Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/11—Aldehydes
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
  • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics

Definitions

• the present invention relates to the use of a composition comprising a combination of active agents selected from 2-dodecenal, nonanal, dodecanal or decanal, as a biocidal agent. It also relates to the therapeutic use of such a composition.
• Staphylococcus aureus is a bacterium that causes many infections or food poisoning. It is particularly feared in hospitals, where it is often involved in so-called nosocomial infections. These infections are all the more dangerous because of the increasing resistance of certain strains of this bacterium to antibiotics.
• the pathogenicity of Staphylococcus aureus is due to the development by the bacterium of various substances with necrotic or toxic effects. This bacterium is responsible for some serious infections of foot wounds in diabetic patients. It is accepted that 5 to 10% of diabetics are at risk of amputation. In France, according to data from the PMSI database (Information Systems Medicalization Program), out of 15,353 people who were amputees in 2003, 7,955 (52%) were diabetic. In addition, the 10-year amputee survival rate is less than 10%, and the median survival rate is less than 2.5 years ⁇ Diabetes Care 2006; 29 (10): 2252-6).
• n-dodecanal and n-decanal showed antibacterial activity against gram-positive bacteria such as Bacillus cereus, Staphylococcus aureus, Staphylococcus epidermis.
• the n-decanal activity is, however, described as weak, with a MIC greater than or equal to 1000 ⁇ g / ml, n-dodecanal is more active with a MIC between 125 ⁇ g / ml and 250 ⁇ g / ml.
• n-nonanal another compound of the essential oil
• Mahnoudi et al. Jeobp, 12 (5), 2009, pp 574-579
• n-decanal is also described as having low activity against Staphylococcus aureus.
• composition comprising a combination of active agents, usually contained in an essential oil of Eryngium foetidium, exhibits biocidal agent properties and can be used to prevent or treat an infection caused by a pathogen.
• the present invention relates, in a first aspect, to the use of a composition comprising a combination of active agents selected from 2-dodecenal, nonanal, dodecanal or decanal, as a biocidal agent.
• the invention relates to a composition for its use for preventing or treating an infection caused by a pathogen, characterized in that it comprises a combination of active agents chosen from 2-dodecenal, nonanal, dodecanal or decanal.
• the invention relates to particular compositions.
• the present invention relates to the use of a composition comprising a combination of active agents selected from 2-dodecenal, nonanal, dodecanal or decanal, as a biocidal agent.
• the present invention relates to the use of a composition
• a composition comprising as sole active agents a combination of at least two active agents selected from 2-dodecenal, nonanal, dodecanal or decanal and at least one excipient, as biocidal agent.
• the combination of active agents used according to the invention does not consist in the decanal with the nonanal or in the decanal with the dodecanal.
• biocidal agent denotes a composition having properties enabling it to destroy or moderate the growth of a living organism, the concentration of active agents of which is between 0.2 ⁇ g / ml. and 50 ⁇ g / ml, preferably 25 ⁇ g / ml.
• composition according to the invention is particularly effective against a living organism chosen from a fungus, a virus or a bacterium.
• fungi examples include Aspergillus niger and Candida albicans.
• composition according to the invention can be used as antibacterial agent.
• antibacterial agent refers to a compound having antibacterial properties enabling it to inhibit the proliferation of a bacterium. Without being bound by any theory, the inventors are of the opinion that the antibacterial properties of the composition according to the invention results from bactericidal rather than bacteriostatic properties.
• composition according to the invention may be used as an antibacterial agent for a bacterium, in particular a gram-negative bacterium chosen from Escherichia coli and Salmonella enteritidis or a Gram-positive bacterium chosen from Bacilius cereus, Bacilius subtilis, Lactobacillus plantarum, Listeria monocytogenes and Staphylococcus aureus.
• a bacterium in particular a gram-negative bacterium chosen from Escherichia coli and Salmonella enteritidis or a Gram-positive bacterium chosen from Bacilius cereus, Bacilius subtilis, Lactobacillus plantarum, Listeria monocytogenes and Staphylococcus aureus.
• composition according to the invention can be used as an antibacterial agent against Staphylococcus aureus.
• composition according to the invention can advantageously be used for disinfection or preservation.
• the composition used according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably from 0.9 ⁇ g / ml to ⁇ g / ml to 1.1 ⁇ g / ml nonanal in combination with minus another active agent chosen from 2-dodecenal or dodecanal, or in combination with at least 2 other active agents chosen from decanal, 2-dodecenal or dodecanal.
