唾液酸及其分析方法研究进展
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摘要
随着糖生物学和糖组学研究的不断深入,已阐明了碳水化合物对生物识别系统的巨大作用。唾液酸是糖基化的一种主要表现形式,涉及机体的多种生理和病理过程,尤其在作为肿瘤和癌症疾病的药物靶标方面发挥了重大作用。论文从唾液酸的基本结构、连接形式、化学衍生化方式及其分析检测方法等方面对唾液酸的主要分析方法进行综述,对唾液酸及其多糖衍生物的物质结构和生物学功能有了更全面的认识,有助于发现基于唾液酸的生物标记和药物靶标,用于临床疾病诊断或监测治疗效果,对未来的生物学研究和医学实践提供了一条新的研究途径。
With the development of glycobiology and glycomics,it has been clarified that carbohydrates play an important role in biological recognition system.Sialic acid is a major form of glycosylation,involving a variety of physiological and pathological processes of the body,especially in the direction of drug targets for cancer.In this paper,the main research methods of sialic acid were reviewed from the aspects of basic structure,linkages,chemical derivatization and analytical detection methods for comprehensively understanding the material structure and biological functions of sialic acid and its polysaccharide derivatives.It is helpful to discover biomarkers and drug targets based on sialic acid for clinical diagnosis or monitoring of therapeutic effects,and provides a new way for future biological research and medical practice.
With the development of glycobiology and glycomics,it has been clarified that carbohydrates play an important role in biological recognition system.Sialic acid is a major form of glycosylation,involving a variety of physiological and pathological processes of the body,especially in the direction of drug targets for cancer.In this paper,the main research methods of sialic acid were reviewed from the aspects of basic structure,linkages,chemical derivatization and analytical detection methods for comprehensively understanding the material structure and biological functions of sialic acid and its polysaccharide derivatives.It is helpful to discover biomarkers and drug targets based on sialic acid for clinical diagnosis or monitoring of therapeutic effects,and provides a new way for future biological research and medical practice.
引文
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[25] Nishikaze T,Tsumoto H,Sekiya S,et al.Differentiation of sialyl linkage isomers by one-pot sialic acid derivatization for mass spectrometry-based glycan profiling[J].Anal Chem,2017,89(4):2353-2360.
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[27] Li H,Gao W,Feng X,et al.MALDI-MS analysis of sialylated N-glycan linkage isomers using solid-phase two step derivatization method[J].Anal Chim Acta,2016,924:77-85.
[28] 黄江铭,曹纬倩,杨芃原.基于质谱的糖蛋白/糖链定量技术研究进展[J].分析科学学报,2014,30(5):749-754.
[29] Pett C,Nasir W,Sihlbom C,et al.Effective assignment of α2,3/α2,6-sialic acid isomers by LC-MS/MS-based glycoproteomics.[J].Angew Chem,2018,57(30):9320-9324.
[30] Hu Y,Zhou S,Khalil S I,et al.Glycomic Profiling of Tissue Sections by LC-MS[J].Anal Chem,2013,85(8):4074-4079.
[31] Damerell D,Ceroni A,Maass K,et al.Annotation of glycomics MS and MS/MS spectra using the glyco workbench software tool[J].Methods Mol Biol,2015,1273:3-15.
[32] Varki A,Etzler M E,Cummings R D,et al.Discovery and Classification of Glycan-Binding Proteins[M]// Essentials of Glycobiology,Cold Spring Harbor (NY):Cold Spring Harbor Laboratory Press,2015-2017.
[33] Zhang L,Luo S,Zhang B.The use of lectin microarray for assessing glycosylation of therapeutic proteins[J].Mabs,2016,8(3):524-535.
[34] Hennig R,Rapp E,Kottler R,et al.N-glycosylation fingerprinting of viral glycoproteins by xCGE-LIF[J].Methods Mol Biol,2015,1331:123-143.
[35] Dias A M,Almeida C R,Reis C A,et al.Studying T Cells N-Glycosylation by Imaging Flow Cytometry[A]// Imaging Flow Cytometry:Methods and Protocols,Methods Mol Biol,2016:167-176.
[36] Veluraja K,Selvin J F A,Jasmine A,et al.Three Dimensional Structures of Carbohydrates and Glycoinformatics:An Overview[A]// Current Trends in Bioinformatics:An Insight,2018:55-87.
[2] Zlatina K,Saftenberger M,Kühnle A,et al.Polysialic acid in human plasma can compensate the cytotoxicity of histones[J].Int J Mol Sci,2018,19(6):1679-1688.
[3] Ferrerbatallé M,Llop E,Ramírez M,et al.Comparative study of blood-based biomarkers,α2,3-sialic acid PSA and PHI,for high-risk prostate cancer detection[J].Int J Mol Sci,2017,18(4):845-856.
[4] Lan Y,Hao C,Zeng X,et al.Serum glycoprotein-derived N-and O-linked glycans as cancer biomarkers[J].Am J Cancer Res,2016,6(11):2390-2415.
[5] Galuska S P.Advances in sialic acid and polysialic acid detection methodologies[EB/OL].https://www.researchgate.net/publication/257961314_Advances_in_Sialic_Acid_and_Polysialic_Acid_Detection_Methodologies,2013.DOI:10.2174/9781608053865113010016.
[6] Xie R,Dong L,Du Y,et al.In vivo metabolic labeling of sialoglycans in the mouse brain by using a liposome-assisted bioorthogonal reporter strategy[J].Proc Natl Acad Sci U S A,2016,113(19):5173-5178.
