| Orginal Article |
|
|
|
|
| Advance in Application of Polysialic Acid,a Non-GAGs, Non-immunogenic Biomaterial |
Jian-rong WU( ),Xing-qiao PENG,Xiao-bei ZHAN |
| The Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China |
|
|
|
Abstract Polysialic acid is a strongly negatively charged, linear homopolymer linked by N-neuraminic acid, present in the human body, animal cells and a few pathogens. Polysialic acid is commonly found in glycoprotein (nerve cell adhesion molecules) and glycolipids. Polysialic acid is a non-glycosaminoglycan, non-immunogenic and biodegradable biomaterial. Polysialic acid can be used as biomaterials in tissue engineering and drug controlled release. Also it can be compounded with other macromolecules to form multi-functional materials. The biological functions, fermentative production and application of polysialic acid are reviewed, in order to provide a hint for the further application of polysialic acid.
|
|
Received: 07 June 2017
Published: 16 December 2017
|
|
|
|
|
| [1] |
Azurmendi H F, Vionnet J, Wrightson L , et al. Extracellular structure of polysialic acid explored by on cell solution NMR. PNAS, 2007,104(28):11557-11561.
doi: 10.1073/pnas.0704404104
pmid: 17609375
|
|
|
| [2] |
黎娜, 王华锋, 曾旭辉 . 唾液酸对精子的作用. 中国细胞生物学学报, 2015,37(5):734-739.
|
|
|
| [2] |
Li N, Wang H F, Zeng X H . Role of sialic acid on sperm. Chinese Journal of Cell Biology, 2015,37(5):734-739.
|
|
|
| [3] |
Tecle E, Gagneux P . Sugar-coated sperm: Unraveling the functions of the mammalian sperm glycocalyx. Mol Reprod Dev, 2015,82(9):635-650.
doi: 10.1002/mrd.22500
pmid: 26061344
|
|
|
| [4] |
Miyata S, Sato C, Kitamura S , et al. A major flagellum sialoglycoprotein in sea urchin sperm contains a novel polysialic acid, an α2,9-linked poly-N-acetylneuraminic acid chain, capped by an 8-O-sulfated sialic acid residue. Glycobiology, 2004,14(9):827-840.
doi: 10.1093/glycob/cwh100
|
|
|
| [5] |
Cress B F, Englaender J A, He W , et al. Masquerading microbial pathogens capsular polysaccharides mimic host-tissue molecules. FEMS Microbiol Rev, 2014,38(4):660-697.
doi: 10.1111/1574-6976.12056
pmid: 24372337
|
|
|
| [6] |
McGowen M M, Vionnet J, Vann W F . Elongation of alternating alpha 2,8/2,9 polysialic acid by the Escherichia coli K92 polysialyltransferase. Glycobiology, 2001,11(8):613-620.
doi: 10.1093/glycob/11.8.613
pmid: 11479272
|
|
|
| [7] |
Kleene R, Schachner M . Glycans and neural cell interactions. Nat Rev Neurosci, 2004,5(3):195-208.
doi: 10.1038/nrn1349
pmid: 14976519
|
|
|
| [8] |
Yabe U, Sato C, Matsuda T , et al. Polysialic acid in human milk CD36 is a new member of mammalian polysialic acid-containing glycoprotein. J Biol Chem, 2003,278(16):13875-13880.
doi: 10.1074/jbc.M300458200
|
|
|
| [9] |
Simon P, Baumner S, Busch O , et al. Polysialic acid is present in mammalian semen as a posttranslational modification of the neural cell adhesion molecule NCAM and the polysialyltransferase ST8SiaII. J Biol Chem, 2013,288(26):18825-18833.
doi: 10.1074/jbc.M113.451112
pmid: 3696658
|
|
|
| [10] |
Tanaka F, Otake Y, Nakagawa T , et al. Expression of polysialic acid and STX,a human polysialyltransferase,is correlated with tumor progression in non-small cell lung cancer. Cancer Res, 2000,60(11):3072-3080.
doi: 10.1097/00002820-200006000-00012
pmid: 10850459
|
|
|
| [11] |
Sato C, Kitajima K . Disialic, oligosialic and polysialic acids: distribution, functions and related disease. J Bioechm, 2013,154(2):115-136.
