55804-65-4Relevant articles and documents
A novel fluorescent probe with extremely low background fluorescence for sensing hypochlorite in zebrafish
Dai, Xiaoting,Dong, Lianghuan,Han, Zhixiang,Jiang, Shu,Long, Lingliang,Sun, Fan,Zhang, Min
, (2020)
Development of an efficient fluorescent probe for sensing hypochlorite in water samples and biological samples is highly demanded. However, the currently reported fluorescent probes for hypochlorite frequently suffered from the problem of high background fluorescence. Herein, based on the combined effect of two different fluorescence quenching groups, we rationally developed a novel fluorescent probe for hypochlorite with extremely low background fluorescence. Notably, due to the doubly quenching groups, the probe could even keep low background fluorescence in a solution with high viscosity. Furthermore, the probe displayed highly sensitive and selective response to hypochlorite, with the detection limits calculated to be 10.5 nM. Practical application demonstrated that the probe was able to quantitatively detect hypochlorite in various water samples with good recovery. Significantly, the probe showed extremely low background fluorescence in living cells and was capable of detecting minor variation of endogenous hypochlorite in RAW 264.7 cells. Moreover, the fluorescence imaging different concentration of hypochlorite in zebrafish has been successfully conducted. The probe developed herein will be widely used as a reliable tool to accurately monitor the variation of hypochlorite in living organism.
A julolidine-fused coumarin-NBD dyad for highly selective and sensitive detection of H2S in biological samples
Ismail, Ismail,Wang, Dawei,Wang, Zhenghua,Wang, Dan,Zhang, Changyu,Yi, Long,Xi, Zhen
, p. 700 - 706 (2019)
A new julolidine-fused coumarin-NBD probe 2 for H2S detection is rationally designed based on the DFT caculations. This improved probe exhibits faster and larger off-on response as well as higher sensitivity compared with the previous coumarin-NBD probe 1. Moreover, 2 possesses excellent selectivity and good biocompatibility, which can be employed to image H2S in living cells and in zebrafish.
Convenient Retinoid X Receptor Binding Assay Based on Fluorescence Change of the Antagonist NEt-C343
Yukawa-Takamatsu, Kayo,Wang, Yifei,Watanabe, Masaki,Takamura, Yuta,Fujihara, Michiko,Nakamura-Nakayama, Mariko,Yamada, Shoya,Kikuzawa, Shota,Makishima, Makoto,Kawasaki, Mayu,Ito, Sohei,Nakano, Shogo,Kakuta, Hiroki
, p. 861 - 870 (2021)
Retinoid X receptor (RXR) modulators (rexinoids) are considered to have therapeutic potential for multiple diseases, such as Alzheimer's disease and Parkinson's disease. To overcome various disadvantages of prior screening methods, we previously developed an RXR binding assay using a fluorescent RXR ligand, CU-6PMN (4). However, this ligand binds not only at the ligand-binding domain (LBD) but also at the dimer-dimer interface of hRXRα. Here, we present a new fluorescent RXR antagonist 6-[N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carboxamido)phenyl)amino]nicotinic acid (NEt-C343, 7), which emits strong fluorescence only when bound to the RXR-LBD. It allows us to perform a rapid, simple, and nonhazardous binding assay that does not require bound/free separation and uses a standard plate reader. The obtained Ki values of known compounds were correlated with the Ki values obtained using the standard [3H]9cis-retinoic acid assay. This assay should be useful for drug discovery as well as for research on endocrine disruptors, functional foods, and natural products.
Ratiometric Fluorescent Probe for Vicinal Dithiol-Containing Proteins in Living Cells Designed via Modulating the Intramolecular Charge Transfer-Twisted Intramolecular Charge Transfer Conversion Process
Wang, Yuanyuan,Zhong, Yaogang,Wang, Qin,Yang, Xiao-Feng,Li, Zheng,Li, Hua
, p. 10237 - 10244 (2016)
Vicinal dithiol-containing proteins (VDPs) play a significant role in maintaining the cellular redox homeostasis and are implicated in many diseases. To provide new chemical tools for VDPs imaging, we report here a ratiometric fluorescent probe CAsH2 for VDPs using 7-diethylaminiocoumarin as the fluorescent reporter and cyclic 1,3,2-dithiarsenolane as the specific ligand. CAsH2 shows peculiar dual fluorescence emission from the excited intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT) states in aqueous media. However, upon selective binding of protein vicinal dithiols to the trivalent arsenical of CAsH2, the probe was brought from the polar water media into the hydrophobic protein domain, causing the excited state ICT to TICT conversion to be restricted; as a result, an increase from the ICT emission band and a decrease from the TICT emission band were observed simultaneously. The designed probe shows high selectivity toward VDPs over other proteins and biological thiols. Preliminary experiments show that CAsH2 can be used for the ratiometric imaging of endogenous VDPs in living cells. So far as we know, this is a rare example of the ratiometric fluorescent probe designed via modulating the ICT-TICT conversion process, which provides a new way to construct various protein-specific ratiometric fluorescent probes.
