1. 辽宁工业大学 化学与环境工程学院, 辽宁 锦州 121001
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吴红梅, 郭宇, 曹建芳等. 用于检测氨基葡萄糖的金属-有机大环化合物的合成及光谱分析[J]. 发光学报, 2018,39(8): 1163-1169
WU Hong-mei, GUO Yu, CAO Jian-fang etc. Synthesis and Spectral Analysis of Metal-organic Macrocyclic Compound for Detection of Glucosamine[J]. Chinese Journal of Luminescence, 2018,39(8): 1163-1169
吴红梅, 郭宇, 曹建芳等. 用于检测氨基葡萄糖的金属-有机大环化合物的合成及光谱分析[J]. 发光学报, 2018,39(8): 1163-1169 DOI: 10.3788/fgxb20183908.1163.
WU Hong-mei, GUO Yu, CAO Jian-fang etc. Synthesis and Spectral Analysis of Metal-organic Macrocyclic Compound for Detection of Glucosamine[J]. Chinese Journal of Luminescence, 2018,39(8): 1163-1169 DOI: 10.3788/fgxb20183908.1163.
以5-氨基异酞酸为初始原料,通过酯化、肼解和席夫碱等反应合成了双三齿配体LD,并通过与锌离子(Zn,2+,)自组装构筑了金属(锌)-有机大环化合物LD-Zn,利用紫外-可见光谱、核磁、电喷雾质谱等表征手段研究了LD-Zn对氨基葡萄糖的识别作用。核磁光谱和电喷雾质谱测试表明,氨基葡萄糖分子能够进入到大环LD-Zn内部,并且LD-Zn以1:1的比例包合了氨基葡萄糖分子。紫外-可见光谱表明,当向LD-Zn中加入氨基葡萄糖后,373 nm处的吸收峰强度增加,269 nm和303 nm处的吸收峰强度降低,平衡常数,K,达到4.1910,3, L/mol,最低检测限为5.010,-6, mol/L。通过对比测试发现,LD-Zn只对氨基葡萄糖有紫外光谱响应,而对葡萄糖和三乙胺无任何响应,说明氨基葡萄糖的结构与大环化合物LD-Zn的空腔更匹配,LD-Zn对氨基葡萄糖的识别不是单纯羟基(氢键)或者氨基(碱性)引起的,而是由LD-Zn限域的空腔效应和氨基的氢键协同作用实现了对氨基葡萄糖的识别。
Double-tridentate ligand LD was synthesized by 5-aminophthalic acid through esterification, hydrazinolysis and Schiff's base reactions. Then, a novel metal-organic macrocyclic LD-Zn was built by the assembly of LD and zinc ions for the recognition of glucosamine. The detection mechanism of glucosamine with LD-Zn was studied by UV-Vis,1,H NMR and ESI-MS. The results of ,1,H NMR and ESI-MS indicate that the glucosamine molecules could enter the LD-Zn. Moreover, 1:1 stoichiometric host-guest complexation between glucosamine and LD-Zn was formed. UV-Vis spectra show that the intensity of the absorption peak at 373 nm increased significantly after addition of glucosamine into LD-Zn. However, the absorption intensity at 269 nm and 303 nm decreases. The equilibrium constant ,K, reaches 4.1910,3, L/mol, and the minimum detection limit is 5.010,-6, mol/L. For comparison, the detection tests of glucose and triethylamine with LD-Zn were carried out. The UV-Vis spectra do not show any response when glucose and triethylamine are added to LD-Zn. These results indicate that the structure of glucosamine is more compatible with the cavity of the macrocycle LD-Zn compared to glucose and triethylamine. The recognition of glucosamine by using LD-Zn is not attributed to pure hydroxyl(hydrogen bonding) or amino(alkaline), it is mainly caused by the joint effect of confined cavity of LD-Zn molecular and hydrogen bonds of amino.
氨基葡萄糖大环化合物光谱分析检测
glucosaminemacrocyclic compoundspectral analysisdetection
ZAHEDIPOUR F, DALIRFARDOUEI R, KARIMI G, et al.. Molecular mechanisms of anticancer effects of glucosamine[J]. Biomed. Pharmacot., 2017, 95:1051-1058.
ZHANG P, ROYTRAKUL S, SUTHEERAWATTANANONDA M. Production and purification of glucosamine and angiotensin-I converting enzyme (ACE) inhibitory peptides from mushroom hydrolysates[J]. J. Funct. Foods, 2017, 36:72-83.
DALIRFARDOUEI R, KARIMI G, JAMIALAHMADI K. Molecular mechanisms and biomedical applications of glucosamine as a potential multifunctional therapeutic agent[J]. Life Sci., 2016, 152:21-29.
HONG P K, NDAGIJIMANA M, BETTI M. Salty and savory enhancing properties of hydrolyzed poultry protein glycated with glucosamine[J]. Meat Sci., 2016, 112:127-128.
TSAI W, TSAI H, WONG Y, et al.. Preparation and characterization of gellan gum/glucosamine/clioquinol film as oral cancer treatment patch[J]. Mater. Sci. Eng. C, 2018, 82:317-322.
VONGNAM K, MUANGNOI C, ROJSITTHISAK P, et al.. A highly selective turn-on fluorescent sensor for glucosamine from amidoquinoline-napthalimide dyads[J]. Biosens. Bioelectron., 2016, 86:472-476.
HAN L, LIU S G, ZHANG X F, et al.. A sensitive polymer dots-manganese dioxide fluorescent nanosensor for "turn-on" detection of glutathione in human serum[J]. Sens. Actuators B:Chem., 2018, 258:25-31.
LI X Z, WU J G, CHEN L Y, et al.. Engineering an iridium-containing metal-organic molecular capsule for induced-fit geometrical conversion and dual catalysis[J]. Chem. Commun., 2016, 52:9628-9631.
COHEN S M. Postsynthetic methods for the functionalization of metal-organic frameworks[J]. Chem. Rev., 2012, 112(2):970-1000.
TASHIRO S, KOBAYASHI M, FUJITA M. Folding of an Ala-Ala-Ala tripeptide into a beta-turn via hydrophobic encapsulation[J]. J. Am. Chem. Soc., 2006, 128(29):9280-9281.
WU H M, HE C, LIN Z H, et al.. Metallohelical triangles for selective detection of adenosine triphosphate in aqueous media[J]. Inorg. Chem., 2009, 48(2):408-410.
HE G J, YANG L, QIAN X L, et al.. A coumarin-based fluorescence resonance energy transfer probe targeting matrix metalloproteinase-2 for the detection of cervical cancer[J]. Int. J. Mol. Med., 2017, 39(6):1571-1579.
FERRAND Y, CRUMP M P, DAVIS A P. A synthetic lectin analog for biomimetic disaccharide recognition[J]. Science, 2007, 318:619-622.
KAMIYA N, TOMINAGA M, SATO S, et al.. Saccharide-coated M12L24 molecular spheres that form aggregates by multi-interaction with proteins[J]. J. Am. Chem. Soc., 2007, 129(13):3816-3817.
HE C, LIN Z H, HE Z, et al.. Metal-tunable nanocages as artificial chemosensors[J]. Angew. Chem. Int. Ed., 2008, 47(5):877-881.
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