doi: 10.1093/jb/mvt057
pmid: 23788662
|
|
|
| [12] |
Murray H C, Low V F, Swanson M E , et al. Distribution of PSA-NCAM in normal, Alzheimer’s and Parkinson’s disease human brain. Neuroscience, 2016,330(8):359-375.
doi: 10.1016/j.neuroscience.2016.06.003
pmid: 27282086
|
|
|
| [13] |
Rodriguez-Aparicio L B, Reglero A, Ortiz A I , et al. Effect of physical and chemical conditions on the production of colominic acid by Escherichia coli in a defined medium. Appl Microbiol Biotechnol, 1988,27(5):474-483.
doi: 10.1007/BF00451616
|
|
|
| [14] |
Rode B, Endres C, Ran C , et al. Large-scale production and homogenous purification of long chain polysialic acids from E. coli K1. J Biotechnol, 2008,135(2):202-209.
doi: 10.1016/j.jbiotec.2008.03.012
pmid: 18482777
|
|
|
| [15] |
Kapre S V, Shaligram U . Process for the preparation of highly pure polysialic acid of high molecular weights: WO Patent, 0353732008. 2012
|
|
|
| [16] |
Zhan X B, Zhu L, Wu J R , et al. Production of polysialic acid from fed-batch fermentation with pH control. Biochem Eng J, 2002,11(2-3):201-204.
doi: 10.1089/thy.2006.16.403
|
|
|
| [17] |
Wu J R, Liu J L, Zhan X B , et al. Enhancement of polysialic acid yield by reduction of initial phosphate and feeding of ammonia water with Escherichia coli CCTCC M208088. Biotechnol Bioproc Eng, 2010,15(4):657-663.
doi: 10.1007/s12257-009-3128-7
|
|
|
| [18] |
Zheng Z Y, Wang S Z, Li G S , et al. A new polysialic acid production process based on dual-stage pH control and fed-batch fermentation for higher yield and resulting high molecular weight product. Appl Microbiol Biotechnol, 2013,97(6):2405-2412.
doi: 10.1007/s00253-012-4503-4
pmid: 23090056
|
|
|
| [19] |
Chen F, Tao Y, Jin C , et al. Enhanced production of polysialic acid by metabolic engineering. Appl Microbiol Biotechnol, 2015,99(6):2603-11.
doi: 10.1007/s00253-015-6391-x
pmid: 25620366
|
|
|
| [20] |
付旭东, 吴剑荣, 蒋芸 , 等. 乙酸与钾离子强度对聚唾液酸合成及过程分子量变化的影响.食品与发酵工业. 2017, doi: 10.13995/j.cnki.11-1802/ts.013824.
doi: 10.13995/j.cnki.11‐ 1802/ts.013824
|
|
|
| [20] |
Fu X D, Wu J R, Jiang Y , et al. Food and Fermentation Industries, 2017, dOI: 10.13995/j.cnki.11‐ 1802/ts.013824
doi: 10.13995/j.cnki.11‐ 1802/ts.013824
|
|
|
| [21] |
Puente-Polledo L, Reglero A, González-Clemente C , et al. Biochemical conditions for the production of polysialic acid by Pasteurella haemolytica A2. Glycoconjugate J, 1998,15(9):855-861.
doi: 10.1023/A:1006902931032
|
|
|
| [22] |
Lin S L, Inoue Y, Inoue S . Evaluation of high-performance anion-exchange chromatography with pulsed electrochemical and fluorometric detection for extensive application to the analysis of homologous series of oligo- and polysialic acids in bioactive molecules. Glycobiology, 1999,9(8):807-814.
doi: 10.1093/glycob/9.8.807
|
|
|
| [23] |
Nomoto H, Iwasaki M, Endo T , et al. Sturctures of carbohydrate units isolated from trout egg polysialoglycoproteins: short-cored units with oligosialosyl groups. Arch Biochem Biophys, 1982,218(1):335-341.
doi: 10.1016/0003-9861(82)90352-6
pmid: 7149739
|
|
|
| [24] |
Liu J L, Zhan X B, Wu J R , et al. An efficient and large-scale preparation process for polysialic acid by Escherichia coli CCTCC M208088. Biochem Eng J, 2010,53(1):97-103.
