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. The present invention provides a cancer cell inhibitory drug comprising at least one compound represented by general formula (1) as an active ingredient.

1 . A cancer cell inhibitory drug represented by general formula (1): 
       
         
           
           
               
               
           
         
         where R 1  and R 2  each independently represent an alkyl group, a carboxylalkyl group, an alkoxycarbonylalkyl group or an alkylcarbonyloxyalkyl group; R 3  to R 10  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, a carbamoyl group or a N-alkylcarbamoyl group; R 3  and R 4 , R 5  and R 6 , R 7  and R 8 , and R 9  and R 10  may be each independently cyclized to form a benzene ring; 
         X 1   −  represents an anionic group; 
         Y 1  is a group including *1, *2, and *5 and represents any one of: 
         *1-S—*5-*2, *1-O—*5-*2, *1-C(—R 11 ,—R 12 )—*5-*2, and *1-*5-CH═CH—*2, 
         where R 11  and R 12  each independently represent an alkyl group, and R 11  and R 12  may bind together to form a ring; 
         Y 2  is a group including *3, *4, and *6 and represents any one of: 
         *4=*6-S—*3, *4=*6-O—*3, *4=*6-C(—R 51 ,—R 52 )—*3, *4=*6-CH═CH—*3, and *4=CH—CH═*6-*3, 
         where R 51  and R 52  each independently represent an alkyl group, and R 51  and R 52  may bind together to form a ring; and 
         a group including A to carbon atoms represented by *5 and *6 is represented by general formula (2) or (3): 
       
       
         
           
           
               
               
           
         
         where R 13  to R 15  each independently represent a hydrogen atom, an alkyl group or an aryl group; n represents an integer of 0 to 2; 
         R 16  represents a hydrogen atom, a phenyl group, a thiol group, an alkoxy group, an aryloxy group or a halogen atom; and 
         R 17  and R 18  each independently represent a hydrogen atom, an alkyl group or an alkyloxycarbonyl group. 
       
     
     
         2 . The cancer cell inhibitory drug according to  claim 1 , wherein the general formula (1) is represented by general formula (4): 
       
         
           
           
               
               
           
         
         where R 19  and R 20  each independently represent an alkyl group, a carboxylalkyl group, an alkylcarbonyloxyalkyl group or an alkoxycarbonylalkyl group; R 21  to R 28  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 21  and R 22 , R 23  and R 24 , R 25  and R 26 , and R 27  and R 28  may be each independently cyclized to form a benzene ring; 
         R 29  to R 31  each independently represent a hydrogen atom, an alkyl group or an aryl group; m represents an integer of 0 to 2; X 2   −  represents an anionic group; and 
         Y 3  and Y 4  each independently represent an oxygen atom, a sulfur atom or an alkylene group, and the alkylene group may have a substituent being alkyl groups, wherein if the alkylene group has two or more substituents being alkyl groups they may bind together to form an aliphatic ring. 
       
     
     
         3 . The cancer cell inhibitory drug according to  claim 1 , wherein the general formula (1) is represented by general formula (5): 
       
         
           
           
               
               
           
         
         where R 34  and R 35  each independently represent an alkyl group, a carboxylalkyl group or an alkoxycarbonylalkyl group, R 36  to R 43  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 36  and R 37 , R 38  and R 39 , R 40  and R 41 , and R 42  and R 43  may be each independently cyclized to form a benzene ring; 
         R 44  represents a hydrogen atom, a phenyl group, a thiol group, an alkoxy group, an aryloxy group or a halogen atom; R 45  and R 46  each independently represent a hydrogen atom, an alkyl group or an alkyloxycarbonyl group; X 3   −  represents an anionic group; and 
         Y 5  and Y 6  each independently represent an oxygen atom, a sulfur atom or an alkylene group, and the alkylene group may have substituents being alkyl groups which may bind together to form an aliphatic ring. 
       
     
     
         4 . The cancer cell inhibitory drug according to  claim 1 , wherein the general formula (1) is represented by general formula (6): 
       
         
           
           
               
               
           
         
         where R 49  and R 50  each independently represent an alkyl group, a carboxylalkyl group, an alkylcarbonyloxyalkyl group or an alkoxycarbonylalkyl group; and X 4   −  represents anionic group. 
       
     
     
         5 . The cancer cell inhibitory drug according to  claim 1 , wherein a 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 the cancer cell inhibitory drug according to  claim 6  as an active ingredient.