WO2016169373A1 - Composition topique renfermant une sinoménine et procédé de contrôle de la carbonylation des protéines - Google Patents

Composition topique renfermant une sinoménine et procédé de contrôle de la carbonylation des protéines Download PDF

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Publication number
WO2016169373A1
WO2016169373A1 PCT/CN2016/076825 CN2016076825W WO2016169373A1 WO 2016169373 A1 WO2016169373 A1 WO 2016169373A1 CN 2016076825 W CN2016076825 W CN 2016076825W WO 2016169373 A1 WO2016169373 A1 WO 2016169373A1
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Prior art keywords
sinomenine
topical composition
skin
subject
carbonylation
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PCT/CN2016/076825
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English (en)
Chinese (zh)
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韩强
张翌
李廷钊
杜军
李波
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捷通国际有限公司
韩强
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Publication of WO2016169373A1 publication Critical patent/WO2016169373A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • 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

Definitions

  • the present invention generally relates to a sinomenine-containing topical composition for inhibiting skin protein carbonylation in a subject, and more particularly to a topical composition comprising sinomenine and inhibiting the skin protein carbonyl of a subject using the topical composition (or denaturation) method.
  • a major contributor to skin yellowing associated with aging is believed to be the protein denaturation process known as "carbonylation" in the dermis.
  • protein denaturation is the result of binding between lipid degradation products produced by ultraviolet ("UV)" ray damage and dermal proteins.
  • UV ultraviolet
  • the resulting discoloration is a major factor contributing to the yellowing of the skin with the age of the individual and is particularly problematic for Asians.
  • a lipid can interact with an aldehyde that causes carbonylation of the dermal protein, resulting in a carbonylated protein.
  • sugars can cause saccharification of dermal proteins, resulting in glycated proteins. It is believed that carbonylation produces a yellower skin relative to saccharification.
  • a topical composition is disclosed.
  • the topical composition can be used on the skin of a subject.
  • the topical composition comprises sinomenine.
  • the sinomenine is present in an amount effective to inhibit skin protein carbonylation in the subject after administration.
  • the active ingredient of the topical composition consists of sinomenine.
  • the topical composition consists of sinomenine.
  • a cosmetic method of inhibiting skin protein carbonylation in a subject includes the step of applying sinomenine to the skin of the subject.
  • the topical compositions are typically applied in an amount and/or time sufficient to inhibit skin protein carbonylation.
  • topical compositions are also used for skin lightening (or whitening), particularly for inhibiting melanin synthesis, eliminating melanin and/or inhibiting tyrosinase.
  • Figure 1 is a line graph illustrating cytotoxicity data ("Data 1");
  • Figure 2 is a line graph illustrating carbonylation inhibition data ("data 2");
  • Figure 3 is another line graph illustrating cytotoxicity data ("Data 3");
  • Figure 5 is a line graph illustrating melanin elimination rate data ("data 5");
  • Figure 6 is a line graph illustrating tyrosinase inhibition rate data ("data 6").
  • composition for inhibiting skin protein carbonylation. More specifically, the composition can be used to inhibit skin protein carbonyl in a subject Chemical.
  • the skin layer includes the epidermis and the dermis, and protein carbonylation generally occurs in at least the dermis.
  • the composition is applied directly to the epidermis, such as the stratum corneum.
  • the composition can also be applied indirectly to the epidermis, such as by a patch that carries/delivers the composition to the skin. At least a portion of the composition or active ingredient thereof, such as sinomenine, migrates from the stratum corneum through the epidermis and to the dermis to inhibit protein carbonylation therein.
  • Subjects are usually human and can include men and women of all ages.
  • the composition is not limited to the location of the skin of a particular subject or subject. For example, a person can apply the composition to his face, neck, arms, hands, chest, torso, legs, feet, and the like, or any combination thereof. Such areas of the skin may be damaged or not damaged. Black spots, yellowing, sagging, and/or wrinkles generally indicate skin damage, such as UV rays or light damage. Methods of using the compositions are further described below.
  • compositions of the present disclosure generally comprise extracts from plants of the genus Geochelone, more typically from plants of the species Sinomenium acutum.
  • sinomenine is the active substance of the extract and is believed to be an effective compound for inhibiting protein carbonylation.
  • reference to the genus Wind Dragon can be used interchangeably with Wind Dragon, and vice versa. The same is true for the mention of sinomenine and genus (or wind dragon) extract.