doi: 10.1016/j.bej.2010.09.015
|
|
|
| [25] |
Chen R, John J, Rode B , et al. Comparison of polysialic acid production in Escherichia coli K1 during batch cultivation and fed-batch cultivation applying two different control strategies. J Biotechnol, 2011,154(4):222-229.
doi: 10.1016/j.jbiotec.2011.04.009
pmid: 21530596
|
|
|
| [26] |
Gregoriadis G, Fernandes A I . Synthesis, characterization and properties of sialylated catalase. Biochim Biophy Acta, 1996,1293(1):90-96.
doi: 10.1016/0167-4838(95)00227-8
pmid: 8652633
|
|
|
| [27] |
Fernandes A I, Gregoriadis G . Polysialylated asparaginase: preparation, activity and pharmacokinetics. Biochim Biophy Acta, 1997,1341(1):26-34.
doi: 10.1016/S0167-4838(97)00056-3
pmid: 9300806
|
|
|
| [28] |
Jain S, Hreczuk-Hirst D H, McCormack B, , et al. Polysialylated insulin: synthesis, characterization and biological activity in vivo. Biochim Biophy Acta, 2003,1622(1):42-49.
doi: 10.1016/S0304-4165(03)00116-8
pmid: 12829260
|
|
|
| [29] |
Constantinou A, Epenetos A A, Hreczuk-Hirst D , et al. Modulation of antibody pharmacokinetics by chemical polysialylation. Bioconjug Chem, 2008,19(3):643-650.
doi: 10.2164/jandrol.108.005074
pmid: 18307285
|
|
|
| [30] |
Constantinou A, Epenetos A A, Hreczukhirst D , et al. Site-specific polysialylation of an antitumor single-chain Fv fragment. Bioconjug Chem, 2009,20(5):924-931.
doi: 10.1021/bc8005122
pmid: 19402707
|
|
|
| [31] |
Zhang R S, Jain S, Rowland M , et al. Development and testing of solid dose formulations containing polysialic acid insulin conjugate: next generation of long-acting insulin. J Diabetes Sci Technol, 2010,4(3):1-8.
doi: 10.1177/193229681000400101
pmid: 2825618
|
|
|
| [32] |
Wu J R, Lin Y, Zheng Z Y , et al. Improvement of the CuZn-superoxide dismutase enzyme activity and stability as a therapeutic agent by modification with polysialic acids. Biotechnol Lett, 2010,32(12):1939-1945.
doi: 10.1007/s10529-010-0382-x
pmid: 20820880
|
|
|
| [33] |
Wu J R, Lu S Z, Zhan X B , et al. Modification with polysialic acid-PEG copolymer as a new method for improving the therapeutic efficacy of proteins. Prep Biochem Biotechnol, 2016,46(8):788-797.
doi: 10.1080/10826068.2015.1135463
pmid: 26829568
|
|
|
| [34] |
Wu J R, Zhan X B, Lin Y . Preparation and application of PEG-PSA block copolymer: CN Patent, 201010111612.X. 2008
|
|
|
| [35] |
Bruns S, Stark Y, Poker S , et al. Collagen biomaterial doped with colominic acid for cell culture applications with regard to peripheral nerve repair. Biomaterial, 2007,28(131):335-345.
doi: 10.1016/j.biomaterials.2006.06.013
pmid: 16854461
|
|
|
| [36] |
Berski S, van Bergeijk J, Schwarzer D , et al. Synthesis and biological evaluation of a polysialic acid-based hydrogel as enzymatically degradable scaffold material for tissue engineering. Biomacromolecules, 2008,9(9):2353-2359.
doi: 10.1021/bm800327s
pmid: 18690740
|
|
|
| [37] |
Haile Y, Berski S . The effect of modified polysialic acid based hydrogels on the adhesion and viability of primary neurons and glial cells. Biomaterials, 2008,29(12):1880-1891.
doi: 10.1016/j.biomaterials.2007.12.030
pmid: 18255143
|
|
|
| [38] |
Masand S N, Chen J, Perron I J , et al. The effect of glycomimetic functionalized collagen on peripheral nerve repair. Biomaterials, 2012,33(33):8353-8362.
