CN114667130A - Hybrid inorganic-organic complex and use thereof for maintaining the microbial balance of skin and/or cosmetic and/or dermopharmaceutical compositions - Google Patents
Hybrid inorganic-organic complex and use thereof for maintaining the microbial balance of skin and/or cosmetic and/or dermopharmaceutical compositions Download PDFInfo
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- CN114667130A CN114667130A CN202080053365.4A CN202080053365A CN114667130A CN 114667130 A CN114667130 A CN 114667130A CN 202080053365 A CN202080053365 A CN 202080053365A CN 114667130 A CN114667130 A CN 114667130A
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- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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Abstract
A hybrid inorganic-organic composite is disclosed comprising a silica colloid covalently grafted with at least one antimicrobial peptide or antimicrobial precursor thereof.
Description
Technical Field
The present invention relates to a hybrid compound and its use for maintaining the microbial balance of skin and/or cosmetic or dermopharmaceutical compositions by reducing or inhibiting the activity of bacterial proliferation.
Background
The skin consists of several layers: the epidermis is the outermost layer, and the dermis and subcutaneous tissue constitute the deepest layer. The organ is the interface between the organism and the external environment. In particular, the epidermis is protective against physical (uv radiation, temperature, etc.), chemical (solvents, allergens, etc.) and even biological (pathogens) attacks. The term applied here is the epidermal barrier.
To combat pathogen attack, the epidermis has a primary immune defense mechanism. Thus, keratinocytes and langerhans cells recognize pathogenic microorganisms and become active to eliminate them by phenomena such as phagocytosis and presentation of microbial antigens to lymphocytes or by production of antimicrobial peptides.
This immune component is complemented by a second structural defense mechanism: desquamation processes, which ensure the elimination of superficial keratinocytes and resident microorganisms.
In the rest of the text, the term "microorganism" refers to living organisms that are not visible to the naked eye, corresponding to various life forms, including bacteria, fungi and even archaea.
The ecosystem consisting of saprophytic flora also provides the barrier function of the skin.
The saprophytic bacteria flora is natural and permanent on the skin surface. The number of bacteria on the skin surface is estimated at 10 per square centimeter of skin2To 105Between individual bacteria. The most representative species are staphylococci (in particular staphylococcus epidermidis), coagulase-negative and related (Micrococcus) and aerobic (corynebacteria), Brevibacterium (Brevibacterium) or anaerobic (Propionibacterium acnes)rium acnes)). These bacteria build up in the outermost layer of the epidermis, called the stratum corneum, which adheres to keratinocytes, forming a protective biofilm.
This saprophytic flora therefore acts as a barrier, since it occupies the adhesion sites of other microorganisms, which may be pathogenic, thus limiting their proliferation.
However, in the case of skin deterioration, such as in the case of pathological (atopic dermatitis, acne or psoriasis) or severe or repeated skin attacks, the deterioration of the skin barrier promotes the appearance of bacterial, viral and/or fungal skin infections.
Meanwhile, the skin may be a place where microorganisms are propagated by contacting daily supplies (especially, cosmetics).
Conventional cosmetic compositions are susceptible to contamination by various microorganisms both during their manufacture and during their use by consumers.
Therefore, the cosmetic industry places great importance on maintaining the microbiological integrity of its products, both for the safety needs of the consumer and for maintaining the good functionality and good physicochemical aspects of its products.
Due to their use and storage techniques, cosmetics are subject to temperature changes, resulting in a moisture evaporation-condensation cycle, which can alter the concentration of ingredients in the formulation. These products are also subject to humidity variations during their distribution, storage and/or use. During their use, the products are contaminated by contact with the external environment or with the skin. This risk is particularly evident with canned products, which have a larger exposed surface and are therefore more accessible to airborne pathogenic microorganisms. Without a suitable preservative system, cosmetics are substrates for the growth of various microorganisms such as Enterobacter (Enterobacter spp.) (e.cloacae) or Enterobacter agglomerans), Pseudomonas spp (Pseudomonas putida), Pseudomonas aeruginosa (p.aeruginosa) or Pseudomonas fluorescens), Bacillus spp (Bacillus spp.), and Staphylococcus spp (Staphylococcus aureus (s.aureus) or Staphylococcus saprophyticus (s.saprophyticus).
Among the many parameters that affect the storage of cosmetics, water activity plays an important role. In order to grow in cosmetics, microorganisms must be present in a certain amount of free water.
For the purposes of the present invention, the term "free water" means water molecules that are not complexed with other molecules used in the formulation of the composition. This amount of free water is called the "water activity" and is denoted aw。
A for microbial growthwThe minimum of (c) depends on their kind. However, a reduction in water activity tends to slow the growth of these pathogens.
For the remainder of the present disclosure, the terms "compound," "component," and "ingredient" are used interchangeably.
In order to reduce the amount of water, especially free water, in conventional cosmetic formulations, the current solution is to add specific components, such as humectants, which can reduce the amount of free water by forming hydrogen bonds between their hydrophilic functional groups and free water molecules.
Agents for altering the rheology of cosmetic formulations may also be used. These are, for example, gums (guar, xanthan, etc.) which can form a three-dimensional network, thereby reducing the mobility of free water molecules. However, gums, in turn, are often the primary source of bacterial and fungal contamination of products into which they are incorporated.
Each microorganism has an optimal growth pH, typically between 5 and 8. Thus, another solution used in conventional compositions is to change the pH of the formulation to less than 5. Thus, the microorganisms are under stress conditions that are not conducive to any growth. However, the addition of acidic compounds to cosmetic compositions is aggressive to the skin and can lead to skin irritation.
An alternative to the above preservative solutions is to add a preservative to the formulation. They may be synthetic preservatives, essential oils or even vegetable oils.