  • embodiments of the present disclosure generally relate to topical compositions comprising an extract of a plant of the genus Rhododendron, such as an extract of a plant of the genus Dragon, wherein the sinomenine is sufficient to reduce/inhibit protein carbonylation in the subject after administration.
  • the amount exists.
  • the composition comprises sinomenine.
  • the active ingredient of the composition consists of sinomenine.
  • the composition may further consist of one or more additional components and/or inactive components.
  • the composition consists of sinomenine.
  • the composition can include plant material from the genus Geochelone, including plant material from the genus.
  • the wind dragon is a genus of the family. It includes only one known species, Wind Dragon, produced in China, northern India, Nepal, Japan and northern Thailand.
  • the wind dragon can also be called the Sinomenium acutum (Thunb.) Rehd.et Wils.
  • the active substances of the wind dragon include alkaloids such as sinomenine, isoflavone, sinomenine, L-paraffin and chlorhexidine, and ⁇ -phytosterol and stigmasterol.
  • sinomenine is considered to be an effective compound for inhibiting protein carbonylation (or denaturation).
  • One or more other active substances may also be used for this effect, but it is considered that sinomenine is most effective for protein carbonylation inhibition.
  • Sinomenine CAS Number 115-53-7, molecular weight ⁇ 329g / mol, and the molecular formula C 19 H 23 NO 4.
  • Sinomenine can be obtained commercially as a standard sample or can be obtained by extracting a material of the genus Rhododendron.
  • Standard samples of sinomenine may have a purity of at least about 90%, at least about 95%, at least about 99%, and up to 99.99%. Other levels of purity are also available and used.
  • Genus plant can be used to obtain sinomenine for use in the composition, including but not limited to roots, stems, rhizomes, leaves, flowers, fruits, and/or extracts of these portions.
  • Sinomenine is generally present in the roots of the wind dragon, whereby root extracts are generally most useful for the purposes of the present disclosure.
  • the genus Rhododendron can be used in its original form, in a suspended form, in a dehydrated form, in a concentrated form or in the form of an extract.
  • the genus Dragon is in a dry or liquid form.
  • the other components of the extract and/or composition of the genus Dragon can be obtained by conventional extraction methods known in the art, such as extraction by water (e.g., steam) or by solvent (e.g., alcohol).
  • extraction methods known in the art, such as extraction by water (e.g., steam) or by solvent (e.g., alcohol).
  • solvent e.g., alcohol
  • the compositions of the present disclosure are not limited to a particular extraction method and are not necessarily extracted because sinomenine can be readily obtained from many commercial suppliers. An exemplary extraction method is described below.
  • the composition comprises an extract from the genus.
  • “Dragonfly extract” generally refers to extracts from the genus Rhododendron, including from the genus. Wind Dragon extracts are commercially available from a variety of sources.
  • suitable extracts of the genus Rhododendron can be obtained by using any conventional extraction technique.
  • a polar solvent such as an alcohol (for example methanol, ethanol, butylene glycol), an ether (for example diethyl ether), a ketone (for example acetone), an ester (for example ethyl acetate), water or a mixture thereof is available.
  • a polar solvent such as an alcohol (for example methanol, ethanol, butylene glycol), an ether (for example diethyl ether), a ketone (for example acetone), an ester (for example ethyl acetate), water or a mixture thereof.
  • Suitable non-polar solvents include, but are not limited to, ethyl acetate, hexane, dichloromethane, chloroform or mixtures thereof.
  • extraction methods that can be used to produce extracts suitable for the composition. These methods include, but are not limited to, the extraction methods disclosed in U.S. Patent No. 7,897,184 to Rana, et al. While the extraction solvent described specifically refers to ethanol, it should be understood that other alcohols such as, but not limited to, isopropanol, ethyl alcohol, and/or methyl alcohol may be used in addition to or in place of ethanol.
  • Exemplary alcoholic solvents include, but are not limited to, a C 1 to C 4 alcohols such as methanol, ethanol, propanol, isopropanol and butanol; water - alcohol or mixture of alcohols and water, including water - ethanol (hydro-ethanol); Multi Hydroxy alcohols such as propylene glycol and butylene glycol; and fatty alcohols. Any of these alcohol solvents can be used. Other solvents such as, but not limited to, acetone can also be used as the extraction solvent. Any ratio of solvent-water admixtures such as alcohol-water and/or acetone-water admixtures can also be used.
  • the extract of the genus Rhododendron can be obtained using an organic solvent extraction technique.
  • continuous extraction of the solvent can be used to obtain the extract of the genus.
  • the total water-ethanol extraction technique it is called a one-time extraction.
