MXPA97009769A - Inhibition of exoprotein in article absorbe - Google Patents
Inhibition of exoprotein in article absorbeInfo
- Publication number
- MXPA97009769A MXPA97009769A MXPA/A/1997/009769A MX9709769A MXPA97009769A MX PA97009769 A MXPA97009769 A MX PA97009769A MX 9709769 A MX9709769 A MX 9709769A MX PA97009769 A MXPA97009769 A MX PA97009769A
- Authority
- MX
- Mexico
- Prior art keywords
- clause
- absorbent article
- compound
- alkyl group
- laureth
- Prior art date
Links
- 230000002401 inhibitory effect Effects 0.000 title claims description 22
- 239000002250 absorbent Substances 0.000 claims abstract description 104
- 230000002745 absorbent Effects 0.000 claims abstract description 104
- -1 amine compound Chemical class 0.000 claims abstract description 80
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 claims abstract description 44
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 40
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 36
- 241000192125 Firmicutes Species 0.000 claims abstract description 28
- ULUAUXLGCMPNKK-UHFFFAOYSA-L 2-sulfobutanedioate Chemical compound OS(=O)(=O)C(C([O-])=O)CC([O-])=O ULUAUXLGCMPNKK-UHFFFAOYSA-L 0.000 claims abstract description 20
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 19
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 239000011780 sodium chloride Substances 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- VILAVOFMIJHSJA-UHFFFAOYSA-N Dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims abstract description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000008054 sulfonate salts Chemical class 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 231100000776 Exotoxin Toxicity 0.000 claims abstract description 6
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- 239000002095 exotoxin Substances 0.000 claims abstract description 6
- 150000002462 imidazolines Chemical class 0.000 claims abstract description 4
- 210000001124 Body Fluids Anatomy 0.000 claims abstract description 3
- 239000010839 body fluid Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 74
- 101710037438 TST Proteins 0.000 claims description 29
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 claims description 27
- 241000894006 Bacteria Species 0.000 claims description 21
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 21
- 239000011734 sodium Substances 0.000 claims description 19
- 229910052708 sodium Inorganic materials 0.000 claims description 19
- 239000002594 sorbent Substances 0.000 claims description 19
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 18
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 17
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 15
- 239000011591 potassium Substances 0.000 claims description 15
- 229910052700 potassium Inorganic materials 0.000 claims description 15
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 14
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 14
- 101710011036 stiI Proteins 0.000 claims description 13
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 9
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 9
- 229940116335 LAURAMIDE Drugs 0.000 claims description 9
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- 235000021314 Palmitic acid Nutrition 0.000 claims description 9
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
- 239000000600 sorbitol Substances 0.000 claims description 9
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 9
- FKMHSNTVILORFA-UHFFFAOYSA-N 2-[2-(2-dodecoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCO FKMHSNTVILORFA-UHFFFAOYSA-N 0.000 claims description 8
- 229920002884 Laureth 4 Polymers 0.000 claims description 8
- 229940057905 Laureth-3 Drugs 0.000 claims description 8
- LAPRIVJANDLWOK-UHFFFAOYSA-N Pentaethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCO LAPRIVJANDLWOK-UHFFFAOYSA-N 0.000 claims description 8
- 235000021355 Stearic acid Nutrition 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229940061515 laureth-4 Drugs 0.000 claims description 8
- GBXRUYNQDDTQQS-UHFFFAOYSA-N 3-dodecoxypropane-1,2-diol Chemical compound CCCCCCCCCCCCOCC(O)CO GBXRUYNQDDTQQS-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- MTNDZQHUAFNZQY-UHFFFAOYSA-N 2-Imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 6
- FXALIOUHXMVTMJ-UHFFFAOYSA-N CCCCCCCCCCCC([Na])=O Chemical compound CCCCCCCCCCCC([Na])=O FXALIOUHXMVTMJ-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229940071089 sarcosinate Drugs 0.000 claims description 6
- FSYKKLYZXJSNPZ-UHFFFAOYSA-M sarcosinate Chemical compound CNCC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-M 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecan-1-amine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 229940071190 laureth sulfosuccinate Drugs 0.000 claims description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
- IGRVZEVKOQUHMQ-UHFFFAOYSA-N 2-(2-dodecyl-4,5-dihydroimidazol-1-yl)ethanol Chemical compound CCCCCCCCCCCCC1=NCCN1CCO IGRVZEVKOQUHMQ-UHFFFAOYSA-N 0.000 claims description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- JNYAEWCLZODPBN-CTQIIAAMSA-N Sorbitan Chemical compound OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 claims description 4
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 claims description 4
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 claims description 4
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- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229940057950 sodium laureth sulfate Drugs 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims 7
- YGAXLGGEEQLLKV-UHFFFAOYSA-L disodium;4-dodecoxy-4-oxo-2-sulfonatobutanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOC(=O)CC(C([O-])=O)S([O-])(=O)=O YGAXLGGEEQLLKV-UHFFFAOYSA-L 0.000 claims 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- TWMFGCHRALXDAR-UHFFFAOYSA-N N-[3-(dimethylamino)propyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCCN(C)C TWMFGCHRALXDAR-UHFFFAOYSA-N 0.000 claims 3
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- 229940071188 lauroamphodiacetate Drugs 0.000 claims 3
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- 150000003385 sodium Chemical group 0.000 claims 3
- HGPNKTHAVDVUNT-UHFFFAOYSA-M 2-dodecylpyridine;chloride Chemical compound [Cl-].CCCCCCCCCCCCC1=CC=CC=N1 HGPNKTHAVDVUNT-UHFFFAOYSA-M 0.000 claims 1
- YCSMVPSDJIOXGN-UHFFFAOYSA-N CCCCCCCCCCCC[Na] Chemical compound CCCCCCCCCCCC[Na] YCSMVPSDJIOXGN-UHFFFAOYSA-N 0.000 claims 1
- 229940079868 disodium laureth sulfosuccinate Drugs 0.000 claims 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 abstract description 3
- 125000001033 ether group Chemical group 0.000 abstract 1
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Abstract
The present invention relates to absorbent articles, such as catamenial plugs, for absorbing body fluids which include an effective amount of a thioether, amine or amide composition, either alone or in combination to essentially inhibit the production of Exotoxins by Gram positive bacteria. The composition of the ether has the general formula: R1-O-R2 wherein R1 is a straight or branched alkyl group having a chain of 18 to 18 carbon atoms and R2 is selected from an alcohol, a salt of polyalkoxylated sulfate and a salt of polyalkoxylated sulfosuccinate. The amine compound has the general formula (a) wherein R3 is an alkyl group having from about 8 to about 18 carbon atoms, and R4 and R5 may be the same or different and are selected from hydrogen and a group of alkyl having from 1 to about 18 carbon atoms and which may have one or more substituent halides selected from dehydroxyl, carboxyl and carboxyl and imidazoline salts. The amide compound has the general formula (b) wherein R7 is an alkyl group having from 8 to 18 carbon atoms, inclusive of the carbonyl carbon and R8 and R9 may be the same or different, R8 and R9 are selected from hydrogen , an alkyl group having from 1 to about 12 carbon atoms and may contain one or more substituent groups selected from ether, ether, amine, hydroxyl, carboxyl, carboxyl salts, sulfonate, sulfonate salts and combinations thereof. A method to inhibit the exoprotein production of gram-positive bacteria is also described
Description
INHIBITION OF EXOPROTEIN IN THE ABSORBENT ARTICLE
FIELD OF THE INVENTION
The present invention relates to the inhibition of exoprotein in an absorbent article, such as vaginal plugs and sanitary napkins. More particularly, the invention relates to the incorporation of ether compounds, amide compounds, and amine compounds either alone or in combination in such absorbent articles and for the effects of these compounds on gram-positive bacteria.
BACKGROUND OF THE INVENTION
Disposable absorbent devices for the absorption of human exudates are widely used. These disposable devices typically have a compressed mass of absorbent formed in the desired shape, which is typically dictated by the use for the intended consumer. In the area of a menstrual plug, the device is intended to be inserted into a body cavity for the absorption of body fluids generally discharged during a woman's menstrual period.
