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  1. Article ; Online: Naturally occurring quercetin and myricetin as potent inhibitors for human ectonucleotide pyrophosphatase/phosphodiesterase 1

    Peeradon Duangiad / Bodee Nutho / Thawatchai Chaijarasphong / Noppawan Phumala Morales / Thunyarat Pongtharangkul / Itaru Hamachi / Akio Ojida / Jirarut Wongkongkatep

    Scientific Reports, Vol 14, Iss 1, Pp 1-

    2024  Volume 13

    Abstract: Abstract Ecto-nucleotide pyrophosphatases/phosphodiesterases 1 (ENPP1) is a key enzyme in purinergic signaling pathways responsible for cell-to-cell communications and regulation of several fundamental pathophysiological processes. In this study, Kyoto ... ...

    Abstract Abstract Ecto-nucleotide pyrophosphatases/phosphodiesterases 1 (ENPP1) is a key enzyme in purinergic signaling pathways responsible for cell-to-cell communications and regulation of several fundamental pathophysiological processes. In this study, Kyoto Green, a rapid chemical sensor of pyrophosphate, was employed to screen for effective ENPP1 inhibitors among five representative flavonoids (quercetin, myricetin, morin, kaempferol, and quercetin-3-glucoside), five nucleosides (adenosine, guanosine, inosine, uridine, and cytidine), and five deoxynucleosides (2′- and 3′-deoxyadenosine, 2′-deoxyguanosine, 2′-deoxyinosine, and 2′-deoxyuridine). Conventional colorimetric, fluorescence, and bioluminescence assays revealed that ENPP1 was effectively inhibited by quercetin (K i ~ 4 nM) and myricetin (K i ~ 32 nM) when ATP was used as a substrate at pH 7.4. In silico analysis indicated that the presence of a chromone scaffold, particularly one containing a hydroxyl group at the 3′ position on the B ring, may promote binding to the active site pocket of ENPP1 and enhance inhibition. This study demonstrated that the naturally derived quercetin and myricetin could effectively inhibit ENPP1 enzymatic activity and may offer health benefits in arthritis management.
    Keywords Medicine ; R ; Science ; Q
    Subject code 572
    Language English
    Publishing date 2024-01-01T00:00:00Z
    Publisher Nature Portfolio
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  2. Article ; Online: Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions

    Noriaki Nakamura / Shohei Uchinomiya / Kazuya Inoue / Akio Ojida

    Molecules, Vol 25, Iss 2153, p

    2020  Volume 2153

    Abstract: Self-immolative linker is a useful building block of molecular probes, with broad applications in the fields of enzyme activity analysis, stimuli-responsive material science, and drug delivery. This manuscript presents N -methyl dimethyl methyl (i.e., ... ...

    Abstract Self-immolative linker is a useful building block of molecular probes, with broad applications in the fields of enzyme activity analysis, stimuli-responsive material science, and drug delivery. This manuscript presents N -methyl dimethyl methyl (i.e., trimethyl) carbamate as a new class of self-immolative linker for the fluorescence detection of enzyme reactions. The trimethyl carbamate was shown to spontaneously undergo intramolecular cyclization upon formation of a carboxylate group, to liberate a fluorophore with the second time rapid reaction kinetics. Interestingly, the auto-cleavage reaction of trimethyl carbamate was also induced by the formation of hydroxyl and amino groups. Fluorescent probes with a trimethyl carbamate could be applicable for fluorescence monitoring of the enzyme reactions catalyzed by esterase, ketoreductase, and aminotransferase, and for fluorescence imaging of intracellular esterase activity in living cells, hence demonstrating the utility of this new class of self-immolative linker.
    Keywords fluorescent probe ; self-immolative linker ; trimethyl carbamate ; enzyme detection ; Organic chemistry ; QD241-441
    Subject code 540
    Language English
    Publishing date 2020-05-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  3. Article ; Online: Improved polarized light microscopic detection of gouty crystals via dissolution with formalin and ethylenediamine tetraacetic acid

    Ruedee Hemstapat / Peeradon Duangiad / Borwornporn Tangketsarawan / Thitiya Phuagpan / Sinthida Chienwiwattanawong / Nuttinee Tangsrianugul / Akio Ojida / Jirarut Wongkongkatep

    Scientific Reports, Vol 13, Iss 1, Pp 1-

    2023  Volume 11

    Abstract: Abstract Conventional polarized light microscopy has been widely used to detect gouty crystals, but its limited sensitivity increases the risk of misidentification. In this study, a number of methods were investigated to improve the sensitivity of ... ...

