89048-25-9Relevant articles and documents
Rational design, synthesis and biological evaluation of ubiquinone derivatives as IDO1 inhibitors
Ding, Yuyang,Tang, Fei,Xue, Xiaoqian,Luo, Jinfeng,Hussain, Muzammal,Huang, Yanhui,Wang, Zhen,Jiang, Hao,Tu, Zhengchao,Zhang, Jiancun
supporting information, (2019/05/21)
Indoleamine 2,3-dioxygenase 1 (IDO1) is an attractive therapeutic target for the treatment of cancer, chronic viral infections and neurological disorders characterized by pathological immune stimulation. Herein, a series of known metal-chelating ubiquinone derivatives were designed, synthesized and evaluated for the IDO1 inhibiting activities. The docking studies showed that the compounds 11, 16, 18 and coenzyme-Q1 exhibited different binding modes to IDO1 protein. Among these compounds, the most active compound is 16d with an IC50 of 0.13 μM in enzymatic assay. The results reveal that a possible halogen bonding interaction between the bromine atom (3-Br) and Cys129 significantly enhances the inhibition activity against IDO1. This study provides structural insights of the interactions between ubiquinone analogues and IDO1 protein for the further modification and optimization.
Efficient synthesis of 2,3,4,5-tetramethoxy-6-methylbenzoic acid
Wang, Jin,Zhou, Rong-Guang,Liao, Teng-Huo-Sheng,Yang, Jian
, p. 6393 - 6396 (2015/08/18)
Abstract The title compound (5), a key intermediate for preparing Coenzyme Q analogues, was prepared in a good yield by a reaction sequence starting from the 2, 3, 4, 5-Tetramethoxytoluene (1) via Blanc Reaction, Kornblum oxidation, and 30 % H2
Practical synthesis of 2,3-dimethoxy-5-hydroxymethyl-6-methyl-1,4-benzoquinone
Wang, Jin,Li, Shuo,Yang, Tao,Zeng, Jin-Rong,Yang, Jian
, p. 486 - 489 (2015/02/19)
2,3-dimethoxy-5-hydroxymethyl-6-methyl-1,4-benzoquinone (V) was prepared with a 75 % yield by means of a reaction sequence starting from 2,3,4,5-tetramethoxytoluene via Blanc chloromethylation reaction, Kornblum oxidation, NaBH4 reduction and c
Practical synthesis of 2,3-dimethoxy-6-methyl-1,4-benzoquinone-5-carboxylic acid
Fan, Lei,Chen, Hai-Yan,Gao, Xiao-Qiang,Gao, Xiao-Juan
, p. 408 - 409 (2014/08/05)
2,3-Dimethoxy-6-methyl-1,4-benzoquinone-5-carboxylic acid was prepared in high yield by a reaction sequence starting from 2,3,4,5-tetramethoxytoluene (1) via a Blanc reaction, potassium dichromate oxidation, 30% H2O 2 oxidation and ceric ammonium nitrate oxidation.
Alkyne-tag Raman imaging for visualization of mobile small molecules in live cells
Yamakoshi, Hiroyuki,Dodo, Kosuke,Palonpon, Almar,Ando, Jun,Fujita, Katsumasa,Kawata, Satoshi,Sodeoka, Mikiko
, p. 20681 - 20689 (2013/02/23)
Alkyne has a unique Raman band that does not overlap with Raman scattering from any endogenous molecule in live cells. Here, we show that alkyne-tag Raman imaging (ATRI) is a promising approach for visualizing nonimmobilized small molecules in live cells. An examination of structure-Raman shift/intensity relationships revealed that alkynes conjugated to an aromatic ring and/or to a second alkyne (conjugated diynes) have strong Raman signals in the cellular silent region and can be excellent tags. Using these design guidelines, we synthesized and imaged a series of alkyne-tagged coenzyme Q (CoQ) analogues in live cells. Cellular concentrations of diyne-tagged CoQ analogues could be semiquantitatively estimated. Finally, simultaneous imaging of two small molecules, 5-ethynyl-2′-deoxyuridine (EdU) and a CoQ analogue, with distinct Raman tags was demonstrated.
In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues
Ma, Wei,Zhou, Hao,Ying, Yi-Lun,Li, Da-Wei,Chen, Guo-Rong,Long, Yi-Tao,Chen, Hong-Yuan
, p. 5990 - 6000 (2011/09/19)
Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV-vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure-activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4′-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 μM and 6.2 μM. This would make them as valuable candidates for future pharmacological studies.
Reversible redox of NADH and NAD+ at a hybrid lipid bilayer membrane using ubiquinone
Ma, Wei,Li, Da-Wei,Sutherland, Todd C.,Li, Yang,Long, Yi-Tao,Chen, Hong-Yuan
, p. 12366 - 12369 (2011/10/02)
Here, we report the reversible interconversion between NADH and NAD + at a low overpotential, which is in part mediated by ubiquinone embedded in a biomimetic membrane to mimic the initial stages of respiration. This system can be used as a platform to examine biologically relevant electroactive molecules embedded in a natural membrane environment and provide new insights into the mechanism of biological redox cycling.
Design and synthesis of novel quinone inhibitors targeted to the redox function of apurinic/apyrimidinic endonuclease 1/redox enhancing factor-1 (Ape1/Ref-1)
Nyland II, Rodney L.,Luo, Meihua,Kelley, Mark R.,Borch, Richard F.
scheme or table, p. 1200 - 1210 (2010/07/18)
The multifunctional enzyme apurinic endonuclease 1/redox enhancing factor 1 (Ape1/ref-1) maintains genetic fidelity through the repair of apurinic sites and regulates transcription through redox-dependent activation of transcription factors. Ape1 can therefore serve as a therapeutic target in either a DNA repair or transcriptional context. Inhibitors of the redox function can be used as either therapeutics or novel tools for separating the two functions for in vitro study. Presently there exist only a few compounds that have been reported to inhibit Ape1 redox activity; here we describe a series of quinones that exhibit micromolar inhibition of the redox function of Ape1. Benzoquinone and naphthoquinone analogues of the Ape1-inhibitor E3330 were designed and synthesized to explore structural effects on redox function and inhibition of cell growth. Most of the naphthoquinones were low micromolar inhibitors of Ape1 redox activity, and the most potent analogues inhibited tumor cell growth with IC50 values in the 10-20 μM range.
2,3-Dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4-naphthoquinones: Glycation inhibitors with lipid peroxidation activity
Jung, Young-Sik,Joe, Bo-Young,Cho, Sung Ju,Konishi, Yasuo
, p. 1125 - 1129 (2007/10/03)
Anti-glycation activity of our anti-oxidant quinone library was measured and several 2,3-dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4- naphthoquinones were identified as novel inhibitors of glycation, of which 2,3-dimethoxy-5-methyl-1,4-benzoquinones 13b is the most potent glycation inhibitor with around 50 μM of the IC50 value.
