一种锌基-类杯[3]芳烃化合物对氨基葡萄糖的识别
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摘要
设计合成了一种锌基-类杯[3]芳烃化合物Zn-Lg1,实现了对氨基葡萄糖的高灵敏度识别.利用紫外-可见光谱和荧光光谱等研究了Zn-Lg1对氨基葡萄糖的识别过程与机理.紫外-可见光谱表明,向Zn-Lg1中加入氨基葡萄糖后,波长423 nm处的吸收峰下降, 320和281 nm处吸收峰增强,等吸收点为360 nm,说明氨基葡萄糖分子已经进入Zn-Lg1内部,主客体计量比为1∶1,平衡常数为1.6×103L/mol.通过对比研究无磺酰胺基团的类杯[3]芳烃化合物Zn-Lg2对氨基葡萄糖的识别效果,分析了Zn-Lg1中磺酰胺部分的氢键在识别中的作用.荧光光谱表明,向Zn-Lg1中加入氨基葡萄糖后,激发波长为360 nm,发射波长从516 nm略蓝移至513 nm,荧光强度增强,最低检测限达到5.0μmol/L.
A zinc-based calix[3]arene-like compound Zn-Lg1 was designed and synthesized to achieve a high-sensitivity detection of glucosamine. The recognition process and mechanism of glucosamine by ZnLg1 were studied by ultraviolet-visible spectroscopy(UV-vis) and fluorescence spectroscopy. UV-vis spectra showed that the intensity of the absorption peak at 423 nm decreased upon addition of glucosamine to Zn-Lg1, the intensity of the absorption peak at 320 and 281 nm increased. The isobestic point at360 nm was obtained, revealing that glucosamine molecules had entered the inner structure of Zn-Lg1 compound. Titration data gave excellent fits to a 1∶1 binding model between the host and guest, and the equilibrium constant was 1.6 × 103 L/mol. For comparison and to analyze the effect of hydrogen bonds of the sulfonamide moiety, the other zinc-based calix[3]arene-like compound Zn-Lg2 without sulfonamide groups was synthesized and applied in the recognition of glucosamine. It indicated that the recognition performance of Zn-Lg1 to glucosamine was better than that of Zn-Lg2, due to the sulfonamide groups on Zn-Lg1. Fluorescence spectra showed that the emission wavelength was slightly blue shifted to513 nm from 516 nm with the excitation wavelength of 360 nm after the addition of glucosamine to Zn-Lg1, and the fluorescence intensity increased. The detection limit was up to 5.0 μmol/L.
A zinc-based calix[3]arene-like compound Zn-Lg1 was designed and synthesized to achieve a high-sensitivity detection of glucosamine. The recognition process and mechanism of glucosamine by ZnLg1 were studied by ultraviolet-visible spectroscopy(UV-vis) and fluorescence spectroscopy. UV-vis spectra showed that the intensity of the absorption peak at 423 nm decreased upon addition of glucosamine to Zn-Lg1, the intensity of the absorption peak at 320 and 281 nm increased. The isobestic point at360 nm was obtained, revealing that glucosamine molecules had entered the inner structure of Zn-Lg1 compound. Titration data gave excellent fits to a 1∶1 binding model between the host and guest, and the equilibrium constant was 1.6 × 103 L/mol. For comparison and to analyze the effect of hydrogen bonds of the sulfonamide moiety, the other zinc-based calix[3]arene-like compound Zn-Lg2 without sulfonamide groups was synthesized and applied in the recognition of glucosamine. It indicated that the recognition performance of Zn-Lg1 to glucosamine was better than that of Zn-Lg2, due to the sulfonamide groups on Zn-Lg1. Fluorescence spectra showed that the emission wavelength was slightly blue shifted to513 nm from 516 nm with the excitation wavelength of 360 nm after the addition of glucosamine to Zn-Lg1, and the fluorescence intensity increased. The detection limit was up to 5.0 μmol/L.
引文
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[2] Solanki A, Das M, Thakore S. A review on carbohydrate embedded polyurethanes:an emerging area in the scope of biomedical applications[J]. Carbohydrate Polymers,2018, 181:1003-1016.
[3] Striegler S. Selective carbohydrate recognition by synthetic receptors in aqueous solution[J]. Current Organic Chemistry, 2003, 7(1):81-102.
[4] Inoue M, Senoo N, Sato T, et al. Effects of the dietary carbohydrate-fat ratio on plasma phosphatidylcholine profiles in human and mouse[J]. The Journal of Nutritional Biochemistry, 2017, 50(4):83-94.
[5] Bruyere O, Reginster J Y. Glucosamine and chondroitin sulfate as therapeutic agents for knee and hip osteoarthritis[J]. Drugs and Aging, 2007, 24(7):573-580.
[6] Zhang P, Roytrakul S, Sutheerawattananonda M. Production and purification of glucosamine and angiotensin-I converting enzyme(ACE)inhibitory peptides from mushroom hydrolysates[J]. Journal of Functional Foods, 2017,36(1):72-83.
[7] Zahedipour F, Dalirfardouei R, Karimi G, et al. Molecular mechanisms of anticancer effects of glucosamine[J].Biomedicine&Pharmacotherapy, 2017, 95(3):1051-1058.
[8] Good T A, Bessman S P. Determination of glucosamine and galactosamine using borate buffers for modification of the Elson-Morgan and Morgan-Elson reactions[J]. Analytical Biochemistry, 1964, 9(3):253-262.
[9] Xiong Bo, Wang Ling-ling, Li Qiong, et al. Parallel microscope-based fluorescence, absorbance and time-offlight mass spectrometry detection for high performance liquid chromatography and determination of glucosamine in urine[J]. Talanta, 2015, 144(6):275-282.
[10] Li Xue-zhao, Wu Jin-guo, Chen Li-yong, et al. Engineering an iridium-containing metal-organic molecular capsule for induced-fit geometrical conversion and dual catalysis[J]. Chemical Communications, 2016, 52(62):9628-9631.
[11] Wu Hong-mei, He Cheng, Lin Zhi-hua, et al. Metallohelical triangles for selective detection of adenosine triphosphate in aqueous media[J]. Inorganic Chemistry,2009, 48(2):408-410.
[12] Khan B, Hameed A, Minhaz A, et al. Synthesis and characterisation of calix[4]arene based bis(triazole)-bis(hexahydroquinoline):probing highly selective fluorescence quenching towards mercury(Hg2+)analyte[J]. Journal of Hazardous Materials, 2018, 347(5):349-358.
[13] Erdemir S, Tabakci B. Highly sensitive fluorometric detection of Zn2+ion by calix[4]arene derivative appended 4-biphenylcarbonitrile[J]. Dyes and Pigments, 2018,151(2):116-122.
[14] Wang Jian, Wu Hong-mei, He Cheng, et al. Metal-organic cyclohelicates as optical receptors for glutathione:syntheses, structures, and host-guest behaviors[J]. Chemistry-Asian Journal, 2011, 6(1):1225-1233.