    Abstract Abstract Conventional polarized light microscopy has been widely used to detect gouty crystals, but its limited sensitivity increases the risk of misidentification. In this study, a number of methods were investigated to improve the sensitivity of polarized light microscopy for the detection of monosodium urate monohydrate (MSUM) and calcium pyrophosphate dihydrate (CPPD) crystals. We found that coating glass slides with poly-L-lysine, a positively charged polymer, improved the attachment of crystals to the glass surface, resulting in clearer crystal images compared to non-coated slides. Additionally, the sensitivity of detection was further enhanced by selective dissolution, in which 40% v/v formalin phosphate buffer was employed to dissolve MSUM crystals but not CPPD while 10% ethylenediamine tetraacetic acid (EDTA) was employed to dissolved CPPD but not MSUM. The other possible interferences were dissolved in both EDTA and formalin solution. These methods were successfully applied to detect gouty crystals in biological milieu, including spiked porcine synovial fluid and inflamed rat subcutaneous air pouch tissues.
    Keywords Medicine ; R ; Science ; Q
    Subject code 500
    Language English
    Publishing date 2023-05-01T00:00:00Z
    Publisher Nature Portfolio
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  4. Article ; Online: Fluorescence Differentiation of ATP-Related Multiple Enzymatic Activities in Synovial Fluid as a Marker of Calcium Pyrophosphate Deposition Disease Using Kyoto Green

    Nattha Yongwattana / Nutsara Mekjinda / Tulyapruek Tawonsawatruk / Itaru Hamachi / Akio Ojida / Jirarut Wongkongkatep

    Molecules, Vol 25, Iss 5, p

    2020  Volume 1116

    Abstract: Calcium pyrophosphate deposition disease (CPPD) is a crystal induced inflammation in joints, and causes severe pain in elderly people. The accumulation of pyrophosphate (PPi) in synovial fluid (SF) results from several enzymatic reactions, especially the ...

    Abstract Calcium pyrophosphate deposition disease (CPPD) is a crystal induced inflammation in joints, and causes severe pain in elderly people. The accumulation of pyrophosphate (PPi) in synovial fluid (SF) results from several enzymatic reactions, especially the highly activated e-NPPs, which catalyze the conversion of ATP to PPi. This study demonstrates the detection of relative catalytic activity of 3 enzymes—ecto-nucleotide pyrophosphatase/phosphodiesterases (e-NPPs), tissue nonspecific alkaline phosphatase (TNAP), and ecto-nucleoside triphosphate diphosphohydrolases (e-NTPDases)—using a single molecular sensor called Kyoto Green. Kyoto Green exhibits excellent performance in sensing the catalytic activity of the commercial representatives of the e-NPPs, TNAP, and e-NTPDases, which are ENPP1, PPase, and apyrase, respectively, in both single-enzyme and multi-enzyme assays. Analysis of SF enzymes in 19 SF samples from human and swine revealed moderate activity of e-NPPs, high activity of e-NTPDases, and low activity of TNAP. Our newly developed method for analysis of multiple enzymatic activities using Kyoto Green in biological SF will assist improvement in accuracy of the CPPD prognosis/diagnosis, which will minimize unnecessary medical procedures.
    Keywords cppd ; pseudogout ; enpp1 ; ppase ; apyrase ; synovial fluid ; fluorescence detection ; molecular sensor ; Organic chemistry ; QD241-441
    Language English
    Publishing date 2020-03-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  5. Article ; Online: A multicolor and ratiometric fluorescent sensing platform for metal ions based on arene–metal-ion contact

    Anna Kanegae / Yusuke Takata / Ippei Takashima / Shohei Uchinomiya / Ryosuke Kawagoe / Kazuteru Usui / Akira Yamashita / Jirarut Wongkongkatep / Manabu Sugimoto / Akio Ojida

    Communications Chemistry, Vol 4, Iss 1, Pp 1-

    2021  Volume 10

    Abstract: Fluorescent probes can detect metal ions with high sensitivity, but their design typically relies on a limited number of sensing mechanisms. Here the use of arene–metal-ion contact as a sensing mechanism allows ratiometric detection of metal ions across ... ...