There is a woman's body a complex process to maintain the vagina and physiologically related areas in a healthy state. In a woman between the age of menopause in menopause, the normal vagina provides an ecosystem for a variety of microorganisms. Bacteria are the predominant type of microorganisms present in the vagina; Most women harbor around 109 bacteria per gram of vaginal exudate. The bacterial flora of the vagina is composed of both aerobic and anaerobic bacteria. The bacteria most commonly isolated are the species Lactobacillus, corynebacteria, Gardnerella vaginalis species, Staphylococcus species, Peptococus species. Aerobic and streptococcal anaerobic species. and the bacteroid species. Other microorganisms that have been isolated from the vagina occasionally include ferment (Candida albicans), protozoa (Trichomonas vaginalis). Mycoplasma (Mycoplasma Hominis), Chlamydia (Chlamydia trachomatis) and visus (Herpes simplex). These last organisms are usually associated with vaginitis or venereal disease, even though these may be present in low numbers without causing symptoms.
Physiological, social and idiosyncratic factors affect the amount and species of bacteria present in the vagina. Physiological factors include age, days of the menstrual cycle and pregnancy. For example, vaginal flora present in the vagina through the menstrual cycle may include lactobacilli, corynebacteria, ureaplasma, and mycoplasma. Social and ideosyncratic factors include a method of birth control, sexual practices, systemic disease (eg, diabetes) and medication.
Bacterial proteins and metabolic products produced in the vagina can affect other microorganisms and the human host. For example, the vagina between menstrual periods is mildly acidic with a pH ranging from around 3.8 to around 4.5. This pH range is generally considered the most favorable condition for the maintenance of normal flora. At that pH, the vagina normally harbors numerous species of microorganisms in a balanced ecology, playing a beneficial role in providing protection and resistance to infections and rendering the vagina unmanageable for some species of bacteria such as Staphylococcus aureus (S. aureus). ). The low pH is a consequence of the growth of lactobacilli and their production of acidic products. Microorganisms in the vagina can also produce antimicrobial compounds such as hydrogen peroxide and bactericides targeted to other bacterial species. An example is that of lactocinos, the lactobacillus bacteriocin type products directed against other lactobacillus species.
Some microbial products can affect the human host. For example, S. Aureus can produce and secrete within its environment a variety of ecoproteins including enterotoxins, toxin-1 toxic shock syndrome (TSST-1) and enzymes such as proteases and lipase.
The S. Aureus is found in the vagina and approximately 16% of healthy women at menstrual age. Approximately 25% of S. Aureus isolated from the vagina sen capable of producing TSST-1. TSST-1 and some of the staphylococcal enterotoxins have been identified as causing the toxic shock syndrome.
The menstrual fluid has a pH of about 7.3. During menstrual periods, the pH of the vagina moves towards neutral and can be made slightly alkaline. This change allows microorganisms whose growth is inhibited by an acidic environment to proliferate. For example, S. Aureus is most frequently isolated from the scouring pads collected during menstrual periods.
There have been numerous attempts to reduce or eliminate the pathogenic microorganisms and the TSS that occurs menstrually by incorporating within a stopper one or more biostatic, biocidal and / or detoxifying compounds. For example, L-ascorbic acid has been applied to the menstrual plug to detoxify the toxin found in a woman's vagina during menstruation.
It has been suggested to incorporate the glyceryl triacetate into a stopper. The glyceryl triacetate is easily broken into glycerol and acetic acid by the enzymatic action of esterase. Esterase is present in the vaginal epithelium and menstrual fluid. The enzymatic action of esterase is controlled in turn by the pH of the environment, being more active when the pH is on the alkaline side. Since the pH of the vagina moves towards the alkaline side during menstruation, the enzymatic activity of the esterase automatically increases and attacks the glyceryl triacetate. This rapidly releases acetic acid, which has the potential to reduce the pH and enzymatic activity of esterase. However, the menstrual fluid is irrigated and the acetic acid is not effective in lowering the pH of the menstrual fluid.
Others have incorporated monoesters and diesters of polyhydric aliphatic alcohols and fatty acids containing from 8 to 18 carbon atoms. For example, glycerol monolaurate (GML) has been used to inhibit J production. aureus enterotoxins and TSST-1. However, as noted above, esterase is abundantly present in vaginal epithelium and menstrual fluid. This esterase, in combination with the esterase and lipase produced by bacteria can enzymatically degrade the esters into ineffective compounds.
Until now, people with a skill in the art have not appreciated the effects of lipase and esterase on ester compounds. Thus, one or more ester compounds may be added to the absorbent article, such as the plug, in sufficiently high concentrations to detrimentally affect the normal flora present in the vaginal area. When the natural condition is altered, the overgrowth of the pathogens can take place resulting in a condition known as vaginitis.
Therefore there is a need for an absorbent product that incorporates there a compound that will effectively inhibit the production of exoproteins, such as TSST-1 from gram-positive bacteria; that it is not affected essentially by the enzymes lipase and esterase, and that it does not alter essentially the natural flora found in the vaginal area.
SYNTHESIS OF THE INVENTION
Briefly, the present invention is based upon the discovery that when the effective amount of one or more ether compounds or nitrogen containing compounds, such as the amine and amide compositions, either alone or in combination, are incorporated into an absorbent article. , such as a catamenial plug, the exoprotein production of gram-positive bacteria is substantially inhibited.
The ether compounds of the invention can be represented by the following formula:
R_-0-R2
wherein R x is a straight or branched chain alkyl group having from 8 to 18 carbon atoms and R 2 is selected from an alcohol, a polyalkoxylated sulfate salt or a polyalkoxylated sulfosuccinate salt. It has been found that when these ether compounds are incorporated into an absorbent article, such as a catamenial plug, the production of the exoprotein in the gram-positive bacteria is essentially inhibited.
The amine compounds of the invention can be represented by the general formula:
R3-N-R4 I R?
wherein R3 is an alkyl group having from about 8 to about 18 carbon atoms; and R4 and Rs may be the same or different and are independently selected from the hydrogen and alkyl groups having from 1 to about 18 carbon atoms. The alkyl groups of R 4 and R 5 may include one or more substitution groups selected from hydroxyl, carboxyl, and carboxyl and imidazoline salts. It is also within the scope of this invention that the nitrogen-containing compound includes an amine salt. It has been found that amine compounds and salts thereof are effective in essentially inhibiting the exoprotein production of gram-positive bacteria.
The amide compositions of the invention can be represented by the formula:
? R7-CN-Rβ I R,
wherein R7, inclusive of the carbonyl carbon is an alkyl group having 8 to 18 carbon atoms, and R, and R, may be the same or different. Preferably, R8 and R9 are selected from hydrogen and from alkyl group having from 1 to about 12 carbon atoms. The alkyl group of R8 and R9 may contain one or more substituent groups selected from ester, ether, amine, hydroxyl, carboxyl, carboxyl salts, sulfonate and sulfonate salts.
It is a general object of the invention to provide an absorbent article which inhibits the exoprotein production of the gram-positive bacterium. A more specific object of the invention is to provide a catamenial plug incorporating one or more of ether, amide, or amine compounds, either alone or in combination, which act to essentially inhibit the production of TSST-1 and enterotoxin B by S. aureus.
Another object of the invention is to provide a catamenial stopper having one or more of ether, amine or amine compounds incorporated therein, either alone or in combination which will substantially inhibit the exoprotein production of gram-positive bacteria without significantly unbalancing the natural flora present in the vaginal tract.
Another object of the invention is to provide a method for inhibiting the production of exoprotein produced by the gram-positive bacterium in an absorbent article.
Other objects and advantages of the invention, and modifications thereof, will become apparent to persons skilled in the art without departing from the inventive concepts defined in the appended claims.
