EP3558287A2 - N-acetyldiaminobutyric acid-containing composition - Google Patents
N-acetyldiaminobutyric acid-containing compositionInfo
- Publication number
- EP3558287A2 EP3558287A2 EP17872888.7A EP17872888A EP3558287A2 EP 3558287 A2 EP3558287 A2 EP 3558287A2 EP 17872888 A EP17872888 A EP 17872888A EP 3558287 A2 EP3558287 A2 EP 3558287A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- acetyldiaminobutyric
- composition
- acetyldiaminobutyric acid
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/007—Preparations for dry skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
Definitions
- composition containing N-acetyldiaminobutyric acid The invention relates to a composition comprising N-acetyldiaminobutyric acid, a salt or an ester of this compound.
- Ectoine (2-methyl-1, 4,5,6-tetrahydropyrimidine-4-carboxylic acid) and hydroxyectoine (5-hydroxy-2-methyl-1, 4,5,6-tetrahydropyrimidine-4-carboxylic acid) are compatible solutes which be synthesized under stress conditions of extremophilic, especially halophilic microorganisms.
- ectoine and hydroxyectoine various applications have hitherto been described, for example as a moisturizer, for the treatment of vascular leak syndrome (VLS) (DE 10 2006 056 766 A1) or for the treatment of atopic dermatitis (DE 103 30 243 A1).
- ectoine is usually obtained by continuous fermentation of the halophilic bacterium Halomonas elongata and subsequent "bacterial milking."
- the environmental conditions for the bacteria are abruptly changed, whereupon they deliver the produced ectoine to the environment.
- the biosynthesis is based on aspartate-ß-semialdehyde. First, it is catalyzed by a transaminase L-2,4-diaminobutyric acid. This is acetylated by an acetyltransferase to NY-acetyl-L-2,4-diaminobutyric acid (NADA). Finally, there is an intramolecular condensation reaction to ectoine catalyzed by ectoine synthase.
- N-Y-acetyl-2,4-diaminobutyric acid or ⁇ - ⁇ -acetyl-2,4-diaminobutyrate As an intermediate thus u. a. Run through N-Y-acetyl-2,4-diaminobutyric acid or ⁇ - ⁇ -acetyl-2,4-diaminobutyrate. So far, no emphasis has been placed on this molecule, but surprisingly, it has been found that N-acetyldiaminobutyric acid is able to exert physiological effects and to be used in therapeutic, prophylactic and cosmetic treatments of the human or animal body. Such effects of N-acetyldiaminobutyric acid have heretofore been unknown. Canovas et al., Appl. Environ. Microbiol.
- N-Y-acetyl-2,4-diaminobutyric acid can thus be used as a medicament, pharmaceutical, medical device and cosmetic.
- N-acetyldiaminobutyric acid is an intermediate in the extraction of ecto-but it can also be easily obtained by alkaline hydrolysis from commercially available ectoine.
- ectoine can be reacted with a 2 M KOH solution to give about 80% ⁇ -acetyl-L-2,4-diaminobutyric acid ((2S) -4-acetamido-2-aminobutyric acid) and ca. 20% Na-acetyl-L-2,4-diaminobutyric acid ((2S) -2-acetamido-4-amino-butanoic acid). Both isomers, ie the ⁇ - and the ⁇ -isomer, have been shown to be physiologically active.
- N-acetyldiaminobutyric acid in addition to N-acetyldiaminobutyric acid, corresponding derivatives may also be used, in particular salts or esters.
- ester derivatives the COOH group of N-acetyldiaminobutyric acid is replaced by a carboxylic acid ester function COOR, where R is saturated or unsaturated, straight-chain or branched alkyl, cycloalkyl, aryl, heteroaryl, alkylaryl, arylalkyl, alkoxyalkyl , Alkylthioalkyl, aryloxyalkyl or arylthioalkyl groups.
- esters may be in ionic or zwitterionic form, i. the invention includes the use of salts of said esters.
- Suitable pharmacologically acceptable salts are, for example, alkali metal, alkaline earth metal and ammonium salts, in particular potassium, sodium, magnesium and calcium salts.
- NADA N-acetyldiaminobutyric acid
- N-acetyldiaminobutyric acid is able to significantly improve the barrier function of epithelium.
- Epithelium in addition to connective tissue, muscle tissue and nerve tissue, is one of four major types of tissue found in the human body. It consists of largely gapless epithelial cells arranged in one or more layers. Epithelial tissue is used in particular Protection and limitation of the body surface (skin) and the lining of organs, blood vessels etc. In addition to the protective function, epithelium also fulfills functions such as absorption and secretion. The epithelium is separated from the underlying connective tissue via a basal membrane.
- a variety of diseases is associated with a disruption of the barrier function of the epithelium and strengthening the barrier function can protect against unwanted external influences. Once they have overcome the epithelial barrier, they are often the trigger of an inflammatory cascade.
- the stabilization of the barrier by N-acetyldiaminobutyric acid or corresponding derivatives thus proves to be useful for use in a number of methods for the treatment of the human or animal body.
- N-acetyldiaminobutyric acid The stabilization of the barrier by N-acetyldiaminobutyric acid appears to be due to the molecule being cosmotropic, i. promoting the formation of hydrogen bonds. As a result, the native form of biomolecules, such as proteins, is also promoted. In contrast, N-acetyldiaminobutyric acid is excluded from the hydration shell of biomolecules; Lipid membranes become fluid. Accordingly, both membranes and proteins are stabilized against a wide variety of influences. Disturbed integrity of Tissue Association structures and membrane structures is restored.
- N-acetyldiaminobutyric acid Another effect of N-acetyldiaminobutyric acid is the up-regulation of claudins. These are membrane proteins as part of tight junctions, narrow bands that surround epithelial cells and communicate with the bands of neighboring cells. The loss of interstices between the cells of the epithelium creates a barrier. This controls the penetration of molecules across the epithelium. The upregulation of pore-closing claudins, which play the most important role as occludins as membrane proteins, leads to greater tightness of the epithelial membrane. The permeability is thus reduced.
- the invention relates to both the therapeutic and the cosmetic use of N-acetyldiaminobutyric acid and its derivatives.
- a composition containing N-acetyldiaminobutyric acid is for use in a method for the treatment and / or prevention of dry skin or mucosa. Moisturizing properties were demonstrated by an assay based on the SIRC cell line.
- N-acetyldiaminobutyric acid exhibits a care efficacy in the treatment of dry, very dry, irritated and flaky skin.
- N-acetyldiaminobutyric acid can also be used to treat dry, inflamed skin, e.g. B. in atopic dermatitis (atopic dermatitis).
