US2011039792A1PendingUtilityA1

Selective Targeting Agents for Mitochondria

56
Assignee: WIPF PETERPriority: Jan 6, 2006Filed: Mar 31, 2010Published: Feb 17, 2011
Est. expiryJan 6, 2026(expired)· nominal 20-yr term from priority
A61K 47/55A61K 31/7048A61K 31/555A61K 47/54A61K 31/7034A61K 31/4468C07K 5/10C07K 7/06C07K 5/08A61K 47/64
56
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Claims

Abstract

The present invention provides a composition and related methods for delivering cargo to a mitochondria which includes (a) a membrane active peptidyl fragment having a high affinity with the mitochondria and (b) cargo. The cargo may be selected from a wide variety of desired cargos which are to be delivered to the mitochondria for a specific purpose. Compositions and methods are disclosed for treating an illness that is caused or associated with cellular damage or dysfunction which is caused by excessive mitochondrial production of reaction oxygen species (ROS). Compositions which act as mitochondria-selective targeting agents using the structural signaling of the β-turn recognizable by cells as mitochondria) targeting sequences are discussed. Mitochondria and cell death by way of apoptosis is inhibited as a result of the ROS-scavenging activity, thereby increasing the survival rate of the patient. In a preferred embodiment, the compositions and methods may be administered therapeutically in the field to patients with profound hemorrhagic shock so that survival could be prolonged until it is feasible to obtain surgical control of the bleeding vessels. In further preferred embodiments, the composition for scavenging radicals in a mitochondria membrane includes a radical scavenging agent and a membrane active compound having a high affinity with said mitochondrial membrane and associated methods. In another embodiment, the cargo transported by mitochondrial-selective targeting agents may include an inhibitor of nitric oxide synthase (NOS) enzyme activity.

Claims

exact text as granted — not AI-modified
1 . A composition for delivering cargo to a mitochondria comprising:
 a. a membrane active peptidyl fragment having a high affinity with the mitochondria; and   b. cargo.   
     
     
         2 - 77 . (canceled) 
     
     
         78 . A compound having the structure: 
       
         
           
           
               
               
           
         
       
       in which R1 is a cargo, R2 and R3 are independently one of a tert-butyl oxycarbonyl (t-Boc) and a benzyloxycarbonyl (Cbz) group, and A is one of 
       
         
           
           
               
               
           
         
       
       where R4 is H, F or methyl. 
     
     
         79 . The compound of  claim 78  having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         80 . The compound of  claim 78  having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         81 . The compound of  claim 78  having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         82 . The compound of  claim 78  in which R1 is a reactive oxygen species (ROS) scavenger. 
     
     
         83 . The compound of  claim 82  in which the ROS scavenger comprises a nitroxide radical. 
     
     
         84 . The compound of  claim 78  in which R1 is 2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine (AMT). 
     
     
         85 . The compound of  claim 78 , having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         86 . The compound of  claim 85 , having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         87 . The compound of  claim 85  having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         88 . The compound of  claim 85  having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         89 . The compound of  claim 85  in which R1 is a reactive oxygen species (ROS) scavenger. 
     
     
         90 . The compound of  claim 89  in which the ROS scavenger comprises a nitroxide radical. 
     
     
         91 . The compound of  claim 85  in which R1 is 2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine (AMT). 
     
     
         92 . A method for delivering a cargo to mitochondria comprising contacting the mitochondria with a compound having the structure: 
       
         
           
           
               
               
           
         
       
       in which R1 is a cargo, R2 and R3 are independently one of a tert-butyl oxycarbonyl (t-Boc) and a benzyloxycarbonyl (Cbz) group, and A is one of 
       
         
           
           
               
               
           
         
       
       where R4 is H, F or methyl. 
     
     
         93 . The method of  claim 92 , the compound having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         94 . The method of  claim 92 , the compound having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         95 . The method of  claim 92 , the compound having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         96 . The method of  claim 92  in which R1 is a reactive oxygen species (ROS) scavenger. 
     
     
         97 . The method of  claim 96  in which the ROS scavenger comprises a nitroxide radical. 
     
     
         98 . The method of  claim 92  in which R1 is 2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine (AMT). 
     
     
         99 . The method of  claim 92 , the compound having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         100 . The method of  claim 99 , the compound having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         101 . The method of  claim 99 , the compound having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         102 . The method of  claim 99 , the compound having the structure: 
       
         
           
           
               
               
           
         
       
     
     
         103 . The method of  claim 99  in which R1 is a reactive oxygen species (ROS) scavenger. 
     
     
         104 . The method of  claim 103  in which the ROS scavenger comprises a nitroxide radical. 
     
     
         105 . The method of  claim 99  in which R1 is 2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine (AMT).

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