DETAILED DESCRIPTION OF THE PREFERRED MODALITIES
This invention will be described in detail in connection with a catamenial stopper but it will be understood by those skilled in the art that it may be applicable to other disposable absorbent articles such as: sanitary napkins, panty liners, incontinent adult undergarments, diapers, medical bandages and plugs such as those intended for medical, dental, surgical and / or nasal use where the inhibition of gram-positive bacterial exoproteins would be beneficial.
The vaginal plugs suitable for use in this invention are usually made of absorbent fibers, including natural and synthetic fibers, compressed into unitary body of a size which can easily be inserted into the vaginal cavity. These are usually made in an elongated cylindrical shape so that they can have a sufficiently large body of material to provide the required absorbent capacity, but can be made in a variety of ways. The plug may or may not be compressed, although compressed types are now generally preferred. The plug can be made of various fiber blends including absorbent and non-absorbent fibers, which may or may not have a suitable cover or wrap.
It has been found that certain ether compounds can essentially inhibit the production of gram-positive bacteria, more specifically the production of TSST-1 and the
Enterotoxin B of S. aureus bacteria. The ether compounds of the present invention have the general formula:
where R? is a straight or branched chain alkyl group having a chain of 8 to 18 carbon atoms and R2 is selected from an alcohol, a polyalkoxylated sulfate salt or a polyalkoxylated sulfosuccinate salt.
The RL group of the ether compounds useful herein can be derived from saturated and unsaturated fatty acid compounds. Suitable compounds include the Cβ-C18 fatty acids and preferably, the fatty acids include, without limitation, caprylic, capric, lauric, myristic, palmitic and stearic acid whose carbon chain lengths are 8, 10, 12, 14, 16 and 18, respectively. Highly preferred materials include capric, lauric and myristic.
Preferred unsaturated fatty acids are those having one or two cis-type double bonds and mixtures of these materials. Suitable materials include the myristoleic, palmitoleic, linoleic and mixtures thereof.
Desirably, the R2 group is an aliphatic alcohol which can be ethoxylated or propoxylated for use in ether compositions of the present invention. Suitable aliphatic alcohols include glycerol, sucrose, glucose sorbitol, sorbitan and derivatives thereof. Preferred ethoxylated and propoxylated alcohols include glycols such as ethylene glycol, propylene glycol, polyethylene glycol and propylene glycol.
The aliphatic alcohols can be ethoxylated or propoxylated by conventional ethoxylating or propoxylating compounds and techniques. The compounds are preferably selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof, and similar ring compounds that provide a material which is effective. More preferably, the ethoxylation compound selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof.
The R2 moiety may further include polyalkoxylated sulfate and polyalkoxylated sulfosuccinate salts. The salts may have one or more cations. Preferably, the cations are sodium, potassium or both.
Preferred ether compounds of the present invention include laureth-3, laureth-4, laureth-5, PPG-5 lauryl ether, 1-0-dodecyl-rac-glycerol, sodium laureth sulfate, potassium laureth sulfate, laureth sulfosuccinate (3 ) disodium, diphosphate laureth (3) sulfosuccinate and sorbitol ether of oxide
(2) polyethylene.
In accordance with this invention, the plug contains an effective amount of the inhibiting ether compound to essentially inhibit the formation of TSST-1 when the plug is exposed to the S bacterium. aureus. Effective amounts have been found to be at least 0.005 millimoles of ether compound per gram of sorbent. Preferably, the ether compound ranges from about 0.005 millimoles per gram of sorbent to about 2 millimoles per gram of sorbent and more preferably 0.005 millimoles per gram of sorbent to about 0.2 millimoles per gram of sorbent. Even when the "compound" is used in the singular, an expert in the art will understand that it includes the plural. That is, the absorbent article can include more than one ether compound.
In another embodiment of the invention certain nitrogen-containing compounds can essentially inhibit the exoprotein production of gram-positive bacteria, and more specifically the production of TSST-1 and enterotoxin B from S bacteria. aureus. Specifically, the nitrogen-containing compounds of the invention are amines and their salts have the general formula:
R3-N-R4 1 Rs
wherein R3 is an alkyl group having from about 8 to about 18 carbon atoms; and R4 and R5 may be the same or different and are selected from hydrogen and alkyl group (s) having from 1 to about 18 carbon atoms. The alkyl groups of R4 and R5 may include one or more substitution moieties selected from hydroxyl, carboxyl, and carboxyl and imidazoline salts. The amine compounds of the invention are effective to essentially inhibit the exoprotein production of gram-positive bacteria.
It is critical for the invention that the R3 group is an alkyl group having from about 8 to about 18 carbon atoms. Desirably, the alkyl group is derived from the fatty acid compounds which include, without limitation, caprylic, capric, lauric, myristic and palmitic acid whose carbon chain lengths are 8, 10, 12, 14, 16 and 18 respectively. Highly preferred materials include capric, lauric and myristic. Preferred unsaturated fatty acids are those having one or two double cis-type bonds and mixtures of these materials. Suitable materials include myristoleic, palmitoleic and linoleic and mixtures thereof.
The alkyl groups R4 and R5 may further include one or more substitution moieties selected from hydroxyl, carboxyl, carboxyl salts, and R3 and R4 may form an unsaturated heterocyclic ring containing a nitrogen that is connected through a double bond to the alpha carbon of the R5 group to form a substituted imidazolino. The carboxyl salts may have one or more cations selected from sodium, potassium or both. The alkyl groups R3-R5 can be straight or balanced and can be saturated or unsaturated.
In other embodiments, the amine compound may be a salt. The salt can be represented by the general formula:
R6 R3 + -N-R4 R5
wherein R3 is an anionic group associated with the amine and is derived from an alkyl group having from about 8 to about 18 carbon atoms. Desirably, R3 is polyalkoxylated alkyl n-sulfate. The group R6 is the mist * ao as described above for the halves R4 and Rs. The alkyl groups R 3 -Rβ can be straight or branched and can be saturated or unsaturated. A preferred illustrative compound of an amine salt is laureth sulfate TEA.
Preferred amine compounds of the present invention which can be incorporated in the absorbent article or the cap thereof include laureth sulfate TEA, lauramine, propionic lauramino acid, sodium dipropionic laurimino acid, lauryl hydroxyethyl imidazoline and mixtures thereof .
According to the invention, the stopper contains an effective amount of the inhibiting nitrogen containing compound to essentially inhibit the TSST-1 form when the stopper is exposed to the S bacterium. aureus. Effective amounts have been found to be at least about 1 x (10 ~ 5) millimoles of the amine compound per gram of sorbent. Preferably, the amine compound ranges from about 0.005 millimoles per gram of sorbent to about 2 millimoles per gram of sorbent and more preferably from 0.005 millimoles per gram of sorbent to about 0.2 millimoles per gram of sorbent. Even when the "compound" is used in the singular, an expert in the art will understand that this includes the plural. That is, the absorbent article may include more than one amine compound.
In another embodiment of the invention, the nitrogen-containing compounds of the invention have the general formula:
? R7-CN-R8 I R «
wherein R7, inclusive of the carbonyl carbon is an alkyl group having 8 to 18 carbon atoms, and R1 and R, may be the same or different. R8 and R9 are selected from hydrogen and from an alkyl group having from 1 to about 12 carbon atoms which may contain one or more substituent groups selected from ester, ether, amine, hydroxyl, carboxyl, carboxyl salts, sulfonate and salts of sulfonate.
The alkyl group, which includes the carbonyl carbon, can be derived from the saturated and unsaturated fatty acid compounds. Suitable compounds include the C8-C18 fatty acids, and preferably, the fatty acids include, without limitation, caprylic, capric, lauric, myristic, palmitic and stearic acids whose carbon chain lengths are 8, 10, 12, 14 , 16 and 18, respectively. Highly preferred materials include capric, lauric and myristic.
Preferred unsaturated fatty acids are those having one or two cis-type double bonds and mixtures of these materials. Suitable materials include myristoleic, palmitoleic, linoleic and mixtures thereof.
