Water-soluble fluorescence compound and method for preparing the same

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.).

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: