磷脂是一类非常重要的生物分子，它是细胞膜的主要组成部分，同时也在诸多生命活动（如细胞激活、代谢维持和激素分泌等）中发挥着不可替代的作用。磷脂种类繁多，且具有自组装能力强、生物相容性好、无细胞毒性、易于获得等一系列优点。作为一种最典型的界面材料，磷脂膜特殊的双层结构及出色的生物学性能引起了科研人员的广泛关注，其能够模拟生物膜结构，有助于研究界面上的分子特征及作用行为。此外，磷脂可被用作生物医学材料，改性磷脂以及磷脂与纳米颗粒的复合物在肿瘤成像技术、药物靶向递送系统等方面具有良好的发展前景，显著促进了新型生物材料的开发与进步。本文先归纳了磷脂的分类，并比较了磷脂在不同基底的吸附行为；之后重点分析了磷脂膜界面的选择性识别功能以及与多肽、酶、蛋白质等生物分子之间的相互作用；最后对基于磷脂膜的生物材料在生物传感、药物研究和成像技术中的应用作出了展望。
As a class of crucially important biomolecules, phospholipids are key building blocks of cytomembrane and play indispensable roles in a variety of life activities, such as cell activation, metabolism maintenance, hormone secretion, and so on. There are a variety of phospholipids, most of which display remarkable advantages in strong self-assembly ability, excellent biocompatibility, no cytotoxicity and easy availability. As the most typical interfacial materials, the unique bilayer structures and outstanding biological performances of phospholipid membranes have attracted researchers' interests, which provide an excellent platform to investigate molecular characteristics and interfacial interactions on cell membranes. In addition, phospholipids can be also used as biomedical materials. Various chemically modified phospholipids and phospholipid-nanoparticle composites display good prospects for development in biomedical fields of tumor imaging technology and drug targeting delivery, which greatly promotes the development of new-generation biomaterials. In this review, the classification of phospholipids has been summarized and their adsorption behaviors on different substrates are also discussed. Then special interests are placed on selective recognition capacities of the phospholipid bilayers and the interfacial interactions between phospholipid bilayers and various biomolecules, such as peptides, enzymes and proteins. Finally, the enticing prospects of phospholipid-based biomaterials in bio-sensing, drug research and bio-imaging technology are demonstrated.
Contents
1 Introduction
2 Classification of phospholipids
2.1 Natural phospholipids
2.2 Synthetic phospholipids
2.3 Phospholipid-based composites
3 Assembly behaviors of phospholipids on different surfaces
3.1 Mica surface
3.2 Silicon dioxide surface
3.3 Gold surface
3.4 Thiolated gold surface
4 Effect of phospholipid bilayers on biomolecules
4.1 Selective recognition at biointerface
4.2 Effect on self-assembly of peptide
4.3 Effect on enzyme catalysis
4.4 Effect on protein
5 Bio-applications of phospholipids
5.1 Bio-sensing
5.2 Drug targeted transport
5.3 Biological imaging technology
5.4 Drug release
6 Conclusion
[1] Nafday O A, Lowry T W, Lenhert S. Small, 2012, 8:1021.
[2] Tu Y, Lv M, Xiu P, Huynh T, Zhang M, Castelli M, Liu Z, Huang Q, Fan C, Fang H, Zhou R. Nat. Nanotechnol., 2013, 8:594.
[3] Suetsugu S, Kurisu S, Takenawa T. Physiol. Rev., 2014, 94:1219.
[4] Mapstone M, Cheema A K, Fiandaca M S, Zhong X, Mhyre T R, MacArthur L H, Hall W J, Fisher S G, Peterson D R, Haley J M, Nazar M D, Rich S A, Berlau D J, Peltz C B, Tan M T, Kawas C H, Federoff H J. Nat. Med., 2014, 20:415.
[5] Hoogevest P V, Wendel A. Eur. J. Lipid Sci. Technol., 2014, 116:1088.