The halves R8 and R9 may be the same or different and each is selected from hydrogen and an alkyl group having a carbon chain having from 1 to about 12 carbon atoms. The alkyl groups R7-R9 can be straight or branched and can be saturated or unsaturated. When R8 and / or R9 are an alkyl moiety having a carbon chain of at least two carbons, the alkyl group may include one or more substituent groups selected from ester, ether, amine, hydroxyl, carboxyl, carboxyl salts , sulfonate and sulfonate salts. The salts may have one or more cations selected from sodium, potassium or both.
Preferred amide compounds of the present invention include sarcosinate lauroyl sodium, MEA lauramide, DEA lauramide, dimethylamine lauramidopropyl, sulfasauccinate MEA lauramido disodium. and disodium lauroamphodiacetate.
According to the invention, the stopper contains an effective amount of the nitrogen-containing inhibitor compound to essentially inhibit the formation of TSST-1 when the stopper is exposed to the S bacterium. aureus. Effective amounts have been found to be about 5 x (10"*. Millimoles of the amine compound per gram of sorbent.) Preferably, the amide compound ranges from about 0.005 millimoles per gram of sorbent to about 2 millimoles. per gram of absorbent, more preferably the amide compound ranges from about 0.005 millimoles per gram of sorbent to about 0.2 millimoles per gram of sorbent Even though the "compound" is used in the singular, an artisan will understand that this includes the plural, that is, the absorbent article may include more than one amine compound.
The compositions of the present invention can be prepared and applied in any suitable form, but are preferably prepared in forms including, without limitation, aqueous solutions, lotions, balms, gels, ointments, semisolid preparations, pills, suppositories and the like.
The compositions can be applied to the absorbent article using conventional methods to apply an inhibiting agent to the desired absorbent article. For example, unitary plugs without separate wraps can be embedded directly into a liquid bath having the agent and then can be air dried, if necessary to remove any volatile solvents. For compressed plugs, the impregnation of any of its elements is done before the compression. The compositions when incorporated into and / or within the plug materials may be fugitive, loosely adhered, bonded or by any combination thereof. As used herein the term "fugitive" means that the composition is capable of migrating through the materials of the plug.
It is not necessary to impregnate the complete absorbent body of the stopper with the inhibitory agent. Optimum results both economically and functionally can be obtained by concentrating the material at or near the outer surface where it will be most effective during use.
The essentially inhibitory composition may additionally employ one or more conventional compatible pharmaceutically acceptable carrier materials useful for the desired application. The carrier may be able to co-dissolve or suspend the materials used in the composition. Carrier materials suitable for use in the present composition, therefore, include those well known for use in the cosmetic and medical arts as a base for ointments, lotions, creams, semi-solid solutions, aerosols, suppositories, gels and the like.
The inhibitory compositions of the present invention may additionally employ auxiliary components conventionally found in pharmaceutical compositions in their established form in the art and at the levels set forth in the art. For example, the composition may contain additional compatible pharmaceutically active materials for a combination therapy, such as complementary antimicrobials, antiparasitic agents, antipluritics, astringents, local anesthetics or anti-inflammatory agents.
The present invention can be easily understood by considering the following examples which are illustrative of the specific embodiments. The examples are given to serve as a guide for carrying out the invention and should not be considered as a limitation or limitations of the invention. It should be understood that various changes or modifications may be made, as will be apparent to those skilled in the art without departing from the spirit of the invention or the scope of the appended claims.
EXAMPLES 1-3
The efficacy of the test compounds in the production of TSST-1 was determined by placing the desired concentration, expressed in millimoles / milliliters
(millimolar hereafter mM) of the active compound in 10 ml of an average growth of each test compound in a Corning 50 ml conical polystyrene tube. The polystyrene tube is available from Scientific Product Division, Baxter Diagnostics Incorporated, 1430 Waukegan Road, McGaw Park, Illinois 60085-6787.
The Growth Medium was prepared as follows: brain heart infusion broth (BHI), available from Becton Dickinson Microbiology Systems, Cockeysville, Maryland 21030 was dissolved and sterilized according to the manufacturer's instructions. 90 milliliters of the BHI broth was supplemented with 10 ml of fetal bovine serum (FBS), available from Sigma Chemical Company, from P.O. Box 14508, St. Louis, Missouri 63178-9916. One milliliter of a sterile 0.02 molar solution of the magnesium chloride hexahydrate, available from Sigma Chemical Company, was added to the BHI-FBS mixture. One milliliter of 0.027 molar sterile L-glutamine solution available from Sigma Chemical Company was also added to the BHI-FBS mixture.
If the test compound was not soluble in water or miscible in water, it was first dissolved at 50 times the desired concentration in 10 ml of isopropanol, and then diluted to the desired final concentration in 10 ml of the growth medium. The growth medium tubes with an equivalent amount of isopropanol, but not the test compound, were prepared as controls.
In preparation for the inoculation of the Growth Medium tubes containing the test compound, an inoculation broth was prepared as follows. The S. aureus (MN__) was striated on a sheep blood agar plate and incubated at 37 ° C. The test organism in this example was obtained from Dr. Pat Schlievert, Department of Microbiology, University of Minnesota, School of Medicine,
Minneapolis, Minnesota. After 24 hours of incubation, 3 to 5 individual colonies were taken with a sterile inoculation loop and used to inoculate 10 ml of the growth medium. The inoculated growth medium tube was ® ® capped with a S / P diaSPo plug available from Scientific Products
Division of Baxter Diagnostics, Incorporated and were incubated
37 ° C in the atmospheric air having 5% by volume of CC2. After 24 hours of incubation, the culture was removed from the incubator and mixed well on a vertex mixer S / P brand. A second tube containing 10 ml of the growth medium was inoculated with 0.5 ml of the 24-hour culture mentioned above and re-incubated at 37 ° C in atmospheric air having 5% by volume of CO2. After 24 hours of incubation the culture was removed from the incubator and mixed well in an S / P brand vertex blender. Each tube of the growth medium containing a test compound and the growth control tubes cor. or without isopropanol were inoculated with 0.1 ml of the prepared inoculant broth. The initial colony forming units (CFJ) per milliliter of growth medium were approximately 1 x 107. The tubes were capped with S / P® plugs. "® diSPo and incubated at 37 ° C in atmospheric air taking 5% by volume Co2.
After 24 hours of incubation the tubes were removed from the incubator and the culture fluid was tested for the number of colony forming units of S. aureus and prepared for the TSST-1 analysis by the method described below.
The number of colony forming units per milliliter after incubation was determined by a standard plate count procedure. The culture fluid broth was centrifuged and the supernatant subsequently filtered and sterilized through an Acrodisc ® syringe filter unit available from Scientific Products Division of
Baxter Diagnostics, Inc. The resulting fluid was frozen at -80 ° C until assayed.
The amount of TSST-1 per milliliter was determined by a non-competitive sandwich enzyme-linked immunosorbent assay (ELISA). Samples of the culture fluid and standard reference TSST-1 were tested in triplicate. The method employed was as follows: Four reagents, rabbit polyclonal anti-TSST-1 IgG (# LTI-101), rabbit polyclonal anti-TSST-1 IgG conjugated to horseradish peroxidase (# LTC-101), TSST- 1 (# TT-606), and free normal anti-TSST-1 certified rabbit serum (# NRS-10) were purchased from Toxin Technology Incorporated, 7165 Curtis Avenue, Sarasota Florida 34231. Sixty-two microliters of anti-TSST Polyclonal rabbit IgG-1 (# LTI-101) was appropriately diluted so that a dilution of 1: 100 gave an absorbance of 0.4 to 650 nanometers. This was added to 6.5 milliliters of 0.5 molar carbonate buffer, a pH of 9.6, and 100 microliters of this solution were pipetted into the inner walls of polystyrene # 439454 microconcentration plates, obtained from Nunc-Denmark. The plates were covered and incubated overnight at 37 ° C. The dissociated antitoxin was removed by three washes with phosphate buffered salt water solution (pH 7.2) (0.011 molar NaH2P04 and 0.9% [weight / volume] NaCl both available from Sigma Chemical Company) containing 0.5% [volume / volume] of Tween 20 (PBS-Tween), also available from Sigma Chemical Company. The plates were treated with 100 microliters of 1% [w / v] of bovine serum albumin solution (BSA) available from Sigma Chemical Company, covered and incubated at 37 ° C for 1 hour. The unbound BSA was removed by six washes with PBS-Tween. The standard reference TSST-1, was diluted from 1-10 ng / ml in PBS-Tween, the test samples were treated with 10% normal rabbit serum
[volume / volume] final concentration and reagent controls were pipetted in 100 microliter volumes to their respective wells. This was followed by incubation for 2 hours at 37 ° C and three washes to remove the unbound toxin. Rabbit polyclonal anti-TSST-1 IgG conjugated to strong horseradish peroxidase and diluted according to the manufacturer's instructions were added (100 microliter volumes) to each microconcentration well. The plates were covered and incubated at 37 ° C for 1 hour.