    Abstract Fluorescent probes can detect metal ions with high sensitivity, but their design typically relies on a limited number of sensing mechanisms. Here the use of arene–metal-ion contact as a sensing mechanism allows ratiometric detection of metal ions across a broad wavelength range.
    Keywords Chemistry ; QD1-999
    Language English
    Publishing date 2021-07-01T00:00:00Z
    Publisher Nature Portfolio
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  6. Article ; Online: Fluorescence Detection of Deoxyadenosine in Cordyceps spp. by Indicator Displacement Assay

    Arinta Agnie Dewantari / Nattha Yongwattana / Panwajee Payongsri / Sawinee Seemakhan / Suparerk Borwornpinyo / Akio Ojida / Jirarut Wongkongkatep

    Molecules, Vol 25, Iss 2045, p

    2020  Volume 2045

    Abstract: A rapid, sensitive and reliable indicator displacement assay (IDA) for specific detection of 2′- and 3′-deoxyadenosine (2′-dAde and 3′-dAde), the latter is also known as cordycepin, was established. The formation of inclusion complex between protonated ... ...

    Abstract A rapid, sensitive and reliable indicator displacement assay (IDA) for specific detection of 2′- and 3′-deoxyadenosine (2′-dAde and 3′-dAde), the latter is also known as cordycepin, was established. The formation of inclusion complex between protonated acridine orange (AOH + ) and cucurbit[7]uril (CB7) resulted in the hypochromic shift of fluorescent emission from 530 nm to 512 nm. Addition of cordycepin to the highly fluorescent AOH + /CB7 complex resulted in a unique tripartite AOH + /CB7/dAde complex with diminished fluorescence, and such reduction in emission intensity serves as the basis for our novel sensing system. The detection limits were 11 and 82 μM for 2′- and 3′-deoxyadenosine, respectively. The proposed method also demonstrated high selectivity toward 2′- and 3′-deoxyadenosine, owing to the inability of other deoxynucleosides, nucleosides and nucleotides commonly found in Cordyceps spp. to displace the AOH + from the AOH + /CB7 complex, which was confirmed by isothermal titration calorimetry (ITC), UV-Visible and proton nuclear magnetic resonance ( 1 H-NMR) spectroscopy. Our method was successfully implemented in the analysis of cordycepin in commercially available Ophiocordyceps and Cordyceps supplements, providing a novel and effective tool for quality assessment of these precious fungi with several health benefits.
    Keywords cordycepin ; fungi ; indicator displacement assay ; fluorescence ; detection ; cucurbit uril ; Organic chemistry ; QD241-441
    Subject code 333
    Language English
    Publishing date 2020-04-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  7. Article: Intracellular delivery of chemical probes using a glutathione-responsive traceless tag

    Aoyama, Eriko / Hirokazu Fuchida / Yuji Oshikawa / Shohei Uchinomiya / Akio Ojida

    Chemical communications. 2016 June 8, v. 52, no. 49

    2016  

    Abstract: A new glutathione (GSH)-responsive traceless tag that facilitates intracellular delivery of small molecule chemical probes has been developed. ...

    Abstract A new glutathione (GSH)-responsive traceless tag that facilitates intracellular delivery of small molecule chemical probes has been developed.
    Keywords chemical compounds ; chemical reactions ; glutathione
    Language English
    Dates of publication 2016-0608
    Size p. 7715-7718.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/c6cc03336a
    Database NAL-Catalogue (AGRICOLA)

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  8. Article ; Online: Electron Microscopic Detection of Single Membrane Proteins by a Specific Chemical Labeling

    Shigekazu Tabata / Marijo Jevtic / Nobutaka Kurashige / Hirokazu Fuchida / Munetsugu Kido / Kazushi Tani / Naoki Zenmyo / Shohei Uchinomiya / Harumi Harada / Makoto Itakura / Itaru Hamachi / Ryuichi Shigemoto / Akio Ojida

    iScience, Vol 22, Iss , Pp 256-

    2019  Volume 268

    Abstract: Summary: Electron microscopy (EM) is a technology that enables visualization of single proteins at a nanometer resolution. However, current protein analysis by EM mainly relies on immunolabeling with gold-particle-conjugated antibodies, which is ... ...

