Bacteriochlorin imides

Abstract

Compound of Formula I: are described, along with compositions containing the same and methods of use thereof.

That which is claimed is: 
     
         1 . A compound of Formula I: 
       
         
           
           
               
               
           
         
       
       wherein:
 M is a metal or is absent; 
 each X is independently selected from the group consisting of Se, NH, CH 2 , O and S; 
 Z is O, S or a covalent bond; 
 R and each R 1  and R 2  is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups; or R 1  and R 2  together are ═O or spiroalkyl; 
 each R 3  and R 4  is independently selected from the group consisting of alkyl, cycloalkyl, aryl, and arylalkyl; 
 each R 5  is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups; and 
 R 6 , R 6a  and R 7a  are each independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups; and 
 R 8  is selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups; 
 or a pharmaceutically acceptable salt thereof. 
 
     
     
         2 . The compound of  claim 1 , wherein M is present and is selected from the group consisting of Pd, Pt, Mg, Zn, Al, Ga, In, Sn, Cu, Ni, and Au. 
     
     
         3 . The compound of  claim 1 , wherein each X is NH. 
     
     
         4 . The compound of  claim 1 , wherein Z is O. 
     
     
         5 . The compound of  claim 1 , wherein Z is S. 
     
     
         6 . The compound of  claim 1 , wherein Z is a covalent bond. 
     
     
         7 . A compound of  claim 1  wherein said targeting group is selected from the group consisting of proteins, peptides, and nucleic acids. 
     
     
         8 . In a method of detecting cells or particles by flow cytometry, wherein said cells or particles are labelled with a detectable luminescent compound, the improvement comprising utilizing a bacteriochlorin as the luminescent compound, wherein said bacteriochlorin is a compound of  claim 1 . 
     
     
         9 . A composition consisting of a compound of  claim 1 , optionally in a solvent, wherein: said composition has a peak molar absorption coefficient in solution of 10,000 to 300,000 M −1  cm −1  at a wavelength between 700 and 1000 nanometers; and/or said composition has a loss of not more than 20 percent of said compound when stored in a sealed vessel at room temperature in the absence of ambient light for at least 3 months. 
     
     
         10 . A pharmaceutical composition comprising a compound of  claim 1  in a pharmaceutically acceptable carrier. 
     
     
         11 . A method for treating a target in a subject in need thereof, comprising: (i) administering to said subject the compound of  claim 1  or a pharmaceutically acceptable conjugate thereof that preferentially associates with the target, and (ii) irradiating the target with light of a wavelength and intensity sufficient to treat said target. 
     
     
         12 . A photodynamic therapy method for treating hyperproliferative tissue in a subject in need thereof, comprising: (i) administering to said subject a compound of  claim 1  or a pharmaceutically acceptable conjugate thereof that preferentially associates with the hyperproliferative tissue, and (ii) irradiating the target with light of a wavelength and intensity sufficient to activate the compound, and thereby treat said hyperproliferative tissue. 
     
     
         13 . A method for detecting the presence of a hyperproliferative tissue in a subject, comprising: (i) administering to the subject a compound of  claim 1  or a pharmaceutically acceptable conjugate thereof that preferentially associates with the hyperproliferative tissue; and then (ii) visualizing the compound within the patient. 
     
     
         14 . A kit to treat hyperproliferative disorders, comprising the compound of  claim 1  or a pharmaceutically acceptable conjugate thereof and instructions teaching a method of photodynamic therapy. 
     
     
         15 . In a light harvesting rod, the improvement comprising utilizing a compound of  claim 1  as at least one chromophore therein. 
     
     
         16 . In a solar cell, the improvement comprising utilizing a compound of  claim 1  as the chromophore or photosensitizer therein; wherein said compound of  claim 1  is in monomeric form or is optionally linked to at least one additional chromophore to form a light harvesting rod. 
     
     
         17 . In an information storage device utilizing a charge storage molecule in monomeric or polymeric form, the improvement comprising utilizing as said charge storage molecule a compound of  claim 1 . 
     
     
         18 . A method of making a compound of  claim 1 , comprising:
 Reacting a compound of Formula II:   
       
         
           
           
               
               
           
         
         with a compound of the formula R 8 NH 2  and carbon monoxide in an organic solvent in the presence of a base and a transition metal catalyst to produce a compound of  claim 1 , wherein: 
         X′ is halo; 
         R′ is loweralkyl; and 
         the remaining substituents are as given in  claim 1 .