  • the extract produced in this process will contain a wide range of phytochemicals present in the extracted material, including fat soluble and water soluble phytochemicals. After collecting the extraction solution, the solvent was evaporated to obtain an extract.
  • Total ethanol extraction can also be used. This technique uses ethanol as a solvent.
  • the extract produced by the extraction technique may include a fat-soluble and/or lipophilic compound in addition to the water-soluble compound.
  • Total methanol extraction can also be used in a similar manner with similar results.
  • the extract of the genus Rhododendron is obtained by extracting the plant material of the genus.
  • SFE supercritical carbon dioxide supercritical fluid extraction
  • the material to be extracted is not exposed to any organic solvent. Rather, the extraction solvent is carbon dioxide (CO 2 ) in a supercritical state (eg, >31.3 ° C and >73.8 bar) with or without a conditioning agent.
  • CO 2 carbon dioxide
  • a supercritical state eg, >31.3 ° C and >73.8 bar
  • temperature and pressure conditions can be varied to achieve optimal extract yield.
  • This technique produces extracts of fat-soluble and/or lipophilic compounds similar to total hexane and ethyl acetate extraction techniques, which can also be used.
  • the extract of the genus Dioscorea can be added to the composition in any amount, provided that it is present in an amount effective to inhibit protein carbonylation.
  • sinomenine is present in an amount effective to reduce the formation of carbonyl derivatives of the skin of the subject.
  • carbonyl derivatives typically comprise an aldehyde, a ketone or a combination thereof.
  • sinomenine is present in an amount from about 5 to about 500, or from about 25 to about 350, g/mL of the topical composition. In a particular embodiment, the sinomenine is present in an amount of from about 10, about 20, about 25, about 50, about 75, about 100, about 200, or about 300 [mu]g/mL of the composition. Individual subranges and amounts of from about 5 to about 500 [mu]g/mL of composition, as well as amounts less than or greater than these amounts, are also contemplated.
  • sinomenine present in the composition can depend on several factors, including the level of protein carbonylation inhibition desired, the level of protein carbonylation inhibition in a particular extract or composition, and other factors.
  • sinomenine is present in an amount from about 0.01 to about 20 pbw based on 100 parts by weight ("pbw") of the composition.
  • the sinomenine is present in an amount of from about 0.05 to about 10 pbw based on the 100 pbw of the composition.
  • Other extracts or ingredients, which are optionally used in the compositions of the present disclosure, are described in U.S.
  • Patent No. 5,747,006 to Dornoff et al. and U.S. Patent Nos. 5,980,904, 6,994,874, 7, 060,304, 7, 247, 321 and 7, 364, 759 to Leverett et al. Into this article.
  • the composition is free of other actives.
  • "Other active substances” herein generally means that the composition does not contain other types of traditional Chinese medicines (“TCM”; or “Chinese medicine”) other than the genus Rhododendron.
  • TCM traditional Chinese medicines
  • Other types of TCM are understood in the art. Examples of other types of TCMs are generally described as "biologically active substances" in International Publication No. WO 01/22934 A2, the contents of which are incorporated herein in entirety by reference.
  • the composition may comprise the following inactive materials. If used, inactive materials are different from other types of TCM.
  • compositions can be formulated to contain a cosmetically acceptable carrier (or vehicle) and prepared and/or packaged and labeled to inhibit protein carbonylation, reduce skin yellowing, and/or skin lightening (or whitening).
  • a cosmetically acceptable carrier or vehicle
  • the composition can be administered topically.
  • cosmetically acceptable carriers include, but are not limited to, water, glycerin, waxes, various alcohols such as ethanol, propanol, vegetable oils, mineral oils, silicones such as silicone oils, fatty esters, fatty alcohols, glycols, polyglycols or Any combination thereof.
  • Such components are generally considered to be inactive components.
  • the final composition may be in any form suitable for topical application to the skin such as, but not limited to, aerosol sprays, gels, creams, dispersions, lotions, foams, liquids, lotions, mousses, patches, balms, Powder, pump spray, solid, solution, stick or towel.
  • the emulsions may include oil-in-water emulsions, water-in-oil emulsions, and water-in-silicone emulsions.
  • compositions of the present disclosure can be prepared using a variety of methods known in the art.
  • the method of preparation comprises the step of extracting the plant material of the genus Dioscorea zingiberensis to obtain the extract of fenglong, i.e., obtaining sinomenine (with or without other active compounds).
  • the method of preparation further comprises the step of combining one or more of sinomenine with a cosmetically acceptable carrier such as the above carrier.
  • the components can be combined using conventional production methods and devices such as mixers, blenders, and the like.