• the composition used according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably from 0.9 ⁇ g / ml to ⁇ g / ml to 1.1 ⁇ g / ml of dodecanal in combination with at least one other active agent chosen from 2-dodecenal or nonanal, or in combination with at least 2 other active agents chosen from 2-dodecenal, nonanal or the decanal.
• the composition used according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably from 0.7 ⁇ g / ml to ⁇ g / ml to 0.9 ⁇ g / ml of decanal, in combination with 2-dodecenal, or in combination with at least 2 other active agents chosen from nonanal, 2-dodecenal or dodecanal.
• the composition used according to the invention comprises a combination of 2-dodecenal and an active agent chosen from nonanal, dodecanal or decanal.
• the composition used according to the invention comprises a combination of nonanal and dodecanal.
• the composition used according to the invention comprises a combination of 2-dodecenal, nonanal, dodecanal and decanal.
• the dodecenal is the majority compound.
• the active agent which is said to be the majority in the composition is the active agent which is present in the greatest amount by weight in the composition. It may represent less than 50% by weight, of the total content of active agents, when there are more than 2 active agents.
• the composition comprises from 0.1 ⁇ g / ml to 10 ⁇ g / ml of 2-dodecenal, from 0.1 ⁇ g / ml to 5 ⁇ g / ml of nonanal, from 0.1 ⁇ g / ml to 5 ⁇ g / ml of dodecanal and from 0.1 ⁇ g / ml to 5 ⁇ g / ml of decanal.
• it contains from 2 ⁇ g / ml to 7 ⁇ g / ml of 2-dodecenal, from 0.5 ⁇ g / ml to 2 ⁇ g / ml of nonanal, from 0.5 ⁇ g / ml to 2 ⁇ g / ml of dodecanal and from 0.5 ⁇ g / ml to 2 ⁇ g / ml of decanal.
• it contains from 5 ⁇ g / ml to 5.5 ⁇ g / ml of 2-dodecenal, from 0.9 ⁇ g / ml to 1.1 ⁇ g / ml of nonanal, from 0.9 ⁇ g / ml to 1, 1 ⁇ g / ml of dodecanal and 0.75 ⁇ g / ml at 0.85 ⁇ g / ml of decanal. It is understood that in these compositions, the total concentration of active agents is less than or equal to 25 ⁇ g / ml.
• the composition according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably still from 0.9 ⁇ g / ml. / ml at 1.1 ⁇ g / ml of nonanal in combination with another active agent selected from 2-dodecenal or dodecanal.
• the composition according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably still from 0.9 ⁇ g / ml. / ml at 1.1 ⁇ g / ml of dodecanal in combination with another active agent selected from 2-dodecenal or nonanal.
• the composition according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably still from 0.7 ⁇ g / ml at 0.9 ⁇ g / ml of decanal, in combination with 2-dodecenal.
• the composition used according to the invention comprises a combination of 2-dodecenal and an active agent chosen from nonanal, dodecanal or decanal.
• the composition according to the invention comprises a combination of nonanal and dodecanal.
• the total concentration of active agents is less than or equal to 50 ⁇ g / ml, preferably less than 25 ⁇ g / ml.
• composition may further comprise at least one excipient of physiologically acceptable formulation.
• composition may further comprise at least one food grade formulation excipient.
• physiologically acceptable formulation excipient refers to a compound whose physicochemical properties do not alter the physiology of the user of the composition.
• the term "food grade formulation excipient” refers to a compound that is nontoxic to the user of the composition.
• the synergy resulting from the combination of active agents in the composition makes it possible to broaden the spectrum of living organisms against which said composition is effective. In particular, it makes it possible to widen the spectrum of bacteria, and their strain, against which the composition is effective.
• composition can be applied identically regardless of the use mentioned above. It can thus be used by surface application, by spraying or by diffusion.
• the use by surface application can be carried out by formulating the composition in the form of cream, soap, gel, etc. or by impregnating a surface with a bandage, wipe, patch or patch.
• the volatility of the active agents of the composition makes it possible to formulate it in the form of a liquid solution in order to use it advantageously by spraying or by diffusion, using a spray or a diffuser. Such formulations also make it possible to administer the composition by nasal or pulmonary route.
• the composition can thus clean the air in a hospital environment.
• the composition may further comprise a suitable solvent.
