Amine-containing lipidoids and uses thereof

Abstract

Provided herein are lipidoids that may be prepared from the conjugate addition of alkylamines to acrylates. In some embodiments, provided lipidoids are biodegradable and may be used in a variety of drug delivery systems. Given the amino moiety of the lipidoids, they are well-suited for the delivery of polynucleotides, in addition to other agents. Nanoparticles containing the inventive lipidoids and polynucleotides have been prepared and have been shown to be effective in delivering siRNA.

1 - 126 . (canceled) 
     
     
         127 . A compound of formula: 
       
         
           
           
               
               
           
         
         or a salt thereof, wherein:
 each R A  is, independently, branched or unbranched, C 1-6  alkyl, C 3-7  cycloalkyl, or branched or unbranched, C 4-12  cycloalkylalkyl, each of which is, independently, optionally substituted with one or more fluorine radicals; 
 each R is, independently, hydrogen or —CH 2 CH 2 C(═O)OR B ; and 
 each R B  is, independently, branched or unbranched, C 10-14  alkyl optionally substituted with one or more fluorine radicals; 
 provided that at least one R group is —CH 2 CH 2 C(═O)OR B . 
 
       
     
     
         128 . The compound of  claim 127 , wherein all R A  groups are the same. 
     
     
         129 . The compound of  claim 127 , wherein the R A  groups are different. 
     
     
         130 . The compound of  claim 127 , wherein each R A  is, independently, branched or unbranched, C 1-6  alkyl. 
     
     
         131 - 132 . (canceled) 
     
     
         133 . The compound of  claim 127 , wherein each R A  is, independently, branched or unbranched, C 1-3  alkyl. 
     
     
         134 . (canceled) 
     
     
         135 . The compound of  claim 127 , wherein each R A  is, independently, C 3-7  cycloalkyl. 
     
     
         136 . The compound of  claim 135 , wherein R A  is cyclohexyl. 
     
     
         137 . The compound of  claim 127 , wherein each R A  is, independently, branched or unbranched, C 4-12  cycloalkylalkyl. 
     
     
         138 . The compound of  claim 127 , wherein the compound is of formula: 
       
         
           
           
               
               
           
         
         or a salt thereof, wherein
 each R B  is, independently, branched or unbranched, C 10-14  alkyl. 
 
       
     
     
         139 . The compound of  claim 127 , wherein at least three R groups are —CH 2 CH 2 C(═O)OR B . 
     
     
         140 . The compound of  claim 127 , wherein all R groups are —CH 2 CH 2 C(═O)OR B . 
     
     
         141 . The compound of  claim 127 , wherein all R B  groups are the same. 
     
     
         142 . The compound of  claim 127 , wherein each R B  is, independently, branched or unbranched, C 10-14  alkyl. 
     
     
         143 . The compound of  claim 127 , wherein each R B  is, independently, unbranched C 10-14  alkyl. 
     
     
         144 - 146 . (canceled) 
     
     
         147 . A compound of formula: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         or a salt thereof. 
       
     
     
         148 . (canceled) 
     
     
         149 . A nanoparticle comprising a compound of  claim 127 , or a salt thereof, and one or more agents to be delivered. 
     
     
         150 - 181 . (canceled) 
     
     
         182 . A composition comprising one or more compounds of  claim 127 , or a salt thereof, and an excipient. 
     
     
         183 - 194 . (canceled) 
     
     
         195 . A method of administering an agent, the method comprising:
 administering to a subject in need thereof a therapeutically effective amount of a composition comprising:   a compound of  claim 127 , or a salt thereof; and   an agent to be delivered.   
     
     
         196 - 200 . (canceled) 
     
     
         201 . The compound of  claim 127 , wherein the compound is of formula: 
       
         
           
           
               
               
           
         
         or a salt thereof. 
       
     
     
         202 . The compound of  claim 127 , wherein the compound is of formula: 
       
         
           
           
               
               
           
         
         or a salt thereof. 
       
     
     
         203 . The compound of  claim 127 , wherein the compound is of formula: 
       
         
           
           
               
               
           
         
         or a salt thereof. 
       
     
     
         204 . The compound of  claim 127 , wherein the compound is of formula: 
       
         
           
           
               
               
           
         
         or a salt thereof. 
       
     
     
         205 . The compound of  claim 127 , wherein the compound is of formula: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         or a salt thereof.