  • the composition can be used in various ways to inhibit protein carbonylation.
  • a cosmetic method for inhibiting skin protein carbonylation in a subject includes the step of applying sinomenine to the skin of the subject.
  • Sinomenine can be applied in a variety of ways, including applying the composition to the skin of a subject, wherein the composition comprises an extract from the species.
  • the composition can be applied directly or indirectly to the skin, such as by hand, applicator, patch, and the like.
  • the composition can be applied as needed, daily, several times a day or any suitable protocol to achieve the desired result.
  • the frequency of topical application can depend on several factors, including the level of protein carbonylation inhibition desired.
  • the regimen includes applying the composition to the skin once or twice daily to include morning application and/or evening application.
  • the amount of the composition applied to the skin in each application may depend on several factors, including the level of the desired result and the particular composition.
  • oxidative stress is associated with the production of reactive oxygen species by protein carbonylation, a process in which a reactive aldehyde or ketone is introduced into a protein by oxidation.
  • the protein carbonyl is the major product of protein oxidation and can be formed by oxidative cleavage of the protein, direct oxidation of the amino acid residue, or covalent reaction with an aldehyde derived from lipid peroxidation.
  • Protein carbonylation occurs generally by direct metal catalyzed oxidation of the amino acid side chain ("primary protein carbonylation") or by addition of a reactive aldehyde to the amino acid side chain (“secondary protein carbonylation”). Oxidative degradation of polyunsaturated fatty acids that are ubiquitous in the human body can lead to the formation of various aldehydes such as acrolein and 4-hydroxyfurfural (“4-HNE”). Studies have shown that major protein carbonylation plays a role in reactive oxygen species (“ROS”) signaling mechanisms. Specifically, major protein carbonylation mediates cellular signaling and major protein carbonylation is reversible.
  • ROS reactive oxygen species
  • Major protein carbonylation involves direct metal catalyzed oxidation of amino acid side chains, particularly on four susceptible amino acid residues: valine, arginine, lysine, and threonine.
  • Oxidation of the proline or arginine side chain results in the formation of a glutamic acid semialdehyde, while lysine oxidizes to produce an aminoadipate semialdehyde, thereby introducing a carbonyl group into the protein structure.
  • Oxidation also converts the hydroxyl group of the threonine side chain to a carbonyl group to form 2-amino-3-butanone acid.
  • the secondary protein carbonylation mechanism involves a Michael addition reaction of a reactive aldehyde with a side chain of lysine, histidine and a cysteine residue, and a substitution of a reducing sugar with an amino group on lysine and arginine.
  • Baseline leading to high carbonyl The increase in the final product of the base.
  • Protein carbonyls are found in a variety of oxidative stress and disease conditions. In addition to protein inactivation, carbonylated cellular proteins undergo proteasome-dependent degradation. It is believed that major protein carbonylation plays a role in labeling damaged proteins during oxidative stress to eliminate them from biological systems. The formation of carbonyl proteins is a hallmark of oxidative stress, for example as an external factor, such as UV radiation induced factors or external application of oxidizing chemicals, or as an intrinsic factor, a reactive carbonyl derived from lipid peroxide degradation. Chemical attack.
  • UV rays or light damaged skin are characterized by various features such as dark spots, wrinkles and sagging. Older people, especially Asians, tend to show changes in the color of yellow skin that age with light. In China, yellowing generally means lack of pink or dull complexion. Common clinical signs of photodamage or aging include the appearance of a characteristic pale or yellow skin. Face yellow is often irreversible, so prevention is ideal.
  • sinomenine has no cytotoxic risk based on safety assessment by CTG cell levels (see data / Figure 1). Moreover, the inventors have discovered that sinomenine has the efficacy and function of skin anti-carbonylation based on in vitro bioassay data (see data / Figure 2). Cell-based assays by model cell HepG2 were performed and inhibition of carbonylation activity was monitored. Vitamin C is considered to be a positive control for carbonylation inhibition. Those skilled in the art understand this type of model cell HepG2 cell-based assay.
  • Luminescent cell viability assay is a uniform method for determining the number of viable cells in culture, based on the quantification of ATP present as an indicator of metabolically active cells.
  • Sinomenine has no cytotoxic risk based on the safety evaluation of CTG cell levels as illustrated by Data 1 and Figure 1.
  • sinomenine has outstanding anti-carbonylation inhibitory potency compared to the positive control vitamin C in the cellular HepG2 model without the risk of cytotoxicity. This data set is generally obtained by the assay methods listed below.
