- A benzothioate native chemical ligation-based cysteine-selective fluorescent probe
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A turn-on fluorescent probe for the detection of cysteine (Cys), an essential amino acid in biological systems, is developed based on Cys-mediated O-phenyl benzothioate native chemical ligation (NCL) for the first time. Cys plays important roles in many p
- Kim, Na Hee,Moon, Heejo,Kim, Jeong Hee,Huh, Youngbuhm,Kim, Yong Jun,Kim, B. Moon,Kim, Dokyoung
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- A Ratiometric Fluorescent Probe Based on a Through-Bond Energy Transfer (TBET) System for Imaging HOCl in Living Cells
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A simple ratiometric probe (Naph-Rh) has been designed and synthesized based on a through-bond energy transfer (TBET) system for sensing HOCl. In this probe, rhodamine thiohydrazide and naphthalene formyl were connected by simple synthesis methods to construct a structure of monothio-bishydrazide. Free probe Naph-Rh showed only the emission of naphthalene. When probe Naph-Rh reacted with HOCl, monothio-bishydrazide could be converted into 1,2,4-oxadiazole, which not only ensured that the donor and the acceptor were connected with electronically conjugated bonds, but also resulted in the spiro-ring opening and the emission of rhodamine. Therefore, a typical TBET process took place. The probe possessed high-energy transfer efficiency and large pseudo-Stokes shifts. As the first TBET probe for HOCl, Naph-Rh showed excellent selectivity and sensitivity toward HOCl over other reactive oxygen species (ROS)/reactive nitrogen species (RNS), and could respond fast to a low concentration of HOCl in the real sample. In addition, the probe was suitable for imaging HOCl in living cells due to its real-time response, excellent resolution, and reduced cytotoxicity.
- Zhang, Yan-Ru,Meng, Ning,Miao, Jun-Ying,Zhao, Bao-Xiang
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- An uridine derivative containing a hydrophobic fluorescent probe at the 2'-position: Synthesis and its incorporation into oligonucleotides
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The synthesis of 2'-(6-dimethylamino-2-naphthamide)uridine [U(DAN)] has been described. The nucleoside was converted to the 5'-dimethoxytrityl nucleoside phosphoramidite which could be used for incorporation of U(DAN) into the desired positions of the oligonucleotide sequence.
- Yamana, Kazushige,Mitsui, Tuneo,Hayashi, Haruhisa,Nakano, Hidehiko
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- Iridium-Catalyzed Direct C-H Amidation Producing Multicolor Fluorescent Molecules Emitting Blue-to-Red Light and White Light
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We report a powerful strategy, iridium-catalyzed direct C-H amidation (DCA) for synthesizing various fluorescent sulfonamides that emit light over the entire visible spectrum with excellent efficiency (up to 99% yields). By controlling electronic characters of the resulting sulfonamides, a wide range of blue-to-red emissions was predictably obtained via an excited-state intramolecular proton-transfer process. Furthermore, we even succeeded in a white-light generation, highlighting that this DCA is an excellent synthetic method to prepare a library of fluorophores.
- Hwang, Soon-Hyeok,Choi, Tae-Lim
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supporting information
p. 2935 - 2940
(2020/04/20)
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- Two-photon ratiometric fluorescent probe compound for detecting aminopeptidase N, and preparation method thereof
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The invention discloses a preparation method of a two-photon ratiometric fluorescent probe compound for detecting aminopeptidase N. The structure of the fluorescent compound is represented by formulaI. The probe compound is designed based on the principle of fluorescence resonance energy transfer, a two-photon naphthalene derivative is selected as an energy donor, a p-methylaminophenol fluorophore is used as an energy acceptor, and alanine is introduced as an aminopeptidase N specific recognition unit. The aminopeptidase N is used to preferentially hydrolyze an N-terminal alanyl group, whichcauses the proportional change in a fluorescence emission signal. The compound has the advantages of high sensitivity, high selectivity, large emission shift, and quickness in detection of the aminopeptidase N, can be successfully applied to two-photon fluorescence imaging in living cells and tissues, and provides a potential tool for clinical detection of kidney injuries.
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Paragraph 0014
(2019/10/23)
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- Discovery of a sensitive, selective, and tightly binding fluorogenic substrate of bovine plasma amine oxidase
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(Chemical Equation Presented) We report a novel fluorogenic substrate of bovine plasma amine oxidase (BPAO), namely, (2-(6-(aminomethyl)naphthalen-2- yloxy)ethyl)trimethylammonium (ANETA), which displays extremely tight binding to BPAO (Km 183 ± 14 nM) and yet is metabolized fairly quickly (kcat 0.690 ± 0.010 s-1), with the aldehyde turnover product (2-(6-formylnaphthalen-2-yloxy)ethyl)trimefhylammonium serving as a real time reporting fluorophore of the enzyme activity. This allowed for the development of a fluorometric noncoupled assay that is 2 orders of magnitude more sensitive than the spectrophotometric benzylamine assay. The discovery of ANETA involved elaboration of the lead compound 6-methoxy-2-naphthalene- methaneamine by structure-based design, which recognized the ancillary cation binding site of BPAO as the most significant structural features controlling binding affinity. Structure-based design further ensured a high level of selectivity: ANETA is a good substrate of BPAO but is not a substrate of either porcine kidney diamine oxidase (pkDAO) or rat liver monoamine oxidase (MAO-B). ANETA represents the first highly sensitive, selective, and tight binding fluorogenic substrate of a copper amine oxidase that is able to respond directly to the enzyme activity in real time.
- Ling, Ke-Qing,Sayre, Lawrence M.
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supporting information; experimental part
p. 339 - 350
(2009/04/11)
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- Prodan-containing nucleotide and use thereof
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A compound represented by formula (1): wherein R1 is a substituent represented by formula (2): wherein R2 is ═O or —NH2, with the proviso that when R2 is ═O, H is attached to the 1-position N of the pyrimidine ring, and the bond between the 1-position N and the 6-position C is a single bond; or a substituent represented by formula (3): wherein R3 is —OH, ═O, or —NH2, with the proviso that when R3 is —OH or —NH2, R4 is H; when R3 is ═O, R4 is —NH2; and when R3 is ═O, H is attached to the 1-position N of the purine ring, and the bond between the 1-position N and the 6-position C is a single bond.
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Page/Page column 18; sheet 2
(2008/06/13)
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- Monitoring of microenvironmental changes in the major and minor grooves of DNA by dan-modified oligonucleotides
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(Graph Presented) We describe the synthesis of new environmentally sensitive fluorescence probes to elucidate DNA structures. DNA oligonucleotides containing fluorophore dan (6-(dimethylamino)-2-acylnaphthalene)-modified dC or dG were able to monitor the
- Kimura, Takumi,Kawai, Kiyohiko,Majima, Tetsuro
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p. 5829 - 5832
(2007/10/03)
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- A general method for the alkaline cleavage of enolisable ketones
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An efficient method is described for the cleavage of enolisable aryl methyl and aryl ethyl ketones using an excess of KOH in DMF at an elevated temperature. It presents a general hydrolytic method yielding aromatic carboxylic acids, and is complementary to the widely used oxidative methods for ketone cleavage.
- Zabjek, Alenka,Petric, Andrej
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p. 6077 - 6078
(2007/10/03)
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