Research Progress on Encapsulation Efficiency of Liposomes

doi:10.3969/j.issn.2095-1396.2016.06. 002

Abstract

Abstract: Liposomes are vesicles composed of phospholipid bilayers surrounding an aqueous compartment. It is possible to encapsulate not only hydrophilic drugs in the inner aqueous compartment， but also lipophilic compounds in the lipidic double layer. Lipidic double layer is ideal for drug delivery to the human body， due to the similarity with natural cells. Its application is important to the diagnosis and treatment of nervous system diseases，malignant tumors， hereditary diseases and so on. When designing and developing a liposome formulation， it is important to control the encapsulation efficiency. High drug encapsulation is a very important characteristic. Furthermore， evaluation of EE is a regulatory requirement. Herein， our aim is to review the relevant papers in the literature on method for determination of entrapment efficiency and discuss the effect of the lipid membrane composition， phospholipid chain length， charge， and different liposome preparation methods on the encapsulation efficiency.

Key words: liposomes, entrapment efficiency, column switching chromatography system, supercritical CO2 technology

ZHAO Kai-yan， ZHANG Dan-shen. Research Progress on Encapsulation Efficiency of Liposomes[J]. Acta Neuropharmacologica, 2016, 6(6): 23-30.

References

[1] Filomana Oliverio, Edurne Nuin, Inmaculada Andreu, et al. Assessment of drug entrapment within liposomes using photophysical probes[J]. Eur J Pharm Biopharm, 2014, 88(2): 551-555.

[2] Marian Vila-Caballer, Gaia Codolo, Fabio Munari, et al. A pH-sensitive stearoyl-PEG-poly(methacryloyl sulfadimethoxine)-decorated liposome system for protein delivery: An application for bladder cancer treatment[J]. J Control Release, 2016, 238: 31-42

[3] Khairunnisa Abdul Ghaffar, Nirmal Marasini, Ashwini Kumar Giddam, et al. Liposome-based intranasal delivery of lipopeptide vaccine candidates againstgroup A streptococcus[J]. Acta Biomater, 2016, 41:161-168.

[4] Fatemeh Movahedi, Rebecca G Hu, David L Becker, et al. Stimuli-responsive liposomes for the delivery of nucleic acid therapeutics[J]. Nanomedicine, 2015, 11(6): 1575-1584.

[5] 陈召红, 刘皈阳, 魏亚超. 脂质体包封率测定方法研究进展[J]. 解放军药学学报, 2011, 27(1): 79-82.

[6] 陈蓓, 袁明奎, 王建华, 等. 葡聚糖凝胶柱色谱法测定阿苯达唑纳米脂质体包封率的方法研究[J]. 中国药房, 2012, 23(45): 4281-4284.

[7] Yann Pellequer, Michel Ollivon, Gillian Barratt. Methodology for assaying recombinant interleukin-2 associated with liposomes by com-bined gel exclusion chromatography and fluorescence[J]. J Chromatogr B Analyt Technol Biomed Life Sci, 2003, 783(1): 151-162.

[8] 李可欣, 陈大为, 商捷, 等. 脂质体中蛋白类药物包封率的测定[J]. 沈阳药科大学学报, 2010, 27(9): 680-685.

[9] 王传金. 冬凌草甲素长循环脂质体的研究[D]. 南京：南京理工大学, 2009.

[10] 陈建霞, 徐缓, 于涛, 等. 微柱离心-紫外分光光度法测定超氧化物歧化酶模拟物脂质体的包封率[J]. 中国新药杂志, 2011, 20(10): 928-931.

[11] Liu Yan, Luo Xiao, Xu Xiao-chao, et al. Preparation, characterization and in vivopharmacokinetic study of PVP-modified oleanolic acid liposomes[J]. Int J Pharm, 2017, 517(1-2): 1-7.

[12] 陈孝储, 郭一沙, 宋菲, 等. 微柱离心结合胆固醇浓度变化测定水溶性药物脂质体包封率[J]. 沈阳药科大学学报, 2014, 31(11): 851-855.

