Selenocysteine vs Cysteine: Tuning the Derivatization on Benzenesulfonyl Moiety of a Triazole Linked Dansyl Connected Glycoconjugate for Selective Recognition of Selenocysteine and the Applicability of the Conjugate in Buffer, in Serum, on Silica Gel, and in HepG2 Cells,Analytical Chemistry

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Selenocysteine vs Cysteine: Tuning the Derivatization on Benzenesulfonyl Moiety of a Triazole Linked Dansyl Connected Glycoconjugate for Selective Recognition of Selenocysteine and the Applicability of the Conjugate in Buffer, in Serum, on Silica Gel, and in HepG2 Cells
Analytical Chemistry ( IF 6.7 ) Pub Date : 2016-06-28 00:00:00 , DOI: 10.1021/acs.analchem.6b01518
Sivaiah Areti ₁ , Surendra Kumar Verma ₁ , Jayesh Bellare ₁ , Chebrolu Pulla Rao ₁

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A dansyl derivatized triazole linked glucopyranosyl conjugate (^NO2L) has been synthesized and characterized and was used in the present study. The conjugate ^NO2L releases a fluorescent product upon reaction by Cys-SeH in aqueous PBS buffer by exhibiting a ∼210-fold fluorescence enhancement even in the presence of 20 other amino acids with a minimum detection limit of (1.5 ± 0.2) × 10^–7 M. The selectivity of the Cys-SeH to ^NO2L was further proven by extending the fluorescence study to different other selenium compounds. The role of para-nitrobenzenesulfonyl (pNBS) center in ^NO2L in the selective recognition of Cys-SeH was confirmed when the fluorescence emission studies were carried out using five different derivatizations possessing two NO₂, five fluoro, two fluoro, one fluoro, and no fluoro groups. The nucleophilic substitution reaction of Cys-SeH on ^NO2L has been clearly demonstrated on the basis of ¹H NMR, ESI-MS, and absorption spectroscopy, and the heat changes were monitored by isothermal titration calorimetry. The application potential of ^NO2L has been demonstrated by studying its selectivity toward Cys-SeH in aqueous PBS buffer, in bovine serum, and on the silica gel surface that lead to minimum detection limits of (25 ± 2), (80 ± 5), and (168 ± 16) ppb, respectively. The biological applicability of ^NO2L for Cys-SeH was further demonstrated in HepG2 cells by fluorescence microscopy. Thus, ^NO2L is aqueous soluble and a biologically acceptable probe for Cys-SeH.

中文翻译：

硒代半胱氨酸与半胱氨酸：调整三唑连接的丹磺酰基连接的糖缀合物的苯磺酰基部分的衍生化，用于硒代半胱氨酸的选择性识别和缀合物在缓冲液，血清，硅胶和HepG2细胞中的适用性

丹磺酰基衍生的三唑连接的吡喃葡萄糖基共轭物（^NO2 L）已被合成和表征，并用于本研究。所述缀合物^NO2大号释放当在PBS水溶液被Cys-SEH反应的荧光产物通过即使在其他20个氨基酸的存在下与（1.5±0.2）×10的最小检测极限呈现~210倍荧光增强缓冲^{- 7} M.上的Cys-SEH到的选择性^NO2大号通过延长荧光研究，以不同的其它硒化合物进一步证实。的作用对-nitrobenzenesulfonyl（pNBS）中心^NO2大号当使用具有两个NO ₂，五个氟，两个氟，一个氟和没有氟基团的五个不同的衍生基团进行荧光发射研究时，证实了Cys-SeH选择性识别中的“ Cys-SeH”选择性。通过¹ H NMR，ESI-MS和吸收光谱，清楚地证明了Cys-SeH在^NO2 L上的亲核取代反应，并通过等温滴定量热法监测了热变化。^NO2 L的应用潜力通过研究其在PBS水溶液，牛血清中和硅胶表面上对Cys-SeH的选择性已证明了这一点，该选择性导致最低检测限为（25±2），（80±5）和（168±16））ppb。通过荧光显微镜进一步证实了HyG2细胞中^NO2 L对Cys-SeH的生物学适用性。因此，^{NO 2} L是水溶性的，并且是Cys-SeH的生物学上可接受的探针。

更新日期：2016-06-28

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