[6] Park S H, Das B B, Casagrande F, Tian Y, Nothnagel H J, Chu M, Kiefer H, Maier K, Angelis A D, Marassi F M, Opella S J. Nature, 2012, 491:779.
[7] Hagn F, Etzkorn M, Raschle T, Wagner G. J. Am. Chem. Soc., 2013, 135:1919.
[8] Cordeiro R M. Biochim. Biophys. Acta Biomembr., 2014, 1838:438.
[9] Shao S, Geng J, Yi H A, Gogia S, Neelamegham S, Jacobs A, Lovell J F. Nat. Chem., 2015, 7:438.
[10] Robison A D, Sun S, Poyton M F, Johnson F A, Pellois J P, Jungwirth P, Vazdar M, Cremer P S. J. Phys. Chem. B, 2016, 120:9287.
[11] Salzano G, Riehle R, Navarro G, Perche F, De R G, Tor-chilin V P. Cancer Lett., 2014, 343:224.
[12] Davies S S, Guo L. Chem. Phys. Lipids, 2014, 181:1.
[13] Noyhouzer T, L'Homme C, Beaulieu I, Mazurkiewicz S, Kuss S, Kraatz H B, Canesi S, Mauzeroll J. Langmuir, 2016, 32:4169.
[14] Yu F, Ao M, Zheng X, Li N, Xia J, Li Y, Li D, Hou Z, Qi Z, Chen X D. Drug Delivery, 2017, 24:825.
[15] Park J H, Cho H J, Yoon H Y, Yoon I S, Ko S H, Shim J S, Cho J H, Park J H, Kim K, Kwon I C, Kim D D. J. Control. Release, 2014, 174:98.
[16] Pattni B S, Chupin V V, Torchilin V P. Chem. Rev., 2015, 115:10938.
[17] Zhang Z, Sohgawa M, Yamashita K, Noda M. Electroanalysis, 2016, 28(3):620.
[18] Wang T, Feng Y, Jin X, Fan X, Crommen J, Jiang Z. J. Pharm. Biomed. Anal., 2014, 96:263.
[19] Liu Q, Boyd B J. Analyst, 2013, 138:391.
[20] Shen Y X, Saboe P O, Sines I T, Erbakan M, Kumar M. J. Membr. Sci., 2014, 454:359.
[21] Kuang H, Ku S H, Kokkoli E. Adv. Drug Delivery Rev., 2017, 110:80.
[22] Oberli M A, Reichmuth A M, Dorkin J R, Mitchell M J, Fenton O S, Jaklenec A, Anderson D G, Langer R, Blankschtein D. Nano Lett., 2017, 17:1326.
[23] Peng R, Wang H, Lyu Y, Xu L, Liu H, Kuai H, Liu Q, Tan W. J. Am. Chem. Soc., 2017, 139:12410.
[24] Shi K, Li J, Cao Z, Yang P, Qiu Y, Yang B, Wang Y, Long Y, Liu Y, Zhang Q, Qian J, Zhang Z, Gao H, He Q. J. Control. Release, 2015, 217:138.
[25] Qu W, Zuo W, Li N, Hou Y, Song Z, Gou G, Yang J. J. Drug Targeting, 2017, 25:661.
[26] Li J, Wang X, Zhang T, Wang C, Huang Z, Luo X, Deng Y. Asian J. Pharm. Sci., 2015, 10:81.
[27] Singh R P, Gangadharappa H V, Mruthunjaya K. J. Drug Delivery Sci. Technol., 2017, 39:166.
[28] 闫媛媛(Yan Y Y), 张康逸(Zhang K Y), 黄健花(Huang J H), 刘元法(Liu Y F), 王兴国(Wang X G). 中国油脂(China Oils and Fats), 2012, 37(5):61.
[29] Hama S, Ogino C, Kondo A. Appl. Microbiol. Biotechnol., 2015, 99:7879.