[13] 邵红霞, 奉建芳, 龙晓英. 脂质体包封率的测定方法[J]. 中南药学, 2009, 7(3): 212-215.

[14] 陈颖翀, 李翔, 张婧, 等. 硫酸长春新碱脂质体含量测定及3种包封率测定方法的比较[J]. 中国药房, 2014, 25(37): 3504-3507.

[15] 张一鸣, 刘靖新, 周颖琳, 等. 固相萃取-高效液相色谱法测定紫杉醇脂质体的包封率[J]. 分析科学学报, 2014, (05): 705-708.

[16] 吴琼. 聚乙二醇修饰的多西他赛长循环脂质体的研究[D]. 广州：广州中医药大学, 2013.

[17] Debasis Nayak, Ankita Boxi, Sarbani Ashe, et al. Stavudine loaded gelatinliposomes for HIV therapy: Preparation, characterization and in vitro cytotoxicevaluation[J]. Mater Sci Eng C Mater Biol Appl, 2017, 73: 406-416.

[18] Zhang Lin, Zhang Zhi-qing, Dong Wei-chong, et al. Accuracy assessment on the analysis of unbound drug in plasma by comparing traditional centrifugal ultrafiltration with hollow fiber centrifugal ultrafiltration and application in pharmacokinetic study[J]. J Chromatogr A, 2013, 1318: 265-269.

[19] Dong Wei-chong, Zhang Zhi-qing, Jiang Xin-hui, et al. Effect of volume ratio of ultrafiltrate to solution on the analysis of free drug and measurement of free carbamazepine in clinical drug monitoring[J]. Eur J Pharm Sci, 2013, 48(1-2): 332-338.

[20] Li Jun-Mei, Jiang Ye, Sun Ting, et al. Hollow-fiber ultrafiltration then centrifugation for LC analysis of water-soluble sucrose in a water-soluble high-molecular-mass gel matrix[J]. Chromatographia, 2009, 70: 1023-1030.

[21] Li Jun-Mei, Li Cen, Jiang Ye, et al. Pretreatment of plasma samples by a novel hollow fiber centrifugal ultrafiltrate device for the determination of cefaclor concentrations in human plasma[J]. J Chromatogr A, 2010, 1217(44): 6824-6828.

[22] Ran C, Chen D, Xu M, et al. A study on characteristic of different sample pretreatment methods to evaluate the entrapment efficiency of liposomes[J]. J Chromatogr B Analyt Technol Biomed Life Sci, 2016, 1028: 56-62.

[23] 武晓玉, 王荣, 谢华, 等. 柱切换技术-高效液相色谱法快速检测大鼠血浆中的普萘洛尔对映体[J]. 色谱, 2011, (12): 1205-1209.

[24] Naozumi Ohnishi, Shota Tanaka, Kohei Tahara, et al. Characterization of insulin-loaded liposome using column-switching HPLC[J]. Int J Pharm. 2015, 479(2): 302-305.

[25] 裘丹. 油溶性Fe3O4纳米颗粒—脂质体的结构、性质及功能研究[D]. 上海：华东理工大学, 2013.

[26] Anumita Chaudhury, Surajit Das, Ronald F S Lee, et al. Lyophilization of cholesterol-free PEGylated liposomes and its impact on drug loading by passiveequilibration[J]. Int J Pharm, 2012, 430(1-2): 167-175.

[27] Wang Yue, Su Wen-ya, Li Qin, et al. Preparation and evaluation of lidocaine hydrochloride-loaded TAT-conjugated polymeric liposomes for transdermal delivery[J]. Int J Pharm, 2013, 441(1-2): 748-756.

[28] Josimar Oliveira Eloy, Marina Claro de Souza, Raquel Petrilli, et al. Liposomes as carriers of hydrophilic small molecule drugs: strategies to enhance encapsulation and delivery [J]. Colloids Surf B Biointerfaces, 2014, 123(19): 345-363.

[29] Mariusz Kepczyński, Kinga Nawalany, Marta Kumorek, et al. Which physical and structural factors of liposome carriers control their drug-loading efficiency[J]. ChemPhysLipids, 2008, 155(1): 7-15.

