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WO2013039308A3 - A water-soluble fluorescence compound and method for preparing the same - Google Patents

A water-soluble fluorescence compound and method for preparing the same Download PDF

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Publication number
WO2013039308A3
WO2013039308A3 PCT/KR2012/007137 KR2012007137W WO2013039308A3 WO 2013039308 A3 WO2013039308 A3 WO 2013039308A3 KR 2012007137 W KR2012007137 W KR 2012007137W WO 2013039308 A3 WO2013039308 A3 WO 2013039308A3
Authority
WO
WIPO (PCT)
Prior art keywords
water
soluble
preparing
fluorescent
same
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2012/007137
Other languages
French (fr)
Other versions
WO2013039308A2 (en
Inventor
Seong Keun Kim
Il Seung Yang
Seon Jin Hwang
Jung Eun Lee
Jong Woo Lee
Jun Hee Kang
Eun Hak LIM
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SNU R&DB Foundation
Original Assignee
SNU R&DB Foundation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020120083376A external-priority patent/KR101244176B1/en
Application filed by SNU R&DB Foundation filed Critical SNU R&DB Foundation
Priority to US14/344,574 priority Critical patent/US9708237B2/en
Publication of WO2013039308A2 publication Critical patent/WO2013039308A2/en
Publication of WO2013039308A3 publication Critical patent/WO2013039308A3/en
Anticipated expiration legal-status Critical
Priority to US15/384,241 priority patent/US10077399B2/en
Priority to US16/861,294 priority patent/USRE49223E1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
    • A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0052—Small organic molecules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0054—Macromolecular compounds, i.e. oligomers, polymers, dendrimers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/06—Radiation therapy using light
    • A61N5/0613—Apparatus adapted for a specific treatment
    • A61N5/062—Photodynamic therapy, i.e. excitation of an agent
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • C07C49/248—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Luminescent Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention provides a water-soluble fluorescent compound of resveratrone 6-O-β-glucoside [(E)-4-(8-hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)naphthalen-2-yl)but-3-en-2-one] and its derivatives of Forumula 1 which have at least one water-soluble substituent, and a method for preparing the same by a photochemical reaction of resveratrol 3-O-β-glucoside and its derivatives of having Formula 3 which are not fluorescent. Said new water-soluble fluorescent compounds has single-photon absorptive characteristics and/or two-photon absorptive characteristics as well as no or little toxicity, and can be usefully utilized in fields that requires water-soluble fluorescent characteristics (diagnosis, fluorescent probe, in vivo imaging, display, etc.).
PCT/KR2012/007137 2011-09-16 2012-09-05 A water-soluble fluorescence compound and method for preparing the same Ceased WO2013039308A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US14/344,574 US9708237B2 (en) 2011-09-16 2012-09-05 Water-soluble fluorescence compound and method for preparing the same
US15/384,241 US10077399B2 (en) 2011-09-16 2016-12-19 Water-soluble fluorescence compound and method for preparing the same
US16/861,294 USRE49223E1 (en) 2011-09-16 2020-04-29 Water-soluble fluorescence compound and method for preparing the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20110093191 2011-09-16
KR10-2011-0093191 2011-09-16
KR10-2012-0083376 2012-07-30
KR1020120083376A KR101244176B1 (en) 2011-09-16 2012-07-30 A water-soluble fluorescence compound and method for preparing the same

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US14/344,574 A-371-Of-International US9708237B2 (en) 2011-09-16 2012-09-05 Water-soluble fluorescence compound and method for preparing the same
US15/384,241 Continuation US10077399B2 (en) 2011-09-16 2016-12-19 Water-soluble fluorescence compound and method for preparing the same

Publications (2)

Publication Number Publication Date
WO2013039308A2 WO2013039308A2 (en) 2013-03-21
WO2013039308A3 true WO2013039308A3 (en) 2013-05-10

Family

ID=47883872

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/007137 Ceased WO2013039308A2 (en) 2011-09-16 2012-09-05 A water-soluble fluorescence compound and method for preparing the same

Country Status (2)

Country Link
US (1) USRE49223E1 (en)
WO (1) WO2013039308A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101294993B1 (en) 2011-09-16 2013-08-13 서울대학교산학협력단 A high efficiency fluorescence compound and method for preparing the same
WO2013039308A2 (en) 2011-09-16 2013-03-21 Snu R&Db Foundation A water-soluble fluorescence compound and method for preparing the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090041632A (en) * 2007-10-24 2009-04-29 한국생명공학연구원 Water soluble photochromic compound for biomolecule labeling and biomolecule detection method using the same
US20100081724A1 (en) * 2007-01-30 2010-04-01 Andre Arigony Souto Process of obtainment of trans-resveratrol and/or emodin and nutraceuticcal compositions containing them

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5847225A (en) * 1997-04-25 1998-12-08 Albemarle Corporation Production of naphthyl-substituted ketones from naphthaldehydes
US20020102309A1 (en) * 1999-09-14 2002-08-01 Jane C. I. Hirsh Controlled release formulation for administration of an anti-inflammatory naphthalene derivative
WO2013039308A2 (en) 2011-09-16 2013-03-21 Snu R&Db Foundation A water-soluble fluorescence compound and method for preparing the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100081724A1 (en) * 2007-01-30 2010-04-01 Andre Arigony Souto Process of obtainment of trans-resveratrol and/or emodin and nutraceuticcal compositions containing them
KR20090041632A (en) * 2007-10-24 2009-04-29 한국생명공학연구원 Water soluble photochromic compound for biomolecule labeling and biomolecule detection method using the same

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KIM, H. M. ET AL.: "Two-Photon Fluorescent Turn-On Probe for Lipid Rafts in Live Cell and Tissue", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 130, no. 13, 2008, pages 4246 - 4247 *
LEMHADRI, M. ET AL.: "Palladium-catalyzed Heck reactions of alk-1-en-3-ones with aryl bromides: a very simple access to (E)-1-arylalk-1-en-3-ones", SYNTHESIS, no. 6, 2009, pages 1021 - 1035 *

Also Published As

Publication number Publication date
WO2013039308A2 (en) 2013-03-21
USRE49223E1 (en) 2022-09-27

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