20571-42-0Relevant academic research and scientific papers
Silver-catalyzed facile decarboxylation of coumarin-3-carboxylic acids
Jafarpour, Farnaz,Jalalimanesh, Nafiseh,Olia, Mina Barzegar Amiri,Kashani, Asieh Otaredi
, p. 9508 - 9511 (2010)
A simple and highly efficient protocol with mild reaction conditions has been developed that allows the smooth protiodecarboxylation of diversely functionalized coumarin-3-carboxylic acids. In the presence of catalytic amounts of Ag2CO3 and acetic acid, even un-activated coumarin-3-carboxylic acids were converted in good to excellent yields and with great preparative ease to the corresponding coumarin derivatives.
Structure-efficiency relationship of newly synthesized 4-substituted donor-π-acceptor coumarins for dye-sensitized solar cells
Jadhav, Manoj M.,Vaghasiya, Jayraj V.,Patil, Dinesh S.,Soni, Saurabh S.,Sekar, Nagaiyan
, p. 5267 - 5275 (2018)
Four (MC1-MC4) 4-substituted coumarin dyes having N,N-diethyl aniline as donor and rhodanine-3-acetic acid as acceptor have been synthesized for use in nano-crystalline TiO2-based dye-sensitized solar cells (DSSCs). The alteration at the 4-position of coumarin was carried out by substituting H atom by chlorine (-Cl), piperidine (-NC5H10), and cyano group (-CN) to study the effect of substitution on the efficiency of the DSSCs. All the dyes were characterised by 1H-NMR and 13C-NMR spectroscopy and CHN analysis. The absorption and emission spectra of these coumarin dyes were recorded in eight different solvents and show positive solvatochromism. The TiO2-based DSSCs were fabricated using the four dyes and their photovoltaic properties were estimated. A maximum efficiency of 4.60% was obtained for the MC4 device, which has an electron-withdrawing cyano group at the 4-position of coumarin, while 2.64% efficiency was obtained for the MC1 device, which has only hydrogen at the 4-position. The efficiencies of the MC2 and MC3 devices lie between those of MC1 and MC4, suggesting the significance of substitution at the 4-position. The introduction of a cyano group, which acts as an electron trap, increases the electron-withdrawing capacity of the dye; thus, more electron density is withdrawn from the donor, resulting in enhanced efficiency. These dyes were studied by using density functional theory (DFT) and time dependent density functional theory (TD-DFT) to obtain the vertical excitation, HOMO-LUMO energy levels, band gap and electron distribution in the ground and excited state. The calculated values showed good correlation with the experimental values. Our results suggest that substitution at the 4-position is essential for enhancing the efficiency of coumarin-based DSSCs.
A novel hydrazide Schiff base self-assembled nanoprobe for selective detection of human serum albumin and its applications in renal disease surveillance
Li, Qing-Zhong,Liu, Hai-Bo,Liu, Wei,Wang, Zhi-Gang,Xie, Cheng-Zhi,Xu, Jing-Yuan,Yan, Xiao-Jing,Zhang, De-Long
, p. 8346 - 8355 (2020)
Human serum albumin (HSA) is considered as a biomarker for the early diagnosis of renal disease, therefore identifying and detecting HSA in biological fluids (especially urine) with an easy method is of great importance. Herein, we report a novel hydrazide Schiff base fluorescent probe N′-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)pyrazine-2-carbohydrazide (NPC), which self-assembled into nanoparticles in aqueous solution. Based on disassembly-induced emission and the site-specific recognition mechanism, the binding of NPC with HSA resulted in a fluorescence "turn-on"response. Probe NPC exhibited superior selectivity and sensitivity toward HSA with a detection limit of 0.59 mg L-1 in PBS and 0.56 mg L-1 in the urine sample. The site-binding mechanism of NPC with HSA was explored by fluorescence quenching study, Job's plot analysis, HSA destruction, site marker displacement and molecular docking. Fluorescence imaging of HSA in MCF-7 cells was achieved by using a non-toxic NPC probe, suggesting that NPC could be applied to visualize the level of HSA in vivo. More importantly, further practical applications of probe NPC in human urine samples were achieved with satisfactory results by using a fluorometer or test paper, which could provide extensive application in clinical diagnosis.
