79418-41-0Relevant academic research and scientific papers
Catalyst-free conjugation and in situ quantification of nanoparticle ligand surface density using fluorogenic Cu-free click chemistry
Jolck, Rasmus I.,Sun, Honghao,Berg, Rolf H.,Andresen, Thomas L.
, p. 3326 - 3331 (2011)
A highly efficient method for functionalizing nanoparticles and directly quantifying conjugation efficiency and ligand surface density has been developed. Attachment of 3-azido-modifed RGD-peptides to PEGylated liposomes was achieved by using Cu-free click conditions. Upon coupling a fluorophore is formed, which could be utilized to monitor conjugation efficiency and the obtained ligand surface density in situ, without prior purification. Copyright
Coumarin-based fluorescent probe for the detection of glutathione and nitroreductase
Tian, Xue,Kumawat, Lokesh K.,Bull, Steven D.,Elmes, Robert B.P.,Wu, Luling,James, Tony D.
, (2021)
With this research we set out to develop a coumarin-based novel fluorescent probe NTR-AHC for the detection of biological thiols and nitroreductase (NTR). Probe NTR-AHC was constructed by attaching the NTR trigger moiety (p-nitrobenzyl) and biothiol accep
A novel highly selective colorimetric sensor for Ni(II) ion using coumarin derivatives
Jiang, Jinqiang,Gou, Chao,Luo, Jing,Yi, Chenglin,Liu, Xiaoya
, p. 12 - 15 (2012)
A new coumarin based colorimetric nickel sensor 1 with high selectivity and sensitivity toward Ni2+ ion was reported. The absorption maximum of 1 shows a large red shift from 341 nm to 540 nm (Δ = 200 nm) in the presence of Ni2+ ion, and the resulted color change from colorless to pink upon addition of Ni2+ is very easily observed by the naked eye, while other metal ions, such as Zn2+, Cd2+, Cu 2+, Fe3+, Ag+, Pb2+, alkali metal and alkaline earth metal cations do not induce such a change. By the "naked eye", the detection limit of Ni2+ is as low as 0.5 μM in solution, which is lower than the current American Environmental Protection Agency (EPA) standard for drinking water. As far as we are aware of, this is the first reported colorimetric chemosensor capable of detecting Ni2+ ion.
Coumarin Thiourea-Based Fluorescent Turn-on Hg2+ Probe That Can Be Utilized in a Broad pH Range 1–11
Pan, Zhixiu,Xu, Zhenxiang,Chen, Jie,Hu, Luping,Li, Hongqi,Zhang, Xin,Gao, Xucheng,Wang, Mengxuan,Zhang, Jian
, p. 505 - 514 (2020)
A novel coumarin-thiourea conjugate was synthesized facilely. It served as a fluorescent turn-on chemosensor for selective detection of Hg2+ ion over other common competitive metal ions including Li+, Na+, K+, Ag+, Cu2+, Fe2+, Zn2+, Co2+, Ni2+, Mn2+, Sr2+, Ca2+, Mg2+, Al3+, Cr3+ and Fe3+ ions based on the Hg2+-promoted desulfurization and cyclization reactions. Addition of Hg2+ ion to the sensor solution in 2:8 EtOH/H2O induced a hypsochromic shift of the UV–Vis absorption band from 360?nm to 340?nm accompanying distinct enhancement in the absorption intensity while addition of other metal ions failed to bring about substantial change in the absorption spectra. Addition of Hg2+ to the sensor solution also caused marked increase in the fluorescence emission intensity and most common competitive metal ions did not interfere with the selective sensing of Hg2+ ion by the sensor. The detection limit of Hg2+ ion by the probe was calculated to be 1.46 × 10?7?M and the probe could be utilized for selective detection of Hg2+ ion by fluorescence turn-on mode over a broad pH range of 1–11.
Synthesis and characterization of a novel fluorescent and colorimetric probe for the detection of mercury (II) even in the presence of relevant biothiols
García-Beltrán, Olimpo,Rodríguez, Alejandra,Trujillo, Ariel,Ca?ete, Alvaro,Aguirre, Pabla,Gallego-Quintero, Sebastián,Nu?ez, Marco T.,Aliaga, Margarita E.
, p. 5761 - 5766 (2015)
We present here a novel probe, coumarin 3-azomethine derivative (AGB), which can detect selectively mercuric ions (Hg2+) via a hydrolysis reaction promoted by these ions. Interestingly, the probe can be used to assess the response to Hg2+ even in the presence of the most important biothiols-glutathione and cysteine - and could be used in the Hg2+ - imaging in living cells.
Orchestration of dual cyclization processes and dual quenching mechanisms for enhanced selectivity and drastic fluorescence turn-on detection of cysteine
Tong, Hongjuan,Zhao, Jianhong,Li, Xiangmin,Zhang, Yajun,Ma, Shengnan,Lou, Kaiyan,Wang, Wei
, p. 3583 - 3586 (2017)
We reported a new approach to achieve enhanced selectivity with a drastic turn-on fluorescence response for the detection of Cys through dual intramolecular cyclization processes and dual PET and ICT quenching mechanisms by the incorporation of an acrylate and a maleimide group onto two opposite sides of a single coumarin fluorophore.
