20050-74-2Relevant academic research and scientific papers
7-Hydroxycoumarins Are Affinity-Based Fluorescent Probes for Competitive Binding Studies of Macrophage Migration Inhibitory Factor
Xiao, Zhangping,Chen, Deng,Song, Shanshan,Van Der Vlag, Ramon,Van Der Wouden, Petra E.,Van Merkerk, Ronald,Cool, Robbert H.,Hirsch, Anna K. H.,Melgert, Barbro N.,Quax, Wim J.,Poelarends, Gerrit J.,Dekker, Frank J.
, p. 11920 - 11933 (2020/11/26)
Macrophage migration inhibitory factor (MIF) is a cytokine with key roles in inflammation and cancer, which qualifies it as a potential drug target. Apart from its cytokine activity, MIF also harbors enzyme activity for keto-enol tautomerization. MIF enzymatic activity has been used for identification of MIF binding molecules that also interfere with its biological activity. However, MIF tautomerase activity assays are troubled by irregularities, thus creating a need for alternative methods. In this study, we identified a 7-hydroxycoumarin fluorophore with high affinity for the MIF tautomerase active site (Ki = 18 ± 1 nM) that binds with concomitant quenching of its fluorescence. This property enabled development of a novel competition-based assay format to quantify MIF binding. We also demonstrated that the 7-hydroxycoumarin fluorophore interfered with the MIF-CD74 interaction and inhibited proliferation of A549 cells. Thus, we provide a high-affinity MIF binder as a novel tool to advance MIF-oriented research.
Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
Hu, Yuheng,Wang, Bing,Yang, Jie,Liu, Teng,Sun, Jie,Wang, Xiaojing
, p. 15 - 30 (2018/10/31)
A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs) formation inhibitory. Most compounds exhibited significant antioxidant and AGEs formation inhibitory activities. Anti-diabetic activity studies showed that compounds 11 and 17 were equipotent to the standard drug glibenclamide in vivo. According to the experimental results, the target compound 35 can be used as a lead compound for the development of new anti-diabetic drugs. The whole experiment showed that anti-diabetic activity is prevalent in 3-arylcoumarins, which added a new natural skeleton to the development of anti-diabetic active drugs.
Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents
Yang, Jie,Zhang, Pingping,Hu, Yuheng,Liu, Teng,Sun, Jie,Wang, Xiaojing
, p. 651 - 656 (2019/02/19)
Alzheimer's disease, a neurodegenerative illness, has the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited high activity; therefore 3-arylcoumarin compounds have the potential as drug candidates for the treatment of Alzheimer's disease.
Molecular Docking-Based Design and Development of a Highly Selective Probe Substrate for UDP-glucuronosyltransferase 1A10
Juvonen, Risto O.,Rauham?ki, Sanna,Kortet, Sami,Niinivehmas, Sanna,Troberg, Johanna,Petsalo, Aleksanteri,Huuskonen, Juhani,Raunio, Hannu,Finel, Moshe,Pentik?inen, Olli T.
, p. 923 - 933 (2018/03/13)
Intestinal and hepatic glucuronidation by the UDP-glucuronosyltransferases (UGTs) greatly affect the bioavailability of phenolic compounds. UGT1A10 catalyzes glucuronidation reactions in the intestine, but not in the liver. Here, our aim was to develop se
Rational design of slightly twisted coumarin molecules with remarkable solution and solid dual efficient luminescence
Sun, Yue,Wu, Tong,Zhang, Fang,Zhang, Rong,Wu, Min,Wu, Yuezhen,Liang, Xiaozhong,Guo, Kunpeng,Li, Jie
, p. 73 - 81 (2017/10/09)
Endowing slightly twisted molecules highly emissive in both solution and solid state is of great importance for understanding the principle of maximizing the luminescent efficiency of luminophores. To this end, a series of slightly twisted coumarin luminophores CMs with different alkoxyl substituents at the 7-positions were synthesized. The effect of the substitutes on the diversity photophysical properties of the four compounds in solution, THF/H2O mixtures and solid state were investigated. Comparing to the referenced compound CM (3-p-tolyl-2H-chromen-2-one) that without a substitute, the introduced electron-rich alkoxyl substitutes not only enhanced the intramolecular charge transfer (ICT) effect, but also significantly modified their molecular packing patterns in the crystals. The combined effect of increasing the radiative and suppressing the nonradiactive pathways boosted the luminescence efficiency of CM1-CM3 in solution and the solid state simultaneously. Eventually, compound CM2 with an ethoxyl substitute exhibited the strongest blue emission with fluorescence quantum yields as high as 73.2% and 96.7% in solution and the solid state, respectively. This work presents an efficient strategy towards dual strong fluorescent luminophores in both solution and the solid state.
Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions
Chauhan, Parul,Ravi, Makthala,Singh, Shikha,Prajapati, Prashant,Yadav, Prem P.
, p. 109 - 118 (2016/01/09)
A facile regioselective metal-free direct α-arylation of coumarins and 2-pyridones is achieved by the reaction of coumarins and 2-pyridones with phenylhydrazine in good yields. The reaction proceeds at room temperature under mild conditions using inexpensive reagents and without the need for step intensive activating groups. The methodology is operationally simple, practically viable and also allows the coupling of similar nitrogen heterocycle aza-coumarins without prerequisite N-protection.
Through-bond energy transfer cassettes with minimal spectral overlap between the donor emission and acceptor absorption: Coumarin-rhodamine dyads with large pseudo-stokes shifts and emission shifts
Lin, Weiying,Yuan, Lin,Cao, Zengmei,Feng, Yanming,Song, Jizeng
supporting information; experimental part, p. 375 - 379 (2010/04/06)
Chemical Equation Presented Cassette recording: A new class of coumarin-rhodamine through-bond energy-transfer (TBET) cassettes with minimal spectral overlap between the donor emission and the acceptor absorption (see picture) show large pseudo-Stokes shifts (up to 230 nm) and emission shifts (up to 170 nm). The utility of this TBET platform for TBET-based probe development was demonstrated by a new ratiometric fluorescence pH probe.
