Self-assembled active agents

Abstract

A self-assembled active agent may be formed by a process including covalently bonding at least a first component molecule and a second component molecule, the two component molecules displaying synergy such that the effective amount of the self-assembled active agent is lower than the sum of the effective amounts of the first component molecule and the second component molecule. The component molecules may be chosen such that the covalent bonding is reversible, for example through a hydrazone bond between an amine and an aldehyde. The active agent may thus have controllable activity such as an antimicrobial agent, a biocide, an antiviral agent, a preservative, an antifouling agent, a disinfectant, or a sensor agent, such as for a particular molecule or for pH.

We claim: 
     
         1 . A method of treating for a pathogen or microbe, the method comprising applying an effective amount of an active agent to a designated area or object, wherein the active agent is a compound of the formula: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 3  are, independently, optionally substituted one or more times, 
         wherein in the case of either of R 1  or R 3  having at least one substitution, a first substitution is one of an alcohol group, an aldehyde group, a 5-member ring, a 6-member ring, a halide, a halide-diol, an ether, and a straight or branched, saturated or unsaturated aliphatic group, 
         wherein n is at least 2, and 
         wherein R 1  is one of the following: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R 2  is: 
       
       
         
           
           
               
               
           
         
         and wherein R 3  is one of: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         2 . The method of treating for a pathogen or microbe of  claim 1 , wherein the active agent is one of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         and an analog thereof. 
       
     
     
         3 . An active agent,
 wherein the active agent is formed by a process comprising covalently bonding at least a first component molecule and a second component molecule,   wherein an effective amount of the active agent is lower than the sum of an effective amount of the first component molecule when used individually and an effective amount of the second component molecule when used individually,   wherein the first component molecule is an amine and the second component molecule is one of an aldehyde and a ketone, and   wherein the covalent bonding between the first component molecule and the second component molecule includes the formation of a hydrazone bond.   
     
     
         4 . The active agent of  claim 3 , wherein the active agent is formed by self-assembly of the first component molecule and the second component molecule. 
     
     
         5 . The active agent of  claim 3 , wherein the first component molecule has two or more amine functional groups. 
     
     
         6 . The active agent of  claim 3 , wherein the first component molecule is 1,3-diaminoguanidine or aminoguanidine. 
     
     
         7 . The active agent of  claim 3 , wherein the second component molecule has two or more aldehyde functional groups. 
     
     
         8 . The active agent of  claim 3 ,
 wherein the second component molecule has the following chemical structure:   
       
         
           
           
               
               
           
         
         wherein R 1  is —CHCO, and 
         wherein R 2 , R 3 , R 4 , R 5 , and R 6  are, independently, one of H, —CHCO, a saturated or unsaturated branched or unbranched aliphatic, a halide, a halide-diol, or —OH. 
       
     
     
         9 . The active agent of  claim 8 , wherein at least one of R 3 , R 4 , and R 5  is —CHCO. 
     
     
         10 . The active agent of  claim 9 , wherein R 3  and R 5  are both —CHCO. 
     
     
         11 . The active agent of  claim 3 , wherein the second component is one of glyoxal, glutaraldehyde, benzylaldehyde, phthalaldehyde, terephthalaldehyde, isophthalaldehyde, benzene-1,3,5-tricarboxaldehyde, 2-bromoisophthalaldehyde, 4-tBu-2,6-diformylphenol, 4-Me-2,6-diformylphenol, 3,5-diformyl-2-propoxyphenylboronic acid, 2,5-thiophenedialdehyde, and 2,5-furandialdehyde. 
     
     
         12 . A method of killing a microbe, the method comprising:
 treating a growth of the microbe with an effective amount of an active agent,   an effective amount of the active agent being achieved by adding a combination of a pre-determined amount of a first component molecule and a pre-determined amount of a second component molecule,   wherein the first component molecule and the second component molecule are capable of self-assembly via the formation of a hydrazone covalent bond.   
     
