Self-assembled active agents

Patent metadata

Field	Value
Publication number	US-2022015367-A1
Application number	US-202117469773-A
Country	US
Kind code	A1
Filing date	Sep 8, 2021
Priority date	Mar 6, 2017
Publication date	Jan 20, 2022
Grant date	—

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.

First claim

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, ind

Assignees

• Us Agriculture
• Method Products Pbc

Inventors

• Hart-Cooper William M
• Orts William J
• Johnson Kaj
• Lynn Lauren E
• Franquivillanueva Diana M

Classifications

• C07C281/16

  Compounds containing any of the groups [IMAGE cpc-sch-C07C-0974.gif], e.g. aminoguanidine · CPC title

• A01N55/08

  containing boron · CPC title

• A01N49/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group [IMAGE cpc-sch-A01N-0948.gif], wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group [IMAGE cpc-sch-A01N-0949.gif], wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof (containing hydrocarbons A01N27/00) · CPC title

• A01N47/44 Primary

  Guanidine; Derivatives thereof · CPC title

• C07C281/18

  the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones · CPC title