[30] 张斌. 不同磷脂膜材对脂质体稳定性的影响[D]. 河南：河南工业大学, 2016.

[31] Clavas-Dodov M, Fredro-Kumbaradzi E, Coracinova K, et al. The effects of lyophilization on the stability of liposomes containing 5-FU[J]. J Pharm, 2005, 291(1-2):79-86.

[32] Sun Wei-Tong, Zhang Na, Li Ai-guo, et al. Preparation and evaluation of N3-0-toluyl-fluorouracil-loaded liposomes[J]. J Pharm, 2008, 353 (1-2): 243-250.

[33] Xia Shu-qin, Tan Chen, Zhang Ya-ting, et al. Modulating effect of lipid bilayer–carotenoid interactions on the property of liposome encapsulation[J]. Colloids and Surfaces B: Biointerfaces, 2015, 128: 172-180.

[34] Eiichi Kajiwara, Kumi Kawano, Yoshiyuki Hattori, et al. Long-circulating liposome-encapsulated ganciclovir enhances the efficacy of HSV-TK suicide gene therapy[J]. J Control Release, 2007, 120(1-2): 104-110.

[35] Ruozi B, Riva G, Belletti D, et al. Cidofovir-loaded liposomes: an intro-study using BCBL-1 cell line asa model for primary effusion lymphoma[J]. Eur J Pharm Sci, 2010, 41(2): 254-264.

[36] Jonathan D Castile, Kevin M G Taylor. Factors affecting the size distribution of liposomesproduced by freeze-thaw extrusion[J]. Int J Pharm, 1999, 188(1): 87-95.

[37] 邱瑞桂, 靳世英, 徐和, 等. 薄膜分散联合冻融法制备小菜蛾抗菌肽脂质体研究[J]. 环球中药, 2012, 5(12): 904-907.

[38] Elorza B, Elorza MA, Frutos G, et al. Characterization of 5-fluorouracilloaded liposomes prepared by reverse-phase evaporation or freezing-thawingextrusion methods: study of drug release[J]. Biochim Biophys Acta, 1993, 1153(2): 135-142.

[39] 李中桂. 吉西他滨脂质体的研究[D]. 广州：广州中医药大学, 2011.

[40] Zhao Li-Sha, Feral Temelli. Preparation of anthocyanin-loaded liposomes using an improved supercritical carbon dioxide method[J]. Innovative Food Science & Emerging Technologies, 2017, 39: 119-128.

[41] 张志丽, 张志云, 张维, 等. 超临界流体技术制备姜黄素脂质体的工艺考察[J]. 沈阳药科大学学报, 2014, 31(02): 81-86+93.

[42] 侯丽芬, 谷克仁，吴永辉. 不同制剂脂质体制备方法的研究进展[J]. 河南工业大学学报：自然科学版, 2016, 37(05): 118-124.

[43] Xia Fei, Jin He-yang, Zhao Ya-ping, et al. Supercritical antisolvent-based technology foi preparation of vitamin D3 proliposome and its characteristics[J]. Chin J ChemEng, 2011, 19(6): 1039-1046.

[44] Zhao Li-sha, Feral Temelli. Preparation of liposomes using supercritical carbon dioxide via depressurization of the supercritical phase[J]. J Food Eng, 2015, 158: 104-112.

[45] Trucillo P, Campardelli R, Reverchon E. Supercritical CO2 assisted liposomes formation: Optimization of the lipidic layer for an efficient hydrophilic drug loading[J]. JCO2 Utilization, 2017, 18: 181-188.

[46] Roberta Campardelli, Islane Espirito Santo, Elaine Cabral-Albuquerque, et al. Efficient encapsulation of proteins in submicro liposomes using a supercritical fluid assisted continuous process[J]. J Supercritical Fluids. 2016, 107: 163-169.

[47] Tatsuhiro Ishida, Yoshihiro Talcanashi, Hisako Doi, et al. Encapsulation of an antivasospastic drug, fasudil, into liposomes, and in vitro stability of the fasudil-loaded liposomes[J]. Int J Pharnl, 2002, 232(1-2): 59-67.

