluble complexes of curcumin with cyclodextrins: Characterization by FT-Raman spectroscopy , 2012 .

[4]  P. Mukherjee,et al.  Curcumin-phospholipid complex: Preparation, therapeutic evaluation and pharmacokinetic study in rats. , 2007, International journal of pharmaceutics.

[5]  Y. Kawashima,et al.  Enteral Absorption of Insulin in Rats from Mucoadhesive Chitosan-Coated Liposomes , 1996, Pharmaceutical Research.

[6]  R. G. Ackman,et al.  Remarks on official methods employing boron trifluoride in the preparation of methyl esters of the fatty acids of fish oils , 1998 .

[7]  Hyun Jin Park,et al.  Preparation of chitosan-coated nanoliposomes for improving the mucoadhesive property of curcumin using the ethanol injection method. , 2013, Journal of agricultural and food chemistry.

[8]  Y. Kawashima,et al.  Mucoadhesive properties of carbopol or chitosan-coated liposomes and their effectiveness in the oral administration of calcitonin to rats. , 2003, Journal of controlled release : official journal of the Controlled Release Society.

[9]  Q. Ping,et al.  Chitosan-coated liposomes: characterization and interaction with leuprolide. , 2003, International journal of pharmaceutics.

[10]  E. Arab-Tehrany,et al.  Structural, hydration, and phase transition properties of phosphatidylcholine from salmon heads , 2011 .

[11]  T. Nagai,et al.  Characterization of dipalmitoylphosphatidylcholine liposomes containing a soybean-derived sterylglucoside mixture by differential scanning calorimetry, Fourier transform infrared spectroscopy, and enzymatic assay. , 1996, Journal of pharmaceutical sciences.

[12]  Na Li,et al.  Development and evaluation of a novel phytosome-loaded chitosan microsphere system for curcumin delivery. , 2013, International journal of pharmaceutics.

[13]  E. Arab-Tehrany,et al.  Oxidative kinetics of salmon oil in bulk and in nanoemulsion stabilized by marine lecithin , 2010 .

[14]  A. Sum,et al.  The role of fatty acid unsaturation in minimizing biophysical changes on the structure and local effects of bilayer membranes. , 2009, Biochimica et biophysica acta.

[15]  M. Nair,et al.  Modulation of liposomal membrane fluidity by flavonoids and isoflavonoids. , 2000, Archives of biochemistry and biophysics.

[16]  M. R. Mozafari,et al.  Microscopical investigations of nisin-loaded nanoliposomes prepared by Mozafari method and their bacterial targeting. , 2007, Micron.

[17]  Mei-Hwa Lee,et al.  Stability and characterisation of phospholipid-based curcumin-encapsulated microemulsions , 2009 .

[18]  K. Gowthamarajan,et al.  Optimization of curcumin nanoemulsion for intranasal delivery using design of experiment and its toxicity assessment. , 2014, Colloids and surfaces. B, Biointerfaces.

[19]  N. Kučerka,et al.  Small-Angle Scattering from Homogenous and Heterogeneous Lipid Bilayers , 2010 .

[20]  Diana M. Ahmadieh,et al.  Effect of Curcumin on Liposome: Curcumin as a Molecular Probe for Monitoring Interaction of Ionic Liquids with 1,2‐Dipalmitoyl‐sn‐Glycero‐3‐Phosphocholine Liposome , 2012, Photochemistry and photobiology.

[21]  G. Gregoriadis.  Liposomes as drug carriers : recent trends and progress , 1988 .

[22]  Ali Hossain Khan,et al.  Interactions between Catanionic Vesicles and Oppositely Charged PolyelectrolytesPhase Behavior and Phase Structure , 1999 .

[23]  D. Hincha,et al.  Specific effects of fructo- and gluco-oligosaccharides in the preservation of liposomes during drying. , 2002, Glycobiology.

[24]  Rupesh Kumar Basniwal,et al.  Curcumin nanoparticles: preparation, characterization, and antimicrobial study. , 2011, Journal of agricultural and food chemistry.

[25]  J. Feijen,et al.  The preparation of monodisperse biodegradable polyester nanoparticles with a controlled size. , 2003, Journal of biomedical materials research. Part B, Applied biomaterials.

[26]  C. Jacobsen,et al.  Oxidative stability of dispersions prepared from purified marine phospholipid and the role of α-tocopherol. , 2012, Journal of agricultural and food chemistry.