     
         13 . The method of killing a microbe of  claim 12 , wherein the first component molecule is 1,3-diaminoguanidine or aminoguanidine. 
     
     
         14 . The method of killing a microbe of  claim 12 , wherein the second component molecule has two or more aldehyde functional groups. 
     
     
         15 . The method of killing a microbe of  claim 12 ,
 wherein the second component molecule has the following chemical structure:   
       
         
           
           
               
               
           
         
         wherein R 1  is —CHCO, and 
         wherein R 2 , R 3 , R 4 , R 5 , and R 6  are, independently, one of H, —CHCO, a saturated or unsaturated branched or unbranched aliphatic, a halide, a halide-diol, or —OH. 
       
     
     
         16 . The method of killing a microbe of  claim 15 , wherein at least one of R 3 , R 4 , and R 5  is —CHCO. 
     
     
         17 . The method of killing a microbe of  claim 16 , wherein R 3  and R 5  are both —CHCO. 
     
     
         18 . A method of producing a self-assembled active agent, the method comprising combining a first component with a second component in a solution,
 wherein the first component is a molecule with an amine functional group and the second component is a molecule with an aldehyde or a ketone functional group,   wherein the first component, the second component, and the combination of the first component and the second component each has a bioactivity, and   wherein the bioactivity of the combination of the first component and the second component is greater than the sum of the bioactivity of the first component and the bioactivity of the second component.   
     
     
         19 . The method of producing a self-assembled active agent of  claim 18 , wherein the first component and the second molecule are capable of self-assembly via the formation of a hydrazone covalent bond. 
     
     
         20 . The method of producing a self-assembled active agent of  claim 18 , wherein the first component has two or more amine functional groups. 
     
     
         21 . The method of producing a self-assembled active agent of  claim 18 , wherein the second component has two or more aldehyde functional groups. 
     
     
         22 . The method of producing a self-assembled active agent of  claim 18 , wherein the second component molecule has the following chemical structure: 
       
         
           
           
               
               
           
         
         wherein R 1  is —CHCO, and 
         wherein R 2 , R 3 , R 4 , R 5 , and R 6  are, independently, one of H, —CHCO, a saturated or unsaturated branched or unbranched aliphatic, a halide, a halide-diol, or —OH. 
       
     
     
         23 . The method of producing a self-assembled active agent of  claim 22 , wherein at least one of R 3 , R 4 , and R 5  is —CHCO. 
     
     
         24 . The method of producing a self-assembled active agent of  claim 23 , wherein R 3  and R 5  are both —CHCO. 
     
     
         25 . A composition comprising at least one compound of the formula 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  independently are
 (1) hydrogen (—H), or 
 (2) an aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, or 
 (3) an aromatic functional group wherein one or more —H is substituted with an alkyl, aliphatic groups, OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, 
 R 3 , R 4  and R 5  independently are aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters or halogens. 
 
       
     
     
         26 . The composition of  claim 25 , wherein the compound is an active agent. 
     
     
         27 . The composition of  claim 26 , wherein the active agent is formed by self-assembly of a first component molecule and a second component molecule. 
     
     
         28 . The composition of  claim 26 , wherein the active agent has antimicrobial activity. 
     
     
         29 . The composition of  claim 25 , wherein said compound is a compound in  FIG. 10  or  FIG. 11 . 
     
     
         30 . A method for killing microorganisms on or in an object or area, said method comprising contacting said object or area with an effective microorganisms killing amount of a composition comprising at least one compound of  claim 25 . 
     
     
         31 . The method of  claim 49 , wherein said compound is a compound in  FIG. 10  or  FIG. 11 . 
     
     
         32 . An active agent,
 wherein the active agent is formed by a process comprising covalently bonding at least a first component molecule and a second component molecule, and   wherein an effective amount of the active agent is lower than the sum of an effective amount of the first component molecule when used individually and an effective amount of the second component molecule when used individually; wherein said active agent is a compound of  claim 25 .   
     