A highly selective and sensitive fluorescent thiol probe through dual-reactive and dual-quenching groups
Zhang, Huatang,Zhang, Changyu,Liu, Ruochuan,Yi, Long,Sun, Hongyan
, p. 2029 - 2032 (2015)
A new fluorescent probe installed with dual-reactive and dual-quenching groups was rationally designed for highly selective and sensitive sensing of biothiols. The sensitivity of the probe toward thiols was significantly improved by dual-quenching effects. Furthermore the selectivity of the probe was also greatly enhanced by installation of dual-reactive groups. This journal is
Development of an ‘OFF-ON-OFF’ fluorescent pH sensor suitable for the study of intracellular pH
Hirano, Tomoya,Noji, Yuki,Shiraishi, Takuya,Ishigami-Yuasa, Mari,Kagechika, Hiroyuki
, p. 4925 - 4930 (2016)
Changes of pH in living organisms are closely related to various physiological functions, so fluorescent sensors of pH would be useful as experimental tools and possibly also for medical diagnosis. We previously reported a pH sensor with ‘OFF-ON-OFF’ -type fluorescence change, which would be potentially more useful than conventional sensors with ‘OFF-ON’ type change. It can be utilized as a sensor for a specific range of pH, however, the range with strong fluorescence is relatively wide, around pH 7–10, which renders it impractical for use in biological studies. So in the present work, we adjusted the pH detection range by the introduction of chloro groups at the ortho-positions to the phenolic hydroxyl groups, whose deprotonation could control fluorescence change, and obtained a sensor specifically responsive to pH around 6. This sensor was confirmed to be suitable for fluorescence imaging of changes of intracellular pH in living cells.
Design and synthesis of a solvent-dependent fluorescent probe for dual selective detection of Mg2+ ion and Zn2+ ion
Fu, Zhen-Hai,Qin, Jing-Can,Wang, Min,Zhang, Zhi-Hong
, (2020/10/20)
A solvent-dependent fluorescent probe QC for the dual detection of Mg2+ ion and Zn2+ ion has been constructed based on a Schiff base compound, in which 8-hydroxyquinoline served as not only a fluorophore but also a recognition group. Among the various tested metal ions, this probe exhibited high sensitivity and good selectivity toward Mg2+ ion in acetonitrile and Zn2+ ion in EtOH-H2O (9:1, v/v), respectively. With the treatment of Mg2+ ion or Zn2+ ion, 1:2 complex was formed between QC and Mg2+ ion, which inhibited the PET processes caused by the lone pair electrons from the nitrogen atom of the -C = N group and the nitrogen atom of quinoline moiety, resulting in the fluorescence enhancement for Mg2+ ion. Whereas a 1:1 complex was formed between QC and Zn2+ ion, which inhibited the PET process only caused by the lone pair electrons from the nitrogen atom of the -C = N group, resulting in the fluorescence enhancement at a shorter wavelength. The detection limit was calculated as low as 6.28 × 10?8 M for Mg2+ ion and 2.36 × 10?7 M for Zn2+ ion. DFT analysis further supported this concept to design the probe.
Myeloperoxidase inhibitory and antioxidant activities of (E)-2-hydroxy-α-aminocinnamic acids obtained through microwave-assisted synthesis
Rivera-Antonio, Astrid,Rosales-Hernández, Martha Cecilia,Balbuena-Rebolledo, Irving,Santiago-Quintana, José Martín,Mendieta-Wejebe, Jessica Elena,Correa-Basurto, José,García-Vázquez, Juan Benjamín,García-Báez, Efrén Venancio,Padilla-Martínez, Itzia I.
, (2021/06/16)
Myeloperoxidase (MPO) is an enzyme present in human neutrophils, whose main role is to provide defenses against invading pathogens. However, highly reactive oxygen species (ROS), such as HOCl, are generated from MPO activity, leading to chronic diseases. Herein, we report the microwave-assisted synthesis of a new series of stable (E)-(2-hydroxy)-α-aminocinnamic acids, in good yields, which are structurally analogous to the natural products (Z)-2-hydroxycinnamic acids. The radical scavenging activity (RSA), MPO inhibitory activity and cytotoxicity of the reported compounds were evaluated. The hydroxy derivatives showed the most potent RSA, reducing the presence of DPPH and ABTS radicals by 77% at 0.32 mM and 100% at 0.04 mM, respectively. Their mechanism of action was modeled with BDEOH, IP and ?EH-L theoretical calculations at the B3LYP/6 ? 31 + G(d,p) level. Compounds showed in vitro inhibitory activity of MPO with IC50 values comparable to indomethacin and 5-ASA, but cytotoxicities below 15% at 100–200 μM. Docking calculations revealed that they reach the amino acid residues present in the distal cavity of the MPO active site, where both the amino and carboxylic acid groups of the α-aminopropenoic acid arm are structural requirements for anchoring. (E)-2-hydroxy-α-aminocinnamic acids have been synthesized for the first time with a reliable method and their antioxidant properties demonstrated.