Comparative study of two near-infrared coumarin-BODIPY dyes for bioimaging and photothermal therapy of cancer
Zhang, Yuandong,Song, Nan,Li, Yuanyuan,Yang, Zhiyu,Chen, Li,Sun, Tingting,Xie, Zhigang
, p. 4717 - 4724 (2019)
Near-infrared (NIR) responsive agents for cancer bioimaging and photothermal therapy are available and significant. Herein, we employed two easily available dyes, boron-dipyrromethane and coumarin, to synthesize a pair of coumarin-borondipyrromethane dyes with different conjugate degrees (BDC and BSC). The difference in conjugate degree made their photophysical properties poles apart. After the self-assembling of BDC and BSC, the newly constructed nanoparticles (BDC NPs and BSC NPs) demonstrated good biocompatibility. Moreover, BDC NPs exhibited a good photothermal effect under irradiation of 808 nm laser, which could effectively inhibit the growth of HeLa cells, and BSC NPs could quickly show a conspicuous fluorescence in the HeLa cells. The exploration demonstrates that the two organic dyes prepared with different conjugation degrees could provide new options for photothermal therapy of cancer and rapid bioimaging.
A colorimetric and ratiometric fluorescence probe for rapid detection of SO2 derivatives bisulfite and sulfite
Xiang, Kaiqiang,Chang, Shunzhou,Feng, Jingjing,Li, Changjiang,Ming, Wei,Liu, Ziyan,Liu, Yunchang,Tian, Baozhu,Zhang, Jinlong
, p. 190 - 197 (2016)
As one of the main atmospheric pollutants, sulfur dioxide (SO2) can be easily inhaled and turned into sulfite and bisulfite, which is harmful to both human health and ecological environment. Therefore, it is of significance to develop an effective method to detect the trace SO2 derivatives—SO32? and HSO3?. Herein, we synthesized a semi-cyanine-coumarin hybrid dye for detection of SO32? and HSO3?. Based on the nucleophilic addition of HSO3?/SO32? to the vinyl group, Probe 1 showed high response speed, selectivity, and sensitivity towards SO32? and HSO3?. Upon addition of HSO3?/SO32?, color obviously changes from blue to yellow which can be differentiated by naked eyes. Probe 1 displays colorimetric and ratiometric response toward HSO3? and SO32?. The detection limit is as low as 27.6?nM and the signal-to-background ratio in fluorescence intensity can reach 35-folds. Moreover, Probe 1 showed high selectivity and anti-interference ability in the co-existence of the environmental and biologic species.
A new fluorescence "turn-on" type chemosensor for Fe3+ based on naphthalimide and coumarin
Li, Zhengqian,Zhou, Ying,Yin, Kai,Yu, Zhu,Li, Yan,Ren, Jun
, p. 7 - 11 (2014)
A new Fe3+-selective "turn-on" chemosensor 1 based on coumarin and naphthalimide was designed and synthesized. The chemosensor exhibits high selectivity for Fe3+ over other ions (Mn2+, Co2+, Ni2+, Cu2+, Ag+, Cd 2+, Pb2+, Ca2+, Al3+, Ba 2+, Hg2+, Li+, Mg2+, Sr 2+, Zn2+ and K+) with fluorescence-enhancement in THF-H2O solution. The binding ratio of 1-Fe3+ complex was determined to be 1:1 according to the Job plot. The association constant Ka of Fe3+ binding with sensor 1 was (2.589 ± 0.206) × 103 M-1. The detection limit was calculated to be 0.388 μM.