[30] Baldassarre F, Allegretti C, Tessaro D, Carata E, Citti C, Vergaro V, Nobile C, Cannazza G, Arrigo P D, Mele A, Dini L, Ciccarella G. ChemistrySelect, 2016, 1:6507.
[31] Cox E, Michalak A, Pagentine S, Seaton P, Pokorny A. Biochim. Biophys. Acta, Biomembr., 2014, 1838:2198.
[32] Slavetinsky C, Kuhu S, Peschel A. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids, 2017, 1862:1310.
[33] Zhou C Y, Wu H, Devaraj N K. Chem. Sci., 2015, 6:4365.
[34] Liu J, Li J, Liu N, Guo N, Gao C, Hao Y, Chen Y, Zhang X. Int. J. Pharm., 2017, 530:291.
[35] Zhuang J, Young A P, Tsung C K. Small, 2017, 32:1700880.
[36] Du B, Tian L, Gu X, Li D, Wang E, Wang J. Small, 2015, 11:2333.
[37] Katagiri K, Imai Y, Koumoto K, Kaiden T, Kono K, Ao-shima S. Small, 2011, 7:1683.
[38] Liao Z, Wang H, Wang X, Zhao P, Wang S, Su W, Chang J. Adv. Funct. Mater., 2011, 21:1179.
[39] Zhang L, Chen Z, Li Y. Int. J. Nanomed., 2013, 8:3689.
[40] Wang F, Liu J. Small, 2014, 10:3927.
[41] Ross E E, Bondurant B, Spratt T, Conboy J C, O'Brien D F, Saavedra S S. Langmuir, 2001, 17:2305.
[42] Richter R P, Bérat R, Brisson A R. Langmuir, 2006, 22:3497.
[43] Watts T H, Brian A A, Kappler J W, Marrack P, Mcconnell H M. Proc. Natl. Acad. Sci. U. S. A., 1984, 81:7564.
[44] Richter R P, Brisson A R. Biophys. J., 2005, 88:3422.
[45] Reimhult E, Zäch M, Höök F, Kasemo B. Langmuir, 2006, 22:3313.
[46] Zhu X, Wang Z, Zhao A, Huang N, Chen H, Zhou S, Xie X. Colloids Surf. B, 2014, 116:459.
[47] Zawisza I, Lachenwitzer A, Zamlynny V, Horswell S L, Goddard J D, Lipkowski J. Biophys. J., 2003, 85:4055.
[48] Toma K, Kano H, Offenhäusser A. ACS Nano, 2014, 8:12612.
[49] Paw?owski J, Juhaniewicz J, Güzelo D?lu A, S?k S. Langmuir, 2015, 31:11012.
[50] Viitala L, Lajunen T, Urtti A O, Viitala T, Murtomäki L. J. Phys. Chem. C, 2015, 119:21395.
[51] Schönherr H, Johnson J M, Lenz P, Frank C W, Boxer S G. Langmuir, 2004, 20:11600.
[52] Hasan I Y, Mechler A. Biointerphases, 2016, 11:031017.
[53] Cajal Y, Svendsen A, De B J, Patkar S A, Alsina M A. Biochimie, 2000, 82:1053.
[54] Cozza G, Rossetto M, Bosello-Travain V, Maiorino M, Roveri A, Toppo S, Zaccarin M, Zennaro L, Ursini F. Free Radical Biol. Med., 2017, 112:1.
[55] Willems N, Lelimousin M, Koldsø H, Sansom M S. Bio-chim. Biophys. Acta, 2017, 1859:340.
[56] Alvares D S, Wilke N, Neto J R, Fanani M L. Chem. Phys. Lipids, 2017, 207:38.
[57] Das D, Pal S K. Chemistryselect, 2017, 2:4779.
[58] Daudey G A, Zope H R, Voskuhl J, Kros A, Boyle A L. Langmuir, 2017, 33:12443.
