«上一篇/Previous Article|本期目录/Table of Contents|下一篇/Next Article»

《厦门大学学报（自然科学版）》[ISSN:0438-0479/CN:35-1070/N]

卷:

58卷

期数:

2019年01期

页码:

19-26

栏目:

研究论文

出版日期:

2019-01-24

文章信息/Info

Title:

Recognition and optical sensing of sialic acid via coumarin-hemicyanine-phenylboronic acid

文章编号:

0438-0479(2019)01-0019-08

作者:

张淑英; 郭林娥; 黎 朝; 江云宝^*

厦门大学化学化工学院,谱学分析与仪器教育部重点实验室,福建 厦门 361005

Author(s):

ZHANG Shuying; GUO Lin’e; LI Zhao; JIANG Yunbao^*

Key Laboratory of Spectrochemical Analysis & Instrumentation,Ministry of Education,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China

关键词:

香豆素-半花菁;  N-乙酰神经氨酸;  分子内电荷转移;  可视化

Keywords:

coumarin-hemicyanine;  N-acetylneuraminic acid;  intramolecular charge transfer;  visual recognition

分类号:

O 657.39

DOI:

10.6043/j.issn.0438-0479.201805024

文献标志码:

A

摘要:

以共轭连接的香豆素和半花菁为信号报告基团,以苯硼酸为识别基团,设计合成了一种对唾液酸具有选择性识别的比色型荧光传感分子,命名为CHB,并采用吸收和荧光光谱方法研究其对唾液酸(N-乙酰神经氨酸)及其他糖类分子(如葡萄糖、蔗糖和麦芽三糖等)的响应.结果表明,CHB仅对N-乙酰神经氨酸表现出显著的吸收和荧光光谱响应,并通过高分辨质谱研究证实二者以1:1计量比通过共价作用结合形成复合物.N-乙酰神经氨酸与苯硼酸的共价作用和静电作用共同影响了香豆素-半花菁共轭体系的分子内电荷转移,从而引起显著的溶液颜色变化和高选择性的光谱响应,因此CHB可用于N-乙酰神经氨酸的可视化检测.

Abstract:

A colorimetric and fluorescent chemosensor CHB was designed and synthesized,using a coumarin-hemicyanine conjugate skeleton as the signal reporter and phenylboronic acid as the receptor.The interactions of CHB with N-acetylneuraminic acid(Neu5Ac)and other saccharides such as glucose,sucrose,maltotriose were investigated using absorption and fluorescence spectroscopy.Significant absorption and fluorescence spectral responses and obvious color changes were only observed in the presence of Neu5Ac,whereas the other saccharides produced weak spectral changes and exerted practically no interference.And it was proved with high resolution mass spectroscopy(HRMS)that CHB and Neu5Ac formed a complex via covalent bonding at a ratio of 1:1.It was suggested that Neu5Ac modulated the intramolecular charge transfer of coumarin-hemicyanine conjugate system in CHB together with the covalent interaction and electrostatic interaction,allowing a highly selective spectral sensing of Neu5Ac,with the potential of visual recognition.

参考文献/References:

[1] HAN S F,COLLINS B E,PAULSON J C.Synthesis of 9-substituted sialicacids as probes for CD22-ligand interactions on B cells[M]∥Frontiers in mordern carbohydrate chemistry.Washington DC:American Chemistry Society,2007:2-14.
[2] 张嘉宁,汪淑晶.唾液酸生物学与人类健康和疾病[J].生命科学,2011,23(7):678-684.
[3] DJANASHVILI K,FRULLANO L,PETERS J A.Molecular recognition of sialic acid end groups by phenylboronates[J].Chemistry,2005,11(13):4010-4018.
[4] TANGVORANUNTAKUL P,GAGNEUX P,DIAZ S,et al.Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid[J].Proc Natl Acad Sci USA,2003,100(21):12045-12050.
[5] MORLEY T J,WITHERS S G.Chemoenzymatic synthesis and enzymatic analysis of 8-modified cytidine monophosphate-sialic acid and sialyl lactose derivatives[J].J Am Chem Soc,2010,132(27):9430-9437.
[6] VARKI A.Sialic acids in human health and disease[J].Trends Mol Med,2008,14(8):351-360.
[7] MATSUMOTO A,SATO N,KATAOKA K,et al.Noninvasive sialic acid detection at cell membrane by using phenylboronic acid modified self-assembled monolayer gold electrode[J].J Am Chem Soc,2009,131(34):12022-12023.
[8] FUKUDA M.Possible roles of tumor-associated carbohydrate antigens[J].Cancer Res,1996,56(10):2237-2244.
[9] BERTOZZI C R,KIESSLING L L.Chemical glycobiology[J].Science,2001,291(5512):2357-2364.
[10] RAMAN R,RAGURAM S,VENKATARAMAN G,et al.Glycomics:an integrated systems approach to structure-function relationships of glycans[J].Nat Methods,2005,2(11):817-824.
[11] RAZ A,MCLELLAN W L,HART I R,et al.Cell surface properties of B16 melanoma variants with differing metastatic potential[J].Cancer Res,1980,40(5):1645-1651.
[12] DOBROSSY L,PAVELIC Z P,BENACKI R J.A correlation between cell surface sialyltransferase,sialic acid,and glycosidase activities and the implantability of B16 murine melanoma[J].Cancer Res,1981,41(6):2262-2266.
[13] PASSANITI A,HART G W.Cell surface sialylation and tumor metastasis.Metastatic potential of B16 melanoma variants correlates with their relative numbers of specific penultimate oligosaccharide structures[J].J Biol Chem,1988,263(16):7591-7603.
[14] SCHAUER R.Chemistry,metabolism,and biological functions of sialic acids[J].Adv Carbohydr Chem Biochem,1982,40(40):131-234.
[15] LACOMBA R,SALCEDO J,ALEGRíA A,et al.Determination of sialic acid and gangliosides in biological samples and dairy products:a review[J].J Pharm Biomed Anal,2010,51(2):346-357.
[16] ROHRER J S.Analyzing sialic acids using high-performance anion-exchange chromatography with pulsed amperometric detection[J].Anal Biochem,2000,283(1):3-9.
[17] SCHAUER R.Analysis of sialic acids[J].Methods Enzymol,1987,138:132-161.
[18] SPICHTIG V,MICHAUD J,AUSTIN S.Determination of sialic acids in milks and milk-based products[J].Anal Biochem,2010,405(1):28-40.
[19] KAKEHI K,SUSAMI A,TAGA A,et al.High-performance capillary electrophoresis of O-glycosidically linked sialic acid-containing oligosaccharides in glycoproteins as their alditol derivatives with low-wavelength UV monitoring[J].J Chromatogr A,1994,680(1):209-215.
[20] LIU H W,LAW WENDELL H T,LEE LAWRENCE C C,et al.Cyclometalated iridium(Ⅲ)bipyridine-phenylboronic acid complexes as bioimaging reagents and luminescent probes for sialic acids[J].Chem Asian J,2017,12(13):1545-1556.
[21] YUAN L,LIN W,SONG J.Ratiometric fluorescent detection of intracellular hydroxyl radicals based on a hybrid coumarin-cyanine platform[J].Chem Commun,2010,46(42):7930-7932.
[22] ELSINGHORST P W,H?RTIG W,GOLDHAMMER S,et al.A gorge-spanning,high-affinity cholinesterase inhibitor to explore β-amyloid plaques[J].Org Biomol Chem,2009,7(19):3940-3946.
[23] LI K T,LIN Y B,YANG D Y.One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multi-component reactions and their molecular switching properties[J].Org Lett,2012,14(5):1190-1193.
[24] OTSUKA H,UCHIMURA E,KOSHINO H,et al.Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid(Neu5Ac)in aqueous solution with varying pH[J].J Am Chem Soc,2003,125(12):3493-3502.
[25] GOPAUL K P,CROOK M A.Sialic acid:a novel marker of cardiovascular disease?[J].Clin Biochem,2006,39(7):667-681.
[26] WU X,LI Z,CHEN X X,et al.Selective sensing of saccharides using simple boronic acids and their aggregates[J].Chem Soc Rev,2013,42(20):8032-8048.[1] HAN S F,COLLINS B E,PAULSON J C.Synthesis of 9-substituted sialicacids as probes for CD22-ligand interactions on B cells[M]∥Frontiers in mordern carbohydrate chemistry.Washington DC:American Chemistry Society,2007:2-14.
