Synthesis, optical properties and binding interactions of a multivalent glycocluster based on a fluorescent perylene bisimide derivative

Synthesis, optical properties and binding interactions of a multivalent glycocluster based on a fluorescent perylene bisimide derivative
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基于荧光苝双酰亚胺衍生物的多价糖簇的合成、光学性质和结合相互作用

DOI:
10.1039/c3ra44675a
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发表时间:
2013-10
期刊:
影响因子:
3.9
通讯作者:
Xiao-Liu Li*
Xiao-Liu Li*
中科院分区:
化学3区
文献类型:
--
作者:
Feng Qian,;Yue-Qing Wang;Jin-Chao Zhang;Xiao-Liu Li*

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合成了接枝有六个甘露糖基团的水溶性荧光苝双酰亚胺衍生物PBI-Cl-Man。通过紫外-可见光谱和荧光光谱研究其光学性质,表明化合物PBI-Cl-Man在低浓度下以单体状态存在,并表现出高荧光,在水中荧光量子产率为59.9%。此外,通过荧光光谱、CD光谱、浊度测定和ELLA实验研究了PBI-Cl-Man与Con A的结合相互作用。与Con A结合后,观察到荧光几乎完全猝灭,结合常数为2.4 × 107 M−1(单体甘露糖为4.0 × 106 M−1,价态校正),比单价甘露糖配体(α-MMP)高近3个数量级。 ELLA实验表明,PBI-Cl-Man作为多价糖簇,与Con A表现出强烈的结合相互作用,IC50值为34 μM(204 μM,价态校正),比参考化合物(α-MMP)强7倍。
A water-soluble fluorescent perylene bisimide derivative, PBI-Cl-Man, grafted with six mannose groups was synthesized. Its optical properties were investigated by UV-vis and fluorescence spectra, which indicated that compound PBI-Cl-Man exists in the monomer state at low concentrations and exhibits high fluorescence with a fluorescence quantum yield of 59.9% in water. Furthermore, the binding interactions of PBI-Cl-Man with Con A were studied by fluorescence spectra, CD spectra, turbidity assays and ELLA experiments. The almost complete quenching of the fluorescence upon binding with Con A was observed, with a binding constant of 2.4 × 107 M−1 (4.0 × 106 M−1 for monomeric mannose, valency corrected), nearly 3 orders of magnitude higher than that of monovalent mannose ligands (α-MMP). The ELLA experiments indicated that PBI-Cl-Man, as a multivalent glycocluster, exhibits a strong binding interaction with Con A with an IC50 value of 34 μM (204 μM, valency corrected), 7 times stronger than that of the reference compound (α-MMP).
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