     
         33 . The active agent of  claim 32 , wherein the active agent is formed by self-assembly of the first component molecule and the second component molecule. 
     
     
         34 . The active agent of  claim 32 , wherein the first component molecule is an amine and the second component molecule is an aldehyde. 
     
     
         35 . The active agent of  claim 32 , wherein the first component molecule is an amine and the second component molecule is a ketone. 
     
     
         36 . The active agent of  claim 32 , wherein the covalent bonding between the first component molecule and the second component molecule includes the formation of a hydrazone bond. 
     
     
         37 . The active agent of  claim 32 , wherein the first component molecule is 1,3-diaminoguanidine or aminoguanidine. 
     
     
         38 . The active agent of  claim 32 ,
 wherein the second component molecule has the following chemical structure:   
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  independently are
 (1) hydrogen (—H), or 
 (2) an aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, or 
 (3) an aromatic functional group wherein one or more —H is substituted with an alkyl, aliphatic groups, OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, and 
 R 3 , R 4  and R 5  independently are aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters or halogens. 
 
     
     
         39 . The active agent of  claim 32 , wherein said active agent is a compound in  FIG. 10  or  FIG. 11 . 
     
     
         40 . A method of killing a microbe on or in an object or area, said method comprising contacting said object or area with an effective microorganisms killing amount of a self-assembled active agent,
 an effective amount of the active agent being achieved by adding a combination of a pre-determined amount of a first component molecule and a pre-determined amount of a second component molecule,   wherein the first component molecule and the second component molecule are capable of self-assembly via the formation of a hydrazone covalent bond.   
     
     
         41 . The method of killing a microbe of  claim 40 , wherein the first component molecule is an amine and the second component molecule is one of an aldehyde and a ketone. 
     
     
         42 . The method of killing a microbe of  claim 40 , wherein the first component molecule is 1,3-diaminoguanidine or aminoguanidine. 
     
     
         43 . The method of killing a microbe of  claim 40 ,
 wherein the second component molecule has the following chemical structure:   
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  independently are
 (1) hydrogen (—H), or 
 (2) an aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, or 
 (3) an aromatic functional group wherein one or more —H is substituted with an alkyl, aliphatic groups, OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, and 
 R 3 , R 4  and R 5  independently are aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters or halogens. 
 
     
     
         44 . The method of killing a microbe of  claim 40 , wherein said active agent is a compound in  FIG. 10  or  FIG. 11 . 
     
     
         45 . A method of producing a self-assembled active agent, the method comprising combining a first component with a second component in a solution,
 wherein the first component is a molecule with an amine functional group and the second component is a molecule with an aldehyde or a ketone functional group,   wherein the first component, the second component, and the combination of the first component and the second component each has a bioactivity, and   wherein the bioactivity of the combination of the first component and the second component is greater than the sum of the bioactivity of the first component and the bioactivity of the second component.   
     
     
         46 . The method of producing a self-assembled active agent of  claim 45 , wherein the first component and the second molecule are capable of self-assembly via the formation of a hydrazone covalent bond. 
     
     
         47 . The method of producing a self-assembled active agent of  claim 45 , wherein the first component is 1,3-diaminoguanidine or aminoguanidine. 
     
     
         48 . The method of producing a self-assembled active agent of  claim 45 , wherein the second component molecule has the following chemical structure: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  independently are
 (1) hydrogen (—H), or 
 (2) an aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, or 
 (3) an aromatic functional group wherein one or more —H is substituted with an alkyl, aliphatic groups, OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters, halogens, or a 1-2 ring heterocycle that contains O, N and/or S as the heteroatom, and 
 R 3 , R 4  and R 5  independently are aliphatic functional group that may be substituted with additional aliphatic groups, —OH groups, ethers, esters, acids, amines, ammoniums, alcohols, thiols, thioesters or halogens. 
 
       
     
     
         49 . The method of producing a self-assembled active agent of  claim 45 , wherein said self-assembled active agent is a compound in  FIG. 10  or  FIG. 11 .