- the composition according to the invention is suitable for maintaining and restoring the normal moisture content of the skin. This is usually regulated by the skin itself, but this self-regulation may be intrinsically or disturbed by external influences such as dry ambient air. There are more dander and small cracks in the skin, which makes the skin more sensitive to other influences. N-acetyldiaminobutyric acid is able to bind water in the skin and thereby increase the moisture content of the skin. Skin within the meaning of the invention is also understood to mean hairy skin, in particular the scalp. Intrinsic skin aging phenomena can also be treated or prevented by the composition according to the invention. These are skin aging phenomena that are not attributable to external influences such as UV radiation or generally solar radiation.
- composition according to the invention can also be used in atopic dermatitis (atopic dermatitis).
- atopic dermatitis This is a chronic, incompletely curable skin disorder characterized by its intense itching. Those affected often respond with scratching, which in turn creates additional skin irritation become.
- the skin is characterized by particular dryness and strong inflammation. It causes the formation of red, scaly eczema on the skin.
- the background of atopic dermatitis is not fully understood; presumably genetic and immunological factors play a role as well as environmental influences. The disease often occurs in childhood and in about 1 to 3% of adults.
- atopic dermatitis is so far essentially symptomatic.
- active substances which fulfill a moisturizing function, for example panthenol or dexpanthenol, which moreover has anti-inflammatory and anti-itch properties.
- glucocorticoids are often used, which also have anti-inflammatory effects, but which are also associated with side effects such as atrophy (thinning of the skin).
- N-acetyldiaminobutyric acid is used, it is unlikely that it will have significantly fewer side effects.
- N-acetyldiaminobutyric acid in the composition with other active ingredients, for example the abovementioned active ingredients (Dex) panthenol or glucocorticoids.
- active ingredients for example the abovementioned active ingredients (Dex) panthenol or glucocorticoids.
- Anti-inflammatory and antibacterial, fungistatic or fungicidal active substances, antibiotics or itching-alleviating substances and analgesics are also generally usable.
- N-acetyldiaminobutyric acid can also be used to treat dry mucous membranes.
- dry nasal mucous membranes oral mucosa, ocular mucosa and vaginal mucosa (vaginal epithelium).
- the nose fulfills important tasks: It cleans the respiratory air of small particles, heats them to body temperature and moisturizes them. In this way, disease-causing factors are eliminated and the gas exchange in the lungs optimally prepared. However, this can only work if the nasal mucous membrane is able to deliver sufficient moisture to the respiratory air.
- dry nose syndrome which is a manifestation of rhinitis sicca and other atrophic rhinitis, may also be a side effect of certain nasal drug treatments and prolonged / repeated exposure to air-conditioned areas, as well as a large contingent of patients with dry nasal mucosa provided by heavy smoker.
- a watery, isotonic saline solution is the first drug of choice to treat a dry nose.
- the treatment in spray form is not always satisfactory and must be repeated quite often.
- higher-viscosity preparations offer characteristic advantages: Compared with water-containing nasal drops or sprays, they remain longer on the nasal mucosa. Thus, the nourishing effect is more intense.
- a disadvantage of the administration of aqueous viscous preparations is that after the evaporation of the water from the viscosity-increasing agent an unpleasant crust is formed.
- the composition according to the invention is well suited for the prevention, treatment and / or care of dry nasal mucous membranes and overcomes the previously described disadvantages of the prior art.
- the composition may include sodium chloride or other moisturizers, for example scleroglucans. Particularly in the case of saline-containing compositions, the thickening is usefully selected so that passage through the pharynx is largely avoided.
- synergistic effects can be achieved by the co-administration of N-acetyldiaminobutyric acid and other active ingredients. So z.
- the decongestant effect of oxymetazoline, xylometazoline or tramazoline can be combined with the action of N-acetyldiaminobutyric acid.
- the effect with the anti-inflammatory effect of other substances such as.
- dexpanthenol or panthenol can be combined.
- antihistamines such as azelastine or cromolyn sodium.
- Another possible combination is with viscosity-increasing substances such as hydroxypropylmethylcellulose, hyetellose, hypromellose or hyaluronic acid or with moistening substances such as sesame oil.
- mucous membrane treatment with the aid of the composition according to the invention is not restricted to the treatment of dry nasal mucous membranes; other mucous membranes can also be effectively moistened with N-acetyldiaminobutyric acid.
- dry mouth xerostomia
- the dryness of the oral mucosa causes dysphagia and speech problems.
- tooth decay is a common consequence, as the teeth-protecting salivary flow is greatly reduced.
- Dryness of the oral mucosa is most common as a result of cancer treatment, either with the help of cytostatics or radiation therapy. Background is that a cancer treatment targeted cells with high rate of division attacks, including the cancer cells and mucosal cells belong.
- the mucous membrane of the eyes may be affected by dryness, which is also referred to as dry eye syndrome, dry eye syndrome or keratoconjunctivitis sicca.
- dryness also referred to as dry eye syndrome, dry eye syndrome or keratoconjunctivitis sicca.
- Related symptoms are a foreign body sensation, burning sensation and redness. In severe cases it can lead to a corneal damage to blindness.
- Keratoconjunctivitis sicca is a common disease affecting approximately 10 to 20% of the adult population. Treatment is often with hyaluronic acid, artificial tears or cellulosics. However, it is often unsatisfactory due to insufficient treatment success or side effects.
- Another form of dry eye is the so-called xerophthalmia, which often affects children, mainly in developing countries.
- the dry eye mucosa can be treated with N-acetyldiaminobutyric acid or corresponding derivatives or a composition containing N-acetyldiaminobutyric acid.
- the composition may contain other active ingredients, for example hyaluronic acid, which also serves to treat keratocunjunctivitis sicca.
- vaginal moisturization i. moistening the vaginal mucosa.
- Vaginal dryness is more prevalent in postmenopausal women due to estrogen deficiency, which is related to the regression of the vaginal epithelium. However, younger women may also be affected. Protection of skin or mucous membrane from external influences
- a composition containing N-acetyldiaminobutyric acid or a corresponding derivative is used in a process for protecting human skin or mucosa from physical, chemical and / or biological influences.
- This may in particular be radiation, particularly UV (ultraviolet) or IR (infrared) radiation, but also, for example, visible light.
- UV radiation The skin damaging effect of UV radiation is well known.
- erythema effect i. the development of a sunburn
- UV radiation also damages collagens, leading to premature skin aging.
- Conventional sunscreens act either physically, such as titanium dioxide, to reflect the light impinging on the skin or chemically by absorbing organic molecules in the sunscreen UV light in the injurious wavelength range.
