Title:
FLUORESCENT COMPOUND RESPONDING TO MITOCHONDRIAL MEMBRANE POTENTIAL
Document Type and Number:
WIPO Patent Application WO/2016/143335
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a compound that is a pigment usable for staining cells, is soluble in water, shows a high emission efficiency and is capable of translocating from mitochondria to nucleus depending on mitochondrial membrane potential.
A compound represented by formula (1) [wherein: R1 represents a C1-C10 alkyl group; Z- represents a counter anion to a pyridinium cation; and X represents any of condensed polycyclic groups represented by the formulae (wherein a wavy line stands for a binding site to an adjacent pyridine ring, provided that a naphthylene group (i) optionally has an electron donating group)], which is soluble in water, shows a high emission efficiency and is capable of translocating from mitochondria to nucleus depending on mitochondrial membrane potential, is usable as a fluorescent pigment for staining cells.
Inventors:
KAWAMATA JUN (JP)
SUZUKI YASUTAKA (JP)
MORITOMO HIROKI (JP)
FUJIKI SHOHEI (JP)
SUZUKI YASUTAKA (JP)
MORITOMO HIROKI (JP)
FUJIKI SHOHEI (JP)
Application Number:
PCT/JP2016/001281
Publication Date:
September 15, 2016
Filing Date:
March 09, 2016
Export Citation:
Assignee:
OTSUKA DENSHI KK (JP)
International Classes:
C07D213/38; C09B6/00; C09B57/00; C09B67/44; G01N21/64; G01N21/78; G01N33/48
Domestic Patent References:
| WO2014069675A1 | 2014-05-08 | |||
| WO2007113321A1 | 2007-10-11 |
Foreign References:
| JP2010116483A | 2010-05-27 | |||
| JP2007171781A | 2007-07-05 |
Other References:
TOMINAGA, M. ET AL.: "A Red Fluorescence Two- photon Absorption Probe for Sensitive Imaging of Live Mitochondria", CHEMISTRY LETTERS, vol. 43, no. 9, 2014, pages 1490 - 1492, XP055313353, ISSN: 0366-7022
MORITOMO, H. ET AL.: "A Biphenyl Type Two-Photon Fluorescence Probe for Monitoring the Mitochondrial Membrane Potential", CELL, vol. 39, no. 2, 2014, pages 125 - 133, XP055313357, ISSN: 1347-3700
NAUD-MARTIN, D. ET AL.: "Acri-2,7-Py, a bright red-emitting DNA probe identified through screening of a distyryl dye library", BIOTECHNOLOGY JOURNAL, vol. 9, no. 2, 2014, pages 301 - 310, XP055224335, ISSN: 1860-6768
ZHANG, SI ET AL.: "A BODIPY-based fluorescent dye for mitochondria in living cells, with low cytotoxicity and high photostability", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 11, no. 4, 2013, pages 555 - 558, XP055313365, ISSN: 1477-0520
TSAI, Y. ET AL.: "Effect of different electronic properties on 9-aryl-substituted BMVC derivatives for new fluorescence probes", JOURNAL OF LUMINESCENCE, vol. 127, no. 1, 2007, pages 41 - 47, XP022082832, ISSN: 0022-2313
MORITOMO, H. ET AL.: "An efficient two-photon induced fluorescent naphthalene derivative sensitive to mitochondrial membrane potential", 95TH ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN IN SPRING (2015) KOEN YOKOSHU IV, 11 March 2015 (2015-03-11), pages 1453, ISSN: 0285-7626
MORITOMO, H. ET AL.: "A Biphenyl Type Two-Photon Fluorescence Probe for Monitoring the Mitochondrial Membrane Potential", CELL, vol. 39, no. 2, 2014, pages 125 - 133, XP055313357, ISSN: 1347-3700
NAUD-MARTIN, D. ET AL.: "Acri-2,7-Py, a bright red-emitting DNA probe identified through screening of a distyryl dye library", BIOTECHNOLOGY JOURNAL, vol. 9, no. 2, 2014, pages 301 - 310, XP055224335, ISSN: 1860-6768
ZHANG, SI ET AL.: "A BODIPY-based fluorescent dye for mitochondria in living cells, with low cytotoxicity and high photostability", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 11, no. 4, 2013, pages 555 - 558, XP055313365, ISSN: 1477-0520
TSAI, Y. ET AL.: "Effect of different electronic properties on 9-aryl-substituted BMVC derivatives for new fluorescence probes", JOURNAL OF LUMINESCENCE, vol. 127, no. 1, 2007, pages 41 - 47, XP022082832, ISSN: 0022-2313
MORITOMO, H. ET AL.: "An efficient two-photon induced fluorescent naphthalene derivative sensitive to mitochondrial membrane potential", 95TH ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN IN SPRING (2015) KOEN YOKOSHU IV, 11 March 2015 (2015-03-11), pages 1453, ISSN: 0285-7626
Attorney, Agent or Firm:
HIROTA, Masanori (JP)
Masaki Hirota (JP)
Masaki Hirota (JP)
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