A hepatocyte-targeting near-infrared ratiometric fluorescent probe for monitoring peroxynitrite during drug-induced hepatotoxicity and its remediation
Fei, Junjie,Jiang, Wen-Li,Li, Chun-Yan,Li, Yongfei,Wang, Wen-Xin,Zhao, Yi-Ting
, p. 14307 - 14310 (2019)
A novel hepatocyte-targeting near-infrared fluorescent probe named Gal-NIR is developed. Gal-NIR shows ratiometric response to ONOO- with high sensitivity and selectivity. Moreover, the probe can accurately target the hepatocyte, and thus is used for assessing drug-induced hepatotoxicity and its remediation by using hepatoprotective medicines in living cells and mice.
A novel two-fluorophore approach to ratiometric sensing of Zn2+
Woodroofe, Carolyn C.,Lippard, Stephen J.
, p. 11458 - 11459 (2003)
We present a small molecule ratiometric Zn2+-sensing system based on two fluorophores excited by visible light, a Zn2+-insensitive reporter fluorophore, coumarin 343, and a Zn2+-sensitive fluorescein-based compound, ZPA-1. The two fluorophores are linked by an ester to give Coumazin-1, a membrane-permeable, essentially nonfluorescent compound. Upon exposure to esterases, Coumazin-1 is hydrolyzed to its constituent fluorophores. Measurement of the ratio of coumarin emission at 488 nm (λexc = 445 nm) and comparison with ZPA-1 emission at 534 nm (λexc = 505 nm) affords information about the amount of sensor present as well as the amount of Zn2+ present. A generally applicable synthetic route to amide-functionalized ZP1 sensors is also described. The Zn2+-sensing properties of one member of this class are similar to those of the parent ZP1 sensor, with slightly tighter binding and lower background signal. Copyright
A PET-based fluorescent probe for monitoring labile Fe(ii) pools in macrophage activations and ferroptosis
Abedi, Syed Ali Abbas,Liu, Xiaogang,Lou, Kaiyan,Ma, Huijuan,Wang, Shanshan,Wang, Wei,Xing, Wanjin,Xu, Hang,Xu, Huan,Zhang, Xingchen
supporting information, p. 2979 - 2982 (2022/03/15)
A fluorescent probe (COU-LIP-1) for monitoring labile Fe(ii) pools (LIP) with high selectivity and sensitivity was developed utilizing coumarin 343 as the fluorophore and 3-nitrophenylazanyl ester as both the reactive group and the fluorescence quenching group. Fe(ii)-induced reductive cleavage of the N-O bond results in a turn-on response via a photo-induced photon transfer (PET) mechanism. The probe was applied for monitoring labile iron(ii) changes in M1 and M2a macrophage activations and also erastin-induced ferroptosis, providing a powerful tool for selectively sensing LIP under both physiological and stressed conditions.
An Activity-Based Probe for Cathepsin K Imaging with Excellent Potency and Selectivity
Bartz, Ulrike,Brajtenbach, Dominik,Breuer, Christian,Horn, Martin,Illies, Annika,Kubatzky, Katharina F.,Lemke, Carina,Beny?ek, Jakub,Bu?a, Michal,Gütschow, Michael,Jílková, Adéla,Mare?, Michael,Ulrychová, Lenka
, p. 13793 - 13806 (2021/09/20)
The cysteine protease cathepsin K is a target for the treatment of diseases associated with high bone turnover. Cathepsin K is mainly expressed in osteoclasts and responsible for the destruction of the proteinaceous components of the bone matrix. We designed various fluorescent activity-based probes (ABPs) and their precursors that bind to and inactivate cathepsin?K. ABP 25 exhibited extraordinary potency (kinac/Ki= 35,300?M-1s-1) and selectivity for human cathepsin K. Crystal structures of cathepsin K in complex with ABP 25 and its nonfluorescent precursor 21 were determined to characterize the binding mode of this new type of acrylamide-based Michael acceptor with the particular orientation of the dibenzylamine moiety to the primed subsite region. The cyanine-5 containing probe 25 allowed for sensitive detection of cathepsin K, selective visualization in complex proteomes, and live cell imaging of a human osteosarcoma cell line, underlining its applicability in a pathophysiological environment.
Preparation method of high-sensitivity hypochlorite fluorescence probe with extremely low background fluorescence (by machine translation)
-
Paragraph 0037-0039, (2020/06/24)
The invention belongs to the technical field of fluorescent probes, and particularly relates to a preparation method of a high-sensitivity hypochlorite fluorescence probe with extremely low background fluorescence. As the concentration of hypochlorite is increased, the -9 - fluorescence intensity of the fluorescent probe is gradually 343 enhanced 4 - at 2 8 - and as the concentration of hypochlorite is increased, the fluorescent probe can be used for detecting hypochlorite content in an actual water sample, detecting exogenous/endogenous hypochlorous acid roots and detecting hypochlorite in zebra fish 488 nm. (by machine translation)
Fluorescently Labeled Amino Acids as Building Blocks for Bioactive Molecules
H?u?ler, Daniela,Gütschow, Michael
, p. 245 - 255 (2016/01/15)
A series of twelve fluorescently labeled amino acids were designed by assembling different coumarin, fluorescein, or nitrobenzo-furazan fluorophores with N-protected lysine or 2-aminopropionic acid. The synthesized amino acids were evaluated with regard to their spectroscopic properties. The easy introduction of the amino acids into peptides and peptidomimetics was exemplarily shown for one coumarin-labeled- amino acid.