    Abstract Summary: Electron microscopy (EM) is a technology that enables visualization of single proteins at a nanometer resolution. However, current protein analysis by EM mainly relies on immunolabeling with gold-particle-conjugated antibodies, which is compromised by large size of antibody, precluding precise detection of protein location in biological samples. Here, we develop a specific chemical labeling method for EM detection of proteins at single-molecular level. Rational design of α-helical peptide tag and probe structure provided a complementary reaction pair that enabled specific cysteine conjugation of the tag. The developed chemical labeling with gold-nanoparticle-conjugated probe showed significantly higher labeling efficiency and detectability of high-density clusters of tag-fused G protein-coupled receptors in freeze-fracture replicas compared with immunogold labeling. Furthermore, in ultrathin sections, the spatial resolution of the chemical labeling was significantly higher than that of antibody-mediated labeling. These results demonstrate substantial advantages of the chemical labeling approach for single protein visualization by EM. : Nanoparticles; Biochemistry Methods; Structural Biology Subject Areas: Nanoparticles, Biochemistry Methods, Structural Biology
    Keywords Science ; Q
    Language English
    Publishing date 2019-12-01T00:00:00Z
    Publisher Elsevier
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  9. Article ; Online: Inhibition of G0/G1 Switch 2 Ameliorates Renal Inflammation in Chronic Kidney Disease

    Naoya Matsunaga / Eriko Ikeda / Keisuke Kakimoto / Miyako Watanabe / Naoya Shindo / Akito Tsuruta / Hisako Ikeyama / Kengo Hamamura / Kazuhiro Higashi / Tomohiro Yamashita / Hideaki Kondo / Yuya Yoshida / Masaki Matsuda / Takashi Ogino / Kazutaka Tokushige / Kazufumi Itcho / Yoko Furuichi / Takaharu Nakao / Kaori Yasuda /
    Atsushi Doi / Toshiaki Amamoto / Hironori Aramaki / Makoto Tsuda / Kazuhide Inoue / Akio Ojida / Satoru Koyanagi / Shigehiro Ohdo

    EBioMedicine, Vol 13, Iss C, Pp 262-

    2016  Volume 273

    Abstract: Chronic kidney disease (CKD) is a global health problem, and novel therapies to treat CKD are urgently needed. Here, we show that inhibition of G0/G1 switch 2 (G0s2) ameliorates renal inflammation in a mouse model of CKD. Renal expression of chemokine (C- ...

    Abstract Chronic kidney disease (CKD) is a global health problem, and novel therapies to treat CKD are urgently needed. Here, we show that inhibition of G0/G1 switch 2 (G0s2) ameliorates renal inflammation in a mouse model of CKD. Renal expression of chemokine (C-C motif) ligand 2 (Ccl2) was increased in response to p65 activation in the kidneys of wild-type 5/6 nephrectomy (5/6Nx) mice. Moreover, 5/6Nx Clk/Clk mice, which carry homozygous mutations in the gene encoding circadian locomotor output cycles kaput (CLOCK), did not exhibit aggravation of apoptosis or induction of F4/80-positive cells. The renal expression of G0s2 in wild-type 5/6Nx mice was important for the transactivation of Ccl2 by p65. These pathologies were ameliorated by G0s2 knockdown. Furthermore, a novel small-molecule inhibitor of G0s2 expression was identified by high-throughput chemical screening, and the inhibitor suppressed renal inflammation in 5/6Nx mice. These findings indicated that G0s2 inhibitors may have applications in the treatment of CKD.
    Keywords Chronic renal disease ; Circadian clock ; G0s2 ; Small compound inhibitor ; Medicine ; R ; Medicine (General) ; R5-920
    Subject code 616
    Language English
    Publishing date 2016-11-01T00:00:00Z
    Publisher Elsevier
    Document type Article ; Online
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