Structurally regular arrangement induced fluorescence enhancement and specific recognition for glutathione of a pyrene chalcone derivative

Yu, Xueying; Wang, Kang‐Nan; Xing, Miaomiao; Sun, Yanan; Li, Mengyuan; Sun, Yongjian; Cao, Duxia; Zhao, Songfang; Liu, Zhi Qiang

doi:10.1016/j.aca.2019.07.052

Cited by 8 publications

(2 citation statements)

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“…Chalcones, a subgroup of flavonoid family, have been applied as fluorescent dyes and fluorescent probes [ 26–28 ] owing to their important optical properties. On the other hand, coumarins attracted a great deal of research interest due to their unique photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12][13][14] In the past few decades, many fluorescent probes for biothiols have been developed based on different fluorophores and various sensing mechanism, such as Michael addition, cleavage reactions, nucleophilic substitution, and conjugated addition cyclization. [15][16][17][18][19][20][21][22][23][24][25] Chalcones, a subgroup of flavonoid family, have been applied as fluorescent dyes and fluorescent probes [26][27][28] owing to their important optical properties. On the other hand, coumarins attracted a great deal of research interest due to their unique photophysical properties.…”

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confidence: 99%

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Photophysical properties and sensing mechanism of fluorescent coumarin–chalcone hybrid for biothiols: A theoretical study

Zhang

Chen

et al. 2022

J of Physical Organic Chem

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The photophysical properties and sensing mechanism of a novel coumarinchalcone hybrid fluorescent probe (CCH) for biothiols were investigated by density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods. The theoretical calculations well reproduced the experimental spectra and clarified the experimental observed fluorescence "on-off" switching. Potential energy surface (PES) results revealed that the excited-state intramolecular proton transfer (ESIPT) process is thermodynamically and kinetically viable for CCH, with the keto form more stable than the enol form.ESIPT process and the significant changes of the orbital energies should be responsible for the red fluorescence of CCH. The results revealed that the lowest lying transition of probe CCH corresponds to electronic transition between HOMO and LUMO with charge transfer (CT) character. The addition of cysteine to CCH breaks the conjugation and the intramolecular CT. A nonclassical photoinduced electron transfer (PET) process should contribute to the fluorescence quenching of CCH-Cys. Thermodynamic and kinetic calculations on the recognition reaction predicted a moderate Gibbs free energy barrier, which proves the possibility of the Michael addition reaction and induces the rapid response of the probe CCH for cysteine.biothiols, coumarin-chalcone hybrids, DFT/TDDFT, photophysical property, sensing mechanism | INTRODUCTIONBiothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), are indispensable functional molecules in biological system, which play vital roles in many physiological processes, such as protein synthesis and metabolism. [1,2] The endogenous concentrations of thiols reflect the functional state of the corresponding enzymes and proteins, and their abnormal levels are associated with many diseases including cancer and Alzheimer's disease. [1][2][3][4] Therefore, it is of great value to detect and sense biothiols.Ling Zhang and Mohan Chen contributed equally.

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Section: Introductionmentioning

confidence: 99%