[27]  S. A. Sande,et al.  Interactions between liposomes and chitosan II : effect of selected parameters on aggregation and leakage , 1997 .

[28]  F. Severcan,et al.  Melatonin strongly interacts with zwitterionic model membranes--evidence from Fourier transform infrared spectroscopy and differential scanning calorimetry. , 2005, Biochimica et biophysica acta.

[29]  M. M. Mady,et al.  Biophysical studies on chitosan-coated liposomes , 2009, European Biophysics Journal.

[30]  D. Mcclements,et al.  Formation, stability and properties of multilayer emulsions for application in the food industry. , 2006, Advances in colloid and interface science.

[31]  L. Misiak,et al.  FTIR, (1)H NMR and EPR spectroscopy studies on the interaction of flavone apigenin with dipalmitoylphosphatidylcholine liposomes. , 2013, Biochimica et biophysica acta.

[32]  A. Bangham,et al.  A Correlation between Surface Charge and Coagulant Action of Phospholipids , 1961, Nature.

[33]  D. Ende,et al.  Rheological Behavior of a Dispersion of Small Lipid Bilayer Vesicles , 1997 .

[34]  J. Irudayaraj,et al.  Characterization of semisolid fats and edible oils by Fourier transform infrared photoacoustic spectroscopy , 2000 .

[35]  J. P. Feitosa,et al.  Sulfated chitosan as tear substitute with no antimicrobial activity. , 2013, Carbohydrate polymers.

[36]  R. Dimova,et al.  Insights on the interactions of chitosan with phospholipid vesicles. Part I: Effect of polymer deprotonation. , 2013, Langmuir : the ACS journal of surfaces and colloids.

[37]  M. Brandl.  Liposomes as drug carriers: a technological approach. , 2001, Biotechnology annual review.

[38]  Xiangyang Shi,et al.  Evaluation of in vitro stability of small unilamellar vesicles coated with collagen and chitosan , 1999 .

[39]  K. Cieślik-Boczula,et al.  The effect of 3-pentadecylphenol on DPPC bilayers ATR-IR and 31P NMR studies. , 2009, Biophysical chemistry.

[40]  J. Fonollosa,et al.  Influence of cholesterol on liposome fluidity by EPR. Relationship with percutaneous absorption. , 2000, Journal of controlled release : official journal of the Controlled Release Society.

[41]  B. Aggarwal,et al.  Curcumin inhibits proliferation, invasion, angiogenesis and metastasis of different cancers through interaction with multiple cell signaling proteins. , 2008, Cancer letters.

[42]  Y. Weng,et al.  Preparation, characterization and anticoagulation of curcumin-eluting controlled biodegradable coating stents. , 2006, Journal of controlled release : official journal of the Controlled Release Society.

[43]  B. Lentz,et al.  Use of fluorescent probes to monitor molecular order and motions within liposome bilayers. , 1993, Chemistry and physics of lipids.

[44]  M. Paoletti,et al.  Current views on fungal chitin/chitosan, human chitinases, food preservation, glucans, pectins and inulin: A tribute to Henri Braconnot, precursor of the carbohydrate polymers science, on the chitin bicentennial , 2012 .

[45]  Hidekazu,et al.  Physical Stability of Size Controlled Small Unilamellar Liposomes Coated with a Modified Polyvinyl Alcohol. , 1998 .

[46]  K. Chennazhi,et al.  Biocompatible, biodegradable and thermo-sensitive chitosan-g-poly (N-isopropylacrylamide) nanocarrier for curcumin drug delivery. , 2011, International journal of biological macromolecules.

[47]  R. Freitas.  What is nanomedicine? , 2005, Nanomedicine : nanotechnology, biology, and medicine.

[48]  M. Linder,et al.  Enrichment of salmon oil with n-3 PUFA by lipolysis, filtration and enzymatic re-esterification , 2002 .

[49]  J. Webster.  Encyclopedia of Medical Devices and Instrumentation , 1988 .

[50]  P. Versluis,et al.  Influence of Salt Concentration and Surfactant Concentration on the Microstructure and Rheology of Lamellar Liquid Crystalline Phases , 2001 .

[51]  J. Robinson,et al.  Bioadhesive-based dosage forms: the next generation. , 2000, Journal of pharmaceutical sciences.

