Fluorescence Turn-on Enantioselective Recognition of both Chiral Acidic Compounds and α-Amino Acids by a Chiral Tetraphenylethylene Macrocycle Amine

In this work, a novel 7-hydroxybenzoxazinone-based fluorescent probe (PBD) for the selective sensing of biothiols is reported. Upon treatment with biothiols, PBD shows a strong fluorescence enhancement (up to 70-fold) and a large Stokes shift (155 nm). Meanwhile, this probe exhibits high resistance to interference from other amino acids and competing species. PBD features good linearity ranges with a low detection limit of 14.5 nM for glutathione (GSH), 17.5 nM for cysteine (Cys), and 80.0 nM for homocysteine (Hcy), respectively. Finally, the potential utility of this probe for biothiol sensing in living HeLa cells is demonstrated.

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Fluorescence turn-on recognition of chiral amino acids using dye incorporated β-CD functionalized AuNPs assembly

Journal of Luminescence ◽

10.1016/j.jlumin.2014.06.001 ◽

2014 ◽

Vol 154 ◽

pp. 541-548 ◽

Cited By ~ 14

Author(s):

B. Aswathy ◽

G. Sony

Keyword(s):

Amino Acids ◽

Turn On ◽

Chiral Amino Acids ◽

Fluorescence Turn On ◽

Functionalized Aunps

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Development of a Novel Benzimidazole-Based Probe and Portable Fluorimeter for the Detection of Cysteine in Human Urine

Biosensors ◽

10.3390/bios11110420 ◽

2021 ◽

Vol 11 (11) ◽

pp. 420

Author(s):

Gyu Seong Yeom ◽

In-ho Song ◽

Shrikant Dashrath Warkad ◽

Pramod B. Shinde ◽

Taewoon Kim ◽

...

Keyword(s):

Amino Acids ◽

Dna Damage ◽

Human Urine ◽

Live Cells ◽

Turn On ◽

Highly Sensitive ◽

Bio Imaging ◽

Fluorescence Turn On ◽

Fluorescence Spectrometer ◽

Excellent Selectivity

The measurement of cysteine in human urine and live cells is crucial for evaluating biological metabolism, monitoring and maintaining the immune system, preventing tissue/DNA damage caused by free radicals, preventing autoimmune diseases, and diagnosing disorders such as cystinuria and cancer. A method that uses a fluorescence turn-on probe and a portable fluorescence spectrometer device are crucial for highly sensitive, simple, rapid, and inexpensive cysteine detection. Herein, we present the synthesis and application of a benzimidazole-based fluorescent probe (ABIA) along with the design and development of a portable fluorescence spectrometer device (CysDDev) for detecting cysteine in simulated human urine. ABIA showed excellent selectivity and sensitivity in detecting cysteine over homocysteine, glutathione, and other amino acids with the response time of 1 min and demonstrated a detection limit of 16.3 nM using the developed CysDDev. Further, ABIA also demonstrated its utility in detecting intracellular cysteine, making it an excellent probe for bio-imaging assay.

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A New Approach to Fluorescence “Turn-On” Sensing of α-Amino Acids

ACS Applied Materials & Interfaces ◽

10.1021/am800093d ◽

2008 ◽

Vol 1 (2) ◽

pp. 232-234 ◽

Cited By ~ 30

Author(s):

Zhong’an Li ◽

Xiaoding Lou ◽

Zhen Li ◽

Jingui Qin

Keyword(s):

Amino Acids ◽

New Approach ◽

Turn On ◽

Fluorescence Turn On

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Enantioselective Recognition of Chiral Acids by Supramolecular Interactions with Chiral AIEgens

Chemical Communications ◽

10.1039/d1cc05618b ◽

2021 ◽

Author(s):

Song Xiang ◽

Panpan Lv ◽

Changsheng Guo ◽

Chunxuan Qi ◽

Jun-Cheng Yang ◽

...

Keyword(s):

Amino Acids ◽

Supramolecular Assembly ◽

Supramolecular Interactions ◽

Amino Groups ◽

Enantioselective Recognition ◽

Acidic Compounds ◽

Optically Pure

Novel chiral AIEgens bearing optically pure amino groups were synthesized and showed excellent discrimination for a series of chiral acidic compounds and amino acids. Interestingly, after supramolecular assembly with 4-sulfocalix[4]arene,...

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A fluorescence turn-on probe for the detection of thiol-containing amino acids in aqueous solution and bioimaging in cells

Tetrahedron ◽

10.1016/j.tet.2014.01.060 ◽

2014 ◽

Vol 70 (11) ◽

pp. 2034-2039 ◽

Cited By ~ 13

Author(s):

Sang-Ho Son ◽

Yongkyun Kim ◽

Min Beom Heo ◽

Yong Taik Lim ◽

Taek Seung Lee

Keyword(s):

Aqueous Solution ◽

Amino Acids ◽

Turn On ◽

Fluorescence Turn On ◽

In Cells

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A Boronic Acid-Based Fluorescence Hydrogel for Monosaccharide Detection

10.26434/chemrxiv.7176989 ◽

2018 ◽

Author(s):

Suying Xu ◽

Adam Sedgwick ◽

Souad Elfecky ◽

Wenbo Chen ◽

Ashley Jones ◽

...

Keyword(s):

Fluorescent Probe ◽

Boronic Acid ◽

Binding Constants ◽

Strong Fluorescence ◽

Fluorescence Response ◽

Turn On ◽

Fluorescence Turn On ◽

Hydrogel System

A boronic acid-based anthracene fluorescent probe was functionalised with an acrylamide unit to incorporate into a hydrogel system for monosaccharide detection. In solution, the fluorescent probe displayed a strong fluorescence turn-on response upon exposure to fructose, and an expected trend in apparent binding constants, as judged by a fluorescence response where D-fructose > D-galactose > D-mannose > D-glucose. The hydrogel incorporating the boronic acid monomer demonstrated the ability to detect monosaccharides by fluorescence with the same overall trend as the monomer in solution with the addition of fructose resulting in a 10-fold enhancement (≤ 0.25 M).

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