For the purposes of the present invention, the term "preservative" means a substance capable of inhibiting the growth of microorganisms in a cosmetic product. In Europe, all regulatory mandated preservatives and their use limit concentrations are included in the list (Annex V of the European Cosmetic Products Directive). However, some compounds not included in this list and not considered as authorized preservatives may contribute to the preservation of cosmetics.
The european directives mandate that preservatives are all synthetic sources with varying physicochemical properties, activities and modes of action. These differences allow the choice of preservative to be adjusted according to the product to be formulated. Preservatives are selected based on various criteria such as spectrum of activity, efficacy at low concentrations, solubility in water, compatibility with other ingredients or safety and ease of use.
However, the use of these preservatives presents a problem because they may be a source of skin irritation and/or sensitization, endocrine disorders, allergies, or even carcinogenic, as some preservatives are suspected of causing cancer.
For example, parabens are one of the approved synthetic preservatives widely used in the cosmetic industry.
Parabens are antimicrobial and antifungal agents, used primarily in cosmetic compositions, but also in food or pharmaceutical products. Their mode of action appears to be through denaturation of microbial and fungal membranes, which is said to result in protein changes. The range of action of parabens includes gram-positive bacteria, such as bacteria of the genus Staphylococcus (Staphylococcus), and some gram-negative bacteria, such as pseudomonas aeruginosa (p. Parabens are also active against yeasts and molds. However, they are very weak against bacterial spores and have no activity against viruses or mycobacteria. That is why they are most often used in combination with other types of preservatives.
However, parabens are suspected to disturb the endocrine system by mimicking the properties of certain hormones and lead to reproductive problems or cancer. In addition, parabens are suspected to be predictive of childhood obesity, or to have allergic and irritant effects.
Other ingredients are also used in conventional cosmetic formulations due to their natural antimicrobial properties. These are natural extracts from plant materials, having antifungal and/or antibacterial properties.
For example, essential oils are used for their antimicrobial activity. In particular, thyme, savory or oregano essential oils contain thymol and carvacrol, or clove essential oil contains eugenol, which are compounds known to be effective against the proliferation of pathogenic microorganisms.
Despite the antimicrobial properties of essential oils, the use of essential oils in cosmetics remains problematic due to their pronounced odor, the presence of allergens, and contraindications for children or pregnant women.
Also, certain cosmetic formulations, soaps and even toothpastes contain antibiotics (e.g. triclosan) as antimicrobial agents. Triclosan is known to increase the risk of allergies, loss of muscle strength, compromised immune systems, and even liver cancer risk factors. In addition, scientists have found that triclosan is often present in consumer products in too small an amount to exert any substantial antimicrobial effect. On the other hand, bacteria exposed to such antibiotics become stronger and more resistant to the antibiotics.
In particular, bacteria such as e.coli (e.coli) increase the activity of their stress response pathways and become more resistant in the presence of triclosan. This is a phenomenon of antibiotic resistance. Then four times more triclosan and eight times more quinolone (antibiotics used against these bacteria) are needed to prevent their proliferation.
Therefore, there is a clear need to develop a new generation of compounds that ensure the inhibition or reduction of the proliferation of microorganisms in cosmetic compositions and/or on the skin and that do not have the drawbacks of the prior art ingredients.
Disclosure of Invention
Applicants have developed a hybrid inorganic-organic composite that can reduce, reduce or even inhibit microbial proliferation in cosmetic compositions and/or on the skin.
The present invention solves the above-mentioned problems of the prior art.
According to a first aspect, the present invention relates to a hybrid inorganic-organic composite comprising a silica colloid covalently grafted by a spacer arm with at least one peptide or precursor thereof.
Silicon dioxide with SiO2Is naturally occurring and is part of many inorganic compositions. It exists in its free state in various crystalline or amorphous forms and in a bound state in silicates.
According to a particular embodiment, the silicate used for the production of the silica colloid according to the invention corresponds to tetraethylorthosilicate.
In practice, the silica according to the invention can be used in purified or isolated form, with a purity at least equal to 60%, preferably at least equal to 70%, advantageously at least equal to 80%, even more advantageously at least equal to 90%, or even 95%, preferably at least 98%, advantageously 99% or even 100%.
Silica colloids are surface-modifiable, biocompatible and exhibit good dispersibility and stability in hydrophilic media.
The size, shape, porosity and crystallinity of the silica colloid may vary depending on the intended application (e.g. in the biomedical, pharmaceutical or cosmetic field). Furthermore, the variety of possible surface modifications allows control of different parameters, such as dispersion, circulation and targeting ability of the silica colloid.
According to the invention, colloid refers to particles in crystalline or amorphous form. In a liquid medium, for example an aqueous medium, the colloid forms a colloidal suspension.
The concept of colloidal grafting is part of the common general knowledge of the skilled person. Grafting corresponds to the formation of covalent bonds, for example, between a peptide or precursor thereof and the surface of the silica colloid.
According to the invention, the covalent grafting is carried out via spacer arms or "linkers".
According to a particular embodiment, the spacer arm may comprise a functional group of the ether, ester, phosphate or amide type, advantageously an ether.
Advantageously, the spacer arm is a linear ether comprising from 3 to 10 carbons (preferably from 4 to 6 carbons).
According to the invention, the spacer has no specific affinity to the microbial plasma membrane (preferably the bacterial plasma membrane).
It goes without saying that grafting is not limited to grafting individual compounds. It is a molecule or molecules of at least one compound grafted onto each silica particle.
The colloids may be synthesized according to conventional techniques, for example by
A method.
Generally, the average size of the colloid is on the order of several nanometers to several tens of nanometers.
