Amphiphilic chitosan derivatives-based liposomes: synthesis, development, and properties as a carrier for sustained release of salidroside.

A novel amphiphilic chitosan derivative of N,N-dimethylhexadecyl carboxymethyl chitosan (DCMCs) was synthesized. The structure of DCMCs was confirmed via FT-IR and (1)H NMR, and the critical micelle concentration (CMC) was investigated by fluorescence spectroscopy. The results indicated that DCMCs has hydrophilic carboxyl and hydrophobic methylene groups and the CMC value was 23.00 mg·L(-1). The polymeric liposomes (DCMCs/cholesterol liposomes, DC-Ls) were developed, and its properties were evaluated. The DC-Ls exhibited multilamellar spheres with positive charge (+73.30 mV), narrow size distribution (PDI = 0.277), and good crystal properties. Salidroside was first to encapsulate into DC-Ls. Compared with traditional liposomes (phosphatidylcholine/cholesterol liposome, PC-Ls), DC-Ls showed higher encapsulation efficiency (82.46%) and slower sustained release rate. The in vitro salidroside release from DC-Ls was governed by two distinct stages (i.e., burst release and sustained release) and was dependent on the pH of the release medium. The case II transport and case I Fichian diffusion were the main release mechanisms for the entire release procedure. These results indicated that DC-Ls may be a potential carrier system for the production of functional foods that contain salidroside or other bioactive food ingredients.

[1]  Hui‐Ming Yu,et al.  Neuroprotective effects of salidroside against beta-amyloid-induced oxidative stress in SH-SY5Y human neuroblastoma cells , 2010, Neurochemistry International.

[2]  Jae-Kwan Hwang,et al.  Characterization of Capsaicin-Loaded Nanoemulsions Stabilized with Alginate and Chitosan by Self-assembly , 2011 .

[3]  Xiaofei Liang,et al.  Synthesis, Structure and Properties of Novel Quaternized Carboxymethyl Chitosan with Drug Loading Capacity , 2008 .

[4]  J. Weiss,et al.  Formation and stability of multiple-layered liposomes by layer-by-layer electrostatic deposition of biopolymers , 2013 .

[5]  Weilin Liu,et al.  Improved physical and in vitro digestion stability of a polyelectrolyte delivery system based on layer-by-layer self-assembly alginate-chitosan-coated nanoliposomes. , 2013, Journal of agricultural and food chemistry.

[6]  Yang Sun,et al.  Protective effects of salidroside on hydrogen peroxide-induced apoptosis in SH-SY5Y human neuroblastoma cells. , 2007, European journal of pharmacology.

[7]  Hua Xiong,et al.  Vanillin cross-linked chitosan microspheres for controlled release of resveratrol , 2010 .

[8]  Xiaofei Liang,et al.  Properties and evaluation of quaternized chitosan/lipid cation polymeric liposomes for cancer-targeted gene delivery. , 2013, Langmuir : the ACS journal of surfaces and colloids.

[9]  Ba-fang Li,et al.  Determination of critical aggregation concentration and aggregation number of acid-soluble collagen from walleye pollock (Theragra chalcogramma) skin using the fluorescence probe pyrene , 2010 .

[10]  S. Chirachanchai,et al.  Amphiphilic chitosan nanospheres: Factors to control nanosphere formation and its consequent pH responsive performance , 2009 .

[11]  Xiguang Chen,et al.  Chitosan/o-carboxymethyl chitosan nanoparticles for efficient and safe oral anticancer drug delivery: in vitro and in vivo evaluation. , 2013, International journal of pharmaceutics.

[12]  Daniel W. Pack,et al.  Design and development of polymers for gene delivery , 2005, Nature Reviews Drug Discovery.

[13]  I. Aranaz,et al.  Chitosan Amphiphilic Derivatives. Chemistry and Applications , 2010 .

[14]  Z. Teng,et al.  Development of carboxymethyl chitosan hydrogel beads in alcohol-aqueous binary solvent for nutrient delivery applications , 2013 .

[15]  Yuanyuan Liu,et al.  Self-assembled nanoparticles of methotrexate conjugated O-carboxymethyl chitosan: Preparation, characterization and drug release behavior in vitro , 2011 .

[16]  Jianping Zhou,et al.  Synthesis and characterization of low-toxic amphiphilic chitosan derivatives and their application as micelle carrier for antitumor drug. , 2010, International journal of pharmaceutics.

[17]  Judith Kuntsche,et al.  Temoporfin-loaded liposomes: physicochemical characterization. , 2010, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[18]  Yangchao Luo,et al.  Recent Advances of Chitosan and Its Derivatives for Novel Applications in Food Science , 2013 .

[19]  Xiaoming Zhang,et al.  Effect of different preparation methods on physicochemical properties of salidroside liposomes. , 2007, Journal of agricultural and food chemistry.

[20]  Zhenyu Liao,et al.  PEG/RGD-modified magnetic polymeric liposomes for controlled drug release and tumor cell targeting. , 2012, International journal of pharmaceutics.

[21]  C. Allen,et al.  Relationship between composition and properties for stable chitosan films containing lipid microdomains , 2007 .

[22]  Harjinder Singh,et al.  Stability during in vitro digestion of lactoferrin-loaded liposomes prepared from milk fat globule membrane-derived phospholipids. , 2013, Journal of dairy science.

[23]  Shiying Xu,et al.  Preparation of salidroside nano-liposomes by ethanol injection method and in vitro release study , 2008 .

[24]  Xiaofei Liu,et al.  Effect of chitosan, O-carboxymethyl chitosan, and N-[(2-hydroxy-3-N,N-dimethylhexadecyl ammonium)propyl] chitosan chloride on overweight and insulin resistance in a murine diet-induced obesity. , 2012, Journal of agricultural and food chemistry.

[25]  Nicholas A. Peppas,et al.  A simple equation for description of solute release II. Fickian and anomalous release from swellable devices , 1987 .

[26]  Jin Chang,et al.  Characterization of novel multifunctional cationic polymeric liposomes formed from octadecyl quaternized carboxymethyl chitosan/cholesterol and drug encapsulation. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[27]  J. Veciana,et al.  Liposomes and other vesicular systems: structural characteristics, methods of preparation, and use in nanomedicine. , 2011, Progress in molecular biology and translational science.

[28]  D. Crommelin,et al.  Hydrolysis of Partially Saturated Egg Phosphatidylcholine in Aqueous Liposome Dispersions and the Effect of Cholesterol Incorporation on Hydrolysis Kinetics , 1993, The Journal of pharmacy and pharmacology.

[29]  Shuifeng Qiu,et al.  Salidroside induces cell-cycle arrest and apoptosis in human breast cancer cells. , 2010, Biochemical and biophysical research communications.

[30]  H. Leuenberger,et al.  In vivo comparison of various liposome formulations for cosmetic application. , 2005, International journal of pharmaceutics.

[31]  Z. Teng,et al.  Development of zein nanoparticles coated with carboxymethyl chitosan for encapsulation and controlled release of vitamin D3. , 2012, Journal of agricultural and food chemistry.

[32]  B. Keller.  Liposomes in nutrition , 2001 .

[33]  San-Yuan Chen,et al.  Self-assembly behavior and doxorubicin-loading capacity of acylated carboxymethyl chitosans. , 2009, The journal of physical chemistry. B.

[34]  N. Parris,et al.  Chitosan/Pectin Laminated Films , 1996 .