• compositions in the above-mentioned formulations can be evaluated according to the activity of living organisms, particularly bacteria, and toxicity results.
• the invention relates to the use as the biocidal agent of the following compositions which contain as sole active agents the following combinations:
• composition comprising a combination of active agents selected from 2-dodecenal, nonanal, dodecanal or decanal, can also be used in the therapeutic field, for the prevention and / or treatment of an infection caused by a pathogen selected from a fungus, a virus, or a bacterium.
• the invention relates to the use of a composition
• a composition comprising at least two active agents chosen from 2-dodecenal, nonanal, dodecanal or decanal and at least one excipient for the treatment and / or preventing an infection caused by a pathogen selected from a fungus, a virus, or a bacterium.
• the composition for its use in the treatment and / or prevention of an infection caused by a pathogen comprises the 2- dodecenal in combination with at least one active agent selected from nonanal, dodecanal or decanal, the amount of 2-dodecenal being predominant in the composition.
• the active agent which is said to be the majority in the composition is the active agent which is present in the greatest amount by weight in the composition. It may represent less than 50% by weight, of the total content of active agents, when there are more than 2 active agents.
• the combination of active agents does not consist of the decanal with the nonanal or of the decanal with the dodecanal.
• the composition comprises the combination of active agents or the combination of active agents with formulation excipients, water and / or a solvent or diluent.
• the formulation excipients, the solvent and the diluent are chosen to be of suitable quality for the use of the composition. If the use of the composition is food (preservative) their quality will be food, if the use is for the disinfection of medical or implantable equipment, their quality is pharmaceutical, and even if their use is therapeutic.
• the combination of active agents is chosen from:
• the different active agents of the combination may be in one or the same formulation, that is to say they may be present simultaneously in the same composition. They may also be in separate forms so that they can be administered or applied not only simultaneously but also separately or sequentially.
• composition according to the invention is particularly effective against an infection caused by a gram-positive bacterium. It is so particularly effective against an infection caused by a gram-positive bacterium mentioned above, and more particularly an infection caused by Staphylococcus aureus.
• Infections caused by Staphylococcus aureus include diarrhea, suppurative skin infections, acute myositis, pneumonia, endocarditis, urinary tract infections, phlebitis, certain types of enteritis, meningitis, osteomyelitis.
• the composition is used for the prevention or treatment of an infection caused by a pathogen in a mammal, in particular a human being, more particularly in a diabetic patient.
• composition When the composition is used for the prevention and / or treatment of an infection caused by a pathogen, said composition may further comprise at least one pharmaceutically acceptable excipient.
• the term "pharmaceutically acceptable excipient” means a compound which is chemically compatible and / or toxicologically compatible with the combination of active agents of the composition and with the mammal treated with the composition.
• the composition is particularly effective for a total active agent concentration of from 0.2 ⁇ g / ml to 50 ⁇ g / ml, preferably from 1 ⁇ g / ml to 25 ⁇ g / ml, more preferably still 1.6 ⁇ g / ml at 15 ⁇ g / ml.
• This low total concentration of active agents in the composition results from a synergy between the different active agents present in the composition.
• the composition used according to the invention comprises from 0.1 ⁇ g / ml to 10 ⁇ g / ml, preferably from 2 ⁇ g / ml to 7 ⁇ g / ml, more preferably from 5 ⁇ g / ml to 5.5 ⁇ g / ml of 2-dodecenal, in combination with at least one other active agent chosen from dodecanal, nonanal, or decanal.
• the composition used according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably from 0.9 ⁇ g / ml to ⁇ g / ml at 1.1 ⁇ g / ml of nonanal in combination with at least one other active agent chosen from 2-dodecenal or dodecanal, or in combination with at least 2 other active agents chosen from decanal, 2-dodecenal or the dodecanal.
• the composition used according to the invention comprises from 0.1 ⁇ / ⁇ 1 to 5 ⁇ / ⁇ 1, preferably from 0.5 ⁇ / ⁇ 1 to 2 ⁇ / ⁇ 1 more preferably still from 0.9 ⁇ / ⁇ 1 to 1.1 ⁇ / ⁇ 1 of dodecanal in combination with at least one other active agent chosen from 2-dodecenal or nonanal, or in combination with at least 2 other active agents selected from 2-dodecenal, nonanal or decanal.