After incubation the plates are washed six times in PBS-Tween. After this, the wells were treated with a solution of 0.075 molar sodium citrate (pH of 4.0), 0.6 millimolar of 2, 2'-Azino-bis- (3-ethylbenzthiazoline-6-sulfonic acid) ammonium salt and 0.009 % [volume / volume] hydrogen peroxide, all available from Sigma Chemical Company. The intensity of the color reaction in each well was evaluated over time using the BioTek Model EL340 Microplate reader (OD ® 405 nm) and Biotek's Kineticalc computer program
Instruments, Inc. The TSST-1 concentrations in the test samples were predicted from the reference toxin regression equations derived during each test procedure.
The efficacy of the ether, amine and amide compounds to inhibit the production of TSST-1 is shown below in Tables I-III respectively.
TABLE I
ELISA Compound: TSST-1
Compound Test M CFU / ml nq / ml
Growth control None 3.3 X 10 »381.8
1-0-dodecyl-rae-glycerol 10.67 1.2 X 10 '19.8
Laureth-3 9.03 2.4 X 10ß 3.7
Laureth-4 10.20 2.4 X 10a 2.3
Sulfate laureth sodium 10.65 2.9 X 103 ND
PPG-5 Laureth-5 7.35 2.0 X 10"1.6
Laureth disdicico sulfosuccinato 9.84 3.4 X 10"2.3
ND = Not detected
The above list of compounds (Trade Name), their percentage of active compound and the seller are as follows:
1-0-dodecyl-rac glycerol from Sigma Chemical Company, 100% P.O. Box 14508, St. Louis, Missouri 63178-9916.
Laureth-3 (Trycol 5966), 97%, Henkle Corporation, Emery Group, 4900 East Avenue, Cincinnati, Ohio 45232.
Laureth-4 (Trycol 5882), 97%, Henkle Corporation, Emery Group, 4900 East Avenue, Cincinnati, Ohio 45232.
Sulfate laureth sodium (Standapol Es-2) 25%, Henkle Corporation. PPG-5 Laureth-5, (Aethoxal B), 100%, Henkle Corporation.
Sulfosuccinate laureth sodium (Standapul SH-124-3), 39%, Henkle Corporation.
According to the present invention, the data in Table I show that S. aureus MN8, when compared to the control, produced significantly less TSST-1 in the presence of the ether compounds. The ether compounds reduced the amount of exotoxin by varying from about 95% to more than 99.6%. However, even when the amount of toxin produced was significantly reduced, in the majority of the ether compounds the number of cells of £ _ was not essentially reduced. aureus.
TABLE II
ELISA Compound: TSST-1
Test compound mM CFU / ml nq / ml
Growth control None 2.5 x 10 '153.2 propidic acid 10.67 No growth < 1.1 laurimine 0.43 Not determined * 24.2 Laurominodide 10.67 1.0 x 103 < 1.1 sodium propionic 2.15 Not determined 2.9 Lauryl hydroxyethyl 10.67 No growth < 1.1 imidazoline 0.43 Not determined 85.9 Sulfate laureth 10.67 6.2 x 102 < 1.1 TEA 2.15 Not determined 4.7 Lauramina 10.67 No growth < 1.1 2.15 Not determined 77.0 * Staphylococcus aureus grew in the culture broth, the amount of growth was not determined.
The above list of compounds (Trade Name), their percentage of active compound and the seller are as follows:
Laurimino Propionic Acid (Mackam 151L), 40% Mclntyre Grou, LTE, 1000 Govermors High University Park, Illinois 60466.
Sodium lauriminodipropionic acid (Deriphat 160-C), 3C% Henkle / Cospha, Cospha Group, 300 Brookside Ave., Ambler, Pennsylvania 19002.
Lauryl hydroxyethyl imidazoline (Schercozoline L), Scher Chemicals, Inc., Industrial West, P: 0: Box 4317, Clifton, New Jersey 07012.
Sulfate laureth TEA (Sulfochem TLES), 39%, Chemron, P.O. Box 2299, Paso-Robles, California 93447.
Lauramide, (Dodecylamine), 99+, Aldrich, 1001 West St. Paul Avenue, Milwaukee, Wisconsin 53233.
In accordance with the present invention, the data of Table II show that S. aureus MN8, when compared to the control, produced significantly less TSST-1 in the presence of the amine compounds. The amine compounds reduced the amount of exotoxin production ranging from about 86% to more than 99.4%.
TABLE III
ELISA Compound: TSST-1
Test compound mM CFU / ml nq / ml
Growth control None 3.1 x 10 '381.8 Lauramide MEA 10.67 1.5 x 10' 51.6 Sarcosinate lauroyl sodium 10.70 1.4 x 103 < 1.1 disodium lauroamphodiacetate 10.74 3.5 x 10 '2.9 Sulfosuccinate MEA Lauramide disodium 10.71 9.1 x 10 * 1.2
The above list of compounds (Trade Name), their percentage of active compound and the seller are as follows:
Lauramide MEA (Comperlan LNN), 98.5%, Henkle Corporation, 300 Brookside Avenue, Ambler, Pennsylvania 19002.
Sarcosinate lauroyl sodium (Hamposyl L-30), 30% Hampshire Chemical Co., 55 Hayden Avenue, Lexington MA 02173.
Disodium Lauroampheracetate (Mackam 2-L), 50% Mclntyre Group, 1000 Govemors High University Park, Illinois 60466.
Sulfosuccinate MEA disodium lauramido (Mackanate LM-40), 40% Mclntyre Group, 1000 Govemors High University Park, Illinois 60466.
In accordance with the present invention, the data of Table III show that S. aureus MN8 when compared to the control, produced significantly less TSST-1 in the presence of the amide compounds. The amide compounds reduced the amount of exotocin production ranging from about 86% to over 99.6%.
EXAMPLES 4-6
The effectiveness of the test compounds in reducing the production of a second S exoprotein. aureus was determined using S. aureus HOCH, a known producer of enterotoxin B. The test organism in this example was obtained from Dr. Pat Schlievert, Department of Microbiology of the
School of Medicine, University of Minnesota, Minneapolis, Minnesota. The experimental procedure to establish the efficacy of the test compounds was carried out on the growth of S. HOCH aureus and for the production of a culture filtrate was the same as established in the
Example A given above.
