Cancer cell inhibitory drug and cancer stem-cell detection probe

Abstract

An object of the present invention is to provide a cancer cell inhibitory drug, particularly a cancer stem-cell inhibitory drug, or a cancer stem-cell detection probe. A cancer cell inhibitory drug containing at least a compound represented by general formula (1).

1 . A cancer cell inhibitory drug comprising at least a compound represented by general formula (1): 
       
         
           
           
               
               
           
         
         where R 1  independently represents an alkyl group, a carboxylalkyl group, an alkoxycarbonylalkyl group or an alkylcarbonyloxyalkyl group; R 2  to R 5  each independently represent a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a halogen atom, an alkoxysulfonyl group, a N-alkylsulfamoyl group, an alkyloxycarbonyl group or a N-alkylcarbamoyl group; R 6  and R 7  each independently represent a hydrogen atom, an alkyl group or a phenyl group; R 8  and R 9  each independently represent a hydrogen atom, an alkyl group, an alkenyl group or a halogen atom; R 10  and R 11  each independently represent an alkyl group, an aryl group or an aralkyl group; R 9  and R 10  may bind together to form a nitrogen atom-containing hetero ring; X 1   −  represents an anionic group; 
         Y 1  represents an oxygen atom, a sulfur atom, a nitrogen atom binding to an alkyl group or —C(R 12 )(R 13 )—, where R 12  and R 13  each independently represent an alkyl group, and R 12  and R 13  may bind together to form an aliphatic ring; and 
         L is absent and carbons at both sides of L are bound through a double bond, is represented by general formula (2) or represents ═C(R 15 )—C(R 16 )═ where R 15  and R 16  each independently represent a hydrogen atom or an alkyl group: 
       
       
         
           
           
               
               
           
         
         where R 14  represents an alkyl group, a carboxylalkyl group, an alkoxycarbonylalkyl group or an alkylcarbonyloxyalkyl group. 
       
     
     
         2 . The cancer cell inhibitory drug according to  claim 1 , wherein the compound represented by the general formula (1) is a compound represented by general formula (3): 
       
         
           
           
               
               
           
         
         where R 17  each independently represents an alkyl group, a carboxylalkyl group, an alkoxycarbonylalkyl group or an alkylcarbonyloxyalkyl group; R 18  to R 21  each independently represent a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a halogen atom, an alkoxysulfonyl group, a N-alkylsulfamoyl group, an alkyloxycarbonyl group or a N-alkylcarbamoyl group; R 22  and R 23  each independently represent a hydrogen atom, an alkyl group or a phenyl group; R 24  represents a hydrogen atom or a halogen atom; R 25  represents an alkyl group, an aryl group or an aralkyl group; X 2   −  represents an anionic group; 
         Y 2  represents an oxygen atom, a sulfur atom, a nitrogen atom binding to an alkyl group or —C(R 26 )(R 27 )—, where R 26  and R 27  each independently represent an alkyl group, and R 26  and R 27  may bind together to form an aliphatic ring; and 
         A represents a cyclopentane ring or a benzene ring. 
       
     
     
         3 . The cancer cell inhibitory drug according to  claim 1 , wherein the compound represented by the general formula (1) is a compound represented by general formula (4): 
       
         
           
           
               
               
           
         
         where R 28  each independently represents an alkyl group, a carboxylalkyl group, an alkoxycarbonylalkyl group or an alkylcarbonyloxyalkyl group; R 29  to R 32  each independently represent a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a halogen atom, an alkoxysulfonyl group, a N-alkylsulfamoyl group, an alkyloxycarbonyl group or a N-alkylcarbamoyl group; R 33  and R 34  each independently represent a hydrogen atom, an alkyl group or a phenyl group; R 35  represents an alkyl group, a carboxylalkyl group, an alkoxycarbonylalkyl group or an alkylcarbonyloxyalkyl group; R 36  represents a hydrogen atom or a halogen atom; R 37  represents an alkyl group, an aryl group or an aralkyl group; X 3   −  represents an anionic group; 
         Y 3  represents an oxygen atom, a sulfur atom, a nitrogen atom binding to an alkyl group or —C(R 38 )(R 39 )—, where R 38  and R 39  each independently represent an alkyl group, and R 38  and R 39  may bind together to form an aliphatic ring; and 
         B represents a cyclopentane ring or a benzene ring. 
       
     
     
         4 . The cancer cell inhibitory drug according to  claim 1 , wherein the compound represented by the general formula (1) is a compound represented by general formula (5): 
       
         
           
           
               
               
           
         
         where R 40  each independently represents an alkyl group, a carboxylalkyl group, an alkoxycarbonylalkyl group or an alkylcarbonyloxyalkyl group; R 41  to R 44  each independently represent a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a halogen atom, an alkoxysulfonyl group, a N-alkylsulfamoyl group, an alkyloxycarbonyl group or a N-alkylcarbamoyl group; R 45  and R 46  each independently represent, an alkyl group or an aryl group; R 35  represents an alkyl group, an aryl group or an aralkyl group; X 4  represents an anionic group; and 
         Y 4  represents an oxygen atom, a sulfur atom, a nitrogen atom binding to an alkyl group or —C(R 47 )(R 48 )—, where R 47  and R 48  each independently represent an alkyl group, and R 47  and R 48  may bind together to form an aliphatic ring. 
       
     
     
         5 . The cancer cell inhibitory drug according to  claim 1 , wherein the compound represented by the general formula (1) is a compound having a luminescence property. 
     
     
         6 . The cancer cell inhibitory drug according to  claim 1 , wherein the cancer cell is a cancer stem cell. 
     
     
         7 . A cancer stem-cell detection probe comprising at least the cancer cell inhibitory drug according to  claim 6  as an active ingredient.