Title:
FLUORESCENT COMPOUND AND AUTOPHAGY DETECTION REAGENT USING SAME
Document Type and Number:
WIPO Patent Application WO/2018/212355
Kind Code:
A1
Abstract:
The fluorescent compound is represented by general formula (I) or (II). In general formulas (I) and (II), R1 and R11 represent an alkyl group or ω-aminoalkyl group; R2 and R12 represent a hydrogen atom or alkyl group; R3 and R13 represent an atomic group represented by the formula -(CH2)m- (m is a natural number not greater than 10); R4 and R14 represent an atomic group represented by the formula -CH2- or -NR6- (-NR16-) (R6 and R16 represent an alkyl group); R5 and R15 represent an atomic group represented by the formula -(CH2)n- (n is a natural number not greater than 10); RN is an atomic group represented by any of formulas -NH2, -NHR7, -NR7R8, and -N+R7R8R9 (-NHR17, -NR17R18 and -N+R17R18R19) (R7, R8, R9, R17, R18, and R19 each independently represent an alkyl group); and when R2 (R12) is an alkyl group and R4 (R14) is the atomic group represented by -NR6- (-NR16-), R2 may be bonded to R6to form a ring (R12 may be bonded to R16 to form a ring).
Inventors:
IWASHITA HIDEFUMI (JP)
SAKAMOTO RYO (JP)
EZOE TAKATOSHI (JP)
OZEKI NOBUYUKI (JP)
ISHIYAMA MUNETAKA (JP)
SAKAMOTO RYO (JP)
EZOE TAKATOSHI (JP)
OZEKI NOBUYUKI (JP)
ISHIYAMA MUNETAKA (JP)
Application Number:
PCT/JP2018/019418
Publication Date:
November 22, 2018
Filing Date:
May 18, 2018
Export Citation:
Assignee:
DOJINDO LABORATORIES (JP)
International Classes:
C07D221/14; A61K49/00; C12Q1/02
Domestic Patent References:
| WO2000031039A1 | 2000-06-02 | |||
| WO2001017356A1 | 2001-03-15 | |||
| WO2017146145A1 | 2017-08-31 |
Foreign References:
| US5917045A | 1999-06-29 | |||
| CN105646346A | 2016-06-08 |
Other References:
GAO, Y. Q. ET AL.: "Theoretical Investigation of the Directional Electron Transfer in 4- Aminonaphthalimide Compounds", JOURNAL OF PHYSICAL CHEMISTRY A, vol. 106, 2002, pages 1956 - 1960, XP055124974, ISSN: 1089-5639
ELBERT, J. E. ET AL.: "A study of 4- (alkylamino)amino substituted 1, 8-naphthalimide fluoroionophores", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY, A: CHEMISTRY, vol. 169, 2005, pages 9 - 19, XP004638576, ISSN: 1010-6030
BANTHIA, S. ET AL.: "Long and Short Brick Network Architecture: Role of Water Molecules Acting as Three-Connecting Spacers", CRYSTAL GROWTH & DESIGN, vol. 6, 2006, pages 360 - 362, XP055550227, ISSN: 1528-7483
MISRA, A. ET AL.: "Microwave-assisted synthesis of 1, 8-naphthalic anhydride and fluorescent probes based on its derivatives", MONATSHEFTE FUER CHEMIE, vol. 140, 2009, pages 1209 - 1215, XP019762257, ISSN: 0026-9247
CARVALHO, C. P. ET AL.: "An aminonaphthalimide- putrescine conjugate as fluorescent probe for cucurbituril host-guest complexes", SUPRAMOLECULAR CHEMISTRY, vol. 25, 2013, pages 91 - 99, XP055550230, ISSN: 1029-0478
GAO, Y. ET AL.: "A naphthalimide-based [12]aneN3 compound as an effective and real-time fluorescence tracking non-viral gene vector", CHEMICAL COMMUNICATIONS, vol. 51, 2015, pages 16695 - 16698, XP055550233, ISSN: 1359-7345
DATABASE REGISTRY [O] 7 July 2016 (2016-07-07), retrieved from STN Database accession no. RN 1947418-80-5
QIAO, Q ET AL.: "A turn-on fluorescent probe for imaging lysosomal hydrogen sulfide in living cells", RSC ADVANCES, vol. 4, 2014, pages 25790 - 25794, XP055550241, ISSN: 2046-2069
LEE, M. H. ET AL.: "Mitochondria-Immobilized pH- Sensitive Off-On Fluorescent Probe", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 136, 2014, pages 14136 - 14142, XP055550248, ISSN: 0002-7863
FEILER, L. ET AL.: "Synthesis of perylene-3, 4- dicarboximides-novel highly photostable fluorescent dyes", LIEBIGS ANNALEN, vol. 7, 1995, pages 1229 - 1244, XP001041286, ISSN: 0947-3440
ZHANG, J ET AL.: "pH-responsive self-assembly of fluorophore-ended homopolymers", CHEMICAL COMMUNICATIONS, vol. 50, 2014, pages 7511 - 7513, XP055550255, ISSN: 1359-7345
IWASHITA, H. ET AL.: "Small fluorescent molecules for monitoring autophagic flux", FEBS LETTERS, vol. 592, 2 February 2018 (2018-02-02), pages 559 - 567, XP055550264, ISSN: 0014-5793
IWASHITA, H. ET AL.: "Live Cell Imaging of Mitochondrial Autophagy with a Novel Fluorescent Small Molecule", ACS CHEMICAL BIOLOGY, vol. 12, 2017, pages 2546 - 2551, XP055550272, ISSN: 1554-8929
ELBERT, J. E. ET AL.: "A study of 4- (alkylamino)amino substituted 1, 8-naphthalimide fluoroionophores", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY, A: CHEMISTRY, vol. 169, 2005, pages 9 - 19, XP004638576, ISSN: 1010-6030
BANTHIA, S. ET AL.: "Long and Short Brick Network Architecture: Role of Water Molecules Acting as Three-Connecting Spacers", CRYSTAL GROWTH & DESIGN, vol. 6, 2006, pages 360 - 362, XP055550227, ISSN: 1528-7483
MISRA, A. ET AL.: "Microwave-assisted synthesis of 1, 8-naphthalic anhydride and fluorescent probes based on its derivatives", MONATSHEFTE FUER CHEMIE, vol. 140, 2009, pages 1209 - 1215, XP019762257, ISSN: 0026-9247
CARVALHO, C. P. ET AL.: "An aminonaphthalimide- putrescine conjugate as fluorescent probe for cucurbituril host-guest complexes", SUPRAMOLECULAR CHEMISTRY, vol. 25, 2013, pages 91 - 99, XP055550230, ISSN: 1029-0478
GAO, Y. ET AL.: "A naphthalimide-based [12]aneN3 compound as an effective and real-time fluorescence tracking non-viral gene vector", CHEMICAL COMMUNICATIONS, vol. 51, 2015, pages 16695 - 16698, XP055550233, ISSN: 1359-7345
DATABASE REGISTRY [O] 7 July 2016 (2016-07-07), retrieved from STN Database accession no. RN 1947418-80-5
QIAO, Q ET AL.: "A turn-on fluorescent probe for imaging lysosomal hydrogen sulfide in living cells", RSC ADVANCES, vol. 4, 2014, pages 25790 - 25794, XP055550241, ISSN: 2046-2069
LEE, M. H. ET AL.: "Mitochondria-Immobilized pH- Sensitive Off-On Fluorescent Probe", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 136, 2014, pages 14136 - 14142, XP055550248, ISSN: 0002-7863
FEILER, L. ET AL.: "Synthesis of perylene-3, 4- dicarboximides-novel highly photostable fluorescent dyes", LIEBIGS ANNALEN, vol. 7, 1995, pages 1229 - 1244, XP001041286, ISSN: 0947-3440
ZHANG, J ET AL.: "pH-responsive self-assembly of fluorophore-ended homopolymers", CHEMICAL COMMUNICATIONS, vol. 50, 2014, pages 7511 - 7513, XP055550255, ISSN: 1359-7345
IWASHITA, H. ET AL.: "Small fluorescent molecules for monitoring autophagic flux", FEBS LETTERS, vol. 592, 2 February 2018 (2018-02-02), pages 559 - 567, XP055550264, ISSN: 0014-5793
IWASHITA, H. ET AL.: "Live Cell Imaging of Mitochondrial Autophagy with a Novel Fluorescent Small Molecule", ACS CHEMICAL BIOLOGY, vol. 12, 2017, pages 2546 - 2551, XP055550272, ISSN: 1554-8929
Attorney, Agent or Firm:
NAKASHIMA Kazuaki (JP)
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