doi: 10.1016/j.biomaterials.2012.08.018
pmid: 22917737
|
|
|
| [39] |
Williams S, Neumann A, Bremer I , et al. Nanoporous silica nanoparticles as biomaterials: evaluation of different strategies for the functionalization with polysialic acid by step-by-step cytocompatibility testing. J Mater Sci-Mater M, 2015,26(3):125-141.
doi: 10.1007/s10856-015-5409-3
pmid: 25690616
|
|
|
| [40] |
Bader R A, Silvers A L, Zhang N . Polysialic acid-based micelles for encapsulation of hydrophobic drugs. Biomacromolecules, 2011,12(2):314-320.
doi: 10.1021/bm1008603
pmid: 21218771
|
|
|
| [41] |
Zhang N, Bader R A . Synthesis and characterization of polysialic acid-N-trimethyl chitosan nanoparticles for drug delivery. Nano LIFE, 2012,2(3):1241003.
doi: 10.1142/S1793984412410036
|
|
|
| [42] |
Greco F, Arif I, Botting R , et al. Polysialic acid as a drug carrier: evaluation of a new polysialic acid-epirubicin conjugate and its comparison against established drug carriers. Polym Chem-UK, 2013,4(5):1600-1609.
doi: 10.1039/c2py20876h
|
|
|
| [43] |
Wilson D R, Zhang N, Silvers A L , et al. Synthesis and evaluation of cyclosporine A-loaded polysialic acid-polycaprolactone micelles for rheumatoid arthritis. Eur J Pharm Sci, 2014,51(1):146-156.
doi: 10.1016/j.ejps.2013.09.013
pmid: 24075961
|
|
|
| [44] |
Wu J R, Zhan X B, Zheng Z Y , et al. Synthesis and characterization of polysialic acid/carboxymethyl chitosan hydrogel with potential for drug delivery. Russ J Bioorg Chem, 2015,41(5):562-567.
doi: 10.1134/S1068162015040135
pmid: 26762102
|
|
|
| [45] |
Zhang W X, Dong D Q, Li P , et al. Novel pH-sensitive polysialic acid based polymeric micelles for triggered intracellular release of hydrophobic drug. Carbohyd Polym, 2016,139(3):75-81.
doi: 10.1016/j.carbpol.2015.12.041
pmid: 26794949
|
|
|
| [46] |
Wu J R, Fu H, Zhan X B , et al. Preparation and characterization of a novel polysialic acid-hyaluronan graft copolymer potential as dermal filler. Int J Biol Macromol, 2017,99(6):692-698.
doi: 10.1016/j.ijbiomac.2017.03.042
|
|
|
| [47] |
Zhang T, Zhou S, Hu L , et al. Polysialic acid-modifying liposomes for efficient delivery of epirubicin, in-vitro characterization and in-vivo evaluation. Int J Pharmaceut, 2016,515(1-2):449-459.
doi: 10.1016/j.ijpharm.2016.10.051
pmid: 27789365
|
|
|
| [48] |
Jung B, Shim M K, Park M J , et al. Hydrophobically modified polysaccharide-based on polysialic acid nanoparticles as carriers for anticancer drugs. Int J Pharmaceut, 2017,520(1-2):111-118.
doi: 10.1016/j.ijpharm.2017.01.055
pmid: 28179099
|
|
|
| [49] |
Wang X J, Gao Y P, Lu N N , et al. Endogenous polysialic acid based micelles for calmodulin antagonist delivery against vascular dementia. Acs Appl Mater Inter, 2016,8(51):35045-35058.
doi: 10.1021/acsami.6b13052
pmid: 27750011
|
|
|
| [50] |
Shahraz A, Kopatz J, Mathy R , et al. Anti-inflammatory activity of low molecular weight polysialic acid on human macrophages. Sci Rep-UK, 2015,5:16800.
doi: 10.1038/srep16800
pmid: 4652165
|
|
|
| [51] |
Neyra C, Paladino J, Le B M . Oxidation of sialic acid using hydrogen peroxide as a new method to tune the reducing activity. Carbohyd Res, 2014,386(316):92-98.
doi: 10.1016/j.carres.2014.01.007
pmid: 24503343
|
|
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