• the composition used according to the invention comprises from 0.1 ⁇ g / ml to 5 ⁇ g / ml, preferably from 0.5 ⁇ g / ml to 2 ⁇ g / ml, more preferably from 0.7 ⁇ g / ml to ⁇ g / ml to 0.9 ⁇ g / ml of decanal, in combination with 2-dodecenal, or in combination with at least 2 other active agents chosen from nonanal, 2-dodecenal or dodecanal.
• the composition used according to the invention comprises a combination of 2-dodecenal and an active agent chosen from nonanal, dodecanal or decanal.
• the composition used according to the invention comprises a combination of nonanal and dodecanal.
• the composition used according to the invention comprises a combination of 2-dodecenal, nonanal, dodecanal and decanal. More specifically, the composition comprises from 0.1 ⁇ g / ml to 10 ⁇ g / ml of 2-dodecenal, from 0.1 ⁇ g / ml to 5 ⁇ g / ml of nonanal, from 0.1 ⁇ g / ml to 5 ⁇ g / ml of dodecanal and from 0.1 ⁇ g / ml to 5 ⁇ g / ml of decanal.
• it contains from 2 ⁇ g / ml to 7 ⁇ g / ml of 2-dodecenal, from 0.5 ⁇ g / ml to 2 ⁇ g / ml of nonanal, from 0.5 ⁇ g / ml to 2 ⁇ g / ml of dodecanal and from 0.5 ⁇ g / ml to 2 ⁇ g / ml of decanal.
• it contains from 5 ⁇ g / ml to 5.5 ⁇ g / ml of 2-dodecenal, from 0.9 ⁇ g / ml to 1.1 ⁇ g / ml of nonanal, from 0.9 ⁇ g / ml to 1, 1 ⁇ g / ml of dodecanal and 0.75 ⁇ g / ml at 0.85 ⁇ g / ml of decanal.
• the total concentration of active agents is less than or equal to 25 ⁇ g / ml.
• the amount of dodecenal is greater than the amount of the other active agents.
• composition used according to the invention can be administered topically, orally, intravenously, intramuscularly, subcutaneously, nasally, percutaneously or pulmonally, in particular orally.
• the percutaneous administration of said composition may be carried out by formulating the composition, in particular in the form of cream, soap or gel, or by impregnating a surface with a net, a dressing, a wipe or a patch or stamp.
• the composition formulated in the form of cream, soap or gel can be used to prevent and / or treat a bacterial infection of a foot wound of a diabetic patient.
• a completely appropriate manner for the prevention and / or the treatment of wounds of diabetic patients, in particular wounds affecting their feet, it is possible to use fillets and / or dressings impregnated with the composition of the invention.
• the volatility of the active agents of the composition makes it possible to formulate it in the form of a liquid solution in order to use it advantageously by spraying or by diffusion, using a spray or a diffuser. Such formulations also make it possible to administer the composition by nasal or pulmonary route.
• the composition can thus treat respiratory tract infections.
• the composition may further comprise a suitable solvent.
• the formulation of the composition in liquid solution form also allows the administration of said composition intravenously, intramuscularly or subcutaneously.
• composition may also be formulated as a capsule, tablet, dragees, granules, syrup, oral suspensions, potions, which allows the administration of said composition orally.
• composition in the above-mentioned formulations can be evaluated according to the activity of living organisms, in particular bacteria, toxicity results, and the patient to be treated.
• the active agents of the composition according to the invention may be synthetic or may be obtained by distillation of a plant of the Apiaceae family selected from Aegopodium podagraria L., Bupleurum prealuminum L., Bupleurum sibthorpianum SS var. Diversifolium, Cnidium silaifolium, Coriandrum sativum, Ducrosia anethifolia, Ducrosia flabellifolia, Eryngium foetidum, Peucedanum alsaticum, Peucedanum cervaria, Lomatopodium staurophyllum and their mixture, preferably Eryngium foetidum.
• the distillation is a hydrodistillation.
• an essential oil obtained by hydrodistillation of a plant of the Apiaceae family selected from Aegopodium podagraria L., Bupleurum prealuminum L., Bupleurum sibthorpianum SS var. Diversifolium, Cnidium silaifolium, Coriandrum sativum, Ducrosia anethifolia, Ducrosia flabellifolia, Eryngium foetidum, Peucedanum alsaticum, Peucedanum cervaria, Lomatopodium staurophyllum and their mixture, preferably Eryngium foetidum.
• the essential oil is itself the composition.