- the less prominent in public perception IR radiation can damage the skin sustainably. This is due to thermal effects that can lead to the denaturation of cell proteins. Protection against further external influences is also possible with the aid of N-acetyldiaminobutyric acid.
- the chemical and biological influences include in particular allergens, heat, irritant or oxidizing or denaturing substances, particulate matter and free radicals. Free radicals arise z. B. by the action of UV radiation, ionizing radiation, cigarette smoke or ozone. Also, reactions with certain environmental substances such as pesticides, herbicides or food ingredients may promote the formation of free radicals. The same applies to stress that a large number of people are exposed to. Free radicals can damage the membrane tissues of the body and thus contribute to the development of diseases. Also, the aging process or the occurrence of aging phenomena such as skin aging are accelerated by free radicals. In particular, protection against free radicals serves to protect against drying out of the skin, dermatoses and age spots.
- N-acetyldiaminobutyric acid is able to stabilize cell membranes of keratinocytes against UV radiation. Furthermore, it could be demonstrated that N-acetyldiaminobutyric acid is able to protect cells from IR radiation, visible light or heat. Likewise, there is protection against other physical, chemical or biological influences, in particular against allergens, irritating or oxidizing or denaturing substances and free radicals. Physical influences also include the action of suspended particles on the skin. In particular, particulate matter (also called particulate matter) with a mean particle size ⁇ 15 ⁇ , especially ⁇ 10 ⁇ can cause aging of the skin. Such suspended dust is often produced by the burning of fossil fuels, but also in the form of sand, spores, pollen, rock dust, in agriculture, in mining, by tobacco consumption, tire wear, brake abrasion or forest fires.
- Other skin diseases can be prevented by means of N-acetyldiaminobutyric acid or corresponding derivatives or they can be treated accordingly.
- these include psoriasis, seborrheic dermatitis, rosacea, hives (urticaria), actinic keratosis, dermatoses (for example light dermatoses), contact dermatitis (for example allergic contact dermatitis), various lichen forms, ichthyosis, diaper dermatitis, diaper sclerosis.
- a composition comprising N-acetyldiaminobutyric acid or corresponding derivatives can also be used for the treatment of diseases, in particular inflammations of the oral or pharyngeal mucosa.
- Treatment of the scalp may also involve intrinsic aspects, thus treating scalp problems that are not directly caused by external influences.
- the scalp is affected by reduced hair growth and graying of the hair.
- the cause of hereditary hair loss is a hypersensitivity of the hair follicles to dihydrotestosterone, the causes the growth phase of the hair is significantly shortened.
- there are also inflammatory hair loss disorders By the graying of the hair, however, men and women are equally affected.
- a composition containing N-acetyldiaminobutyric acid or a corresponding derivative is used in a method for the treatment and / or prevention of respiratory diseases.
- respiratory diseases include airway diseases attributable to particulate matter, in particular diseases of the lungs.
- allergic diseases, bronchial asthma, lung cancer, chronic respiratory disease can all be caused by particulate matter Bronchitis, COPD (chronic obstructive pulmonary disease), silicosis or pulmonary fibrosis.
- COPD includes pulmonary emphysema and chronic obstructive bronchitis.
- allergic or virally caused respiratory diseases can be treated by N-acetyldiaminobutyric acid and corresponding derivatives.
- the diseases include in particular allergic rhinitis, asthma, colds, rhinitis acuta (colds), acute or chronic bronchitis, flu and pneumonia.
- Respiratory diseases often have viral causes. In particular, they are caused by rhinoviruses and adenoviruses. Rhinoviruses infect the mucous membranes of the nasopharynx and lead to acute rhinitis (runny nose), more rarely also to acute bronchitis. The human body responds to the virus attacks with an inflammatory reaction of the nasal mucosa.
- the vessels of the mucous membrane become more permeable and increased secretion of secretion occurs.
- the nasal mucosa swells and obstructs breathing through the nose. There may also be malaise and headaches.
- secondary infection by bacteria in the throat and pharynx often occurs.
- Respiratory diseases caused by adenoviruses range from a common cold to bronchitis to pneumonia (pneumonia).
- ARDS Acute Respiratory Distress Syndrome
- Allergic respiratory diseases have increased significantly in recent decades, especially in industrialized countries.
- An allergic rhinitis can be triggered by different allergens, such as pollen or house dust.
- the disease is based on an inflammation, which is ultimately a defense reaction of the organism against the stimuli caused by the allergens.
- T helper cells Through the action of allergens it comes in the body with the help of T helper cells to the Release of inflammatory mediators, in particular histamine together with interleukin-8, leukotrienes and tumor necrosis factor-alpha (TNF-alpha), which activates the downstream cascade of anti-inflammatory action in the body.
- TNF-alpha tumor necrosis factor-alpha
- an influence on the adhesion molecules of the epithelium affected by the external influence arises, these are produced more or less strongly.
- the strain expresses the ICAM-1 molecule more strongly in the affected cells.
- Respiratory allergens cause reactions in the respiratory tract, typically with mucosal edema and hypersecretion (allergic rhinitis, hay fever) and bronchial asthma. In case of particularly strong allergen exposure, a systemic immediate reaction may occur, which may lead to anaphylactic shock.
- N-acetyldiaminobutyric acid can cure, alleviate or prevent other allergen-induced diseases.
- Other conjunctival inflammations, commonly referred to as conjunctivitis can be treated with N-acetyldiaminobutyric acid, regardless of whether conjunctivitis has bacterial, viral, or mechanical causes, or has been caused by fungi, parasites, or laser treatment.
- the conjunctiva is a mucous membrane; the epithelium of the conjunctiva is protected from external influences by N-acetyldiaminobutyric acid.
- a composition containing N-acetyldiaminobutyric acid or one of the described derivatives can be used for the treatment of respiratory diseases, whether allergic or viral, whitewater-induced or of other causes. Even aging of the lung and senile pulmonary emphysema can be treated.
- the diseases can affect different parts of the respiratory tract, such as the lungs, nose and Throat.
- Respiratory diseases treatable by N-acetyldiaminobutyric acid include rhinitis allergica, allergic or non-allergic bronchial asthma, bronchial hyperresponsiveness, common cold, rhinitis acuta (cold), acute or chronic bronchitis, influenza, pneumonia, COPD, chronic obstructive bronchitis, pulmonary emphysema, lung cancer, acute respiratory distress syndrome (ARDS), cystic fibrosis, pulmonary fibrosis, silicosis and sarcoidosis.