The amount of enterotoxin B of S. aureus per milliliter was determined by a Western Blot assay. The samples of the culture fluid and staphylococcal enterotoxin B (SEB) reference standard were tested in triplicate. The method used was similar to that described in "A Sensitive and Rapid Method for the Detection of Alkaline Phosphatase-Conjugate Antibody on Western Blots" of M.S. Blake, K.H. Johnston, G.J. Russell-Jones and E.C, Gotschlich, Analytical Biochemistry. 136: 175-179, 1984. The description of which is incorporated herein by reference. Enterotoxin B was separated from other proteins in the test samples by polyacrylamide-sodium dodecyl sulfate gel electrophoresis (SDS-PAGE). The upper blow gel used 3% acrylamide, the lower separation gel contained 14% acrylamide gel. The upper gel was prepared with a comb containing 20 lines extending 15.5 cm from the top of the gel. A low molecular weight SDS-PAGE standard, BioRad # 161-0305, available from Bio-Rad Laboratories having offices at 2000 Alfred Nobel Drive, Hercules, California 94547, SEB # BT-202 from Toxin Technology Incorporated and culture extracts as prepared at the top were each mixed 1: 1 with a charge buffer. The charge absorber contained 30% [vol / vol] glycerol, 15%
[vol / vol] mercaptoethanol, 7% [w / vol] base Trizma with a pH of 6.8. The mixtures were boiled for 5 minutes and then twenty-five (25) microliters of each mixture were placed in a line. The SDS-PAGE gel was electrophored (60 to 80 volts) for 90 minutes or until the frontal dye was passed through the crowding gel and for an additional 2.5 hours (160-170 volts) with an electrophoresis buffer of 0.61% [weight / vol] of base Tris, 2.85 [weight / vol] glycine, 0.1% [weight / vol] SDS, pH of 7.85. The proteins were transferred to a nitrocellulose transfer membrane, available from Schleicher and Schull, Inc., of Keene, N.H. 03431, BA 85, overnight for approximately 15 hours at 200 milliamps in a bio-Rad Trans-Blot® cell. The transfer buffer was composed of 0.3% [weight / vol] Tris base, 1.4% [weight / vol] of glycine, 20% [vol / vol] of methane !, pH of 7.6.
The nitrocellulose membrane was treated for 45 minutes at 37 ° C with 3% gelatine [weight / vol] in 0.02 molar Tris buffer, 0.5 molar NaCl, at a pH of 7.5 (TBS) to block non-specific reactions, then washed at 37oc with TBS-0.05% (vol / vol) of Tween 20 (TBS-Tween) for 45 minutes.The membrane was then submerged for 1.5 hours at 37oC in 30 my TBS-Tween containing 0.05 ml of anti-SEB IgG polyclonal rabbit # LBI-202 available from Toxin Technology, Incorporated.
The membrane was washed twice in TBS-Tween and then immersed a second time for 1.5 hours at 37oc in a 50 ml solution of TBS-Tween with 25 microliters of goat anti-rabbit IgG conjugated to alkaline phosphatase. The membrane was washed twice in TBS-Tween and twice in TBS. The spot was developed with a reaction solution consisting of 2 mg of 5-bromo-4-chloroindolyl phosphatase, 100 microliters of N, N-dimethyl formamide, 10 ml of 0.15 molar barbitol buffer, pH of 9.2, 2 mg of tetrazolium nitroblue, and 40 microliters of a 2 molar solution of MgCl2 * 6H20 all available from Sigma. The reaction was stopped with a cold water wash. The amount of SEB produced in the presence of the test compound was estimated by a comparison with the staining intensity produced by a serial dilution of SEB.
The efficacy of the ether, amine and amine compounds to inhibit the production of Enterotoxin B is shown below in Tables IV-VI.
TABLE IV
Western Spot Compound
Test compound mM CFU / ml nq / ml
Growth control None 1.0 X 10 '0.8
1-0-dodecyl-rac-glycerol 10.67 7.0 X 10a 0.8
Laureth-3 9.03 8.3 X 10th ND
Laureth-4 10.20 7.5 X 10a ND
Sulfate laureth sodium 2.13 1.2 X 107 ND
PPG-5 Laureth-5 7.35 6.4 X 10th ND
Laureth disodium sulfosuccinate 9.84 2.1 X 107 ND
ND = Not detected, < 0.16 mg / ml
According to the present invention the data of Table IV show that Stachilococcus aureus HOCH, when compared to the control, produced less SEB in the presence of other compounds. However, even when the amount of toxin produced was essentially reduced, the other compounds ne significantly reduced the number of Staphylococcus aureus cells.
TABLE V
Compound of Western Spot: S? B
Test compound mM CFU / ml nq / ml
Growth control None 7.0 x 10 '0.8 Laurimino 10.67 No growth Not detected propidic acid 0.43 Not determined * Not detected
Sodium 10.67 1.3 x 103 Not detected lauriminodipropionic acid 2.15 Not determined Not detected
Lauryl hydroxyethyl 10.67 No growth Not detected imidazoline 0.43 Not determined Not detected
Sulfate laureth 10.67 5.6 x 102 Not detected
TEA 2.15 Not determined Not detected
Lauramina 10.67 No growth Not detected 2.15 Not determined 0.2
* Staphylococcus aureus grew in the culture broth, the amount of growth was not determined.
According to the present invention, the data in Table II show that Stachilococcus aureus HOCH produced significantly less SEB in the presence of the α-amine compounds. Compared to the control, the amine compounds reduced the amount of exotoxin production below the detectable range of 0.16 milligrams / milliliter.
TABLE VI
Western Spot Compound
Test compound mM CFU / ml nq / ml
Growth control None 1. .5 x 10 '0.8 MEA Lauramida 10.67 3 .7 x 10a Not detected
Sarcosinado lauroil sodium 10.70 * 1 .7 x 103 Not detected
Disodium lauroamphodiacetate 10.74 1 .2 x 10a Not detected
Sulfosuccinate MEA of lauramido disddico 10.71 1 .2 x 10a Not detected
* SEB was not detected at a concentration of 0.43 millimole of lauroyl sodium sarcosinate, no plate count was carried out.
Not detected = < 0.16 mg / ml.
In accordance with the present invention, the data in Table II show that Staphylococcus aureus HOCH when comparing the control produced significantly less SEB in the presence of the amine compounds. However, even when the amount of toxin produced was reduced to below the detectable level, the concentration of the amine compound may be adjusted such that there was little reduction in the number of Staphylococcus aureus cells. The amide compounds reduced the amount of exotoxin production below the detectable range of 0.16 milligrams / milliliter.
Another aspect of the invention is for a method for inhibiting the exoprotein production of Gram-positive bacteria in an absorbent product. The method includes the steps of contacting the absorbent article, such as a plug, with one or more of the inhibitor compositions described above and then placing the absorbent article for use so that the exoprotein production of the Gram positive bacterium is inhibited. The absorbent article may have one or more inhibitor compositions absorbed within or coated onto the fines or coating material. Desirably, the production of TSST-1 and Enterotoxin B are inhibited.
Even when the invention has been described in conjunction with a specific embodiment it will be understood that many alternatives, modifications and variations are apparent to those skilled in the art in light of the foregoing description. Therefore, this invention is intended to encompass all those alternatives, modifications and variations that fall within the spirit and scope of the appended claims.
Claims (66)
1. An absorbent article comprising an effective amount of an ether compound having the formula: R1 - 0 - R2 wherein Rx is a straight or branched alkyl group having a chain of 8 to 18 carbon atoms and R2 is selected from an alcohol, a polyalkoxylated sulfate salt and a polyalkoxylated sulfosuccinate salt, wherein said compound is effective to essentially inhibit the exoprotein production of Gram-positive bacteria.
2. The absorbent article as claimed in clause 1, characterized in that the alkyl group is saturated.
3. The absorbent article as claimed in clause 1, characterized in that the alkyl group is unsaturated.
4. The absorbent article as claimed in clause 1, characterized in that the alkyl group is selected from caprylic, capric, lauric, myristic, palmitic and stearic acids.
5. The absorbent article as claimed in clause 1, characterized in that said alcohol is aliphatic alcohol.
6. The absorbent article as claimed in clause 5, characterized in that said aliphatic alcohol is selected from glycerol, glycol, sucrose, glucose, glucose, sorbitol, sorbitan and derivatives thereof.
7. The absorbent article as claimed in clause 6, characterized in that said glycol is selected from ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol and combinations thereof.
8. The absorbent article as claimed in clause 1, characterized in that the cationic sulfate salt group and said sulfosuccinate salt are selected from sodium, potassium and combinations thereof.