The size of the colloids according to the invention is therefore advantageously between 0.1nm and 1000nm, more advantageously between 0.3nm and 100nm, even more advantageously of the order of 5nm, advantageously measured by DLS.
DLS (dynamic light scattering) is a technique conventionally used to measure the size of colloids in fluids.
According to a particular embodiment, the hybrid compound according to the invention comprises a silica colloid to which at least one peptide having antimicrobial activity or a precursor thereof is covalently grafted.
The grafting of the peptide or antimicrobial precursor thereof on the silica colloid is carried out via a spacer arm or "linker".
According to a particular embodiment, the grafting of the silica colloid with at least one peptide or its precursor (preferably a peptide or its antimicrobial precursor) is carried out by chemical reaction with an alkoxysilane or halosilane (advantageously an alkoxysilane), for example by creating a covalent bond by nucleophilic substitution between the terminal amine of the peptide or its precursor and the reactive end of the spacer arm.
Preferably, the grafting of the silica colloid with at least one precursor or peptide thereof is carried out with (3-glycidoxypropyl) trimethoxysilane.
This is a conventional reaction known to those skilled in the art for grafting silica colloids with spacer arms. This reaction takes place between the surface of the silica colloid comprising Si-OH functional groups and the spacer, which is advantageously an alkoxysilane or halosilane, preferably an alkoxysilane, even more advantageously (3-glycidoxypropyl) trimethoxysilane.
For the purposes of the present invention, the term "peptide" optionally denotes a polymer of amino acids.
For the purposes of the present invention, the term "peptide precursor" denotes an amino acid, i.e. an amino acid monomer, which can be converted into a peptide by natural, biotechnological or artificial peptide synthesis. Synthetic peptides may be modified (e.g., glycosylated, acylated, and/or acetylated), which may modulate their activity and/or properties.
For the purposes of the present invention, the term "peptide or antimicrobial precursor thereof" denotes a peptide or precursor thereof having properties such that it is capable of inhibiting, slowing or reducing the growth of a microorganism (e.g. bacteria, fungi, viruses, yeasts and/or protozoa).
According to a particular embodiment, the peptide or precursor thereof according to the invention is selected from the group comprising: CM15(SEQ ID NO:1), lysine, drosophila rhzomorph (drosocin), cecropin (attacin), diptericin (diptericin), melittin (melittin), cathelicidin (e.g., LL-37), defensin (defensin) (e.g., human beta-defensin-1, human beta-defensin-2 or human beta-defensin-3 (or hBD-1, h-BD-2 or hBD-3)) or a plant defensin from Nicotiana sativa (or NaD1 or NaD2) and mixtures thereof.
According to a particular embodiment, the hybrid compound according to the invention comprises a silica colloid covalently grafted with at least one peptide or precursor thereof, the colloid/peptide or precursor mass ratio of the compound being between 99.9:0.1 and 90:10, advantageously between 99:1 and 90:10, preferably between 93:7 and 94: 6.
According to a particular embodiment, the invention relates to a hybrid compound Comprising Silica Colloids (CSCs) grafted with at least one CM15, the colloid/CM 15 mass ratio of the compound being between 99.9:0.1 and 90:10, advantageously between 99:1 and 90:10, preferably between 93:7 and 94: 6.
CM15 is a 15 amino acid multifunctional hybrid cationic peptide (or MCP) (SEQ ID NO: 1). Specifically, CM15 is a hybrid peptide consisting of 2 peptides, cecropin (cecropin) and melittin (melittin) from the hemolymph of the butterfly-carved crinopsis kefir (Hyalophora cecropia).
According to the present invention, the hybrid compounds comprising CSCs have antimicrobial properties with an advantageous efficacy/minimum inhibitory concentration ratio, which is present in particular in the negative charge carried by the silica colloid. These negative charges are the origin of the phenomenon of element repulsion of microbial membranes, particularly negatively charged bacterial membranes. This phenomenon allows the hybrid complex to cross the membrane of the microorganism (e.g., bacteria) and enter the plasma membrane, particularly bacteria, which leads to degradation of the microorganism.
According to the invention, CSC hybrid complexes allow CM15 to maintain its original conformation in solution and thus increase or improve its efficiency.
According to another particular embodiment, the hybrid compound according to the invention comprises a silica Colloid (CSL) covalently grafted with at least one lysine as peptide precursor.
According to a particular embodiment, the invention relates to a hybrid compound comprising CSL, the colloid/lysine mass ratio of which is between 99:1 and 90:10, advantageously between 95:5 and 94:6, preferably between 93:7 and 94: 6.
Lysine is a positively charged amino acid contained in the composition of proteins. Such amino acids are important building blocks that make up many antimicrobial peptides. For example, cecropin (cecropin) is rich in lysine.
Such amino acids, which are also part of the composition of lysine homopolymers, are called polylysines, which differ in length (25 to 30 amino acids) and possibly in stereochemistry and bond position from each other. Studies have shown that polylysine has antimicrobial properties.
The grafting of lysine onto the silica colloid according to the invention makes it possible to immobilize and electronically stabilize the lysine, which helps to promote the penetration of CSL into the microbial, in particular bacterial, membrane in order to eliminate said microorganisms.
According to another aspect, the present invention relates to a cosmetic or dermopharmaceutical composition comprising the hybrid compound as described above.
According to a particular embodiment, the present invention relates to a cosmetic or dermopharmaceutical composition comprising CSCs and/or CSLs.
Advantageously, the hybrid compound according to the invention (in particular the CSC and/or CSL) represents from 0.001% to 2%, preferably from 0.01% to 1%, alternatively from 0.1% to 1% of the total weight of the composition.
