Title:
NOVEL FLUORESCENT DYE, COMPOSITION FOR LIPID DROPLET STAINING USING SAME, AND METHOD FOR IMAGING INTRACELLULAR LIPID DROPLETS USING SAME
Document Type and Number:
WIPO Patent Application WO/2020/045529
Kind Code:
A1
Abstract:
The present invention discloses a fluorescent dye represented by general formula (I), (II) or (III), which is specific to lipid droplets and enables lipid droplet staining with high sensitivity, while having no cytotoxicity and high intracellular retentivity, and which is applicable for kinetics observation of lipid droplets. The present invention also discloses a composition for lipid droplet staining and a method for imaging intracellular lipid droplets, each of which uses this fluorescent dye. In the formulae, each of R1 and R2 independently represents a hydrogen atom or a group that is selected from the group consisting of a cyano group, a formyl group, an aryl group, a substituted aryl group, a heteroaryl group and a substituted heteroaryl group, with at least one of R1 and R2 being a cyano group, a formyl group, an aryl group, a substituted aryl group, a heteroaryl group or a substituted heteroaryl group; R3 represents a functional group represented by general formula (i), (ii) or (iii); R11 represents a functional group represented by general formula (i); and R12 represents a nitro group, a cyano group, a sulfonyl group, a sulfoxyl group, a carbonyl group or a carboxyl group.
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Inventors:
TATENAKA YUKI (JP)
EZOE TAKATOSHI (JP)
OZEKI NOBUYUKI (JP)
ISHIYAMA MUNETAKA (JP)
EZOE TAKATOSHI (JP)
OZEKI NOBUYUKI (JP)
ISHIYAMA MUNETAKA (JP)
Application Number:
PCT/JP2019/033790
Publication Date:
March 05, 2020
Filing Date:
August 28, 2019
Export Citation:
Assignee:
DOJINDO LABORATORIES (JP)
International Classes:
C09B3/18; C09B57/00; C09B67/20; G01N33/92
Foreign References:
| JP6241014B2 | 2017-12-06 |
Other References:
CASTEL, NELLY ET AL.: "Photophysics and reversible photochemistry of 1, 2-diarylethylenes containing perylenyl or biphenylenyl as an aryl group", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY, A: CHEMISTRY, vol. 57, no. 1-3, 1991, pages 301 - 15, XP055697425, ISSN: 1010-6030
MAEDA, YOSHIHIRO ET AL.: "Photoinduced trans ? cis isomerization and intramolecular-charge-transfer interaction", PHOTOCHEMISTRY AND PICOSECOND LASER SPECTROSCOPY OF 4-SUBSTITUTED BETA-(1-PYRENYL)STYRENES, JOURNAL OF PHYSICAL CHEMISTRY, vol. 88, no. 13, 1984, pages 2714 - 2718, XP055697429, ISSN: 0022-3654
KATRITZKY, ALAN R. ET AL.: "Intramolecular charge transfer properties of dicyanovinyl-substituted aromatics", JOURNAL OF PHYSICAL CHEMISTRY, vol. 95, no. 15, 1991, pages 5737 - 5742, XP055697431, ISSN: 0022-3654
USTINOV, A. V. ET AL.: "Oligonucleotides containing arylacetylene residues: Synthesis and post-synthetic modification via [3+2] cycloaddition", RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION, vol. 55, no. 7, 2006, pages 1268 - 1274, XP019454004, ISSN: 1066-5285, DOI: 10.1007/s11172-006-0410-0
NIU, GUANGLE ET AL.: "Specific Two-Photon Imaging of Live Cellular and Deep-Tissue Lipid Droplets by Lipophilic AIEgens at Ultralow Concentration", CHEMISTRY OF MATERIALS, vol. 30, no. 14, 2 July 2018 (2018-07-02), pages 4778 - 4787, XP055697432, ISSN: 0897-4756