[59] Schulz M, Werner S, Bacia K, Binder W H. Angew. Chem. Int. Ed., 2013, 52:1829.
[60] Biros S M, Ullrich E C, Hof F, Laurent T A, Julius R J. J. Am. Chem. Soc., 2004, 126:2870.
[61] Ishigami T, Suga K, Umakoshi H. ACS Appl. Mater. Interfaces, 2015, 7:21065.
[62] Hirose M, Ishigami T, Suga K, Umakoshi H. Langmuir, 2015, 31:12968.
[63] Okamoto Y, Kishi Y, Suga K, Umakoshi H. Biomacromolecules, 2017, 18:1180.
[64] Okamoto Y, Kishi Y, Ishigami T, Suga K, Umakoshi H. J. Phys. Chem. B, 2016, 120:2790.
[65] 陆时万(Lu S W), 徐祥生(Xu X S), 沈敏健(Shen M J). 植物学(Botany). 北京:高等教育出版社(Beijing:Higher Education Press), 1991. 8.
[66] 王建勋(Wang J X), 秦四勇(Qin S Y), 蔡腾腾(Cai T T). 高等学校化学学报(Chemical Journal of Chinese Universities), 2015, 36(2):201.
[67] Kornmueller K, Lehofer B, Meindl C, Fröhlich E, Leitinger G, Amenitsch H, Prassl R. Biomacromolecules, 2016, 17:3591.
[68] Gao G, Zhang M, Lu P, Guo G, Wang D, Sun T. Angew. Chem., 2015, 127:2273.
[69] Sevigny J, Chiao P, Bussière T, Weinreb P H, Williams L, Maaier M, Dunstan R, Salloway S, Chen T, Ling Y, O'Gorman J, Qian F, Arastu M, Li M, Chollate S, Brennan M S, Quinrero-Monzon O, Scannevin R H, Arnold H M, Engber T, Rhodes K, Ferrero J, Hang Y, Mikulskis A, Grimm J, Hock C, Nitsch R M, Sandrock A. Nature, 2016, 537:50.
[70] 叶明舟(Ye M Z). 浙江大学博士论文(Doctoral Dissertation of Zhejiang University), 2015.
[71] Qing G, Zhao S, Xiong Y, Lv Z, Jiang F, Liu Y, Chen H, Zhang M, Sun T. J. Am. Chem. Soc., 2014, 136:10736.
[72] Gao G, Zhang M, Lu P, Guo G, Wang D, Sun T. Angew. Chem., 2015, 54:2245.
[73] 王悦(Wang Y), 彭蜀晋(Peng S J), 周媛(Zhou Y). 大学化学(University Chemistry), 2011, 26(5):88.
[74] 王镜岩(Wang J Y), 朱圣康(Zhu S K), 徐长法(Xu C F). 生物化学(Biochemistry). 北京:高等教育出版社(Beijing:Higher Education Press), 2002. 319.
[75] Agapakis C M, Boyle P M, Silver P A. Nat. Chem. Biol., 2012, 8:527.
[76] Tabaei S R, Rabe M, Zetterberg H, Zhdanov V P, Höök F. J. Am. Chem. Soc., 2013, 135:14151.
[77] Carvalho C M L, Cabral J M S. Biochimie, 2000, 82:1063.
[78] Anzenbacher P, Anzenbacherová E. Cell. Mol. Life Sci., 2001, 58:737.
[79] Navrátilová V, Paloncyova M, Berka K, Otyepka M. J. Phys. Chem. B, 2016, 120:11205.
[80] 李红春(Li H C). 中国科学技术大学博士论文(Doctoral Dissertation of University of Science and Technology of China), 2015.
[81] Wang L, Gotoh T, Wang Y, Kouyama T, Wang J Y. J. Phys. Chem. C, 2017, 121:19999.
