643755-84-4Relevant academic research and scientific papers
Development of a General Aza-Cope Reaction Trigger Applied to Fluorescence Imaging of Formaldehyde in Living Cells
Bruemmer, Kevin J.,Walvoord, Ryan R.,Brewer, Thomas F.,Burgos-Barragan, Guillermo,Wit, Niek,Pontel, Lucas B.,Patel, Ketan J.,Chang, Christopher J.
, p. 5338 - 5350 (2017)
Formaldehyde (FA) is a reactive signaling molecule that is continuously produced through a number of central biological pathways spanning epigenetics to one-carbon metabolism. On the other hand, aberrant, elevated levels of FA are implicated in disease states ranging from asthma to neurodegenerative disorders. In this context, fluorescence-based probes for FA imaging are emerging as potentially powerful chemical tools to help disentangle the complexities of FA homeostasis and its physiological and pathological contributions. Currently available FA indicators require direct modification of the fluorophore backbone through complex synthetic considerations to enable FA detection, often limiting the generalization of designs to other fluorophore classes. To address this challenge, we now present the rational, iterative development of a general reaction-based trigger utilizing 2-aza-Cope reactivity for selective and sensitive detection of FA in living systems. Specifically, we developed a homoallylamine functionality that can undergo a subsequent self-immolative β-elimination, creating a FA-responsive trigger that is capable of masking a phenol on a fluorophore or any other potential chemical scaffold for related imaging and/or therapeutic applications. We demonstrate the utility of this trigger by creating a series of fluorescent probes for FA with excitation and emission wavelengths that span the UV to visible spectral regions through caging of a variety of dye units. In particular, Formaldehyde Probe 573 (FAP573), based on a resorufin scaffold, is the most red-shifted and FA sensitive in this series in terms of signal-to-noise responses and enables identification of alcohol dehydrogenase 5 (ADH5) as an enzyme that regulates FA metabolism in living cells. The results provide a starting point for the broader use of 2-aza-Cope reactivity for probing and manipulating FA biology.
Polyphosphoric acid terminal fluorescence labeled nucleotide and application thereof
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Paragraph 0046; 0052; 0053, (2019/11/29)
The invention relates to a 5 '-end phosphoric acid fluorescent labeled nucleotide, and provides a molecular structure and a synthesis method. The molecule can be better identified by DNA polymerase, and after the molecule is identified by the DNA polymerase, and reacted with the DNA polymerase for combination, and with the aid of alkaline phosphatase, the transform from the close to open state of a fluorescence signal can be rapidly realized, so that the 5 '-end phosphoric acid fluorescent labeled nucleotide as a polymerase substrate can be used in the nucleic acid sequence determination and other fields.
XANTHINE COMPOUND AND USE THEREOF
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, (2018/11/21)
A fluorescent probe for measurement of CYP3A activity, having an excellent CYP molecular species selectivity and detection sensitivity represented is represented by the following formula: In the formula, R1 represents a monovalent group, R2 represents a hydrogen atom or a monovalent group, R3 and R4 each independently represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group, R5 represents a monovalent group selected so that the ether bond of the O-benzyl moiety at the 6th position of the compound represented by formula (I) is oxidatively cleavable by the molecular species 3A of the cytochrome P-450, n represents an integer from 1 to 5, and when n is 2 or more, all or a part of the plurality of R5s may be the same as each other or different from each other.