- rhinitis allergica allergic or non-allergic bronchial asthma
- bronchial hyperresponsiveness common cold
- rhinitis acuta cold
- acute or chronic bronchitis influenza
- pneumonia COPD
- chronic obstructive bronchitis pulmonary emphysema
- lung cancer acute respiratory distress syndrome
- cystic fibrosis pulmonary fibrosis
- the composition can be present in particular in inhalable form. It may accordingly be a liquid or a solid, wherein the composition is atomized with an inhalation device provided for this purpose into an aerosol and inhaled by the patient.
- an inhalation device provided for this purpose into an aerosol and inhaled by the patient.
- customary, customary for the production of an inhalable composition additives can be used.
- the N-acetyldiaminobutyric acid may be present in water.
- the addition of antiasthmatics, broncholytics or expectorant to the composition is conceivable.
- a composition according to the invention for controlling allergic or virally caused respiratory diseases is administered via the respiratory tract, in particular nasally.
- Particularly preferred is administration in the form of a nasal spray or nasal drops.
- the effect of N-acetyldiaminobutyric acid against rhinitis allergica is attributed to the fact that in the nasal epithelial cells in the context of the inflammatory reaction, which is typical of rhinitis allergica (hay fever), through the interaction of the epithelial cells with the relevant allergen (eg pollen) to an upregulation of adhesion molecules, such as ICAM-1, in these cells, which is the prerequisite for the formation of the clinical symptoms of the cold.
- allergen eg pollen
- the inventors have observed that the upregulation of ICAM-1 can be inhibited by pro-inflammatory stimuli by N-acetyldiaminobutyric acid.
- the ICAM-1 molecule functions not only as an adhesion molecule for other cells, but also as a receptor for the rhinoviruses described above.
- increased expression of ICAM-1 in rhinovirus infection triggered respiratory epithelia.
- the uptake of ICAM-1 molecules in the nasal epithelium and thus the expression of this rhinovirus receptor can be prevented or attenuated by the osmolyte treatment, so that the development and development of rhinovirus infection in humans can be prevented or mitigated.
- the CAR receptor Within the adhesion complex of the cells is the CAR receptor, which is used as a docking site of adenoviruses.
- the different serotypes of Adenoviridae then use different other receptors (integrins, CD46, heparan sulfate glycosaminoglycans, CD80, CD86 and members of MHC-1) to invade the cells.
- the expression change of adhesion molecules by osmolyte treatment can thus also mitigate or even prevent a possibility of the adenoviruses docking or penetrating the cell.
- the N-acetyldiaminobutyric acid may be administered together with other active ingredients, for example, together with anthistamines or corticosteroids, especially glucocorticoids. It has been shown that their side effects can be reduced. Co-administration is also considered to be the case if the active ingredients are not administered in a composition but are coordinated with each other in a timely manner, so that the active ingredients function in a functional manner.
- the invention also relates to a combination preparation (kit of parts), in which a composition contains N-acetyldiaminobutyric acid and a further composition contains at least one antihistamine and / or at least one corticosteroid.
- glucocorticoids such as dexamethasone, budesonide, betamethasone, triamcinolone, fluocortolone, methylprednisolone, deflazacort, prednisolone, prednisone, cloprednol, cortisone, hydrocortisone, fluocortin, clocortolone, clobetasone, alclomethasone, flumethasone, fluopredniden, fluorandrenolone, prednicarbate, mometasone, methylprednisolone, Fluticasone, halomethasone, fluocinolone, diflorasan, desoximethasone, fluocinonide, fludrocortisone, deflazacort, rimexolone, cloprednol, amcinonide, halcinonide, diflucortolone, clobetasol or
- N-acetyldiaminobutyric acid with GM-CSF leukotrienes such as LTB 4 , theophylline (1,3-dimethyl-xanthine), leukotriene antagonists, phosphodiesterase inhibitors (PDE inhibitors, especially PDE4 inhibitors), muscarine receptor antagonists, anticholinergics such as Ipratropium bromide or tiotropium bromide or other drugs.
- composition according to the invention containing N-acetyldiaminobutyric acid or a corresponding derivative is the treatment or prevention of chronic inflammatory diseases of the gastrointestinal tract, in particular Crohn's disease, ulcerative colitis and gastritis. Crohn's disease and ulcerative colitis are chronic inflammations of the intestinal mucosa.
- the N-acetyldiaminobutyric acid thus shows here its anti-inflammatory potential, the substance acting in particular on the intestinal epithelium.
- N-acetyldiaminobutyric acid can be used.
- Crohn's disease is due, among other things, to a disruption of the barrier function of the intestinal epithelium.
- the mucus on the intestinal mucosa shows a lack of anti-infective defensins. Due to the disruption of the barrier function, intestinal bacteria invade the intestinal wall and cause inflammation there, which in turn causes further damage to the barrier.
- the above-mentioned strengthening of the barrier function by N-acetyldiaminobutyric acid is therefore suitable for preventing Crohn's disease or for treating the disease.
- ulcerative colitis a chronic inflammatory bowel disease affecting the large intestine, enhances barrier function significantly.
- composition containing N-acetyldiaminobutyric acid, a salt or an ester of N-acetyldiaminobutyric acid can also be used in a method of treating and / or preventing gastroesophageal reflux disease, inflammation and damage of gastric or duodenal mucosa and / or gastric or duodenal ulcer.
- Gastroesophageal reflux disease may be reflux esophagitis, non-erosive reflux disease or Barrett's esophagus.
- Gastroesophageal reflux diseases are a common phenomenon. In western industrialized countries, the problem occurs among adults in about 10 to 20% of the population at least once a week. In East Asia, the prevalence is 2.5 to 7.8%, in the US, 20% of the adult population weekly, 7% even daily affected by the disease. The disease is primarily due to the fact that gastric acid from the stomach reaches the esophagus. In addition to gastric acid, other gastric contents also enter the esophagus, such as the digestive enzyme pepsin, a peptidase used to digest proteins in food. The damaging effect of stomach acid is enhanced by pepsin.
- the current mainstream treatment option is the use of proton pump inhibitors (PPIs) such as omeprazole and histamine H2 receptor antagonists (H2Ras). Both classes of substances provide suppression of gastric acid production.
- PPIs proton pump inhibitors
- H2Ras histamine H2 receptor antagonists
- antacids ie gastric acid neutralizing substances.
- Alginates provide for the formation of a tough foam in the stomach, which prevents the reflux of gastric acid into the esophagus.
- gastroesophageal reflux disease is associated with cardiac insufficiency. This is a malfunction of the sphincter (esophageal sphincter), which separates the esophagus and stomach, so that gastric contents return to the esophagus. Other reasons may be excessive gastric acid production or abnormal esophageal peristalsis. Particularly often the problem occurs at night, so in a lying position. Desserts or the enjoyment of tobacco and alcohol can also promote the occurrence of reflux symptoms.
