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Reconstructed epidermis/skin equivalent comprising a ceramide 7 and/or 5.5 and lipid lamellar vesicular compositions comprising ceramide 7 and/or 5.5 compounds

a technology of reconstructed epidermis and skin equivalent, which is applied in the direction of drug compositions, artificial cell constructs, skeletal/connective tissue cells, etc., can solve the problems of inability to control the exact nature of the ceramide which will be synthesized in situ, the fragility of the reconstructed skin, and the inability to control the nature of the ceramide. , to achieve the effect of improving the barrier function

Inactive Publication Date: 2007-06-28
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0031] It has also now been determined that a composition based on lipid lamellar vesicles incorporating at least one derivative of the ceramide 7 and / or ceramide 5.5 family makes it possible to improve the barrier function of an epidermis exhibiting a deficiency in 6-hydroxy-4-sphingenine-base ceramides. This is particularly advantageous since it has been shown, in the context of the invention, that dry skin and reconstructed skin (study carried out on the EPISKIN™ model) exhibit a deficiency in the most polar ceramides, which results in a deficiency in 6-hydroxy-4-sphingenine (also called 6-hydroxy-4-sphingosine) sphingoid bases.

Problems solved by technology

However, in using 6-hydroxy-4-sphingenine, it is not possible to control the nature of the ceramide which will be obtained in situ subsequent to its combination with a fatty acid in the epidermis.
In addition, reconstructed skin is a fragile structure whose survival can only be maintained for a limited period of time (approximately 1 month).
In addition, in introducing ascorbic acid or one of its derivatives into the culture medium, it is not possible to control the exact nature of the ceramide which will be synthesized in situ.

Method used

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  • Reconstructed epidermis/skin equivalent comprising a ceramide 7 and/or 5.5 and lipid lamellar vesicular compositions comprising ceramide 7 and/or 5.5 compounds
  • Reconstructed epidermis/skin equivalent comprising a ceramide 7 and/or 5.5 and lipid lamellar vesicular compositions comprising ceramide 7 and/or 5.5 compounds
  • Reconstructed epidermis/skin equivalent comprising a ceramide 7 and/or 5.5 and lipid lamellar vesicular compositions comprising ceramide 7 and/or 5.5 compounds

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0199] Preparation of the Ceramide 7 of Formula (I) by TLC from Human Stratum Corneum:

[0200] Step 1: Turbine Extraction

Starting sample: Epidermis from a normal volunteer

Action: organic solvents (most commonly a 2 / 3 mixture of hexane / ethanol) are passed through the stratum corneum so as to entrain the lipids, by virtue of a turbine.

Final sample: Epidermal lipids in solvated form.

[0201] Step 1a: Extraction Using Tape Stripping

Starting sample: Epidermis from a normal volunteer

[0202] Action: an adhesive strip—lacquer+nylon—is applied to the skin of volunteers, and the whole is torn off, entraining, by the same token, part of the stratum. The strips are then placed in the presence of solvents (of the chloroform / methanol (2 / 1) type, with stirring).

Final sample: Epidermal lipids in solvated form.

[0203] Step 2: Isolation of Ceramides 7

Starting sample: Epidermal lipids in solvated form (total lipids)

Action: Separation of ceramide families

[0204] After concentration, if nece...

example 2

[0213] Preparation of Ceramide 5.5 by TLC from Human Stratum Corneum:

[0214] The preparation of ceramide 5.5 is identical to that of ceramide 7 of Example 1, with the difference that the band isolated after structural analysis of the ceramide content of the various migration bands will be the band containing mainly ceramide 5.5, and with the difference that the latter is generally associated with a greater amount of impurities (ceramides 5) and that obtaining it in a correctly purified form possibly requires repeating purification step 3 one or more times if necessary.

example 3

[0215] Evaluation of the Effectiveness of the Vesicular Dispersions According to the Invention on the Barrier Function of Reconstructed Skin:

[0216] The two suspensions below are prepared:

[0217] Formula with ceramide 7-free niosomes:

Sorbitan palmitate (Span 40 sold by Uniquema)0.225%Cholesterol0.225%N-stearoyl-L-glutamic acid, disodium salt0.050%Propylene glycol3.000%Water qs100.000%

[0218] Formula with niosomes containing ceramide 7:

Sorbitan palmitate0.2250%Cholesterol0.1250%N-stearoyl-L-glutamic acid, disodium salt0.0500%Ceramide 70.0315%Distilled water qs100.0000%

[0219] Procedure:

[0220] In the 2 cases, the lipids are combined beforehand in a methanol / chloroform (50 / 50 by weight) solvent phase. The solvent is then evaporated off under reduced pressure using a rotary evaporator. The lipid film formed on the wall of the round-bottomed flask is then solubilized with an aqueous octylglucoside solution (6%) so as to form octylglucoside / vesicular lipid mixed micelles. This solution...

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Abstract

A reconstructed epidermis / skin equivalent supplemented with at least one ceramide 7 and / or 5.5 compound, suited for reinforcing the barrier function of normal human epidermis and for improving the barrier function of dry skin and of reconstructed skin or skin equivalents, is prepared by introducing the at least one ceramide 7 and / or 5.5 compound into the culture medium of such reconstructed epidermis / skin equivalent and / or topically applying onto the face surface of such reconstructed epidermis / skin equivalent a composition which comprises lipid lamellar vesicles incorporating at least one ceramide 7 and / or 5.5 compound.

Description

CROSS-REFERENCE TO PRIORITY / PROVISIONAL APPLICATIONS [0001] This application claims priority under 35 U.S.C. § 119 of FR 03 / 01058 and FR 03 / 01059, both filed Jan. 30, 2003, and of provisional application Ser. Nos. 60 / 477,049 and 60 / 477,053, both filed Jun. 10, 2003, each hereby expressly incorporated by reference and each assigned to the assignee hereof. This application is also a continuation of said '049 and '053 provisionals.BACKGROUND OF THE INVENTION [0002] 1. Technical Field of the Invention [0003] The present invention relates to a method for preparing a reconstructed epidermis or a skin equivalent supplemented with at least one derivative of ceramide 7 and / or 5.5, comprising introducing at least one derivative of ceramide 7 and / or 5.5 into the culture medium for said reconstructed epidermis or said skin equivalent and / or in topically applying to said reconstructed epidermis or said skin equivalent a composition based on lipid lamellar vesicles incorporating at least one deri...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C12N5/08C12N5/071
CPCA61K8/14A61K8/68A61Q19/005C12N5/0698C12N2500/36C12N2500/38C12N2502/094C12N2502/1323Y10S514/943
Inventor CHOPART, MELANIECASTIEL, ISABELLESIMONNET, JEAN-THIERRY
Owner LOREAL SA
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