[82] Perez L, Mettry M, Hinman S S, Byers S R, McKeating K S, Caulkins B G, Cheng Q, Hooley R J. Soft Matter, 2017, 13:3966.
[83] Shen Y R. Nature, 1989, 337:519.
[84] Yan E C Y, Fu L, Wang Z, Liu W. Chem. Rev., 2014, 114:8471.
[85] Wu H L, Tong Y, Peng Q, Li N, Ye S. Phys. Chem. Chem. Phys., 2016, 18:1411.
[86] Wei F, Ye S, Li H, Luo Y. J. Phys. Chem. C, 2013, 117:11095.
[87] 胡艳军(Hu Y J), 蒋风雷(Jiang F L), 欧阳宇(Ouyang Y),刘义(Liu Y). 中国科学:化学(Scientic Sinica:Chimica), 2010, (9):90.
[88] Graça J S, de Oliveira R F, de Moraes M L, Ferreira M. Bioelectrochemistry, 2014, 96:37.
[89] Lin B, Liu D, Yan J, Qiao Z, Zhong Y, Yan J, Zhu Z, Ji T, Yang C J. ACS Appl. Mater. Interfaces, 2016, 8:6890.
[90] Weingart O G, Loessner M J. Toxicol. Appl. Pharmacol., 2016, 313:16.
[91] Kang D H, Jung H S, Kim K, Kim J. ACS Appl. Mater. Interfaces, 2017, 9:42210.
[92] Kraft J C, Freeling J P, Wang Z, Ho R J. J. Pharm. Sci., 2014, 103:29.
[93] Yan L, Crayton S H, Thawani J P, Amirshaghaghi A, Tsourkas A, Cheng Z. Small, 2015, 11:4870.
[94] Davis B M, Normando E M, Guo L, Turner L A, Nizari S, O'Shea P, Moss S E, Somavarapu S, Cordeiro M F. Small, 2014, 10:1575.
[95] Xu H L, Yang J J, Zhuge D L, Lin M T, Zhu Q Y, Jin B H, Tong M Q, Shen B X, Xiao J, Zhao Y Z. Adv. Healthcare Mater., DOI:10.1002/adhm.201701130.
[96] Tansi F L, Rüger R, Rabenhold M, Steiniger F, Fahr A, Kaiser W A, Hilger L. Small, 2013, 9:3659.
[97] Kim J, Pandya D N, Lee W, Park J W, Kim Y J, Kwak W, Ha Y S, Chang Y, An G I, Yoo J. ACS Med.Chem.Lett., 2014, 5:390.
[98] Gao X, Li C. Small, 2014, 10:426.
[99] Voon S H, Kiew L V, Lee H B, Lim S H, Noordin M I, Kamkaew A, Burgess K, Chung L Y. Small, 2014, 10:4993.
[100] Wang C, Ye Y, Hu Q, Bellotti A, Gu Z. Adv. Mater., 2017, 29.
[101] Sun Q, You Q, Wang J, Liu L, Wang Y, Song Y, Cheng Y, Wang S, Tan F, Li N. ACS Appl. Mater. Interfaces, 2018, 10:1963.
[102] Mazur F, Bally M, Städler B, Chandrawati R. Adv. Colloid Interface Sci., 2017, 249:88.
[103] Liu Q, Boyd B J. Analyst, 2013, 138:391.
[104] Mahmoudi-Badiki T, Alipour E, Hamishehkar H, Golabi S M. J. Biomater. Appl., 2016, 31:273.
[105] Zhu Y, Liao L. J. Nanosci. Nanotechnol., 2015, 15:4753.
[106] Bygd H C, Ma L, Bratlie K M. Mater. Sci. Eng. C, 2017, 79:237.
[107] Goldenbogen B, Brodersen N, Gramatica A, Loew M, Liebscher J, Herrmann A, Egger H, Budde B, Arbuzova A. Langmuir, 2011, 27:10820.