The composition comprising the hybrid compound according to the invention, advantageously the CSC and/or CSL, may be provided in all galenic forms commonly used in cosmetics and dermatology, for example but not limited to in the form of an optionally gelled aqueous solution, a dispersion of the emulsion (deposition) type, an O/W or inverse W/O emulsion (emulsion), a more or less fluid, or a multiple emulsion (e.g. a triple emulsion (W/O/E or O/W/O)), or in the form of a vesicular dispersion of ionic (liposome) and/or non-ionic type, which is a two-phase composition free of emulsifier and gelling agent, the immiscible phases of which separate during storage, frothing, spraying or misting.
According to a particular embodiment, the cosmetic or dermopharmaceutical composition comprising the hybrid compound according to the invention (advantageously the CSC and/or CSL) is in the form of a water-based solution, dispersion, emulsion or emulsion.
According to a particular embodiment, the cosmetic or dermopharmaceutical composition comprising the hybrid compound according to the invention (advantageously the CSC and/or CSL) is an aqueous solution further comprising at least one surfactant.
In a preferred embodiment, the surfactant is a nonionic surfactant selected from the group comprising Alkyl Polyglucosides (APGs), polyglyceryl fatty alcohols, ethoxylated derivatives and polysorbates.
According to a particular embodiment, the alkylpolyglucoside comprises an alkyl group containing from 6 to 30 carbon atoms, preferably from 8 to 16 carbon atoms, and comprises a hydrophilic group (glucoside) preferably containing 1,2 or 3 saccharide units.
Examples of alkylpolyglucosides according to the invention may be, for example, compounds corresponding to the following INCI names:
sucrose stearate, sold under the name Sisterna SP70-C by SISTERNA;
decyl glucoside (or alkyl-C9/C11-polyglucoside (1.4)), by KAO CHEMICALS under the name MYDOLTM10. By BASF under the name PLANTARENTM2000UP, or by SEPPIC under the name ORAMIX NSTM10, selling;
octyl/decyl glucoside, by BASF under the name PLANTACARETM810UP for sale;
lauryl glucoside, by BASF under the name PLANTARENTM1200N and PLANTACARETM1200, sale; and
coco glucoside, by BASF under the name PLANTACARETM818/UP for sale.
As polyglycerin fatty alcohols according to the invention, mention may be made, by way of example, of Tegosoft, a raw material sold by EVONIK and corresponding to the INCI names polyglycerin-4 decanoate and polyglycerin-6 octanoate/polyglycerin-4 decanoate, respectivelyTM PC 41、TegoSolveTM 90MB。
Advantageously, the composition comprising the hybrid compound according to the invention (advantageously the CSC and/or CSL) comprises from 0.5% to 20%, preferably from 1% to 10% or alternatively from 1% to 5% by total weight of the surfactant composition.
According to a particular embodiment, the composition comprising the hybrid compound according to the invention (advantageously CSC and/or CSL) is free of ethoxylated derivatives, preferably free of surfactants derived from polyethylene glycol (PEG).
According to another embodiment, the composition according to the invention comprises an inorganic and organic hybrid complex comprising a silica colloid covalently grafted by a spacer arm with at least one peptide or its precursor (advantageously CSC and/or CSL) and at least one preservative.
Any preservative, authorized or not by regulations applicable to Cosmetic or dermatological compositions (Annex V of the European Cosmetic Products Directive), may be used to formulate compositions comprising the hybrid complex according to the invention (advantageously the CSC and/or CSL).
According to a particular embodiment, the preservative according to the invention is an alkanediol.
Preferably, the preservative according to the present invention is a 1, 2-alkanediol or a 1, 3-alkanediol.
According to a particular embodiment, the alkanediol is selected from the group comprising compounds corresponding to the following INCI names: propylene glycol, 1, 3-propanediol, 2-methyl-1, 3-propanediol, 1, 2-pentanediol, 1, 2-hexanediol, octanediol, 1, 2-decanediol, hexanediol, and mixtures thereof.
These preservatives are available from a variety of cosmetic raw material suppliers.
By way of example, we can cite:
-EVO-100TMpropylene glycol, sold by ARCHER DANIELS MIDLAND COMPANY and corresponding to the INCI name;
-ZEMEATMfrom DUPONT-TATE&LYLE biproducts, marketed and corresponding to INCI name 1, 2-propanediol;
-DUB DIOLTM2-methyl-1, 3-propanediol sold by STEARINERIE DUBOIS and corresponding to the INCI name;
-Hydrolite-5TM、Hydrolite-6TM、Hydrolite-8TMand SymClariol 344028TMMarketed by sym rise and corresponding to INCI names 1, 2-pentanediol, 1, 2-hexanediol, octanediol, and 1, 2-decanediol, respectively;
-HexasolTMhexanediol, sold by ARKEMA and corresponding to the INCI name.
According to another embodiment, the preservative is a quaternary ammonium salt selected from the group consisting of docosanyltrimethylammonium chloride, cetrimonium bromide, myristyltrimethylammonium bromide, cetrimonium chloride, lauryltrimethylammonium bromide, lauryltrimethylammonium chloride, stearyltrimethylammonium bromide, stearyltrimethylammonium chloride, benzethonium chloride, benzalkonium chloride, and mixtures thereof.
According to a particular embodiment, the preservative corresponding to the quaternary ammonium salt is cetrimide and/or myristyl trimethyl ammonium bromide, advantageously cetrimide.
For example, cetrimide is available from MERCK under the trade name RONACARETMCETRIMONIUM BROMIDE, and myristyltrimethylammonium BROMIDEFrom COSPHATECH LLC under the trade name iBact CetrimideTMAnd (5) selling.