KIM, EUNHA ET AL.: "A Seoul-Fluor-based bioprobe for lipid droplets and its application in image-based high throughput screening", CHEMICAL COMMUNICATIONS, vol. 48, no. 17, 2012, pages 2331 - 2333, XP055697435, ISSN: 1359-7345
TATENAKA, YUKI ET AL.: "Monitoring Lipid Droplet Dynamics in Living Cells by Using Fluorescent", BIOCHEMISTRY, vol. 58, no. 6, 2019, pages 499 - 503, XP055697436, ISSN: 0006-2960
OKA, MASAKO ET AL.: "Exogenous Cytokine-Free Differentiation of Human Pluripotent Stem Cells into Classical Brown Adipocytes", CELLS, vol. 8, no. 4, 24 April 2019 (2019-04-24), pages 373, XP055697438, ISSN: 2073-4409, Retrieved from the Internet [retrieved on 20191021]
SONG, CHANG WOOK ET AL.: "A rationally designed polarity-viscosity sensitive probe for imaging lipid droplets", DYES AND PIGMENTS, vol. 171, no. 107718, 17 July 2019 (2019-07-17), pages 1 - 8, XP085790410, ISSN: 0143-7208, Retrieved from the Internet [retrieved on 20191021], DOI: 10.1016/j.dyepig.2019.107718
MAEDA, YOSHIHIRO ET AL.: "Photoinduced trans ? cis isomerization and intramolecular-charge-transfer interaction", PHOTOCHEMISTRY AND PICOSECOND LASER SPECTROSCOPY OF 4-SUBSTITUTED BETA-(1-PYRENYL)STYRENES, JOURNAL OF PHYSICAL CHEMISTRY, vol. 88, no. 13, 1984, pages 2714 - 2718, XP055697429, ISSN: 0022-3654
KATRITZKY, ALAN R. ET AL.: "Intramolecular charge transfer properties of dicyanovinyl-substituted aromatics", JOURNAL OF PHYSICAL CHEMISTRY, vol. 95, no. 15, 1991, pages 5737 - 5742, XP055697431, ISSN: 0022-3654
USTINOV, A. V. ET AL.: "Oligonucleotides containing arylacetylene residues: Synthesis and post-synthetic modification via [3+2] cycloaddition", RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION, vol. 55, no. 7, 2006, pages 1268 - 1274, XP019454004, ISSN: 1066-5285, DOI: 10.1007/s11172-006-0410-0
NIU, GUANGLE ET AL.: "Specific Two-Photon Imaging of Live Cellular and Deep-Tissue Lipid Droplets by Lipophilic AIEgens at Ultralow Concentration", CHEMISTRY OF MATERIALS, vol. 30, no. 14, 2 July 2018 (2018-07-02), pages 4778 - 4787, XP055697432, ISSN: 0897-4756
KIM, EUNHA ET AL.: "A Seoul-Fluor-based bioprobe for lipid droplets and its application in image-based high throughput screening", CHEMICAL COMMUNICATIONS, vol. 48, no. 17, 2012, pages 2331 - 2333, XP055697435, ISSN: 1359-7345
TATENAKA, YUKI ET AL.: "Monitoring Lipid Droplet Dynamics in Living Cells by Using Fluorescent", BIOCHEMISTRY, vol. 58, no. 6, 2019, pages 499 - 503, XP055697436, ISSN: 0006-2960
OKA, MASAKO ET AL.: "Exogenous Cytokine-Free Differentiation of Human Pluripotent Stem Cells into Classical Brown Adipocytes", CELLS, vol. 8, no. 4, 24 April 2019 (2019-04-24), pages 373, XP055697438, ISSN: 2073-4409, Retrieved from the Internet
SONG, CHANG WOOK ET AL.: "A rationally designed polarity-viscosity sensitive probe for imaging lipid droplets", DYES AND PIGMENTS, vol. 171, no. 107718, 17 July 2019 (2019-07-17), pages 1 - 8, XP085790410, ISSN: 0143-7208, Retrieved from the Internet
Attorney, Agent or Firm:
NAKASHIMA Kazuaki (JP)
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