577-85-5Relevant articles and documents
Transient Absorption Study of the Intramolecular Excited-State and Ground-State Proton Transfer in 3-Hydroxyflavone and 3-Hydroxychromone
Itoh, Michiya,Tanimoto, Yoshifumi,Tokumura, Kunihiro
, p. 3339 - 3340 (1983)
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Direct evidence of excited-state intramolecular proton transfer in 2'-hydroxychalcone and photooxygenation forming 3-hydroxyflavone
Chou,Matinez,Cooper
, p. 4943 - 4944 (1992)
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Proton Transfer in Matrix-Isolated 3-Hydroxyflavone and 3-Hydroxyflavone Complexes
Brucker, G. A.,Kelley, D. F.
, p. 2856 - 2861 (1987)
The proton-transfer dynamics of 3-hydroxyflavone (3HF) and 3HF-solvent complexes have been studied in 10 K argon matrices.Both static and picosecond fluorescence spectroscopies were used.The results indicate that proton transfer in bare molecules occurs quite rapidly (10 ps).The 3HF-solvent complexes are formed by codeposition of argon:solvent mixtures (typically 2000:1) with 3HF followed by matrix annealing.Solvents include water, methanol, ethanol, and diethyl ether.The results show that proton transfer is very fast (10 ps) in alkohol and water monosolvates and can be interpreted in terms of cyclically hydrogen-bonded structures.The results also show that the diethyl ether monosolvate undergoes proton transfer in about 40 ps.Solvation with two or more waters or alkohols was found to inhibit proton transfer.
Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
Ashraf, Jamshaid,Mughal, Ehsan Ullah,Sadiq, Amina,Bibi, Maryam,Naeem, Nafeesa,Ali, Anser,Massadaq, Anam,Fatima, Nighat,Javid, Asif,Zafar, Muhammad Naveed,Khan, Bilal Ahmad,Nazar, Muhammad Faizan,Mumtaz, Amara,Tahir, Muhammad Nawaz,Mirzaei, Masoud
, p. 7107 - 7122 (2020/08/21)
To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened for in?vitro against mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis, 1H-, 13C-NMR) and mass spectrometry (EI-MS). The structure of compound 15 was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibiotics i.e. Cefixime and Clotrimazole. Amongst the series, the compounds 2, 4, 5, 6, 7, 10, 11, 14 and 22 exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound 2 (IC50 = 0.280 ± 0.010 μg/ml) was found almost sixfold and derivative 5 (IC50 = 0.230 ± 0.020 μg/ml) about sevenfold more active as compared to standard Kojic acid (IC50 =1.79 ± 0.6 μg/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma.
Simultaneous Two-Color Visualization of Lipid Droplets and Endoplasmic Reticulum and Their Interplay by Single Fluorescent Probes in Lambda Mode
Guo, Lifang,Tian, Minggang,Zhang, Zhiyun,Lu, Qing,Liu, Zhiqiang,Niu, Guangle,Yu, Xiaoqiang
supporting information, p. 3169 - 3179 (2021/03/01)
In living systems, subcellular organelles mutually cooperate and closely contact to form organelle interaction networks. Thus, the simultaneous and discriminative visualization of different organelles is extremely valuable for elucidating their distribution and interplay. However, such meaningful investigations remain a great challenge due to the lack of advanced single fluorescent probes (SF-probes) capable of simultaneous and two-color imaging of two targets. Herein, for the first time, we present two excited-state intramolecular proton transfer (ESIPT) based SF-probes (PPC and EPC) for simultaneous two-color fluorescence imaging of lipid droplets (LDs) and the endoplasmic reticulum (ER) under single-wavelength excitation. Due to the strong electron-donating ability of the side substituents, the fluorescence spectra and colors of these ESIPT probes are highly sensitive to the nuance of water contents between LDs and ER, leading to orange and green fluorescence in LDs and ER, respectively, in the Lambda imaging mode. Using the probe PPC or EPC, the morphology, size, and distribution of LDs and ER have been investigated in live cells and tissues. With the aid of in situ and real-time fluorescence imaging in Lambda mode, we observed the generation of newborn LDs near the ER regions and their close apposition and shared identical fluorescence colors, probably providing a valuable proof for the mainstream hypothesis that LDs originate from the ER. The remarkable imaging performances render these SF-probes as powerful tools to decipher LD-ER related biological processes.