Further preservatives suitable for use in the composition comprising the hybrid compound according to the invention (advantageously CSC and/or CSL) are, for example:
potassium sorbate (INCI), sodium benzoate (INCI) and benzyl alcohol (INCI), respectively under the name Paratexin from AZELIS UKTM KS、ParatexinTMSBG and ParatexinTMSelling BA;
p-anisic acid (INCI) and levulinic acid (INCI), respectively under the name Cosphaederm from Cosphaec GMBHTMAnd CophadermTMLA-T sales;
dehydroacetic acid (INCI) and polyaminopropylbiguanide (INCI), respectively Geogard by the name LONZATM111A andTMselling CQ;
phenoxyethanol (INCI) under the name Phenoxetol by CLARIANT INTERNATIONAL LTD CosmosilTMAnd (5) selling.
According to a particular embodiment, the composition comprising the hybrid compound according to the invention (advantageously the CSC and/or CSL) comprises from 0.001% to 5%, advantageously from 0.01% to 2%, preferably from 0.1% to 1% of preservative by total weight of the composition.
The composition comprising the hybrid compound according to the invention (advantageously CSC and/or CSL) may also comprise at least one dermocosmetic active ingredient, such as:
-lysine azelaic acid salt or derivatives thereof or azelaic acid salt;
andrographolide, in particular an Andrographis paniculata extract corresponding to the INCI name Andrographis paniculata (Andrographis paniculata) leaf extract;
natural ascorbic acid (vitamin C) or its derivatives, in particular derivatives corresponding to INCI ascorbyl glucoside, ascorbyl ethyl ether, ascorbyl methylsilanol pectate, sodium ascorbyl phosphate and ascorbyl tetraisopalmitate, advantageously ascorbyl glucoside;
arbutin or a plant extract containing it, in particular an extract of arbutin corresponding to the INCI name extract of the leaves of arbutin (Arctostaphylos uva-ursi);
glabridin or plant extracts containing it, in particular licorice extracts corresponding to the INCI name Glycyrrhiza glabra (Glycyrrhiza glabra) root extract, Glycyrrhiza inflata (Glycyrrhiza inflata) root extract, Glycyrrhiza uralensis (Glycyrrhiza uralensis) root extract;
-a biomimetic peptide corresponding to the INCI name hexapeptide-2 and/or nonapeptide-1;
-an aqueous extract of the alga known as Palmaria palmata (Palmaria palmata), in particular an extract corresponding to the INCI name Palmaria palmata extract;
-4-n-butylresorcinol;
-vitamin PP (also known as niacinamide) and its derivatives;
-at least one polyol, in particular selected from xylitol, rhamnose, mannitol and mixtures thereof;
-fructooligosaccharides;
-extracts of the algae Laminaria cuneata (Laminaria ochroleuca), Laminaria japonica (Blidinia minima) and/or Laminaria saccharina (Laminaria saccharana);
-an extract of the plant Zanthoxylum armatum (Zanthoxylum armatum);
-panthenol;
-vitamin E or one of its hydrophilic or lipophilic derivatives, or one of their salts, advantageously tocotrienols or tocopherols;
-salicylic acid or one of its derivatives;
-juniper (cade wood) extract;
-an extract from Boldo tree (Boldo);
-an extract from Meadowsweet (Meadowsweet);
-an agent limiting immunosuppression, advantageously vitamin PP;
-a protectant of the p53 protein, advantageously epigallocatechin gallate (EGCG);
-a karanja oil extract from karanja (pongama gladra);
-ATP (adenosine-5-triphosphate), Gp4G (diguanosine tetraphosphate) or Ap4A (diadenosine tetraphosphate); -peptide extracts of soybean and/or wheat and mixtures thereof;
-an amino acid or amino acid derivative selected from the group consisting of ectoin, creatine, ergothioneine, carnosine, tyrosine, decarboxylated carnosine, glutamine and salts thereof;
-an aqueous Cucumber extract corresponding to the INCI name Cucumber (Cucumis sativus) (cucumer) fruit extract;
-or mixtures thereof.
Advantageously, the composition comprising the hybrid compound according to the invention (advantageously CSC and/or CSL) further comprises from 0.001% to 10%, advantageously from 0.01% to 5%, preferably from 0.1% to 1%, by total weight of the composition, of a skin cosmetic active ingredient.
The composition comprising the hybrid compound according to the invention (advantageously CSC and/or CSL) may also comprise adjuvants conventional in the field considered, for example hydrophilic or lipophilic thickeners or gelling agents, hydrophilic or lipophilic additives, antioxidants, perfumes, fillers, pigments, UV filters, odour absorbers, dyes, humectants, vitamins, essential fatty acids, liposoluble polymers (in particular hydrocarbons), opacifiers, stabilizers, chelating agents, conditioning agents, propellants, fatty substances, organic solvents, silicones, thickeners, emollients, anionic, cationic, nonionic or amphoteric polymers, antifoams, hair conditioning agents (for example proteins, vitamins, dyes), pearlescent agents, sunscreens, especially hydrophilic sunscreens, electrolytes, stabilizers, buffers (for example citric acid/sodium citrate buffer).
According to another aspect, the invention relates to the use of the hybrid compound as described above as an agent for disinfecting skin.
According to the invention, the hybrid compound as skin cleanser can:
-maintaining and rebalancing skin microbiota;
-reducing or inhibiting proliferation of pathogenic bacteria; and/or
-elimination of pathogenic bacteria.
According to another aspect, the invention relates to the use of the hybrid compound as described above as an agent for disinfecting cosmetic or dermopharmaceutical compositions.
According to the invention, the hybrid compound as a disinfectant of the composition may:
-protecting the composition from bacterial contamination;
-reducing or inhibiting the proliferation of pathogenic bacteria; and/or
-elimination of pathogenic bacteria.
