Method for limiting the growth of microorganisms using metal-containing compounds

• US 6,248,733 B1
• Filed: 01/09/1998
• Issued: 06/19/2001
• Est. Priority Date: 01/09/1998
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Landgrebe, Kevin D., Cuny, Gregory D., Shelburne, Charles E., Smith, Terrance P.
• Primary Examiner(s): Dees, Jose′ G.
• Assistant Examiner(s): Pryor, Alton
• Application Number:
  US09/004,892
• Time in Patent Office: 1,257 Days
• Field of Search: 546/2, 514/184, 510/161, 510/179, 510/199, 510/292, 510/180, 540/202, 540/203
• US Class Current: 514/184
• CPC Class Codes: A01N 55/02 containing metal atoms
• CPC Class Codes: A01N 59/16 Heavy metals; Compounds thereof
• CPC Class Codes: A01N 59/20 Copper
• CPC Class Codes: C07F 15/0093 without a metal-carbon linkage

Abstract

This invention relates to the use of compounds having the general structure:

wherein: Z1 and Z2 each independently represent an arene nucleus, which has from 5 to 14 ring atoms; G1 and G2 each independently represent a metal ligating group; R represents a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, a thiol group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an amino group, an alkoxycarbonyl group, an acyloxy group, a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfoxyl group, an arylsulfoxyl group, an aryloxyl group, a hydroxyl group, a thioamido group, a carbamoyl group, a suffamoyl group, a formyl group, an acyl group, a ureido group, an aryloxycarbonyl group, a silyl group, or a sulfoalkoxy group; L1 represents a nitrogen heterocycle; L2 represents a monodentate or polydentate (e.g., bidentate) ligand; X represents nitrogen or a methine (CH) group; M is a divalent or polyvalent transition metal ion where the coordination number is at least 4; and k, m, and n are whole numbers less than or equal to 3 as antimicrobial agents to inhibit the growth or replication of microorganisms such as viruses, bacteria, and fungi.

Claims

1. A method for limiting growth of a microorganism comprising:

exposing a microorganism to an effective amount of a composition comprising a metal-containing compound having the following chemical structure;

 

wherein;

Z1 and Z2 each independently represent an arene nucleus, having from 5 to 14 ring atoms;

G1 and G2 each independently represent a metal ligating group, wherein G1 and G2 may be contained within or pendant from at least one of Z1 and Z2;

R represents a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, a thiol group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an amino group, an alkoxycarbonyl group, an acyloxy group, a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfoxyl group, an arylsulfoxyl group, an aryloxyl group, a hydroxyl group, a thioamido group, a carbamoyl group, a sulfamoyl group, a formyl group, an acyl group, a ureido group, an aryloxycarbonyl group, a silyl group, or a sulfoalkoxy group;

L1 represents a nitrogen heterocycle, substituted with R1 or R2 or both R1 and R2;

R1 and R2 each independently represent a hydrogen, a halogen atom, an alkyl group, including vinyl groups, hydroxyalkyl groups, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, an alkylthio group, an alkylamino group, an alkoxycarbonyl group, an acyloxy group, an alylsulfonyl group, an alkylsulfoxyl group, an alkylcarbamoyl group, an alkylsulfamoyl group, a formyl group, an acyl group, a silyl group, or a sulfoalkoxy group;

L2 represents a monodentate or polydentate ligand;

X represents nitrogen or a methine (CH) group;

M is selected from the group consisting of platinum and palladium; and

k, m, and n are whole numbers less than or equal to 3.

2. The method of claim 1 wherein the method further comprises exposing the composition to light for at least one time.

3. The method of claim 1 wherein the metal-containing compound is compound 1

4. The method of claim 3 wherein the metal-containing compound is selected from the group consisting of compound 5

5. The method of claim 1 wherein the microorganism is a virus.

6. The method of claim 5 wherein the virus is an enveloped virus.

7. The method of claim 6 wherein the virus is HIV.

8. The method of claim 6 wherein the virus is a member of the Herpesvirus group.

9. The method of claim 6 wherein the virus is an Influenza virus.

10. The method of claim 1 wherein the microorganism is a bacterium.

11. The method of claim 10 wherein the bacterium is a gram-positive bacterium.

12. The method of claim 10 wherein the bacterium is a gram-negative bacterium.

13. The method of claim 1 wherein the microorganism is a fungus.

14. The method of claim 13 wherein the fungus is a yeast.

15. The method of claim 1 wherein exposing further comprises contacting a surface with the composition.

16. The method of claim 1 wherein the composition comprises the metal-containing compound in a liquid.

17. The method of claim 1 wherein the composition is added to a liquid.

18. The method of claim 1 wherein exposing further comprises adding the metal-containing compound to a solid.

19. The method of claim 1 wherein replication of the microorganism is inhibited by exposing the microorganism to the effective amount of the composition.

20. The method of claim 1 wherein the microorganism is killed by exposing the microorganism to the effective amount of the composition.

21. The method of claim 15 wherein the metal-containing compound on the surface is exposed to light more than once.

22. The method of claim 16 wherein the liquid is exposed to light more than once.

23. The method of claim 17 wherein the liquid is exposed to light more than once.

24. The method of claim 18 wherein the mctal-containing compound is exposed to light more than once.

25. The method of claim 1 wherein the composition is in a liquid during the exposing step.

26. The method of claim 1 wherein the composition is a solid during exposing of the microorganism to the effective amount of the composition.