[7] Chen X,Varki A.Advances in the biology and chemistry of sialic acids[J].Acs Chem Biol,2010,5(2):163-176.
[8] Sato C.Chain length diversity of sialic acids and its biological significance[J].Trends Glycosci Glyc,2004,16(91):331-344.
[9] 易晨,刘欣.生物质谱分析方法用于豚鼠血清中N-聚糖的测定研究[A]//第二十届全国色谱学术报告会及仪器展览会.陕西西安:中国化学会,2015.
[10] 李恒辉.N-聚糖质谱检测新方法研究及应用[D].湖北武汉:华中科技大学,2016.
[11] 关锋,杨刚龙,谭增琦,等.一种两端标记相对定量分析糖链的方法:中国,104020216 B[P].2014-09-03.
[12] 铁偲,胡婷,张金兰.基于新型衍生化方法的UPLC-HRMS单克隆抗体N-糖基化分析方法[J].药物分析杂志,2015(6):1032-1037.
[13] Kakehi K,Kinoshita M,Kitano K,et al.Lactone formation of N-acetylneuraminic acid oligomers and polymers as examined by capillary electrophoresis[J].Electrophoresis,2015,22(16):3466-3470.
[14] 刘志东,王荫榆,郭本恒,等.唾液酸的研究进展[J].食品工业科技,2010(4):368-373.
[15] Skrisovska L,Schubert M,Allain H T.Recent advances in segmental isotope labeling of proteins:NMR applications to large proteins and glycoproteins[J].J Biomol Nmr,2010,46(1):51-65.
[16] Haverkamp J,Halbeek H,Dorland L,et al.High-resolution 1H-NMR spectroscopy of free and glycosidically linked O-acetylated sialic acids [J].Febs J,2010,122(2):305-311.
[17] 孔晨,徐敦明,黄慧英.基于核磁共振一维氢谱法鉴定燕窝真伪的研究[J].厦门大学学报:自然科学版,2015,54(6):819-824.
[18] 朱婧,石羽杰,吴立芳,等.不同阶段母乳中10种游离低聚糖的检测及含量分析[J].中国食品卫生杂志,2017,29(4):417-422.
[19] 陈思衡.高效液相色谱荧光检测应用于唾液酸分析研究[D].湖北武汉:华中科技大学,2012.
[20] Gohlke M,Blanchard V.Separation of N-glycans by HPLC[J].Methods Mol Biol,2002,446:239-254.
[21] Torii T,Yoshimura T,Narumi M,et al.Determination of major sialylated N-glycans and identification of branched sialylated N-glycans that dynamically change their content during development in the mouse cerebral cortex[J].Glycoconjugate J,2014,31(9):671-683.
[22] 傅青,张秀莉,郭志谋,等.寡糖色谱分离研究进展[J].生命科学,2011,7(7):703-713.
[23] 王承健,王仲孚.糖链的生物质谱分析[J].生命科学,2011,23(6):569-576.
[24] 张莹,焦竞,蔡炎,等.N-糖组质谱分析新方法[A]//第二届全国质谱分析学术报告会会议.陕西西安:中国化学会,2015.
[25] Nishikaze T,Tsumoto H,Sekiya S,et al.Differentiation of sialyl linkage isomers by one-pot sialic acid derivatization for mass spectrometry-based glycan profiling[J].Anal Chem,2017,89(4):2353-2360.
[26] Galuska C E,Kai M,Galuska S P.Mass spectrometric analysis of oligo- and polysialic acids[A]//Glyco-Engineering:Springer New York,2015,1321:417-426.
[27] Li H,Gao W,Feng X,et al.MALDI-MS analysis of sialylated N-glycan linkage isomers using solid-phase two step derivatization method[J].Anal Chim Acta,2016,924:77-85.
[28] 黄江铭,曹纬倩,杨芃原.基于质谱的糖蛋白/糖链定量技术研究进展[J].分析科学学报,2014,30(5):749-754.
[29] Pett C,Nasir W,Sihlbom C,et al.Effective assignment of α2,3/α2,6-sialic acid isomers by LC-MS/MS-based glycoproteomics.[J].Angew Chem,2018,57(30):9320-9324.
[30] Hu Y,Zhou S,Khalil S I,et al.Glycomic Profiling of Tissue Sections by LC-MS[J].Anal Chem,2013,85(8):4074-4079.
[31] Damerell D,Ceroni A,Maass K,et al.Annotation of glycomics MS and MS/MS spectra using the glyco workbench software tool[J].Methods Mol Biol,2015,1273:3-15.
[32] Varki A,Etzler M E,Cummings R D,et al.Discovery and Classification of Glycan-Binding Proteins[M]// Essentials of Glycobiology,Cold Spring Harbor (NY):Cold Spring Harbor Laboratory Press,2015-2017.
[33] Zhang L,Luo S,Zhang B.The use of lectin microarray for assessing glycosylation of therapeutic proteins[J].Mabs,2016,8(3):524-535.
[34] Hennig R,Rapp E,Kottler R,et al.N-glycosylation fingerprinting of viral glycoproteins by xCGE-LIF[J].Methods Mol Biol,2015,1331:123-143.
[35] Dias A M,Almeida C R,Reis C A,et al.Studying T Cells N-Glycosylation by Imaging Flow Cytometry[A]// Imaging Flow Cytometry:Methods and Protocols,Methods Mol Biol,2016:167-176.
[36] Veluraja K,Selvin J F A,Jasmine A,et al.Three Dimensional Structures of Carbohydrates and Glycoinformatics:An Overview[A]// Current Trends in Bioinformatics:An Insight,2018:55-87.