- Gastro-oesophageal reflux disease can manifest as non-erosive reflux disease (NERD), which does not cause esophageal mucosal damage, or erosive reflux disease (erosive esophagitis (ER)) )). In the latter, the mucosa changes in the esophagus and mucosal damage is detectable. Bleeding and ulcers may occur in the transition between the stomach and the esophagus. Another complication of gastroesophageal reflux disease may be a narrowing of the esophagus, which in turn leads to dysphagia.
- a Barrett's esophagus endobrachyosophagus
- a metaplastic transformation of the epithelium of the esophagus is observed and multilayer squamous epithelium of the esophagus transforms into a single-layer, prismatic columnar epithelium in the distal region.
- This transformation may be completely circular, especially in the area of the gastroesophageal junction, i. H. the transition from the stomach to the esophagus.
- columnar epithelium is more resistant to gastric acid and the gastric enzyme pepsin, there is a risk of dysplasia.
- a Barrett's esophagus may therefore be a precursor to the development of esophageal carcinoma (Barrett's carcinoma) and must therefore be observed.
- a Barrett's esophagus can lead to the development of ulcers.
- N-acetyldiaminobutyric acid or salts and esters thereof are capable of a significant improvement in gastroesophageal reflux disease and pyrosis. It has been shown that N-acetyldiaminobutyric acid is able to overcome the negative effects of acid and pepsin on squamous epithelial cells. It has also been found that N-acetyldiaminobutyric acid prevents damage to the stomach or intestinal epithelium and can treat it. In particular, this relates to the treatment and prevention of gastritis (gastritis). The aggressive gastric acid can attack the gastric mucosa, for example, when the production of the protective mucus layer is disturbed by external factors.
- N-acetyldiaminobutyric acid is thus in turn due to the improvement of the barrier function of the epithelium, here the stomach, the esophagus and the intestine. It has been found that N-acetyldiaminobutyric acid and corresponding derivatives are capable of preventing or treating gastritis. Gastritis may develop as a result of reflux oesophagitis.
- Gastritis can lead to gastric ulcers (ulcus ventriculi), which is ultimately also due to the aggressive gastric acid with insufficient protection of the stomach wall and the gastric mucosa against gastric acidity.
- one of the damaging factors is overproduction of stomach acid.
- the formation of gastric ulcers u. a. attributed to damage to the gastric mucosa; insofar as the protection of the gastric mucosa also protects against gastric ulcers.
- duodenum damage to the epithelium of the duodenum (duodenum) can be prevented by N-acetyldiaminobutyric acid, which is why the substances are suitable for the prophylaxis and for the treatment of inflammation of the mucous membrane of the duodenum. Similar to the gastric mucosa, this is a single-layered columnar epithelium.
- the duodenum is the first part of the small intestine that adjoins the stomach. Because it is exposed to the highly corrosive gastric contents of digestive enzymes such as pepsin, it can Inflammation and damage to the duodenum mucosa come.
- duodenal ulcer In addition, the food in the duodenum bile from the liver and gallbladder and pancreatic enzymes are supplied. Damage to the duodenal mucosa can result in a duodenal ulcer (ulcus duodeni), which affects about 2 to 10% of people during their lifetime. Also, the development of a duodenal ulcer is based on an imbalance between the mucosa attacking substances such as gastric acid and certain proteases and the mucosal protective factors such as sufficient mucus formation. The protection of the mucous membrane of the duodenum is therefore important for the prevention and treatment of duodenal ulcers.
- N-acetyldiaminobutyric acid as well as the mentioned derivatives of these compounds are suitable for effectively preventing the development of both gastric and duodenal ulcers and to effectively treat gastric ulcer ulcers. Even though the damage to the stomach / duodenum mucosa has progressed less far than to the ulcer, it is possible to treat and prevent any damage (erosion) that occurs there.
- composition according to the invention can be used for the treatment and / or prophylaxis of gastroesophageal reflux diseases or pyrosis of varying severity, i. H. both for non-erosive reflux diseases and for reflux esophagitis, in which damage to the mucous membranes of the esophagus can already be detected.
- the treatment options extend to Barrett's esophagus, which is a serious disease with an increased risk of cancer.
- the composition is an aqueous solution, mostly for oral administration.
- the composition containing N-acetyldiaminobutyric acid, a salt or an ester of N-acetyldiaminobutyric acid is used in a process for Recovery of injured body tissue.
- This may in particular be a wound or an ulcer, ie an ulcer.
- Injuries to body tissues can come in different ways. In particular, they can be caused by external influences, ie in a traumatic way. In general, such tissue injuries, especially in the area of the skin or mucosa, are also referred to as wounds. In addition to tissue injuries that are due to external influences, non-traumatic injuries are also known as ulcer (ulcer). Body tissue injuries can also occur during surgical and endoscopic procedures. In surgical procedures, so-called postoperative inflammatory stress and pain often occur, which can cause considerable problems for the patient. This inflammatory stress is often a consequence of the mechanical stress caused by the procedure and may not necessarily be the target of the actual procedure.
- postoperative inflammatory stress occurs in abdominal interventions, in particular in the stomach / intestine area, but also in interventions in the liver and kidneys as well as in endoscope examinations.
- abdominal interventions in particular in the stomach / intestine area, but also in interventions in the liver and kidneys as well as in endoscope examinations.
- a mechanical load results from the need to shift intestinal loops during the procedure, to widen the abdomen or, in particular during examinations, to pressurize the intestine itself or the abdomen.
- the resulting symptoms of inflammation and the associated inflammatory stress and pain sometimes last for a long time after the procedure.
- This applies equally to interventions in other parts of the body including tooth extraction, jaw surgery or fracture-related surgery. This includes tooth extraction, jaw surgery and implantation, including teeth and artificial joints, and eye surgery.
- recovery of damaged body tissue naturally begins a short time after the injury.
- the restoration of which can be promoted according to the invention by the N-acetyldiaminobutyric acid-containing compositions it can be in particular skin or mucous membrane.
- the injury can be traumatic. This is understood to mean that the injury is caused by external influences, such as impacts, cuts, stitches, bites or the like. Such mechanically induced wounds can, for. B. caused by accidents or in the context of operations.
- mucositis In the case of damaged mucous membranes, one also speaks of mucositis whose treatment also falls under the promotion of the restoration of injured body tissue according to the invention.
- a mucositis can have different causes. For example, since mucosal cells have a high rate of regeneration, mucositis often occurs as Side effect in the context of cancer treatment by chemo- or radiotherapy on.
- a weakened immune system for example in immunosuppressed patients, causes an increase in infections, which in turn can lead to inflammation of the mucosa.
- the oral mucous membranes and the mucous membranes of the digestive system may be affected.