A coumarin-fused ‘off-on’ fluorescent probe for highly selective detection of hydrazine
Wang, Mei,Wang, Xiaoli,Li, Xueyan,Yang, Ziqi,Guo, Zhenbo,Zhang, Jiangyan,Ma, Jingjun,Wei, Chao
, (2020)
Hydrazine is a kind of widely used industrial raw material and a toxic biochemical reagent. Due to its toxic to organisms, hydrazine has been classified to be a hazardous environmental pollutant. It is urgent to develop fluorescent probe tools for selective sensitivity detection of hydrazine in the environment and the body. We developed here a new coumarin-based fluorescent probe for hydrazine detection. The probe can selectively detect hydrazine over other environmental and endogenous interfering analytes with a large off-on fluorescence response. The detection limit is 8.55 ppb, which is well below the allowed threshold limit value. The sensing mechanism is hydrazine-induced pyrazole ring formation, which is confirmed by HRMS and DFT calculation methods. Additionally, the probe could also be applied for hydrazine imaging in living HeLa cells.
A "turn-off" red-emitting fluorophore for nanomolar detection of heparin
Jana, Palash,Radhakrishna, Mithun,Kanvah, Sriram,Khatua, Saumyakanti
, p. 13263 - 13270 (2018)
A simple fluorophore bearing a diethylaminocoumarin donor and a pyridinium acceptor was synthesized and utilized for the ultra-sensitive detection of heparin. The synthesized dicationic push-pull coumarin derivative emits strongly in the red-region (665 nm) and detects nanomolar concentrations (14.8 nM to 148 nM) of heparin in HEPES buffer and FBS serum solutions. The dication exhibits excellent fluorescence selectivity and sensitivity towards heparin over its analogues such as chondroitin 4-sulfate (CS), hyaluronic acid (HA) and dextran. This fluorescence assay is a convenient, sensitive method for monitoring heparin levels in biological samples. These findings were confirmed using coarse-grained Monte Carlo simulations, which provide us with a rationale for the selective binding of heparin.
A selective thioxothiazolidin-coumarin probe for Hg2+ based on its desulfurization reaction. Exploring its potential for live cell imaging
Aliaga, Margarita E.,Gazitua, Marcela,Rojas-Bola?os, Andrea,Fuentes-Estrada, Marcial,Durango, Diego,García-Beltrán, Olimpo
, (2020)
Sensing the most toxic heavy metal (mercury) has attracted a lot of attention in recent years due to its extreme harmfulness to both human health and the environment. Thus, we reported herein the synthesis, spectroscopic and kinetic characterization, and biological evaluation of a new thioxothiazolidin coumarin derivative (ILA92), which undergoes a desulfurization reaction induced by mercuric ions (Hg2+). This process is the origin of a selective sensing of Hg2+ ions in aqueous solution by colorimetric and fluorescent methods. Furthermore, the probe showed great potential for imaging Hg2+ in living cells.
Design, synthesis and bioactivity evaluation of coumarin-chalcone hybrids as potential anticancer agents
Dong, Junqiang,Gao, Jianbo,Wang, Yu,Zhang, Wenda
, (2020)
The selenoprotein thioredoxin reductases (TrxRs) have been extensively studied as a potential target for the development of anticancer drugs. Herein, we designed, synthesized, and evaluated a series of coumarin-chalcone hybrids as TrxR inhibitors. Most of them exhibited enhancing anticancer activity than Xanthohumol (Xn). The representative Xn-2 (IC50 = 3.6 μM) was a fluorescence agent, wherein drug uptake can be readily monitored in living cells by red fluorescence imaging. Xn-2 down-regulated the expression of TrxR, remarkedly induced ROS accumulation to activate mitochondrial apoptosis pathway. Furthermore, Xn-2 inhibited cancer cell metastasis and abolished the colony formation ability of cancer cells. Taken together, these results highlight that compound Xn-2 may be a promising theranostic TrxR inhibitor for human cancer therapy.
