Water-soluble fluorescence compound and method for preparing the same

Patent metadata

Field	Value
Publication number	US-RE49223-E
Application number	US-202016861294-A
Country	US
Kind code	E1
Filing date	Apr 29, 2020
Priority date	Sep 16, 2011
Publication date	Sep 27, 2022
Grant date	Sep 27, 2022

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 Formula I 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.).

First claim

What is claimed is:

1. A display element comprising a fluorescent compound represented by the following Formula 1:

wherein, R 1 and R 2 are independently selected from the group consisting of a hydrogen atom; straight-chain or branched C1-C10 alkyl; C1-C10 alkylcarbonyl; C3-C6 cycloalkyl; C6-C30 aryl; and C5-C30 heteroaryl comprising:
at least one heteroatom N, O or S;
a residue of a water-soluble natural compound;
a residue of a water-soluble polymer; or
a residue of a water-soluble high molecular organic compound, provided that at least one of R 1 and R 2 represents a residue of a water-soluble natural compound, a residue of a water-soluble polymer or a residue of a water-soluble high molecular organic compound, said water-soluble natural compound, water-soluble polymer or water-soluble high molecular organic compound selected from a group consisting of monosaccharide, disaccharide, oligosaccharide, a water-soluble vitamin, polyethylene glycol, polypropylene glycol, PVA, crospovidone, PVP, and PVP-PVA.

2. A spectrometer, a two-photon absorptive storing device, a laser micro processing apparatus, or a photo dynamic therapy apparatus, comprising a fluorescent compound represented by the following Formula 1:

wherein, R 1 and R 2 are independently selected from the group consisting of a hydrogen atom; straight-chain or branched C1-C10 alkyl; C1-C10 alkylcarbonyl; C3-C6 cycloalkyl; C6-C30 aryl; and C5-C30 heteroaryl comprising:
at least one heteroatom N, O or S;
a residue of a water-soluble natural compound;
a residue of a water-soluble polymer; or
a residue of a water-soluble high molecular organic compound, provided that at least one of R 1 and R 2 represents a residue of a water-soluble natural compound, a residue of a water-soluble polymer or a residue of a water-soluble high molecular organic compound, said water-soluble natural compound, water-soluble polymer or water-soluble high molecular organic compound selected from a group consisting of monosaccharide, disaccharide, oligosaccharide, a water-soluble vitamin, polyethylene glycol, polypropylene glycol, PVA, crospovidone, PVP, and PVP-PVA.

3. A fluorescent compound comprising a compound represented by the following Formula 1:

wherein R 1 is selected from the group consisting of a hydrogen atom; straight-chain or branched C1-C10 alkyl; C1-C10 alkylcarbonyl; C3-C6 cycloalkyl; C6-C30 aryl; and C5-C30 heteroaryl including at least one heteroatom N, O or S;
wherein R 2 is a residue of a water-soluble natural compound or a residue of a water-soluble high molecular organic compound;
wherein said residue of a water-soluble natural compound is a substituent selected from the group consisting of a monosaccharide, and a disaccharide or oligomer thereof; and
wherein said residue of a water-soluble high molecular organic compound is a substituent selected from the group consisting of polyethylene glycol, polypropylene glycol, polyvinyl alcohol, crospovidone, polyvinylpyrrolidone, and PVP-PVA.

4. The fluorescent compound according to claim 3, wherein the fluorescent compound includes the fluorescent compound represented by the following Formula 2:

wherein R 1 is selected from the group consisting of a hydrogen atom; straight-chain or branched C1-C10 alkyl; C1-C10 alkylcarbonyl; C3-C6 cycloalkyl; C6-C30 aryl; and C5-C30 heteroaryl including at least one heteroatom N, O or S.

5. The fluorescent compound according to claim 3,
wherein the fluorescent compound includes the fluorescent compound represented by Formula 6:

6. A fluorescent compound comprising a compound represented by the following Formula 9, or Formula 12:

7. A fluorescent compound comprising a compound represented by the following Formula 13:

Assignees

• Snu R&Db Foundation
• Global Frontier Ct Multiscale Energy Systems

Inventors

• Kim Seong Keun
• Yang Il Seung
• Hwang Seon Jin
• Lee Jung Eun
• Lee Jong Woo
• Kang Jun Hee
• Lim Eun Hak

Classifications

• A61K49/0054

  Macromolecular compounds, i.e. oligomers, polymers, dendrimers · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• A61K49/0021

  the fluorescent group being a small organic molecule · CPC title

• A61K49/0052

  Small organic molecules (oligomers, polymers, dendrimers A61K49/0054) · CPC title

• C07H15/203

  Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems · CPC title