- tissue injury which can also be treated with the aid of the composition according to the invention.
- tissue injury include, for example, thermal wounds due to burns, scalding or frostbite, burns, burns or wounds due to ionizing radiation.
- bruises can also be treated with the aid of the composition according to the invention.
- organs or parts of the body are damaged by mechanical force, without any actual injury to the skin.
- the composition of the invention is also suitable for the treatment of ulcers (ulcers). These can have different causes, for example circulatory disorders, tumors or infections.
- ulcers which can be treated with the aid of the composition according to the invention are ulcus cruris ("open leg"), decubitus (pressure ulcer), malum perforans (foot pressure ulcer), dura ulcer, ulcer ulcer, ulcer rodens, corneal ulcer and others.
- DFS diabetic foot syndrome
- diabetic foot colloquially referred to as diabetic foot.
- minor injuries especially to the foot or lower leg, that would heal easily, but are often permanent due to poor wound healing in diabetic patients.
- the poor wound healing is due among other things to circulatory disorders occurring in diabetic patients.
- ulcers can spread deep into the body part, with the additional risk of infection by germs.
- the number of amputations required annually due to the diabetic foot syndrome is significant, thus resulting in the need to provide an effective treatment option.
- pressure sores Another common tissue damage is known as pressure sores (decubitus ulcer, pressure ulcer).
- Pressure ulcers occur especially in people in need of care, who are tied to the bed and in which certain body parts are exposed to a permanent pressure load. If the pressure acting on the vessels exceeds the capillary pressure of the vessels, the cells are undersupplied with oxygen and nutrients and, consequently, damage to the tissue. While pressure ulcers usually do not occur in healthy people, as they regularly relocate and relieve vulnerable areas of the skin, the corresponding reflexes are sometimes only limitedly available to people in need of care. Pressure ulcers may occur especially at those skin sites where bones are particularly close to the skin surface. Finally, there is also the danger that an open decubitus ulcer leads to the ingress of germs. In view of the number of people in need of care and the considerable consequences of developing pressure ulcers, there is a particular need for treatment options for this indication.
- aphthae Another example of treatable ulcers is aphthae. This is painful damage to the mucosa in the mouth and throat. The causes that lead to aphthae are still largely unexplained. In particular, recurrent aphthae can be very stressful for the patient if they occur, for example, in heavily used areas.
- Other body tissue injuries in which the composition according to the invention can be used are hemorrhoidal injuries or anal fissures, which are usually caused by mechanical stresses.
- haemorrhoidal diseases can be treated with the aid of the composition according to the invention by alleviating itching, inflammation and pain.
- the promotion of the restoration of injured body tissue is also advantageous in that in this way the formation of scars can be prevented. It has been found that wounds, in particular of the skin, heal better and, for reasons of appearance, unwanted scars are avoided by the composition according to the invention.
- the invention relates to the use of a composition comprising N-acetyldiaminobutyric acid, a salt or an ester of N-acetyldiaminobutyric acid as a constituent of a storage solution for the storage of transplant organs, transplant organ systems or transplant tissues.
- transplantation of an organ plays an important role in modern medicine.
- transplantation of an organ may be necessary for chronic renal failure, certain coronary heart disease, or cirrhosis of the liver.
- the majority of transplants are performed with organs from brain-dead donors, so from the time of collection to finding and preparing a suitable recipient, a certain amount of time elapses, so that a preservation of the organ is required.
- the organ thus remains for a certain time without oxygen supply, ie it undergoes an ischemic phase with a corresponding reversible damage.
- the organ is typically stored or transported at a low temperature of about 4 ° C.
- the concentration of N-acetyldiaminobutyric acid should be between 0.1 and 100 mM. Preferred are concentrations between 1 and 10 mM, more preferably 4 to 7 mM and most preferably about 5 mM. At appropriate concentrations, a significant reduction in organ damage was observed.
- a typical aqueous HTK solution contains:
- Histidine hydrochloride monohydrate 18.0 mM
- the principle of the HTK solution is based on the inactivation of organ function by removal of extracellular sodium and calcium, combined with the buffering of the extracellular milieu by histidine / histidine hydrochloride. This prolongs the time that the organs tolerate interrupting the supply of oxygen-containing blood.
- the electrolyte composition of the HTK solution inhibits the activation of energy-consuming activation processes, so that the energy requirement of the organ is reduced.
- the buffer histidine / histidine hydrochloride slows the pH drop during ischemia, which increases the efficiency of anaerobic energy production.
- Potassium hydrogen-2-ketoglutarate serves as a substrate for aerobic energy generation, tryptophan is said to have a membrane protective effect and mannitol prevents the formation of a cell edema.
- the properties of such a solution can be optimized by adding the indicated amount of N-acetyldiaminobutyric acid. The same applies when adding to a UW solution, also known under the name Viaspan.
- the composition is similar to that of the cytosol within the cells.
- the solution is based on the principle that metabolic inert substances such as lactobionic acid or corresponding salts or raffinose maintain the osmotic concentration. Hydroxyethyl starch is used to prevent edema.
- free radical scavengers may be added.
- a typical aqueous UW solution contains:
- a Celsior solution can also be improved by adding N-acetyldiaminobutyric acid.
- the solution contains, among others, mannitol, lactobionic acid, glutamic acid, histidine, calcium chloride, potassium chloride, magnesium chloride, sodium hydroxide and glutathione.
- a typical aqueous composition contains:
- the invention is used in particular in the transplantation of kidney, heart, lung, liver or pancreas.
- tissues to be transplanted for example the cornea or organ systems such as a finger or a hand.
- the storage solution may, especially if it is based on a HTK solution, contain other components known from the prior art.
- the storage solution may contain hydroxamic acid or a hydroxamic acid derivative which may be alkyl or aryl substituted.
- Particularly suitable is deferoxamine, which is a strong iron chelator and has the same three hydroxamic acid functions. In this way, an iron-dependent cold damage is prevented.
- other iron chelators can also be used.
- a buffer may be used based on N-acyl histidine, especially N-acetyl histidine and the corresponding base.
- lysine, arginine or glycine or corresponding derivatives such as lysine, arginine or glycine-containing dipeptides.
- the basic amino acids lysine and arginine or derivatives can be used as base equivalents.
- the storage solution may be glucose added.
- the glucose concentration must be chosen so that excessive glucose uptake by other cells is avoided.
- Other sugars, sugar alcohols or other polyols eg mannitol, raffinose, sucrose, xylitol, sorbitol
- high molecular weight substances such as HES or dextran can also be used to achieve the required physiological osmotic pressure of about 300 mosm / l ,
- Dimethyl sulfoxide can be used as a cryoprotective agent.
