Ultra-highly selective recognition of nucleosides over nucleotides by rational modification of tetralactam macrocycle and its application in enzyme assay

Yao, Huan; Qin, Jian; Wang, Yan-Fang; Wang, Song-Meng; Yi, Liu-Huan; Li, Shi-Yao; Du, Fangfang; Yang, Liu-Pan; Wang, Li-Li

doi:10.1016/j.cclet.2023.109154

Cited by 6 publications

(2 citation statements)

References 44 publications

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“…IDA offers distinct advantages over traditional sensing methods, such as access to many indicators, access to diverse receptors, and flexibility of the detection wavelengths. 8 Several macrocycles, [15,16] cyclophanes, [17,18] metal complexes, [19,20] amphiphiles [21,22] and polymers [23,24] have been successfully employed as ATP sensors based on an IDA strategy. Nevertheless, the availability of water-soluble cage receptors for ATP sensing through the IDA strategy is quite limited.…”

Section: Introductionmentioning

confidence: 99%

Water‐Soluble Triazolium Covalent Cages for ATP Sensing

Maji,

Samanta,

Natarajan

2024

Chemistry A European J

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Water‐soluble organic cages are attractive targets for their molecular recognition and sensing features of biologically relevant molecules. Here, we have successfully designed and synthesized a pair of water‐soluble cationic cages employing click reaction as the fundamental step followed by the N‐methylation of the triazole rings. The rigid and shape‐persistent 3D hydrophobic cavity, positively charged surface, H‐bonding triazolium rings, and excellent water solubility empower both cages to exhibit a superior affinity and selectivity for binding with adenosine‐5’‐triphosphate (ATP) compared to cyclophanes and other macrocyclic receptors. Both cage molecules (PCC·Cl and BCC·Cl) can bind a highly emissive dye HPTS (8‐hydroxypyrene‐1,3,6‐trisulfonic acid trisodium salt) to form non‐fluorescent complexes. The addition of ATP resulted in the stronger cageÌATP complexes with the retention of HPTS emission upon its displacement. The resultant indicator‐displacement assay system can efficiently sense and quantify ATP in nanomolar detection limits in buffer solutions and human serum matrix. Spectroscopic and theoretical studies revealed the synergistic effect of π×××π stacking interaction between the aromatic moiety of the cationic cages and the adenine moiety of ATP, as well as the electrostatic and hydrogen bonding interaction between the phosphate anion of ATP and triazole protons of cages, played the pivotal roles in the sensing process.

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Section: Introductionmentioning

confidence: 99%

Water‐Soluble Triazolium Covalent Cages for ATP Sensing

Maji,

Samanta,

Natarajan

2024

Chemistry A European J

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“…[55] 将该传感器应用于纸基传感检测, 实现了尿酸水平的双模式检测. 随后, 我们课题组用羧基取代了 H1 萘上的四个乙基, 在大环空腔入口处引入了带电链, 合成了一种新的水溶性四内酰胺大环 H2, 从而实现了对生物分子的高结合亲和力和高选择性.…”

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Research Progress on the Construction and Application of Macrocyclic Fluorescent Sensing Platform Based on Indicator Displacement Assay

Shen,

Li,

Yang

et al. 2024

Chinese Journal of Organic Chemistry

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Supramolecular fluorescent sensors can address various detection and bioimaging issues related to the environment and human health. Indicator displacement assay (IDA) is a supramolecular fluorescence sensing method that can convert the chemical changes caused by molecular recognition into easily observed fluorescence signals. It provides a unique and innovative sensing method for the detection of analytes. In recent years, IDA based on non-covalent binding has been developed rapidly due to its advantages of high sensitivity, adjustability, real-time, and low synthesis effort. In order to meet the diverse needs of IDA development, a variety of supramolecular macrocyclic hosts have been involved in the construction of IDA sensors, such as calix[n]arenes, cucurbit[n]uril, pillar[n]arenes, etc. The recent research progress in this field based on different classes of macrocycles is briefly reviewed, focusing on the application in biochemical sensing, and providing a reference for the construction and application of novel fluorescent biochemical sensing platforms based on IDA in the future.

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