[108] Agrawal M, Ajazuddin, Tripathi D K, Saraf S, Saraf S, Antimisiaris S G, Mourtas S, Hammarlund-Udenaes M, Alexander A. J. Control. Release, 2017, 260:61.
[109] Shaw T K, Mandal D, Dey G, Pal M M, Paul P, Chakraborty S, Ali K A, Mukherjee B, Bandyopadhyay A K, Mandal M. Drug Delivery, 2017, 24:346.
[110] Zhang Y, Zhai M, Chen Z, Han X, Yu F, Li Z, Xie X, Han C, Yu L, Yang Y, Mei X. Drug Delivery, 2017, 24:1045.
[111] 于杰(Yu J), 叶超(Ye C), 李臣贵(Li C G), 陈蓉(Chen R), 胡育筑(Hu Y Z). 中国药科大学学报(Journal of China Pharmaceutical University), 2011, 42(4):380.
[112] Wang Y, Wu B, Yang C, Liu M, Sum T C, Yong K T. Small, 2016, 12:534.
[113] Luo D, Li N, Carter K A, Lin C, Geng J, Shao S, Huang W C, Qin Y, Atilla-Gokcumen G E, Lovell J F. Small, 2016, 12:3039.
[114] Luo D, Carter K A, Miranda D, Lovell J F. Adv. Sci., 2017, 4:1600106.
[115] Shao S, Do T N, Razi A, Chitgupi U, Geng J, Alsop R J, Dzikovski B G, Rheinstädter M C, Ortega J, Karttunen M, Spernyak J A, Lovell J F. Small, 2017, 13:1602505.
[116] Bégu S, Aubert-Pou Dëssel A, Polexe R, Leitmanova E, Lerner D A, Devoisselle J M, Tichit D. Chem. Mater., 2009, 21:2679.
[117] Wang Q, O'Hare D. Chem. Rev., 2012, 112:4124.
[118] Yan M, Zhang Z, Cui S, Zhang X, Chu W, Lei M, Zeng K, Liao Y, Deng Y, Zhao C. Asian J. Pharm. Sci., 2016, 11:396.
[119] Lee C H, Kankala R K, Kuthati Y, Liu C L. RSC Adv., 2015, 5:42666.
[120] Zhang Y, Wu X, Mi Y, Li H, Hou W. J. Phys. Chem. Solids, 2017, 108:125.
[121] Nogueira E, Gomes A C, Preto A, Cavaco-Paulo A. Colloids Surf. B, 2015, 136:514.
[122] Sugimoto T, Yamazaki N, Hayashi T, Yuba E, Harada A, Kotaka A, Shinde C, Kumei T, Sumida Y, Fukushima M, Munekata Y, Maruyama K, Kono K. Colloids Surf. B, 2017, 155:449.
[123] Luo D, Carter K A, Razi A, Geng J, Shao S, Giraldo D, Sunar U, Ortega J, Lovell J F. Biomaterials, 2015, 75:193.
[124] Østrem R G, Parhamifar L, Pourhassan H, Clergeaud G, Nielsen O L, Kjær A,Hansen A E, Andresen T L. J. Control. Release, 2017, 262:212.
[125] Nasir M Z M, Jackman J A, Cho N J, Ambrosi A, Pumera M. Anal. Chem., 2017, 89:11753.
[126] Liu X, Wu Z, Zhou F, Li D, Chen H. Colloids Surf. B, 2010, 79:452.
[127] Tang Z, Liu X, Luan Y, Liu W, Wu Z, Li D, Chen H. Polym. Chem., 2013, 4:5597.
[128] Liu J, Cai J, Chen H, Zhang S, Kong J. J. Electroanal. Chem., 2016, 781:103.
[129] Chen Z H, Lv Z Y, Wang X, Yang H, Guang Y Q, Sun T L. NPG Asia Mater. DOI:10.1038/am.2017.241.
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