Hydrazinyl lipidoids and uses thereof

Abstract

The present disclosure is directed to hydrazinyl lipidoids, formulations thereof further comprising at least one active agent, as well as methods of delivering the at least one active agent to a target organism.

1 . A compound of formula (I): 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is, independently, hydrogen, an optionally substituted C 1-20  aliphatic group, or an optionally substituted C 1-20  heteroaliphatic group; 
         R 2  is, independently, an optionally substituted C 1-20  aliphatic group or an optionally substituted C 1-20  heteroaliphatic group; 
         R A  is hydrogen, an optionally substituted C 1-20  aliphatic group, an optionally substituted, C 1-20  heteroaliphatic group, or a group of formula (II): 
       
       
         
           
           
               
               
           
         
         
           wherein 
           R 3  is, independently, hydrogen, an optionally substituted C 1-20  aliphatic group, or an optionally substituted C 1-20  heteroaliphatic group; and 
           R 4  is, independently, an optionally substituted C 1-20  aliphatic group or an optionally substituted C 1-20  heteroaliphatic group; 
         
         R B  is an optionally substituted aryl group, an optionally substituted heteroaryl group, or a group of formula (II): 
       
       
         
           
           
               
               
           
         
         
           wherein R 3  and R 4  are as defined above; and 
         
         wherein any one or more of R 1 , R 2 , R 3 , and R 4  together with another R 1 , R 2 , R 3 , or R 4  or one of R A  and R B  optionally defines a carbocyclic or heterocyclic ring system; and 
         R A  and R B  together optionally define a carbocyclic or heterocyclic ring system. 
       
     
     
         2 . The compound of  claim 1 , wherein R A  and R B  are each a group of formula (II): 
       
         
           
           
               
               
           
         
       
     
     
         3 . The compound of  claim 2 , wherein R 1  and R 3  are identical and R 2  and R 4  are identical. 
     
     
         4 . The compound of  claim 3 , wherein R 1  and R 3  are hydrogen and R 2  and R 4  are an unbranched C 1-20  aliphatic group. 
     
     
         5 . The compound of  claim 4 , wherein R 2  and R 4  are selected from the group consisting of methyl, n-butyl, n-pentyl, n-decanyl, and n-dodecanyl. 
     
     
         6 - 15 . (canceled) 
     
     
         16 . A microparticle or nanoparticle comprising a compound of  claim 1  and an active agent to be delivered. 
     
     
         17 . The microparticle or nanoparticle of  claim 16 , wherein the active agent to be delivered is selected from the group consisting of polynucleotides, oligonucleotides, proteins, peptides, and small molecules. 
     
     
         18 . The microparticle or nanoparticle of  claim 17 , wherein the active agent to be delivered is an oligonucleotide or a polynucleotide. 
     
     
         19 . The microparticle or nanoparticle of  claim 18 , wherein the active agent to be delivered is an RNA. 
     
     
         20 . The microparticle or nanoparticle of  claim 19 , wherein the RNA is a small interfering RNA (siRNA) or a double-stranded RNA (dsRNA). 
     
     
         21 . A formulation comprising the compound of  claim 1  and an active agent to be delivered. 
     
     
         22 . The formulation of  claim 21 , wherein the active agent to be delivered is an oligonucleotide or a polynucleotide. 
     
     
         23 . An herbicidal formulation comprising the compound of  claim 1 , an herbicidal agent to be delivered, and an agriculturally acceptable carrier. 
     
     
         24 . An insecticidal formulation comprising the compound of  claim 1 , an insecticidal agent to be delivered, and an agriculturally acceptable carrier. 
     
     
         25 . A formulation for controlling a plant pathogen, comprising the compound of  claim 1 , an agent to be delivered that controls a plant pathogen, and an agriculturally acceptable carrier. 
     
     
         26 . A method of regulating expression of a gene in an organism, comprising applying the formulation of  claim 21  to the organism. 
     
     
         27 . A method of controlling a weed, comprising delivering to the weed an effective amount of the formulation of  claim 23 . 
     
     
         28 . A method of controlling an insect, comprising delivering to the insect an effective amount of the formulation of  claim 24 . 
     
     
         29 . A method of controlling a plant pathogen, comprising applying the formulation of  claim 25  to the plant pathogen, or to a plant infected with the plant pathogen. 
     
     
         30 . A plant cell, insect cell or mammalian cell comprising the compound of  claim 1 .