[2] 张嘉宁,汪淑晶.唾液酸生物学与人类健康和疾病[J].生命科学,2011,23(7):678-684.
[3] DJANASHVILI K,FRULLANO L,PETERS J A.Molecular recognition of sialic acid end groups by phenylboronates[J].Chemistry,2005,11(13):4010-4018.
[4] TANGVORANUNTAKUL P,GAGNEUX P,DIAZ S,et al.Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid[J].Proc Natl Acad Sci USA,2003,100(21):12045-12050.
[5] MORLEY T J,WITHERS S G.Chemoenzymatic synthesis and enzymatic analysis of 8-modified cytidine monophosphate-sialic acid and sialyl lactose derivatives[J].J Am Chem Soc,2010,132(27):9430-9437.
[6] VARKI A.Sialic acids in human health and disease[J].Trends Mol Med,2008,14(8):351-360.
[7] MATSUMOTO A,SATO N,KATAOKA K,et al.Noninvasive sialic acid detection at cell membrane by using phenylboronic acid modified self-assembled monolayer gold electrode[J].J Am Chem Soc,2009,131(34):12022-12023.
[8] FUKUDA M.Possible roles of tumor-associated carbohydrate antigens[J].Cancer Res,1996,56(10):2237-2244.
[9] BERTOZZI C R,KIESSLING L L.Chemical glycobiology[J].Science,2001,291(5512):2357-2364.
[10] RAMAN R,RAGURAM S,VENKATARAMAN G,et al.Glycomics:an integrated systems approach to structure-function relationships of glycans[J].Nat Methods,2005,2(11):817-824.
[11] RAZ A,MCLELLAN W L,HART I R,et al.Cell surface properties of B16 melanoma variants with differing metastatic potential[J].Cancer Res,1980,40(5):1645-1651.
[12] DOBROSSY L,PAVELIC Z P,BENACKI R J.A correlation between cell surface sialyltransferase,sialic acid,and glycosidase activities and the implantability of B16 murine melanoma[J].Cancer Res,1981,41(6):2262-2266.
[13] PASSANITI A,HART G W.Cell surface sialylation and tumor metastasis.Metastatic potential of B16 melanoma variants correlates with their relative numbers of specific penultimate oligosaccharide structures[J].J Biol Chem,1988,263(16):7591-7603.
[14] SCHAUER R.Chemistry,metabolism,and biological functions of sialic acids[J].Adv Carbohydr Chem Biochem,1982,40(40):131-234.
[15] LACOMBA R,SALCEDO J,ALEGRíA A,et al.Determination of sialic acid and gangliosides in biological samples and dairy products:a review[J].J Pharm Biomed Anal,2010,51(2):346-357.
[16] ROHRER J S.Analyzing sialic acids using high-performance anion-exchange chromatography with pulsed amperometric detection[J].Anal Biochem,2000,283(1):3-9.
[17] SCHAUER R.Analysis of sialic acids[J].Methods Enzymol,1987,138:132-161.
[18] SPICHTIG V,MICHAUD J,AUSTIN S.Determination of sialic acids in milks and milk-based products[J].Anal Biochem,2010,405(1):28-40.
[19] KAKEHI K,SUSAMI A,TAGA A,et al.High-performance capillary electrophoresis of O-glycosidically linked sialic acid-containing oligosaccharides in glycoproteins as their alditol derivatives with low-wavelength UV monitoring[J].J Chromatogr A,1994,680(1):209-215.
[20] LIU H W,LAW WENDELL H T,LEE LAWRENCE C C,et al.Cyclometalated iridium(Ⅲ)bipyridine-phenylboronic acid complexes as bioimaging reagents and luminescent probes for sialic acids[J].Chem Asian J,2017,12(13):1545-1556.
[21] YUAN L,LIN W,SONG J.Ratiometric fluorescent detection of intracellular hydroxyl radicals based on a hybrid coumarin-cyanine platform[J].Chem Commun,2010,46(42):7930-7932.
[22] ELSINGHORST P W,H?RTIG W,GOLDHAMMER S,et al.A gorge-spanning,high-affinity cholinesterase inhibitor to explore β-amyloid plaques[J].Org Biomol Chem,2009,7(19):3940-3946.
[23] LI K T,LIN Y B,YANG D Y.One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multi-component reactions and their molecular switching properties[J].Org Lett,2012,14(5):1190-1193.
[24] OTSUKA H,UCHIMURA E,KOSHINO H,et al.Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid(Neu5Ac)in aqueous solution with varying pH[J].J Am Chem Soc,2003,125(12):3493-3502.
[25] GOPAUL K P,CROOK M A.Sialic acid:a novel marker of cardiovascular disease?[J].Clin Biochem,2006,39(7):667-681.
[26] WU X,LI Z,CHEN X X,et al.Selective sensing of saccharides using simple boronic acids and their aggregates[J].Chem Soc Rev,2013,42(20):8032-8048.

备注/Memo

备注/Memo:

收稿日期:2018-05-17 录用日期:2018-07-25
基金项目:国家自然科学基金(21435003,91427304,21521004,J1310024)
*通信作者:ybjiang@xmu.edu.cn

常用功能

更新日期/Last Update: 1900-01-01