US2021252152A1PendingUtilityA1

Near-infrared (nir) absorbing photosensitizers

Assignee: ORTA DOGU TEKNIK UNIVPriority: Jun 25, 2018Filed: Jun 25, 2018Published: Aug 19, 2021
Est. expiryJun 25, 2038(~11.9 yrs left)· nominal 20-yr term from priority
A61K 49/0021A61K 41/0057C07F 17/02C07F 9/6584A61P 35/00C07F 7/0814C07F 5/022C07F 7/0816
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Claims

Abstract

Near-infrared (NIR) absorbing photosensitizers for imaging and treatment of cancer in a photodynamic therapy (PDT) are provided. Specifically, the NIR photosensitizers are mitochondria targeted and water-soluble, and used as a cytotoxic drug in a photodynamic therapy of the cancer. The NIR photosensitizers are activated with wavelengths of light, wherein the light penetrates through a body not just a skin. Hence the NIR photosensitizers aim to transform PDT from being a specialized treatment to a generally applicable one. PDT is almost completely non-invasive compared to current treatment methods.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A near-infrared (NIR) absorbing photosensitizer, comprising formula A or B; 
       
         
           
           
               
               
           
         
       
       wherein, 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein, 
       R 7 =alkyl and aryl derivatives; 
       R 8 =H, Br, I, any alkyl and aryl derivatives; 
       R 9 =H, Br, I, any alkyl and aryl derivatives; 
       R 10 =H, Br, I, any alkyl and aryl derivatives; 
       R 11 =H, Br, I, any other possible alkyl and aryl derivatives; 
       R 12 =H, Br, I, any other possible alkyl and aryl derivatives; 
       R 13 =H, Br, I, any other possible alkyl and aryl derivatives; 
       R 14 =H, Br, I, any other possible alkyl and aryl derivatives; and 
       R 15 =H, Br, I, any other possible alkyl and aryl derivatives; 
       
         
           
           
               
               
           
         
       
       wherein, 
       R 7 =alkyl and aryl derivatives; 
       R 8 =H, Br, I, any alkyl and aryl derivatives; 
       R 9 =H, Br, I, any alkyl and aryl derivatives; 
       R 10 =H, Br, I, any alkyl and aryl derivatives; 
       R 11 =H, Br, I, any other possible alkyl and aryl derivatives; 
       R 12 =H Br, I, any other possible alkyl and aryl derivatives; 
       R 13 =H, Br, I, any other possible alkyl and aryl derivatives; 
       R 14 =H, Br, I, any other possible alkyl and aryl derivatives; and 
       R 15 =H, Br, I, any other possible alkyl and aryl derivatives. 
     
     
         2 . The NIR absorbing photosensitizer according to  claim 1 , comprising one selected from the group of 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         3 . A NIR absorbing photosensitizer, comprising formula C or D or E or F or G or H: 
       
         
           
           
               
               
           
         
       
       wherein: 
       
         
           
           
               
               
           
         
         wherein 
         R 3 =alkyl and aryl derivatives; 
         R 4 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 = H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 ==—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 11 =—H, —Br, —I, an other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 3 =alkyl and aryl derivatives; 
         R 4 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
       
       wherein: 
       
         
           
           
               
               
           
         
         wherein 
         R 3 =alkyl and aryl derivatives; 
         R 4 =alkyl and aryl derivatives; 
         R 5 =alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 12 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 13 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 5  alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 12 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 13 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
       
       wherein; 
       
         
           
           
               
               
           
         
         wherein 
         R 3 =alkyl and aryl derivatives; 
         R 4 =alkyl and aryl derivatives; 
         R 5 =alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 —H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 12 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 13 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 5 =alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 12 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 13 =—H, —Br, —I, any other possible alkyl, and aryl derivatives; 
       
       
         
           
           
               
               
           
         
       
       wherein; 
       
         
           
           
               
               
           
         
         wherein 
         R 2 =alkyl and aryl derivatives; 
         R 3 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 4 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 6 —H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives 
       
       
         
           
           
               
               
           
         
         wherein 
         R 2 =alkyl and aryl derivatives; 
         R 3 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 4 =—Br, —I, any other possible alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
       
       wherein; 
       
         
           
           
               
               
           
         
         wherein 
         R 3 =alkyl and aryl derivatives; 
         R 4 =alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 12 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 4 =alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 12 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
       
       wherein; 
       
         
           
           
               
               
           
         
         wherein 
         R 3 =alkyl and aryl derivatives; 
         R 4 =alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =—H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 12 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
       
       
         
           
           
               
               
           
         
         wherein 
         R 4 =alkyl and aryl derivatives; 
         R 5 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 6 =—H, —Br, —I, alkyl and aryl derivatives; 
         R 7 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 8 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 9 =—H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 10 =H, —Br, —I, any other possible alkyl and aryl derivatives; 
         R 11 =H, —Br, —I, any other possible alkyl and aryl derivatives; and 
         R 12 =H, —Br, —I, any other possible alkyl and aryl derivatives. 
       
     
     
         4 . The NIR absorbing photosensitizer according to  claim 3 , comprising one selected from the group of 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         5 . The NIR absorbing photosensitizer according to  claim 1 , wherein the NIR absorbing photosensitizer is mitochondria targeted. 
     
     
         6 . The NIR absorbing photosensitizer according to  claim 1 , wherein the NIR absorbing photosensitizer is water-soluble. 
     
     
         7 . A method of using the compounds according to  claim 1 , wherein the compounds are used as a cytotoxic drug in a photodynamic therapy of a cancer. 
     
     
         8 . The NIR absorbing photosensitizer according to  claim 1 , comprising formula I or J or K or L or M or N: 
       
         
           
           
               
               
           
         
         wherein; 
       
       
         
           
           
               
               
           
         
         wherein; 
       
       
         
           
           
               
               
           
         
         wherein: 
       
       
         
           
           
               
               
           
         
         wherein; 
       
       
         
           
           
               
               
           
         
         wherein: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein; 
       
       
         
           
           
               
               
           
         
       
     
     
         9 . The NIR absorbing photosensitizer according to  claim 8 , comprising one selected from the group of 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         10 . A method of using the compounds for an imaging of cancer cells according to  claim 9 . 
     
     
         11 . The NIR absorbing photosensitizer according to  claim 2 , wherein the NIR absorbing photosensitizer is mitochondria targeted. 
     
     
         12 . The NIR absorbing photosensitizer according to  claim 3 , wherein the NIR absorbing photosensitizer is mitochondria targeted. 
     
     
         13 . The NIR absorbing photosensitizer according to  claim 4 , wherein the NIR absorbing photosensitizer is mitochondria targeted. 
     
     
         14 . The NIR absorbing photosensitizer according to  claim 2 , wherein the NIR absorbing photosensitizer is water-soluble. 
     
     
         15 . The NIR absorbing photosensitizer according to  claim 3 , wherein the NIR absorbing photosensitizer is water-soluble. 
     
     
         16 . The NIR absorbing photosensitizer according to  claim 4 , wherein the NIR absorbing photosensitizer is water-soluble.

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