Water-soluble fluorescence compound and method for preparing the same

Patent metadata

Field	Value
Publication number	US-9708237-B2
Application number	US-201214344574-A
Country	US
Kind code	B2
Filing date	Sep 5, 2012
Priority date	Sep 16, 2011
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

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 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.).

First claim

What is claimed is:

1. A method of preparing a fluorescent compound comprising a compound represented by the following Formula 1, characterized in that it comprises a step of dissolving a compound represented by the following Formula 3 in water or an organic solvent, and a step of subjecting to an UV irradiation:

wherein, R 1 and R 2 are independently selected from the group consisting of 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,
characterized in that ascorbic acid, polyphenol or mixture thereof is further added before the UV radiation,
wherein the compound is fluorescent.

2. The method according to claim 1 , characterized in that it is conducted under N 2 atmosphere (N 2 purging).

Assignees

• Kim Seong Keun
• Yang Ii Seung
• Hwang Seon Jin
• Lee Jung Eun
• Lee Jong Woo
• Kang Jun Hee
• Lim Eun Hak
• Snu R&Db Foundation

Inventors

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

Classifications

• C07C49/248 Primary

  having unsaturation outside the aromatic rings · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07H15/203

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• A61K49/0052

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