9. The absorbent article as claimed in clause 1, characterized in that said compound is selected from laureth-3, laureth-4, laureth-5, PPG-5, lauryl ether, 1-0-dodecyl-rac-glycerol, sulfate sodium laureth, potassium laureth sulfate, disodium laureth sulfosuccinate (3), dipotassium laureth sulfosuccinate (3) and sorbitol ether (2) polyethylene oxide.
10. The absorbent article as claimed in clause 1, characterized in that said compound is present in an amount greater than 0.005 millimoles per gram absorbent.
11. The absorbent article as claimed in clause 1, characterized in that said compound is present in an amount of 0.005 millimoles per gram of absorbent to about 2 millimoles per gram of absorbent.
12. An absorbent article comprising an effective amount of an ether compound having the formula: Ra - 0 -R2 wherein Rx is a straight or branched alkyl group having a chain of 8 to 18 carbon atoms selected from caprylic, capric, lauric, myristic, palmitic and stearic acid and R2 is selected from an alcohol, a polyalkoxylated sulfate salt and a polyalkoxylated sulfosuccinate salt, wherein said compound is effective to essentially inhibit the exoprotein production of gram positive bacteria.
13. The absorbent article as claimed in clause 12, characterized in that the alkyl group is saturated.
14. The absorbent article as claimed in clause 12, characterized in that the alkyl group is unsaturated.
15. The absorbent article as claimed in clause 12, characterized in that said alcohol is an aliphatic alcohol.
16. The absorbent article as claimed in clause 15, characterized in that said aliphatic alcohol is selected from glycerol, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, sucrose, glucose, sorbitol, sorbitan and derivatives thereof.
17. The absorbent article as claimed in clause 12, characterized in that said cationic group of sulfate salt and sulfosuccinate salt are selected from sodium, potassium and combinations thereof.
18. The absorbent article as claimed in clause 12, characterized in that said compound is present in an amount greater than about 0.005 millimoles per gram of sorbent and said compound is selected from laureth-3, laureth-4, laureth-5, PPG-5, lauryl ether, 1-0-dodecyl-rac-glycerol, sodium laureth sulfate, potassium laureth sulfate, laureth disodium sulfosuccinate (3), dipotassium laureth sulfosuccinate (3), sorbitol ether (2), and polyethylene oxide and combinations thereof.
19. An absorbent article comprising an effective amount of an ether compound having the general formula: Rx - 0 - R2 wherein Rx is a straight or branched alkyl group having a chain of 8 to 18 carbon atoms selected from caprylic, capric, lauric, myristic, palmitic and stearic acids and R2 is selected from aliphatic alcohol, polyalkoxylated sulfate salt and salt polyalkoxylated sulfosuccinate, said aliphatic alcohol being selected from glycerol, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, sucrose, glucose, sorbitol, sorbitan and derivatives thereof, said compound being effective to essentially inhibit the production of TSST-1 and Enterotoxin B of Staphylococcus aureus bacteria.
20. The absorbent article as claimed in clause 19, characterized in that the cationic group of said sulfate salt and said sulfosuccinate salt is selected from sodium, potassium or both.
21. The absorbent article as claimed in clause 19, characterized in that said compound is selected from laureth-3, laureth-4, laureth-5, PPG-5, lauryl ether, 1-0-dodecyl-rac-glycerol, sulfate sodium laureth, potassium laureth sulfate, laureth disodium sulfosuccinate (3), dipotassium laureth sulfosuccinate (3), and sorbitol ether (2) polyethylene oxide.
22. A method for inhibiting the exoprotein production of Gram-positive bacteria in an absorbent product comprising contacting the absorbent product with an effective amount of an ether compound and exposing said absorbent product to one or more Gram-positive bacteria, said ether compound has the general formula: wherein R x is a straight or branched alkyl group having a chain of 8 to 18 carbon atoms and R 2 is selected from alcohol, a polyalkoxylated sulfate salt and a polyalkoxylated sulfosuccinate salt.
23. A method as claimed in clause 22, characterized in that said ether compound is selected from laureth-3, laureth-4, laureth-5, PPG-5, lauryl ether, 1-0-dodecyl-rac-glycerol, sulfate sodium laureth, potassium laureth sulfate, laureth disodium sulfosuccinate (3), dipotassium laureth sulfosuccinate (3), and sorbitol ether (2) polyethylene oxide.
24. The method as claimed in clause 22, characterized in that said absorbent product is a catamenial stopper.
25. An absorbent article comprising an effective amount of an amine compound wherein said compound is effective to essentially inhibit the exoprotein production of pathogenic organisms.
26. The absorbent article as claimed in clause 25, characterized in that said organisms are Gram-positive bacteria.
27. The absorbent article as claimed in clause 26, characterized in that said Gram-positive bacteria are TSST-1 and Staphylococcus aureus bacteria producing Enterotoxin-B.
28. An absorbent article comprising an effective amount of nitrogen containing a compound having the general formula: R3-N-R4 R5 wherein R3 is an alkyl group having from about 8 to about 18 carbon atoms, and R4 and R5 may be the same or different and are selected from hydrogen and from an alkyl group having from 1 to about 18 carbon atoms and which may have one or more substitution moieties selected from hydroxyl, carboxyl and carboxyl salts, and imidazoline wherein said compound effective in essentially inhibiting the exoprotein production of gram positive bacteria.
29. The absorbent article as claimed in clause 28, characterized in that the alkyl group R3-R5 is straight.
30. The absorbent article as claimed in clause 28, characterized in that the alkyl group R3-R5 is branched.
31. The absorbent article as claimed in clause 28, characterized in that R3 is selected from an alkyl group obtained from caprylic, capric, lauric, myristic, palmitic and stearic acid.
32. The absorbent article as claimed in clause 28, characterized in that said carboxyl salt has a cationic moiety selected from sodium, potassium or both.
33. The absorbent article as claimed in clause 28, characterized in that R3 and R4 form an unsaturated esteroccyclic ring.
34. The absorbent article as claimed in clause 28, characterized in that R4 contains a nitrogen connecting through a double bond to the alpha carbon of said R3 moiety to form a substituted imidazoline.
35. The absorbent article as claimed in clause 28, characterized in that said nitrogen-containing compound is selected from lauramine, lauramino propionic acid, lauryl sodium inodipropionic acid, imidazoline hydroxyethyl lauryl and mixtures thereof.
36. The absorbent article as claimed in clause 28, characterized in that said compound is present in an amount greater than about 1 x (10"5) millimoles per gram of absorbent.
37. The absorbent article as claimed in clause 28, characterized in that said compound is present in an amount ranging from about 0.005 millimoles per gram of sorbent to about 2 millimoles per gram of sorbent.
38. An absorbent article comprising an effective amount of a nitrogen containing salt having the general formula: wherein R3 + is an anionic moiety derived from an alkyl group having from about 8 to about 18 carbon atoms, R4-R6 can be the same or different and are selected from hydrogen and an alkyl group having from 1 to about 18 carbon atoms and which may have one or more substitution moieties selected from hydroxyl, carboxyl and carboxyl salts, and imidazoline wherein said compound is effective to essentially inhibit the exoprotein production of gram positive bacteria.
39. The absorbent article as claimed in clause 38, characterized in that said salt containing nitrogen is laureth sulfate TEA.
40. A method for inhibiting exoprotein production of Gram-positive bacteria in an absorbent product comprising the steps of contacting said absorbent product with an effective amount of a nitrogen-containing compound and exposing said absorbent product to at least one Gram-positive bacterium, said nitrogen-containing compound has the general formula: R3-N-R4 wherein R3 is an alkyl group having from about 8 to about 18 carbon atoms, and R4 and R5 may be the same or different and are selected from hydrogen and the alkyl group having from about 1 to about of 18 carbon atoms and which may have one or more substitution moieties selected from hydroxyl, carboxyl and carboxyl salts, and imidazoline.