In other words, the invention relates to the use of the hybrid compound as described above as an agent for disinfecting the skin and/or a cosmetic or dermopharmaceutical composition.
According to a particular embodiment, the hybrid compound is for use in reducing, reducing or inhibiting the proliferation of pathogenic bacteria on the skin and/or in a cosmetic or dermopharmaceutical composition.
Drawings
The invention and the advantages resulting therefrom will appear more clearly from the following figures and examples, which are given by way of illustration and are not limiting.
Fig. 1 shows the antimicrobial activity of the hybrid complexes corresponding to CSCs according to the present invention compared to the antimicrobial activity of CM15 alone.
FIG. 2 shows the comparison of the antimicrobial activity of the hybrid compound corresponding to CSL according to the invention with the antimicrobial activity of lysine alone.
Detailed Description
1/overview of CSL according to the invention
The compositions used for the synthesis of CSL according to the invention are shown in table 1.
[ Table 1]
Step 1: b was dissolved in A at 60 ℃ for 20 minutes.
Step 2: c was added to the solution obtained in step 1, and the mixture was heated to 60 ℃ and stirred for 20 hours.
Step 3: the suspension obtained in step 2 was cooled to room temperature and then filtered under vacuum through a 0.4 μm filter.
Step 4: d was added to the reaction mixture from step 3, and then the reaction was maintained at 40 ℃ for 16 hours.
Step 5: after a purification step by dialysis of the mixture according to step 4, silica Colloids (CSL) covalently grafted with lysine according to the invention were obtained, first dialyzed against 5g/L of E solution for 15 hours, with 3 changes of stripping solvent, and then against A for 15 hours, with 3 changes of stripping solvent. The dialysis membrane used had an exclusion limit of 3.5 kDa. The dust was removed by filtration through a 0.2 μm cellulose acetate filter.
2/overview of CSC according to the invention
The compositions used to synthesize the CSCs according to the invention are shown in table 2.
[ Table 2]
Step 1: b was dissolved in A at 60 ℃ for 20 minutes. The pH of the solution was about 10.3.
Step 2: c was added to the solution obtained in step 1, and the mixture was heated to 60 ℃ and stirred for 20 hours.
Step 3: the suspension obtained in step 2 was cooled to room temperature and then filtered under vacuum through a 0.4 μm filter.
The solution was then dialyzed against a 1kDa exclusion limit dialysis membrane, first against 5g/L of solution D for 15 hours, with 3 changes of stripping solvent, and then against A for 15 hours with 3 changes of stripping solvent.
The pH of the solution obtained after dialysis was between 8 and 9.5, which was then adjusted between 7.5 and 8 by adding the necessary amount of 0.1M HCl solution.
Step 4: for chemical grafting, E, then F were added to the solution obtained in step 3 in the dark and the reaction was maintained at 40 ℃ for 16 hours in the dark.
Step 5: silica Colloids (CSCs) covalently grafted with CM15 according to the invention were obtained after a purification step by dialysis of the mixture according to step 4 with a for 15 hours. The dialysis membrane used had an exclusion limit of 3.5 kDa. The dust was removed by filtration through a 0.2 μm cellulose acetate filter.
3/evaluation of antimicrobial Properties of CSC and CSL hybrid complexes according to the invention
The antimicrobial capacity of the hybrid CSC and CSL complex according to the invention is determined in vitro according to the ATP assay principle.
This technique involves measuring the amount of ATP present in a sample.
All living organisms contain ATP. ATP is quantified by a bioluminescent reaction using luciferase. This enzyme catalyzes the reaction between fluorescein (substrate), ATP (cofactor) and oxygen, which is responsible for the emission of photons.
In fact, every ATP molecule consumed in the reaction produces a photon. Thus, the light production in this reaction is directly proportional to the amount of biological energy (ATP) present in the sample.
The amount of ATP measured was converted into the number of microorganisms by considering the consensus that the bacteria (e.g.E.coli) contained 0.001pg ATP.
Assessment of the antimicrobial properties of CSC and CSL hybrid complexes is performed using an ATP assay kit comprising lysis buffer that can extract cellular ATP, resin that can capture substances that may interfere with the assay, ATP stabilization buffer (not extracted from live cells) that is pre-solubilized, standard solution of ATP, and luciferase.
The amount of ATP measured after treatment with lysis buffer and resin corresponds to the total amount of ATP contained in the sample.
The value obtained for dissolved ATP is subtracted from the value for total ATP to provide the cellular ATP concentration from which the concentration of viable biomass present in the assay sample can be inferred.
The analysis was performed in the presence of CM15 peptide alone, lysine alone or in a solution comprising CSCs or CSLs according to the invention.
a/sample preparation
1.5mL of each study sample was placed in a 5mL glass vial. All samples were then contaminated with either glucose solution (method 1) or skin contact (method 2).
Method 1-glucose contamination: 1g/L glucose aqueous solution is prepared and stored for 3 days at room temperature to promote the growth of microorganisms. This solution was then added to the sample to be tested at a concentration of 25% by weight of the sample.
Method 2-contamination by skin contact: 100 μ L of the test sample was collected and placed in contact with the palm of the individual's hand (3 inhalations and refluxes). The skin contains 10 per square centimeter2To 105And (4) bacteria. These bacteria belong to either resident (non-pathogenic) or transient (potentially pathogenic) bacteria. Unlike method 1, this technique of contamination ensures that the sample contains as many bacteria as possible in contact with the cosmetic or dermopharmaceutical preparation.
b/determination of the amount of ATP in the sample
Determination of the Total amount of ATP
mu.L of the sample was mixed with 40. mu.L of lysis buffer. After one minute incubation at room temperature, 50. mu.L of the mixture was placed in 200. mu.L of resin. After homogenizing the mixture, the supernatant was analyzed for luminescence by adding 10. mu.L of the mixture to 10. mu.L of luciferase in a 384-well plate.
