Triazole-Linked Quinoline Conjugate of Glucopyranose: Selectivity Comparison among Zn2+, Cd2+, and Hg2+ Based on Spectroscopy, Thermodynamics, and Microscopy, and Reversible Sensing of Zn2+ and the Structure of the Complex Using DFT

被引:11
作者
Areti, Sivaiah [1 ]
Bandaru, Sateesh [1 ,2 ]
Rao, Chebrolu Pulla [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bioinorgan Lab, Mumbai 400076, Maharashtra, India
[2] Beijing Computat Sci Res Ctr, Software Pk 2, Beijing 100084, Peoples R China
关键词
MOLECULAR PROBES; ZINC; SENSOR; IONS; GALVANIZATION; COORDINATION; CHEMOSENSOR; PROTEINS; RECEPTOR; DESIGN;
D O I
10.1021/acsomega.6b00277
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A water-soluble triazole-linked quinoline conjugate of glucopyranose (L) has been synthesized and characterized, and its single-crystal X-ray diffraction (XRD) structure has been established. Binding of L toward different biologically relevant metal ions has been studied using fluorescence and absorption spectroscopy in HEPES buffer at pH 7.4. The conjugate L detects Zn2+ and Cd2+ with 30 +/- 2 and 14 +/- 1-fold fluorescence enhancement, respectively, but in the case of Hg2+, only a fluorescence quench was observed. The stoichiometry of the complex is 1:2 metal ion to the ligand in the case of Zn2+ and Cd2+ resulting in [Zn(L)(2)] and [Cd(L)(2)], and it is 1: 1 in the case of Hg2+, as confirmed from their electrospray ionization mass spectrometry (ESIMS) spectra. Zn2+ shows greater exothermicity over Cd2+, whereas Hg2+ shows endothermicity, which supports the differences in their binding strength and the nature of the corresponding complex. L exhibits rod-shaped particles and upon complexation with Zn2+, it exhibits sphere-like morphological features in scanning electron microscopy (SEM) images. However, clustered aggregates are observed in Cd2+, whereas the [HgL] complex exhibits small fused spherical structures, and therefore the signature of these ions is seen in microscopy images. The computational studies revealed that the syn-[Zn(L)(2)] complex is stabilized by 9.7 kcal mol(-1) more than that in the case of anti-[Zn(L)(2)] owing to the formation of hydrogen bonds between the two glucosyl moieties within the syn-complex. Among the anions studied, [Zn(L)(2)] is sensitive and selective toward the phosphate ion (H2PO4-) with a minimum detection limit of 16 +/- 2 ppb. Similarly, the [HgL] can act as a secondary sensor for CN- while also exhibiting reversibility. Based on the input-output characteristics, INHIBIT logic gate was built in the case of Zn2+ vs H2PO4- and IMPLICATION logic gate was built in the case of Hg2+ vs CN-.
引用
收藏
页码:626 / 635
页数:10
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