[48] Andreas Fritze, Felicitas Hens, Andrea Kimpfler, et al. Remote loading of doxorubicin into liposomes driven by a transmembrane phosphate gradient[J]. Biochim Biophys Acta, 2006, 1758(10): 1633-1640.

[49] Hee Dong Han, Aeri Lee, Chung Kil Song, et al. In vivo distribution and antitumor activity of heparin-stabilized doxorubicin-loadedliposomes[J]. Int J Pharm, 2006, 313(2-1): 181-188.

[50] Nancy Dos Santos, Kelly A Cox, Cheryl A McKenzie, et al. pH gradient loading of anthracyclines into cholesterol-free liposomes: enhancing drug loading rates through use of ethanol[J]. Biochim Biophys Acta, 2004, 1661(1): 47-60.

[51] Wang Chen-yu, Feng Ling-lin, Yang Xian-kun, et al. Folic acid-conjugated liposomal vincristine for multidrug resistant cancer therapy[J]. Asian J Pharmaceutical Sciences, 2013, 8(2): 118-127.

[52] 张立, 何凤田, 高会广, 等. PDP-PEG_(2000)-DSPE修饰的长春新碱脂质体的制备及其包封率测定[J]. 实用预防医学, 2006, 13(03): 480-482.

[53] Raquel Silva Araújo, Ana Leticia Malheiros Silveira, Ericka Lorenna de Sales E Souza, et al. Intestinal toxicity evaluation of long-circulating and pH-sensitive liposomes loaded with cisplatin[J]. Eur J Pharm Sci, 2017, 106: 142-151.

[54] Sergey A Shein, Ilya I Kuznetsov, Tatiana O Abakumova, et al. VEGF-and VEGFR2-Targeted Liposomes for Cisplatin Delivery to Glioma Cells[J]. Mol Pharm, 2016, 13(11): 3712-3723.

[55] Liu Wei-lin, Ye Ai-qian, Liu Wei, et al. Behaviour of liposomes loaded with bovine serum albumin during in vitro digestion[J]. Food Chem, 2016, 175: 16-24.

[56] Yuko Okamoto, Kazuaki Taguchi, Keishi Yamasaki, et al. P-012: Effect of PEGylation on the physicochemical and pharmacokinetic characteristics of bovine serum albumin-encapsulated liposome[J]. Asian J Pharmaceutical Sciences, 2016, 11(1): 112-113.

[57] Cui Meng, Wu Wei, Lars Hovgaard, et al. Liposomes containing cholesterol analogues of botanical origin as drug delivery systems to enhance the oral absorption of insulin[J]. Int J Pharm, 2015, 489(1-2): 277-284.

[58] Se-Jin Park, Soon Gil Choi, Enkhzaya Davaa, et al. Encapsulation enhancement and stabilization of insulin in cationic liposomes[J]. Int J Pharm, 2011, 415(1-2): 275-272.

[59] Christopher Barnier-Quer, Abdelrahman Elsharkawy, Stefan G Romeijn, et al. Adjuvant Effect of Cationic Liposomes for Subunit Influenza Vaccine:Influence of Antigen Loading Method, Cholesterol and Immune Modulators[J]. Pharmaceutics, 2013, 5(3): 392-410.

[60] 乔建斌. 冻融—冻干法制备流感疫苗脂质体及其细胞免疫研究[D]. 昆明：昆明医科大学, 2014.

[61] 叶红艳. 冻融—冻干法制备狂犬疫苗脂质体及其细胞免疫研究[D]. 昆明：昆明医科大学, 2016.

[62] Zhang Y, Li H, Sun J, et al. DC-Chol/DOPE cationic liposomes: A comparative study of the influence factors on plasmid pDNA and siRNA gene delivery[J]. Int J Pharm, 2010, 390(2): 198-207.

[63] 臧新龙, 李季, 李晓巍, 等. 载siRNA阳离子脂质体的制备[J]. 沈阳药科大学学报, 2015, 32(7): 510-516.