- Radical scavengers such as Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) can be used to scavenge intracellular radicals.
- the organ storage solution of the invention can be used not only for the storage of organs, tissues or organ systems, but also for perfusion upon removal of the organ from the donor body.
- the organ is perfused with the storage solution and then stored and transported to the recipient in the storage solution until engraftment.
- composition containing N-acetyldiaminobutyric acid, a salt or an ester of N-acetyldiaminobutyric acid can also be used to treat and / or prevent cell aging phenomena.
- NADA can be a useful ingredient in anti-aging products. Treatment of aural complaints
- aural complaints i. Damage to the ear can be treated with a composition containing N-acetyldiaminobutyric acid, a salt or an ester of N-acetyldiaminobutyric acid.
- this includes otitis externa, i. an inflammation of the outer ear. This is characterized by pain, itching, redness, dandruff and crust formation and secretion. The causes are often mechanical in nature, with minor injuries associated with subsequent bacterial infection. Bacterial infections, for example with pseudomonads, can also occur after swimming or diving. Other bacterial pathogens are staphylococci. A viral, allergic or immune-related background of the otitis externa is also possible.
- pruritus that occurs here, i. Itching. Such is usually due to the release of histamine or other messengers u.a. triggered by mast cells. Other forms of pruritus outside the ear can be treated according to the invention.
- the composition may be present, for example, as a solution, rinse, suspension, ointment, cream, lotion, paste, emulsion, microemulsion, spray, jelly or aerosol.
- the emulsions and microemulsions may be oil-in-water (O / W) or water-in-oil (W / O) emulsions / microemulsions.
- Suitable carriers for liquid administration forms are in particular aqueous systems with or without buffer.
- Suitable carriers for thick or semi-solid preparations such as, for example, ointments, creams or gels, are, for example, paraffin hydrocarbons, vaseline, wool wax products and other pharmaceutically usable, viscosity-increasing base substances, for hydrophilic gels, for example water, glycerol or sorbitol, which are mixed with suitable bulking agents, such as polyacrylic acid, cellulose derivatives, starch or tragacanth gelled.
- Ointments, pastes, creams and gels may contain the usual excipients, e.g. As animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silica, talc and zinc oxide or mixtures of these substances.
- excipients e.g. As animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silica, talc and zinc oxide or mixtures of these substances.
- the composition containing the active ingredient may also be encapsulated in nanostructures or in the form of liposomes. This is particularly advantageous if the composition contains no preservative.
- Corresponding methods for encapsulation are known in principle from the prior art.
- the preparation according to the invention may contain other acceptable pharmaceutical excipients and / or additives which are compatible with the active substances, such as, for example, Filling, stretching, binding, wetting, stabilizing, coloring, buffering, smelling and / or preserving agents, bactericides, solubilizers, vitamins, stabilizers, substances for preventing foaming, thickening agents, dyes, surface-active substances, moisturizing substances , Emulsifiers, viscosity increasing agents, etc.
- other acceptable pharmaceutical excipients and / or additives which are compatible with the active substances, such as, for example, Filling, stretching, binding, wetting, stabilizing, coloring, buffering, smelling and / or preserving agents, bactericides, solubilizers, vitamins, stabilizers, substances for preventing foaming, thickening agents, dyes, surface-active substances, moisturizing substances , Emulsifiers, viscosity increasing agents, etc.
- Preservatives are, for example, thiomersal, organic mercury compounds such as phenylmercury, benzalkonium chloride, chlorhexidine, benzyl alcohol, glucose, ethanol and quaternary ammonium salts.
- examples of viscosity-increasing agents are cellulose ethers such as hydroxyethylcellulose, carboxymethylcellulose, hydroxypropylmethylcellulose, methylpropylcellulose, methylcellulose, methylethylcellulose, ethylcellulose, hydroxyethylmethylcellulose, hydroxypropylcellulose, ethylhydroxyethylcellulose.
- polyethylene glycol polyvinyl alcohols, polyvinylpyrrolidone, glycosaminoglycans, proteoglycans, cetyl alcohol and stearyl alcohol or combinations thereof (cetylstearyl alcohol), polyacrylic acid, polymethacrylic acid, polyacrylamide, polyethers, polyimines, polyamides, alginates, xanthan, polyuronides, alginic acid, carrageenan, chondroitin sulfate, guaran, Hydroxypropylguaran and starch acetate.
- the concentration of the viscosity-increasing agents in the composition is preferably 0.05 to 10% by weight, preferably 0.1 to 3% by weight.
- concentrations for cellulose ethers in the range of 0.2 to 2.5 wt .-%, for polyethylene glycol in the range of 0.2 to 1 wt .-%, for polyvinyl alcohol from 0.1 to 4 wt .-% have been found to be useful. and for polyacrylic acid from 0.1 to 0.3% by weight.
- Moisturizing or moisturizing agents are e.g. Glycerin, sorbitol, trehalose, betaine, dexpanthenol, 1,2-propylene glycol, xylitol or other polyalcohols.
- compositions may contain other active ingredients.
- active ingredients Possible, for example, is the combination of N-acetyldiaminobutyric acid or the abovementioned derivatives with one or more active substances selected from: dexpanthenol or derivatives, Arnica montana extract (Arnica), capsaicin, Capsicum extract, Hypericum perforatum extract (St.
- DIP di-myo-inositol phosphate
- cDPG cyclic 2,3-diphosphoglycerate
- DGP 1,1-di-glycerol phosphate
- DGP 1,1-di-glycerol phosphate
- firoin ⁇ -mannosylglycerate
- Firoin A Mannosyl di-inositol phosphate
- DMIP Mannosyl di-inositol phosphate
- glucosylglycerol taurine
- betaine citrulline
- DAMICA 4,5-dihydro-2-methylimidazole-4-carboxylic acid
- HDMICA 4,5,6,7-tetrahydro-2-methyl- 1 H- [1, 3] - to call diazepine-4-S-carboxylic acid
- homoectin di-myo-inositol phosphate
- cDPG cyclic 2,3-diphosphoglycerate
- Suitable agents are local anti-inflammatories, e.g. Steroids, cyclosporin A, beta-receptor blocker. Also possible is the combination with antipruritic substances, antimycotics, fungistats, fungicides, antivirals and therapeutic peptides. Part of the composition may also be antibiotics. These include gentamicin, kanamycin, neomycon, tobramycin, ciprofloxacin, ofloxacin, chlortetracycline, ciprofloxacin, erythromycin, fusidic acid, lomefloxacin, levofloxacin and oxytetracycline.