[52]  P. Calder,et al.  Understanding Omega-3 Polyunsaturated Fatty Acids , 2009, Postgraduate medicine.

[53]  I. Otsuka,et al.  Elaboration of chitosan-coated nanoparticles loaded with curcumin for mucoadhesive applications. , 2012, Journal of colloid and interface science.

[54]  D. Machin,et al.  A review of the rheology of the lamellar phase in surfactant systems. , 2002, Advances in colloid and interface science.

[55]  E. Kudryashova,et al.  Structure and stability of anionic liposomes complexes with PEG-chitosan branched copolymer , 2014, Russian Journal of Bioorganic Chemistry.

[56]  B. Krajewska,et al.  Chitosan as a lipid binder: a langmuir monolayer study of chitosan-lipid interactions. , 2007, Biomacromolecules.

[57]  E. Arab-Tehrany,et al.  Formulation, characterization and pharmacokinetic studies of coenzyme Q₁₀ PUFA's nanoemulsions. , 2012, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[58]  M. Tlusty,et al.  Effects of dietary DHA and EPA on neurogenesis, growth, and survival of juvenile American lobster, Homarus americanus , 2009 .

[59]  G. Barratt,et al.  Therapeutic applications of colloidal drug carriers. , 2000, Pharmaceutical science & technology today.

[60]  K. S. Parvathy,et al.  Antioxidant, antimutagenic and antibacterial activities of curcumin-β-diglucoside , 2009 .

[61]  S. Mura,et al.  An approach to rheological and electrokinetic behaviour of lipidic vesicles covered with chitosan biopolymer , 2008 .

[62]  B. Timmermann,et al.  The effect of turmeric extracts on inflammatory mediator production. , 2005, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[63]  B. Mukherjee,et al.  Plant Medicines of Indian Origin for Wound Healing Activity: A Review , 2003, The international journal of lower extremity wounds.

[64]  S. Takeoka,et al.  Rheological properties of hemoglobin vesicles (artificial oxygen carriers) suspended in a series of plasma-substitute solutions. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[65]  B. Aliakbarian,et al.  Influence of lecithin-lipid composition on physico-chemical properties of nanoliposomes loaded with a hydrophobic molecule. , 2014, Colloids and surfaces. B, Biointerfaces.

[66]  M. Kępczyński,et al.  Interaction of curcumin with lipid monolayers and liposomal bilayers. , 2011, Colloids and surfaces. B, Biointerfaces.

[67]  Francesco Castelli,et al.  Effects of lipid composition and preparation conditions on physical-chemical properties, technological parameters and in vitro biological activity of gemcitabine-loaded liposomes. , 2007, Current drug delivery.

[68]  N. Škalko-Basnet,et al.  Mucoadhesive chitosan-coated liposomes: characteristics and stability , 2001, Journal of microencapsulation.

[69]  E. Arab-Tehrany,et al.  Optimization and characterization of liposome formulation by mixture design. , 2012, The Analyst.

[70]  S. Kale,et al.  Complexes of cobalt nanoparticles and polyfunctional curcumin as antimicrobial agents , 2012 .

[71]  E. Arab-Tehrany,et al.  Liposome encapsulation of curcumin: physico-chemical characterizations and effects on MCF7 cancer cell proliferation. , 2014, International journal of pharmaceutics.

[72]  J. Brender,et al.  Determining the effects of lipophilic drugs on membrane structure by solid-state NMR spectroscopy: the case of the antioxidant curcumin. , 2009, Journal of the American Chemical Society.

[73]  H. Y. Zhang,et al.  Effects of nanoliposomes based on soya, rapeseed and fish lecithins on chitosan thin films designed for tissue engineering , 2012 .

[74]  C. Valenta,et al.  The influence of selected steroid hormones on the physicochemical behaviour of DPPC liposomes. , 2007, Chemistry and physics of lipids.

[75]  X. Zhu,et al.  Polysaccharides for drug delivery and pharmaceutical applications , 2006 .

[76]  B. Lokesh,et al.  Studies on spice principles as antioxidants in the inhibition of lipid peroxidation of rat liver microsomes , 1992, Molecular and Cellular Biochemistry.

[77]  Robert A Newman,et al.  Bioavailability of curcumin: problems and promises. , 2007, Molecular pharmaceutics.