Limiting the presence of microorganisms using polymer-bound...

Details Limiting the presence of microorganisms using polymer-bound... Limiting the presence of microorganisms using polymer-bound...

2000-07-06

2002-08-13

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Solid synthetic organic polymer as designated organic active...

C424S406000, C514S184000, C540S202000, C540S203000

Reexamination Certificate

active

06432396

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to polymer-bound metal-containing compositions, and the use of such compositions to limit the growth of viruses, bacteria, and fungi.
BACKGROUND OF THE INVENTION
The potential for the presence of pathogenic bacteria and viruses in biological fluids such as saliva, tears, blood, and lymph is of significant concern as is the potential for the transfer of such microorganisms to the surfaces of medical devices (and vice versa). For these reasons, methods for minimizing the transmission of pathogens in the home and in hospitals, as well as in day-care centers, are important.
Microorganisms can be killed or rendered static by a number of physical and chemical methods. Physical methods include heat and radiation. There are a number of chemicals that have been used to limit viral, fungal, and bacterial growth. Examples include alcohols (usually, 70% by volume aqueous ethyl or isopropyl alcohol); phenol and phenol derivatives such as hexachlorophene; formaldehyde; glutaraldehyde; ethylene oxide; ether; detergents; chlorhexidine gluconate; heavy metals such as silver, copper, and mercury; organic compounds of mercury such as mercurochrome; as well as oxidizing agents such as hydrogen peroxide, iodine, hypochlorite, and chlorine.
Antibiotics, such as bacitracin, the cephalosporins, cycloserine, the penicillins, vancomycin, chloramphenicol, the erythromycins, the tetracyclines, the sulfonamides, and the aminoglycosides (such as streptomycin, neomycin, and gentamycin) have traditionally been defined as chemicals made by microorganisms that kill bacteria. Antibiotics have no effect on viruses.
Many of such treatment methods are neither permanent nor continuous. Thus, repeated treatments may be needed to restore sterility during and after use. Polymeric compositions intended for imparting a continuously antimicrobial, self-disinfecting property to surfaces or liquids are known. Typically, these involve an antimicrobial agent and a polymer in a mixture that allows leaching of the antimicrobial agent for controlled release. In some cases, the antimicrobial agent that leaches from the polymer is toxic or imparts undesirable properties to the material in the leached form. Thus, there is considerable interest in autosterile (possessing intrinsic microbicidal activity) non-leaching materials.
There are also examples of polymeric compositions that include an antimicrobial moiety covalently bonded to a polymer. Rose bengal, for example, has been covalently attached to poly(styrene), and porphyrins have been bonded to acrylates, with the resulting polymers in both cases possessing antimicrobial activity with no leaching.
Singlet oxygen is generated in neutrophils and macrophages for use in killing microorganisms of a wide variety. The “photodynamic effect” is the term used to describe destruction of cells and microbes by triplet-sensitizers in the presence of oxygen and light. Singlet oxygen is believed to be the destructive agent under conditions where oxygen concentration is high and there are no reducing agents present. Singlet oxygen is a short-lived excited state of molecular oxygen. In solution, its lifetime of 1 microsecond allows it to diffuse on the order of 0.1 micron before being deactivated to triplet molecular oxygen. In the gas phase in air, the lifetime of singlet oxygen is about 1 millisecond, which allows for diffusion of up to 1 millimeter before deactivation to triplet oxygen. The combinations of certain photosensitizers, oxygen, and light have been shown to be toxic to living tissue, which is believed to be the consequence of the formation of singlet oxygen.
Thus, photosensitizing dyes, such as merocyanines and water-soluble zinc phthalocyanines, have been disclosed for use as antimicrobial agents. Surfaces coated with certain photosensitizers can be made to be autosterile. Due to the catalytic nature of the photosensitizer-oxygen reaction that generates singlet oxygen and regenerates ground-state photosensitizers, the antimicrobial activity of such coatings can be made to be essentially permanent. Additionally, certain immobilized photosensitizers have been shown to exhibit antimicrobial activity at a distance due to diffusion of singlet oxygen.
Use of photosensitizers compounded with or covalently attached to polymers to prepare substantially non-leaching autosterile materials is known. For example, various polymers that include covalently-bound porphyrin, phthalocyanine, and Rose Bengal photosensitizers are known.
U.S. Pat. No. 6,248,733 (Landgrebe et al.) discloses the use of metal-containing compounds in polymeric compositions (e.g., porous fabrics). For certain embodiments of the compounds described therein, specifically, wherein R
1
includes a long chain organic group containing, e.g., 8 or 9 carbon atoms, no antimicrobial activity was observed. These findings are consistent with the theory that leaching of the metal-containing compound is required to impart antimicrobial activity.
SUMMARY OF THE INVENTION
In one aspect, the present invention provides a method for limiting the presence of a microorganism. The method includes contacting the microorganism with a polymer-bound metal-containing composition. The composition includes a compound having the following formula:
wherein:
Z
1
and Z
2
each independently represent an arene nucleus, which has from 5 to 14 ring atoms;
G
1
and G
2
each independently represent a metal ligating group such that G
1
and G
2
may be contained within or pendant from at least one of Z
1
and Z
2
;
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 alkyl- or aryl sulfonyl group, an alkyl- or aryl sulfoxyl group, an aryloxyl group, a hydroxyl group, a thioamido, 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;
L
1
represents a nitrogen heterocycle substituted with R
1
or R
2
or both R
1
and R
2
;
R
1
and R
2
each independently represent a polymer-bound group, a hydrogen, a halogen atom, an alkyl group, a vinyl group, a hydroxyalkyl group, 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; wherein at least one of R
1
and R
2
represents a polymer-bound group;
L
2
represents a monodentate or polydentate ligand;
X represents nitrogen or a methine group;
M represents a platinum or palladium atom; and
k, m, and n are whole numbers less than or equal to 4.
In one embodiment, the polymer-bound metal-containing composition includes a compound of the following formula:
wherein:
R
1
and R
2
each independently represent H or a polymer-bound group, wherein at least one of R
1
and R
2
is a polymer-bound group; X represents nitrogen or a methine group; and M represents a platinum or palladium atom.
In another aspect, the present invention provides a polymer-bound metal-containing compound of the following formula:
wherein:
R
1
and R
2
each independently represent H or a polyurethane-bound group, wherein at least one of R
1
and R
2
represents a polyurethane-bound group;
X represents nitrogen or a methine group; and
M represents a platinum or palladium atom.
In still another aspect, the present invention provides a method of preparing a polymer-bound metal-containing compound that includes reacting a prepolymer or polymer with a metal-containing monomer of the following formula:
wherein:
R
1
and R
2
each independently represent H or CH
2
OH, wherein at least one of R
1
and R
2
represents CH
2
OH;
X represents nitrogen or a methine group; and
M represents a

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