449175-73-9Relevant academic research and scientific papers
Determining Essential Requirements for Fluorophore Selection in Various Fluorescence Applications Taking Advantage of Diverse Structure-Fluorescence Information of Chromone Derivatives
Chen, Yikun,Gao, Yongxin,He, Yujun,Zhang, Gang,Wen, Hui,Wang, Yuchen,Wu, Qin-Pei,Cui, Huaqing
, p. 1001 - 1017 (2021/01/09)
Herein, we report our work exploring the essential requirements for fluorophore selection during the development of various fluorescence applications. We assembled a library of chromone-derived fluorophores with diverse structure-fluorescence properties, which allowed us to choose the fluorophore pairs with similar structures but differing fluorescence properties and compared the performance of the selected fluorophore pairs in three types of commonly used fluorescence applications. We found that the selection standard of a suitable fluorophore is variable depending on the application. (1) In fluorescence imaging, fluorophores with strong and constant fluorescence under various conditions, such as a large pH range, are preferred. Notably, (2) in the detection of bioactive species, fluorophores with relatively lower fluorescence quantum yield favor the detection sensitivity. Furthermore, (3) in enzymatic assays employing fluorescence, the key parameter is the binding affinity between the fluorophore and the enzyme.
Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
Miao, Jianzhuang,Cui, Huaqing,Jin, Jing,Lai, Fangfang,Wen, Hui,Zhang, Xiang,Ruda, Gian Filippo,Chen, Xiaoguang,Yin, Dali
supporting information, p. 881 - 884 (2015/02/19)
Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is
Synthesis and anti-tumor activities of novel oxazinyl isoflavonoids
Wang, Dun,Hou, Like,Wu, Lirong,Yu, Xin
scheme or table, p. 513 - 520 (2012/05/05)
The design, synthesis and biological evaluation of a novel series of oxazinyl isoflavonoids is described. Several analogs were shown to exhibit growth inhibitory effects against SKOV-3, DU-145 and HL-60 human colon cancer cell lines with IC50 values in the micromolar range. The cellular potency of compounds 7e and 12h were found to have greater in vitro inhibitory activities than phenoxodiol, the parental compound currently in late-stage clinical trials for the treatment of cancer. The results shown are suitable for further lead optimization.
Synthesis and structural study on heterocyclic compounds 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones: Crystal structure of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one
Yeap, Guan-Yeow,Yam, Wan-Sinn,Dominiak, Paulina,Ito, Masato M.
experimental part, p. 25 - 33 (2010/06/16)
Six new isoflavone-based esters, 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones, derived from 1,3-benzenediol (resorcinol) and different para substituted phenylacetic acids have been synthesized and characterized. The molecular structures of the title compounds were elucidated with the employment of physical measurements and spectroscopic techniques (FTIR, 1D and 2D NMR). The conformation of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one was determined by single crystal X-ray diffraction analysis of which the title compound crystallized into triclinic lattice with P-1 space group. Crystal structure of the title compound also revealed that the two phenyl rings of the central moiety were planar whilst the heterocyclic ring was found to pucker slightly from the mean plane.
COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH
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Page/Page column 34, (2010/11/30)
The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.
Synthesis of daidzin analogues as potential agents for alcohol abuse
Gao, Guang-Yao,Li, Dian-Jun,Keung, Wing Ming
, p. 4069 - 4081 (2007/10/03)
Daidzin, the active principle of an herbal remedy for 'alcohol addiction', has been shown to reduce alcohol consumption in all laboratory animals tested to date. Correlation studies using structural analogues of daidzin suggests that it acts by raising the monoamine oxidase (MAO)/mitochondrial aldehyde dehydrogenase (ALDH-2) activity ratio (J. Med. Chem. 2000, 43, 4169). Structure-activity relationship (SAR) studies on the 7-O-substituted analogues of daidzin have revealed structural features important for ALDH-2 and MAO inhibition (J. Med. Chem. 2001, 44, 3320). We here evaluated effects of substitutions at 2, 5, 6, 8, 3′ and 4′ positions of daidzin on its potencies for ALDH-2 and MAO inhibition. Results show that analogues with 4′-substituents that are small, polar and with hydrogen bonding capacities are most potent ALDH-2 inhibitors, whereas those that are non-polar and with electron withdrawing capacities are potent MAO inhibitors. Analogues with a 5-OH group are less potent ALDH-2 inhibitors but are more potent MAO inhibitors. All the 2-, 6-, 8- and 3′-substituted analogues tested so far do not inhibit ALDH-2 and/or have decreased potencies for MAO inhibition. This, together with the results obtained from previous studies, suggests that a potent antidipsotropic analogue would be a 4′,7-disubstituted isoflavone. The 4′-substituent should be small, polar, and with hydrogen bonding capacities such as, -OH and -NH2; whereas the 7-substituent should be a straight-chain alkyl with a terminal polar function such as -(CH 2)n-OH with 2≤n ≤6, -(CH2) n-COOH with 5≤n ≤10, or -(CH2)n-NH 2 with n ≥4.