Determination of the amount of dissolved ATP
mu.L of the sample was mixed with 300. mu.L of stabilization buffer. After homogenization and incubation for one minute at room temperature, the luminescence of the solution was analyzed by mixing a volume of 10 μ L of sample with 10 μ L of luciferase in 384-well plates.
The amount of ATP was initially quantified after contamination (T0). The samples were placed in a climate chamber at 40 ℃ and 75% relative humidity for 3 days. Then, ATP was newly quantified (T3 ═ T3 days after contamination).
The values obtained in cellular ATP were converted into microbial equivalents.
comparison of antimicrobial Activity of c/CSC with CM15 alone
CSC (concentration 1X 10) according to the invention-3、1×10-4Or 1X 10-5mg/mL) was compared to the antimicrobial activity of CM15 alone (i.e., in a free, ungrafted state) used at the same concentration.
The results are shown in FIG. 1.
The data indicate that no antimicrobial effect was seen with CM15 alone, regardless of the concentration of CM15 used.
In contrast, the concentrations used were 1X 10 respectively-3、1×10-4Or 1X 10-5The mg/mL CSC significantly inhibited bacterial proliferation by 75.5%, 70.6% and 87.7%.
Comparison of the antimicrobial Activity of d/CSL with lysine alone
The antimicrobial activity of CSL according to the invention (at concentrations of 0.5, 0.2 or 0.05mg/mL) was compared with the antimicrobial activity of lysine alone (i.e. in a free, ungrafted state) used at the same concentration.
The results are shown in FIG. 2.
The data show that at concentrations of 0.5mg/mL or 0.2mg/mL, CSL inhibits bacterial overgrowth as well as lysine alone.
In contrast, the use of CSL at a concentration of 0.05mg/mL significantly inhibited the proliferation of 70% of the bacteria, whereas lysine alone had no inhibitory effect on this proliferation.
4/example of composition-micellar Water, foamed hygiene products and milks comprising CSL or CSC according to the invention
Liquid for treating urinary tract infection
In the table below, the percentages indicated are given in terms of weight of product relative to the total weight of the composition.
The formulation of the composition comprising micellar water of CSL according to the invention is shown in table 3.
[ Table 3]
The formulation of the composition of micellar water comprising the CSCs according to the invention is shown in table 4.
[ Table 4]
The formulation of the composition corresponding to the foaming hygiene article (body wash) comprising the CSL according to the invention is shown in table 5.
[ Table 5]
The formulation of a cosmetic O/W emulsion comprising CSL according to the invention is shown in table 6.
[ Table 6]
| Water (W) | 61.801 |
| Decyl oleate | 13.496625 |
| Glycerol | 10.00 |
| Methyl propylene glycol | 5.00 |
| Behenyl alcohol | 4.50 |
| Hydrogenated castor oil | 2.00 |
| Sucrose laurate | 1.00 |
| Sucrose stearate | 1.00 |
| Dehydro xanthan gum | 0.50 |
| Citric acid sodium salt | 0.50 |
| Citric acid | 0.184 |
| Di-covalently grafted with lysine according to the inventionColloidal silica (example 1) | 0.015 |
| Tocopherol | 0.002194 |
| Hydrogenated palm oil glycerides citrate | 0.001181 |
Sequence listing
<110> Biaonikley Co
<120> hybrid inorganic-organic complexes and their use for maintaining the microbial balance of skin and/or cosmetic and/or dermopharmaceutical compositions
<130> B374-B-55515 PCT
<150> FR1908575
<151> 2019-07-26
<160> 1
<170> BiSSAP 1.3.6
<210> 1
<211> 15
<212> PRT
<213> Artificial sequence
<220>
<223> CM15
<400> 1
Lys Trp Lys Leu Phe Lys Lys Ile Gly Ala Val Leu Lys Val Leu
1 5 10 15
Claims (10)
1. An inorganic-organic hybrid compound comprising a silica colloid covalently grafted via a spacer arm to at least one antimicrobial peptide or antimicrobial precursor thereof.
2. Hybrid compound according to claim 1, characterized in that the spacer arm comprises a functional group of the ether, ester, phosphate or amide type, advantageously an ether, preferably a linear ether comprising 3 to 10 carbons, advantageously 4 to 6 carbons.
3. The hybrid compound according to any one of the preceding claims, characterized in that at least one peptide or its precursor is selected from the group comprising: CM15(SEQ ID NO:1), lysine, drosophila rhzomorph (drosocin), cecropin (attacin), diptericin (diptericin), melittin (melittin), defensin (defensin), cathelicidin and mixtures thereof.
4. The hybrid compound according to any one of claims 1 to 3, characterized in that the colloid/peptide or precursor mass ratio is from 99.9:0.1 to 90:10, advantageously from 93:7 to 94: 6.
5. A cosmetic or dermopharmaceutical composition comprising the hybrid complex of any one of claims 1 to 4.
6. Cosmetic or dermopharmaceutical composition, according to claim 5, characterized in that said hybrid compound represents from 0.001% to 2%, preferably from 0.01% to 1% of the total weight of the composition.
7. Cosmetic or dermopharmaceutical composition, according to claim 5 or 6, characterized in that it is in the form of a water-based solution, dispersion of an emulsion or emulsion.
8. Cosmetic or dermopharmaceutical composition, according to any of claims 5 to 7, characterized in that it is free of surfactants derived from polyethylene glycol.
9. Use of the hybrid compound according to any one of claims 1 to 4 or the cosmetic or dermopharmaceutical composition according to any one of claims 5 to 8 as an agent for disinfecting skin and/or a cosmetic or dermopharmaceutical composition.