• the different active agents are present in this composition in the proportions defined previously.
• Figure 1 is a graph showing the antimicrobial activity of Composition 1 of Example 1 and each of the active agents isolated at their respective concentration in Composition 1 of Example 1 against 5 different strains of Staphylococcus. aureus.
• Figure 2 is a graph showing the antimicrobial activity of Composition 1 of Example 1 and each isolated active agent at a concentration of 12.5 ⁇ g / ml against 5 different strains of Staphylococcus aureus.
• Figure 3 is a graph showing the antimicrobial activity of the 2x compositions of Example 2 against two bacterial strains of Staphylococcus aureus RN 4220 and S 25.
• Example 1 Obtaining a Composition Comprising (E) -2-Dodecenal of Nonanal Dodecanal and Decanal.
• composition is obtained by hydrodistillation of Eryngium foetidum (leaf, root).
• Hydrodistillation process 200 g of dry raw materials (aerial parts) are introduced into a 3 L reactor with 1.5 L of water and a few grains of pumice. The reactor is closed and equipped with a Clevenger. The whole is refluxed for 6 hours. The system is insulated with cotton strips wrapped in aluminum foil. The essential oil is recovered and then dried over MgSO 4 through a pasteur pipette to give Composition 1. The hydrosol is also preserved, the whole is stored protected from light at 4 ° C.
• the concentration of active agents is analyzed by gas chromatography coupled to mass spectroscopy (GC-MS) and by gas chromatography with a flame ionization detector (GC-FID).
• GC-MS gas chromatography coupled to mass spectroscopy
• GC-FID flame ionization detector
• Composition 1 is composed of the following active agents: (E) -2-dodecenal, dodecanal, nonanal and decanal
• the total concentration of active agents in Composition 1 is 12.5 ⁇ g / ml, distributed as follows 5.125 ⁇ g / ml of (E) -2-dodecenal, 1 ⁇ g / ml of dodecanal, 0.9875 ⁇ g / ml of nonanal and 0.8 ⁇ g / ml of decanal.
• Example 2 Study of the antibacterial properties of composition 1 and comparison with each isolated active agent.
• Strains RN 4220 laboratory strain
• S 25 strain isolated from a patient with osteoarticular infection
• NSA 1385 and NSA 739 strains isolated from foot wounds of diabetic patients
• S 1799 strain ST80 MRS A IV Methylcillin-resistant community, currently diffusing in Europe
• S S385 isolated strains of foot wounds of diabetic patients
• Composition 1 and each isolated active agent are tested according to the protocol described below. Control is performed by DMSO.
• the first concentration of each isolated active agent corresponds to the concentration of said active agent in Composition 1.
• the (E) -2-dodecenal is tested diluted in DMSO at a concentration of 5.125 ⁇ g / ml.
• the second concentration is identical for all the isolated active agents, it corresponds to the total concentration of active agents of Composition 1, that is to say to 12.5 ⁇ g / ml.
• Pre-culture is carried out by adding a colony of Staphylococcus aureus in 13 ml of LB culture medium. The LB culture medium is then stirred for 2 h at 37 ° C. 0.5 ⁇ l of Composition 1, or active agent diluted in DMSO at the concentration tested, or DMSO for the control is spot in the bottom of a 96-well flat-bottom plate. 100 ⁇ l of the preculture is added to the multichannel pipette per well (there are 3 wells per sample, 3 control wells, and 3 LB wells. An Optical Density reading at 600 nm is made at T ::::: Oh, 3 pm and 6 pm
• Composition 1 essential oil
• the activity of Composition 1 is much stronger than the activity of each active agent tested in isolation.
• this concentration 5.125 ⁇ g / ml
• neither the (E) -2-dodecenal nor each of the other active agents tested is responsible for the activity of Composition 1 on these strains.
• the activity of Composition 1 therefore comes from a synergistic effect between the different active agents of this Composition 1.
• composition 1 therefore has a bactericidal rather than a bacteriostatic action.
• Example 3 Obtaining 2x compositions, comprising a combination of 2 active agents.
• compositions 2x comprising active agents of Composition 1 are obtained from synthetic compounds (obtained from Sigma-Aldrich). These compositions are presented in the following Table 1.
• compositions 2a, 2b, 2c and 2d are particularly active on the bacterial strains S RN4220 and S S25.
• compositions 2e and 2f do not exhibit the synergistic effects and are not active on bacterial strains S RN4220 and S S25.

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