27. The method of claim 1 wherein the composition further comprises at least one other antimicrobial compound.

28. The method of claim 1 wherein n is a whole number less than or equal to 2.

29. The method of claim 1 wherein the alkyl group of R¹ and R² has less than 8 carbons.

30. A method for disinfecting a surface comprising:

applying a composition comprising a metal-containing compound to a surface, the metal-containing compound having the general structure;

 

wherein;

Z1 and Z2 each independently represent an arene nucleus, having from 5 to 14 ring atoms;

G1 and G2 each independently represent a metal ligating group, wherein G1 and G2 may be contained within or pendant from at least one of Z1 and Z2;

R represents a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, a thiol group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an amino group, an alkoxycarbonyl group, an acyloxy group, a nitro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfoxyl group, an arylsulfoxyl group, an aryloxyl group, a hydroxyl group, a thioamido group, a carbamoyl group, a sulfamoyl group, a formyl group, an acyl group, a ureido group, an aryloxycarbonyl group, a silyl group, or a sulfoalkoxy group;

L1 represents a nitrogen heterocycle, substituted with R1 or R2 or both R1 and R2;

R1 and R2 each independently represent a hydrogen, a halogen atom, an alkyl group, including vinyl groups, hydroxyalkyl groups, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, an alkylthio group, an alkylamino group, an alkoxycarbonyl group, an acyloxy group, an alylsulfonyl group, an alkylsulfoxyl group, an alkylcarbamoyl group, an alkylsulfamoyl group, a formyl group, an acyl group, a silyl group, or a sulfoalkoxy group;

L2 represents a monodentate or polydentate ligand;

X represents nitrogen or a methine (CH) group;

M is selected from the group consisting of platinum and palladium;

and k, m, and n are whole numbers less than or equal to 3.

31. The method of claim 30 further comprising exposing the surface to light.

32. The method of claim 31 wherein the composition further comprises a second antimicrobial agent.

33. The method of claim 32 wherein the second antimicrobial agent is selected from the group consisting of an antiviral agent, an antibacterial agent and an antifungal agent.

34. A method for limiting the growth of a virus, bacterium and/or a fungus comprising:

contacting the virus, bacterium or fungus with a composition comprising a metal-containing compound having the following formula;

 

wherein R1 and R2 are each independently selected from the group consisting of H, CH₂OH, CH═

CH₂ and CH₂CH₃, X is a methine (CH) group, and M is Pt.

35. The method of claim 34 wherein at least one of R1 or R2 is H.

36. A metal-containing compound having the general structure:

wherein R1 is CH₂OH [or CH₂CH₃], R2 is H, [Z] X ia a methine (CH) group, and M is Pt.

37. A method for limiting growth of a microorganism comprising:

exposing a microorganism to am effective amount of a composition comprising a metal-containing compound having a chemical structure of compound 1;

 

wherein;

R1 and R2 each independently represent a hydrogen, a halogen atom, an alkyl group, including vinyl groups, hydroxyalkyl groups, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, an alkylthio group, an alkylamino group, an alkocycarbonyl group, an acyloxy group, an alylsulfonyl group, an alkylsulfoxyl group, an alkylcarbamoyl group, an alkylsulfamoul group, a formyl group, an acyl group, a silyl group, or a sulfoalkoxy group;

X represents nitrogen or a methine (CH) group; and

M is a divalent or polyvalent transition metal ion where the coordination number is at least 4.

38. A method for limiting growth of a virus comprising:

exposing a microorganism to an effective amount of a composition comprising a metal-containing compound having the following chemical structure;

 

wherein;

Z1 and Z2 each independently represent an arene nucleus, having from 5 to 14 ring atoms;

G1 and G2 each independently represent a metal ligating group, wherein G1 and G2 may be contained within or pendant from at least one of Z1 and Z2.

R represents a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, a thiol group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an amino group, an alkoxycarbonyl group, an acyloxy group, a notro group, a cyano group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfoxyl group, an arylsulfoxyl group, an aryloxyl group, a hydroxyl group, a thioamido group, a carbamoyl group, a sulfamoyl group, a formyl group, an acyl group, a ureido group an aryloxycarbonyl group, a silyl group, or a sulfoalkoxy group;

L1 represints a nitrogen heterocycle, substituted with R1 or R2 or both R1 and R2;

R1 and R2 each independently represent a hydrogen, a halogen atom, an alkyl group, including vinyl groups, hydroxyalkyl groups, an acylamino group, an alkoxy group, a sufonamido group, an aryl group, an alkylthio group, an alkylamino group, an alkoxycarbonyl group, an acyloxy group, an alylsulfonyl group, an alkylsulfoxyl group, an alkylcarbamoyl group, an alkylsulfamoyl group, a formyl group, an acyl group, a silyl group, or a sulfoalkoxy group;

L2 represints a monodentate or polydenatee ligand;

X represents nitrogen or methine (CH) group;

M is a divalent or polyvalent transition metal ion where the coordination number is at least 4; and

k, m, and n are whole numbers less than or equal to 3.

39. The method of claim 38 wherein the virus is an enveloped virus.

40. The method of claim 39 wherein the virus is HIV.

41. The method of claim 39 wherein the virus is a member of the Herpesvirus group.

42. The metod of claim 39 wherein the virus is an Influenza virus.