- antibiotics include gentamicin, kanamycin, neomycon, tobramycin, ciprofloxacin, ofloxacin, chlortetracycline, ciprofloxacin, erythromycin, fusidic acid, lomefloxacin, levofloxacin and oxyt
- compositions may also have a pH buffering system to set a particular pH.
- Suitable buffer systems are citrate, phosphate, TRIS, glycine, borate, acetate. These buffer systems can be prepared from substances such as citric acid, monosodium phosphate, disodium phosphate, glycine, boric acid, sodium tetraborate, acetic acid or sodium acetate.
- the N-acetyldiaminobutyric acid is typically present at a level of from 0.001% to 50%, preferably from 0.05% to 20%, more preferably from 0.1% to 10% by weight, based on the total weight of the composition.
- Calcein AM staining (calcein acetoxymethyl ester) was used to determine cell viability.
- Calcein is a fluorescent dye. After transport of calcein-AM into the living cell, the ester groups are cleaved by esterases of the cell, producing calcein, which forms a strongly green fluorescent complex with calcium ions present in the cell. High fluorescence therefore represents high cell viability, since dead cells do not have active esterases that could release the calcein necessary for complexation. A high cell viability in turn stands for good humidification properties of the test substances.
- UV and IR protection A UV protection assay via TEER assay
- a characteristic of both epithelial and endothelial cell layers is the formation of intercellular junctions, resulting in a dense cell barrier separating the basolateral (abluminal) side from the apical (luminal) side.
- the cell layers selectively form permeable interfaces between different compartments, controlling both diffusion in the intercellular space and intracellular transport processes. This is ensured by tight junctions (paracellular barriers in the intercellular space). The integrity of these barriers is determined by the so-called TEER method (transepithelial / transendothelial electrical resistance). In this case, a defined DC voltage is applied to two electrodes on the two sides of the cell layer. The flowing current is measured, resulting in resistance according to Ohm's law.
- HaCaT cells a human keratinocyte cell line, were used. These were applied to PET membranes ( "ThinCerts ®"). It has been maintained until the cells had formed a complete and intact monolayers. The integrity of the monolayers was determined by measuring the TEER value.
- a full thickness skin model from Henkel was used. This is based on a bovine collagen scaffold, which is morphologically equivalent to human skin and allows easy handling during examinations.
- the Phenion skin model was incubated with the test substances for 4 h. These were applied directly on top. Subsequently, the Phenion skin model was exposed to UV-B radiation for 2 hours. The time was chosen longer than with simple cell layers, because the phenion skin model is much more resistant. Thereafter, the skin model was incubated for a further 24 h and the LDH (lactate dehydrogenase) value was determined.
- the LDH value is a measure of the degree of damage to the cells.
- the LDH value before UV exposure is approximately the same for PBS and NADA, while the LDH level after UV exposure is significantly higher for the PBS control.
- NADA thus shows similar UV protection properties as in the cell layer model based on the TEER assay.
- Infrared (IR) radiation causes an increase in skin temperature, which is associated with an increase in the number of free radicals and increased expression of heat shock metalloproteases (MMP). Persistent exposure to IR radiation may result in an increase in cell death rate from apoptosis.
- HaCat cells human keratinocyte cell line
- the membrane-stabilizing effect and thus the strengthening of the barrier function of epithelial cells by NADA was investigated by means of a TR146 cell line.
- This is a buccal human cell line of oral mucosal cells.
- the cells were placed in a 96-well microtiter plate. Once confluence was achieved, the cells were washed with PBS and provided with varying concentrations of N-acetyldiaminobutyric acid.
- the negative control contained only PBS, the positive control cDPG (cyclic 2,3-diphosphoglycerate). After incubation, the cells were washed again with PBS and incubated with 5 ⁇ M calcein AM over a period of 45 min.
- HaCaT cells a keratinocyte cell line
- cell culture medium was changed to PBS with the addition of NADA or comparison substances such Glcosylglycerol, ectoine (28Extremoin) and Myramaze ®, a commercially available anti-aging product.
- the cells were incubated for 5 hours.
- the study examined the upregulation of claudins, membrane proteins as part of tights junctions, which close the interstices between the cells of the epithelium, creating a barrier. This controls the penetration of molecules across the epithelium. Specifically, the pore-occluding Claudin-1 was examined. Increased expression of claudin-1 leads to greater tightness of the epithelial membrane and increased transepithelial electrical resistance (TEER). The permeability is thus reduced.
- TEER transepithelial electrical resistance
- the epithelial cell line (HaCaT) used for the experiment was cultured on a microtiter plate in wells until a closed cell monolayer had formed. Subsequently, the cells were pretreated for 6 h in the cell culture medium with NADA (10, 25, 50, 75, 100 and 175 mM). Thereafter, the cells were suddenly exposed to a temperature of 44 ° C for 30 minutes before being kept at 37 ° C for another 24 or 48 hours. The cells were harvested and the lysate was analyzed using a Claudin-1 specific ELISA (enzyme-linked immunosorbent assay). The result is shown in FIG.
- ectoine 207 g were dissolved in 2 l KOH solution (2 M) and stirred at room temperature over a period of 19 h.
- the resulting solution was neutralized with 25% HCl; KCl was removed by electrodialysis. After concentration and drying, the product was obtained as a colorless powder.
- the reaction product contained less than 1% by weight of ectoine and was composed of 80% by weight of (2S) -4-acetamido-2-aminobutyric acid and 20% by weight of (2S) -2-acetamido-4-aminobutyric acid.
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Abstract
Description
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DE102016125414.2A DE102016125414A1 (en) | 2016-12-22 | 2016-12-22 | Composition containing N-acetyldiaminobutyric acid |
PCT/EP2017/084454 WO2018115475A2 (en) | 2016-12-22 | 2017-12-22 | N-acetyldiaminobutyric acid-containing composition |
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US (1) | US20190380985A1 (en) |
EP (1) | EP3558287A2 (en) |
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WO1993003714A2 (en) * | 1991-08-27 | 1993-03-04 | The Upjohn Company | Method for treatment of metabolic disorders |
DE10262084B4 (en) | 2002-05-17 | 2009-12-24 | Dr. Franz Köhler Chemie GmbH | Protective solution for the prevention of ischemic damage |
DE10330243A1 (en) | 2003-07-03 | 2005-01-20 | bitop Aktiengesellschaft für biotechnische Optimierung | Use of osmolytes derived from extremophilic bacteria for the manufacture of medicines for the external treatment of atopic dermatitis |
DE102006056766A1 (en) | 2006-12-01 | 2008-06-05 | Bitop Ag | Use of compatible solutes |
ES2700613T3 (en) | 2008-07-16 | 2019-02-18 | Bitop Ag | Synthesis of cyclic amidines |
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