41. The method as claimed in clause 40, characterized in that said nitrogen-containing compound is selected from laureth sulfate TEA, lauramine, lauramino propionic acid, sodium lauriminodipropionic acid, lauryl pyridine chloride, lauryl hydroxyethyl imidazoline and mixtures thereof, said compound being present in an amount greater than about tx (10"4) millimoles per gram of absorbent of said stopper.
42. The method as claimed in clause 40, characterized in that said Gram-positive bacterium is a Staphylococcus aureus bacterium producing TSST-1.
43. The method as claimed in clause 40, characterized in that the Gram positive bacterium is a Staphylococcus aureus bacterium producing Enterotoxin B.
44. A method for inhibiting the exoprotein production of Gram-positive bacteria in an absorbent product comprising the steps of contacting said absorbent product with an effective amount of a nitrogen-containing compound and exposing said absorbent product to at least one gram-positive bacterium. said nitrogen-containing compound is selected from laureth sulfate TEA, lauramine, propionic lauramino acid, sodium lauriminodipropionic acid, pyridinium chloride lauryl, lauryl hydroxyethyl imidazoline and mixtures thereof.
45. An absorbent article comprising an effective amount of a nitrogen-containing compound wherein said compound is effective to essentially inhibit the exoprotein production of pathogenic organisms.
46. The absorbent article as claimed in clause 45, characterized in that said nitrogen-containing compound is an amide.
47. The absorbent article as claimed in clause 45, characterized in that said pathogenic organisms are Gram-positive bacteria.
48. An absorbent article comprising an effective amount of a nitrogen-containing compound having the general formula: wherein R7 is an alkyl group having from 8 to 18 carbon atoms, inclusive of carbonyl carbon, and R8 and R9 may be the same or different, R8 and R9 are selected from hydrogen, an alkyl group having from 1 to 12 carbon atoms and may contain one or more substituent groups selected from ester, ether, amine, hydroxyl, carboxyl, carboxyl salts, sulfonate, sulfonate salts and combinations thereof, wherein said compound is effective to essentially inhibit the production of exoprotein of Gram positive bacteria.
49. The absorbent article as claimed in clause 48, characterized in that said alkyl groups of R7-R9 are straight.
50. The absorbent article as claimed in clause 48, characterized in that said alkyl groups of R7-R9 are branched.
51. The absorbent article as claimed in clause 48, characterized in that R7, including the carbonyl carbon is selected from caprylic, capric, lauric, myristic, palmitic and stearic acids.
52. The absorbent article as claimed in clause 48, characterized in that the cationic carboxyl group and said sulfonate salts are selected from sodium, potassium and combinations thereof.
53. The absorbent article as claimed in clause 48, characterized in that said compound is selected from sarcosinate lauroyl sodium, MEA lauramide, DEA lauramide, lauramidopropyl dimethylamine, sulfosuccinate MEA lauramido disodium, lauroamphodiacetate disodium and mixtures thereof.
54. The absorbent article as claimed in clause 48, characterized in that said compound is present in an amount greater than 5 x (10"4) millimoles per gram of absorbent.
55. The absorbent article as claimed in clause 48, characterized in that said compound is present in an amount ranging from about 0.005 millimoles per gram of sorbent to about 2 millimoles per gram of sorbent.
56. An absorbent article comprising an effective amount of a nitrogen containing a compound having the general formula: wherein R7 is an alkyl group having from 8 to 18 carbon atoms, inclusive of carbonyl carbon, obtained from capric, caprylic, lauric, myristic, palmitic and stearic acid and Rβ and R9 may be the same or different, R8 and R9 are selected from hydrogen, an alkyl group having from 1 to 12 carbon atoms and may contain one or more substituent groups selected from ester, ether, amine, hydroxyl, carboxyl, carboxyl salts, sulfonate, sulfonate salts and combinations of the same, wherein said compound is effective to essentially inhibit the exoprotein production of Gram-positive bacteria.
57. The absorbent article as claimed in clause 56, characterized in that the cationic group of the carboxyl salt is selected from sodium, potassium or both.
58. The absorbent article as claimed in clause 56, characterized in that the cationic group of the sulfonate salt is selected from sodium, potassium or both.
59. The absorbent article as claimed in clause 56, characterized in that said compound is selected from sarcosinate lauriloyl sodium, MEA lauramide, DEA lauramide, lauramidopropyl dimethylamine, sulfosuccinate MEA lauramido disodium, lauroamphodiacetate disodium and mixtures thereof.
60. The absorbent article as claimed in clause 56, characterized in that said compound is present in an amount greater than about 5 x (10 ~ 4) millimoles per gram of absorbent.
61. A method for inhibiting the exoprotein production of gram positive bacteria in an absorbent product comprising contacting said absorbent product with an effective amount of a nitrogen containing a compound and exposing an absorbent product to one or more Gram positive bacteria.
62. The method as claimed in clause 61, characterized in that said nitrogen-containing compound has the general formula: wherein R7 is an alkyl group having from 8 to 18 carbon atoms, inclusive of carbonyl carbon and R8 and R9 may be the same or different, R8 and R9 are selected from hydrogen, an alkyl group having from 1 to about 12 carbon atoms and may contain one or more substituent groups selected from ester, ether, amine, hydroxyl, carboxyl, carboxyl salts, sulfonate, sulfonate salts and mixtures thereof.
63. The method as claimed in clause 61, characterized in that the absorbent product is a catamenial stopper.
64. The method as claimed in clause 63, characterized in that said compound is selected from sarcosinate lauroyl sodium, MEA lauramide, DEA lauramide, lauramidopropyl dimethylamine, sulfosuccinate MEA lauramido disodium, lauroamphodiacetate disodium and mixtures thereof, said compound being present on said stopper in an amount greater than about 5 x (10"4) millimoles per gram of absorbent of said stopper.
65. The method as claimed in clause 61, characterized in that said Gram-positive bacterium is Staphylococcus aureus bacteria producing TSST-1.
66. The method as claimed in clause 61, characterized in that said Gram-positive bacterium is Staphylococcus aureus bacteria producing Enterotoxin B. SUMMARIZES Absorbent articles, such as catamenial plugs, are described for absorbing body fluids which include an effective amount of an ether, amine or amide composition, either alone or in combination to essentially inhibit the production of exotoxins by the body. Gram positive bacteria. The ether composition has the general formula: R ^ OR, wherein R 1 is a straight or branched alkyl group having a chain of 18 to 18 carbon atoms and R 2 is selected from an alcohol, a polyalkoxylated sulfate salt and a polyalkoxylated sulfosuccinate salt. The amine compound has the general formula (a) wherein R3 is an alkyl group having from about 8 to about 18 carbon atoms; and R4 and R5 may be the same or different and are selected from hydrogen and an alkyl group having from 1 to about 18 carbon atoms and which may have one or more substituent halides selected from dehydroxyl, carboxyl and carboxyl salts and imidazoline. the amide compound has the general formula (b) wherein R7 is an alkyl group having from 8 to 18 carbon atoms, inclusive of the carbonyl carbon and R8 and R9 may be the same or different, R8 and R9 are selected from hydrogen, an alkyl group having from 1 to about 12 carbon atoms and may contain one or more substituent groups selected from ester, ether, amine, hydroxyl, carboxyl, carboxyl salts, sulfonate, sulfonate salts and combinations thereof . A method for inhibiting the production of exoprotein-positive gram bacteria is also described.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08487876 | 1995-06-07 | ||
US08/487,950 US5612045A (en) | 1995-06-07 | 1995-06-07 | Inhibition of exoprotein in absorbent article |
US08/487,875 US5618554A (en) | 1995-06-07 | 1995-06-07 | Inhibition of exoprotein using amine compositions in absorbent article and method thereof |
US08/487,876 US5685872A (en) | 1995-06-07 | 1995-06-07 | Inhibition of exoprotein using amide compositions in absorbent article |
US487950 | 1995-06-07 | ||
US487875 | 1995-06-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
MX9709769A MX9709769A (en) | 1998-07-31 |
MXPA97009769A true MXPA97009769A (en) | 1998-11-09 |
Family
ID=
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