  • This program describes a standard method for the anti-oxidation assay of HepG2 cells.
  • the assay plates were incubated for 24 hours at 37 ° C, 5% CO 2 under humidified conditions.
  • HBSS Hanks Balanced Salt Solution
  • human skin coloration is determined by the amount and location of melanin on the surface of the skin.
  • Melanin is synthesized by oxidation of amino acid tyrosine to L-3,4-dihydroxyphenylalanine ("L-DOPA") in cells, commonly referred to as melanocytes, present at the dermal-epidermal junction. The oxidation process is catalyzed by tyrosinase.
  • melanogenesis A series of cellular processes by melanocytes are commonly referred to as melanogenesis.
  • Skin coloration is regulated by the amount and type of melanin synthesized by melanocytes. Environmental factors can also affect skin color. A healthy amount of melanin in the skin effectively absorbs UV rays. When the skin is exposed to UV radiation, it generally increases the amount and rate of melanin production and can result in skin blackening or "brown”.
  • Local or general pigmentation disorders such as hyperpigmentation or hypopigmentation, can be derived from a number of factors, including hormone levels in the body, diet, genetic disorders, and medications. Common pigmentation disorders include melasma, freckles, and leukoplakia.
  • compositions have been formulated to address pigmentation disorders and have been contemplated, for example, for treating hyperpigmentation and/or hypopigmentation. Such treatments are often referred to as "skin brightening,” “skin whitening,” or “skin whitening.”
  • skin lightening agents For example, lightening age spots (freckles or aging spots), or preventing blackening of Caucasian and Asian skins (ie, maintaining a bright/white complexion).
  • Some of these formulations have included tyrosinase inhibitors such as hydroquinone, vitamin C, kojic acid, arbutin, glutathione, cysteine, lactic acid, ferulic acid, nicotinamide, and plant extracts.
  • tyrosinase inhibitors such as hydroquinone, vitamin C, kojic acid, arbutin, glutathione, cysteine, lactic acid, ferulic acid, nicotinamide, and plant extracts.
  • sinomenine was found to have efficacy in skin lightening and depigmentation.
  • Assays for this type of model cell-based B16F10 cells are known to those skilled in the art.
  • Arbutin is considered to be a positive control for both melanin synthesis inhibition and tyrosinase activity inhibition, while hydroquinone is used as a positive control for the existing melanin-eliminating activity.
  • sinomenine has the ability to strongly interrupt or reduce the melanin synthesis process in B16F10 cells. This data set is generally obtained by the assay methods listed below.
  • This program describes a standard method for the inhibition of melanin synthesis in B16 F10 cells.
  • the assay plates were incubated for 24 hours at 37 ° C, 5% CO 2 under humidified conditions.
  • % inhibition (maximum signal - compound signal) / (maximum signal - minimum signal) x 100.
  • This program describes a standard method for the determination of melanin in B16 cells.
  • the assay plates were incubated for 24 hours at 37 ° C, 5% CO 2 under humidified conditions.
  • the assay plates were incubated at 37 ° C, 5% CO 2 for 72 hours under humidified conditions.
  • % inhibition (maximum signal - compound signal) / (maximum signal - minimum signal) x 100.
  • Sinomenine exerts excellent tyrosinase inhibitory activity in B16F10 cells, and the inhibition rate is 32.4% at a concentration of 100 ⁇ g/mL. Specifically, as shown in Data 6 and FIG. 6, sinomenine exhibited much better or much better arbutin in tyrosinase inhibitory activity in B16F10 cells.
  • sinomenine has shown great ability to eliminate the presence of melanin assay models.
  • sinomenine has excellent activity as a skin whitening and depigmenting agent, and there is no risk of cytotoxicity for skin care or topical use.
  • the range of "0.1 to 0.9" can be further depicted as a smaller one-third, ie 0.1 to 0.3, the middle third, ie 0.4 to 0.6, and the larger one, ie 0.7 to 0.9, which is individual and generally within the scope of the appended claims, and may be relied upon and provided with sufficient support for the specific embodiments within the scope of the appended claims.
  • languages that define or modify a range such as “at least”, “greater than”, “less than”, “not greater than”, etc., it is to be understood that such language includes sub-ranges and/or upper or lower limits.
  • a range of "at least 10" inherently includes a subrange of at least 10 to 35, a subrange of at least 10 to 25, a subrange of at least 25 to 35, and the like, and each subrange may be in an individual and/or population Sufficient support is provided for the specific embodiments within the scope of the appended claims.
  • individual values within the scope of the disclosure may be relied upon and provide sufficient support for the specific embodiments within the scope of the appended claims.
  • a range of "1 to 9" includes each individual integer, such as 3, and an individual value including a decimal point (or fraction), such as 4.1, which may be relied upon and provide sufficient support for a particular embodiment within the scope of the appended claims. .