10. Use according to claim 9, for reducing, reducing or inhibiting bacterial proliferation on the skin and/or in a cosmetic or dermopharmaceutical composition.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FRFR1908575 | 2019-07-26 | ||
| FR1908575A FR3099060B1 (en) | 2019-07-26 | 2019-07-26 | MINERAL AND ORGANIC HYBRID COMPLEX AND ITS USE FOR MAINTAINING THE MICROBIOLOGICAL BALANCE OF THE SKIN AND/OR OF A COSMETIC AND/OR DERMOPHARMACEUTICAL COMPOSITION |
| PCT/EP2020/070642 WO2021018682A1 (en) | 2019-07-26 | 2020-07-22 | Hybrid mineral-organic complex, and use thereof for maintaining the microbiological balance of the skin and/or of a cosmetic and/or dermopharmaceutical composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114667130A true CN114667130A (en) | 2022-06-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080053365.4A Pending CN114667130A (en) | 2019-07-26 | 2020-07-22 | Hybrid inorganic-organic complex and use thereof for maintaining the microbial balance of skin and/or cosmetic and/or dermopharmaceutical compositions |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP4003269A1 (en) |
| CN (1) | CN114667130A (en) |
| FR (1) | FR3099060B1 (en) |
| WO (1) | WO2021018682A1 (en) |
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| US4927749A (en) * | 1986-04-09 | 1990-05-22 | Jeanette Simpson | Reagent for cell separation |
| WO2002079408A2 (en) * | 2001-03-28 | 2002-10-10 | Helix Biomedix, Inc. | Short bioactive peptides and methods for their use |
| JP2005053852A (en) * | 2003-08-06 | 2005-03-03 | Kao Corp | Cocohesion inhibitor |
| US20090215096A1 (en) * | 2006-08-10 | 2009-08-27 | The Furukawa Electric Co., Ltd. | Collodial silica particle containing light-absorbing susbstance, nano light-absorbing material,absorption labeling nanobead kit, and method for detection or quantification of biological molecule using the colloidal silica particle containing light-absorbing substance |
| CN102391300A (en) * | 2011-08-30 | 2012-03-28 | 上海大学 | Organic/ inorganic composite lamellar compound containing glutathione (GSH) and preparation method thereof |
| FR2992318A1 (en) * | 2012-06-22 | 2013-12-27 | Centre Nat Rech Scient | PEPTIDE-SILICE HYBRID MATERIALS |
| CN106552600A (en) * | 2016-10-18 | 2017-04-05 | 武汉理工大学 | A kind of magnetic shell-core structure nanoparticle and preparation method and application |
-
2019
- 2019-07-26 FR FR1908575A patent/FR3099060B1/en active Active
-
2020
- 2020-07-22 CN CN202080053365.4A patent/CN114667130A/en active Pending
- 2020-07-22 WO PCT/EP2020/070642 patent/WO2021018682A1/en unknown
- 2020-07-22 EP EP20740649.7A patent/EP4003269A1/en active Pending
Patent Citations (7)
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|---|---|---|---|---|
| US4927749A (en) * | 1986-04-09 | 1990-05-22 | Jeanette Simpson | Reagent for cell separation |
| WO2002079408A2 (en) * | 2001-03-28 | 2002-10-10 | Helix Biomedix, Inc. | Short bioactive peptides and methods for their use |
| JP2005053852A (en) * | 2003-08-06 | 2005-03-03 | Kao Corp | Cocohesion inhibitor |
| US20090215096A1 (en) * | 2006-08-10 | 2009-08-27 | The Furukawa Electric Co., Ltd. | Collodial silica particle containing light-absorbing susbstance, nano light-absorbing material,absorption labeling nanobead kit, and method for detection or quantification of biological molecule using the colloidal silica particle containing light-absorbing substance |
| CN102391300A (en) * | 2011-08-30 | 2012-03-28 | 上海大学 | Organic/ inorganic composite lamellar compound containing glutathione (GSH) and preparation method thereof |
| FR2992318A1 (en) * | 2012-06-22 | 2013-12-27 | Centre Nat Rech Scient | PEPTIDE-SILICE HYBRID MATERIALS |
| CN106552600A (en) * | 2016-10-18 | 2017-04-05 | 武汉理工大学 | A kind of magnetic shell-core structure nanoparticle and preparation method and application |
Non-Patent Citations (4)
| Title |
|---|
| GUIJIAN GUAN等: ""Protein-building molecular recognition sites by layer-by-layer molecular imprinting on colloidal particles"", 《ANALYST》, vol. 134, pages 1880, XP055682413, DOI: 10.1039/b820962f * |
| HEEJUN CHOI等: ""Single-cell, real-time detection of oxidative stress induced in Escherichia coli by the antimicrobial peptide CM15"", 《PNAS》, vol. 112, no. 3, pages 303 - 310 * |
| VICTORIA N. SYRYAMINA等: ""Peptides on the Surface:Spin-Label EPR and PELDOR Study of Adsorption of the Antimicrobial Peptides Trichogin GA IV and Ampullosporin A on the Silica Nanoparticles"", 《APPL MAGN RESON》, vol. 47, pages 309 * |
| ZHENGWEI MAO等: ""Tat peptide mediated cellular uptake of SiO2 submicron particles"", 《COLLOIDS AND SURFACES B: BIOINTERFACES》, vol. 75, pages 432, XP026785546, DOI: 10.1016/j.colsurfb.2009.09.017 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP4003269A1 (en) | 2022-06-01 |
| FR3099060A1 (en) | 2021-01-29 |
| FR3099060B1 (en) | 2022-01-14 |
| WO2021018682A1 (en) | 2021-02-04 |
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