XANTHENE COMPOUND AND USE THEREOF
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, (2016/10/10)
PROBLEM TO BE SOLVED: To provide a fluorescence probe for measuring activity of molecular species 3A of cytochrome P-450 having excellent cytochrome P-450 molecular species selectivity and excellent detection sensitivity. SOLUTION: There is provided a xanthene-based fluorescent compound represented by the formula (I), where R1 is a monovalent group, R2 is H or a monovalent group, R3 and R4 are H, a halogen atom or the like, R5 is a monovalent group in which an ether bond of 6-position O-benzyl part of the formula (I) can be oxidation cleaved by cytochrome P-450 molecular species 3A, n is an integer of 1 to 5 and R5s may be same or different when n is 2 or more. COPYRIGHT: (C)2016,JPOandINPIT
Fluorescence probe for lysophospholipase C/NPP6 activity and a potent NPP6 inhibitor
Kawaguchi, Mitsuyasu,Okabe, Takayoshi,Okudaira, Shinichi,Hanaoka, Kenjiro,Fujikawa, Yuuta,Terai, Takuya,Komatsu, Toru,Kojima, Hirotatsu,Aoki, Junken,Nagano, Tetsuo
, p. 12021 - 12030 (2011/10/02)
Nucleotide pyrophosphatases/phosphodiesterases (NPPs) are ubiquitous membrane-associated or secreted ectoenzymes that have a role in regulating extracellular nucleotide and phospholipid metabolism. Among the members of the NPP family, NPP1 and -3 act on nucleotides such as ATP, while NPP2, -6, and -7 act on phospholipids such as lysophosphatidylcholine and sphingomyelin. NPP6, a recently characterized NPP family member, is a choline-specific glycerophosphodiester phosphodiesterase, but its functions remain to be analyzed, partly due to the lack of highly sensitive activity assay systems and practical inhibitors. Here we report synthesis of novel NPP6 fluorescence probes, TG-mPC and its analogues TG-mPC3C, TG-mPC5C, TG-mPENE, TG-mPEA, TG-mPhos, TG-mPA, TG-mPMe, and TG-mPPr. Among the seven NPPs, only NPP6 hydrolyzed TG-mPC, TG-mPC3C, and TG-mPENE. TG-mPC was hydrolyzed in the cell lysate from NPP6-transfected cells, but not control cells, showing that it is suitable for use in cell-based NPP6 assays. We also examined the usefulness of TG-mPC as a fluorescence imaging probe. We further applied TG-mPC to carry out high-throughput NPP6 inhibitor screening and found several NPP6-selective inhibitors in a library of about 80 000 compounds. Through structure-activity relationship (SAR) analysis, we identified a potent and selective NPP6 inhibitor with an IC50 value of 0.21 μM. Our NPP6-selective fluorescence probe, TG-mPC, and the inhibitor are expected to be useful to elucidate the biological function of NPP6.
Fluorescent probe
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Page/Page column 9; 11, (2011/02/17)
A fluorescent probe which is represented by the following formula (I): (wherein, R1 represents a monovalent substituent other than hydrogen atom, carboxy group, or sulfo group; R2 represents hydrogen atom, or a monovalent substituent
Fluorescent probe
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Page/Page column 11-15, (2009/05/29)
A fluorescent probe which is represented by the following formula (I): (wherein, R1 and R2 represent hydrogen atom, or a substituent for trapping proton, a metal ion, or an active oxygen species, or the like; R3 represents
Evolution of fluorescein as a platform for finely tunable fluorescence probes
Urano, Yasuteru,Kamiya, Mako,Kanda, Kojiro,Ueno, Tasuku,Hirose, Kenzo,Nagano, Tetsuo
, p. 4888 - 4894 (2007/10/03)
Fluorescence imaging is the most powerful technique currently available for continuous observation of dynamic intracellular processes in living cells. Suitable fluorescence probes are naturally of critical importance for fluorescence imaging, but only a v
Extension of the applicable range of fluorescein: A fluorescein-based probe for Western blot analysis
Kamiya, Mako,Urano, Yasuteru,Ebata, Nobuyoshi,Yamamoto, Masami,Kosuge, Jyunichi,Nagano, Tetsuo
, p. 5439 - 5441 (2007/10/03)
(Chemical Equation Presented) The new star of Westerns: A highly sensitive fluorescence probe for alkaline phosphatase (ALP) based on a fluorescein derivative has been prepared and found to be suitable for use in Western blot analysis. The probe 1 is nonf