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Abstract

L'invention concerne une composition topique d'inhibition de la carbonylation des protéines cutanées, son procédé de préparation et ses applications. Le principe actif de ladite composition topique est une sinoménine. Le procédé de préparation de ladite composition topique comprend une étape d'obtention de la sinoménine à partir de la plante Sinomenium.
PCT/CN2016/076825 2015-04-22 2016-03-21 Composition topique renfermant une sinoménine et procédé de contrôle de la carbonylation des protéines WO2016169373A1 (fr)

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CN201510194019.9A CN106137782A (zh) 2015-04-22 2015-04-22 包含青藤碱的局部组合物及用于抑制蛋白羰基化的方法
CN201510194019.9 2015-04-22

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FR2913885B1 (fr) * 2007-03-22 2012-07-20 Univ Paris Descartes Utilisation de la citrulline pour le traitement des pathologies liees a une augmentation de la carbonylation des proteines

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ZHANG, XIANZHOU ET AL.: "Study on the Transdermal Penetration of Sinomenine Microemulsion and Gel", CHINESE JOURNAL OF MODERN APPLIED PHARMACY, vol. 20, no. 6, 31 December 2008 (2008-12-31), pages 518 *

Cited By (3)

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Publication number Priority date Publication date Assignee Title
WO2018162368A1 (fr) * 2017-03-06 2018-09-13 Merck Patent Gmbh Utilisation de solutés compatibles
CN110381917A (zh) * 2017-03-06 2019-10-25 默克专利股份有限公司 相容性溶质的用途
CN110381917B (zh) * 2017-03-06 2023-10-31 默克专利股份有限公司 相容性溶质的用途

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