US20100113385A1 - Complex combining an organic silicon derivative with hyaluronic acid calibrated fragments, for preventive and repairing action of cutaneous damages - Google Patents

Complex combining an organic silicon derivative with hyaluronic acid calibrated fragments, for preventive and repairing action of cutaneous damages Download PDF

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Publication number
US20100113385A1
US20100113385A1 US12/572,658 US57265809A US2010113385A1 US 20100113385 A1 US20100113385 A1 US 20100113385A1 US 57265809 A US57265809 A US 57265809A US 2010113385 A1 US2010113385 A1 US 2010113385A1
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United States
Prior art keywords
fragments
kda
complex
molecular weight
hyaluronic acid
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Abandoned
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US12/572,658
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English (en)
Inventor
Marie-Christine Seguin
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Exsymol SAM
EXZYMOL M SA
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EXZYMOL M SA
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Application filed by EXZYMOL M SA filed Critical EXZYMOL M SA
Publication of US20100113385A1 publication Critical patent/US20100113385A1/en
Assigned to EXSYMOL S.A.M. reassignment EXSYMOL S.A.M. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SEGUIN, MARIE CHRISTINE
Priority to US13/649,640 priority Critical patent/US8822433B2/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • 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
    • A61K31/695—Silicon compounds
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/728—Hyaluronic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates

Definitions

  • the invention concerns a complex combining an organic silicon derivative with one or several hyaluronic acid calibrated fragments, and its use in the prevention or the repair of cutaneous damages.
  • hyaluronane Linear polysaccharide constituted of repetitive units of D-glucuronic acid and N-acetyl-D-glucosamine, the hyaluronic acid is found in the extra-cellular matrix of numerous connective tissues (skin, tendons, muscles, etc), more precisely as a polyanion called “hyaluronane”.
  • HA hyaluronic acid
  • the HA synthesized by fibroblasts and keratinocytes (hereafter “native HA”) mainly exists as polymers of very high molecular weight (> to 2.000 kDa) able even to reach 4.000 kDa with a chain of 10.000 disaccharides (Hascall V. C. and al., GlycoForum/Hyaluronan Today (1997), chapter 1).
  • fragmented HA has a different behavior from the native HA, and that according to the size of fragments, in other words their molecular weight, it is observed different biological effects, and even opposite (Noble P. W., Matrix Biol. (2002), vol. 21, pp. 25-29; Asari A., GlycoForum/Hyaluronan Today (2005), chapter 29 and quoted references).
  • HA fragments said of high molecular weight an effect on regeneration and healing, an important role as regulator of the inflammatory process, but also an immunosuppressive effect.
  • oligomers said of low weight are presented as entities able to activate the immune cells and to deliver endogenous signals with respect to stress, but also to be powerful inducers of inflammation and angiogenesis (Stern R., Clin. Dermatol. (2008), vol. 26, pp. 106-122; Krasinski R. et al., Postepy Hig. Med. Dosw (2007), vol. 61, pp. 683-689).
  • FIG. 1 illustrates an agarose gel.
  • the gel displays, for the three times of sampling and reaction (5 min, 15 min and 30 min), a more important distribution of HA with a high molecular weight for the MSH complex according to the invention, compared to fragmented HA non combined.
  • the technical problem that intends to solve the invention is to develop a new active ingredient based on hyaluronic acid fragments, with the double purpose:
  • the applicant's choice settled on a molecular entity under the form of a complex, combining an organic silicon derivative with hyaluronic acid calibrated fragments of molecular weight between 150 and 750 kDa, this for both following reasons.
  • the invention has for object a complex based on an organic silicon derivative characterized in that said derivative is combined, by weak bonds, with one or several hyaluronic acid calibrated fragments of molecular weight between 150 and 750 kDa.
  • the molecular weight of these fragments is between 150 and 600 kDa, in a way even more preferred between 250 and 600 kDa.
  • organic silicon derivative it is meant a compound defined by the following general formula (I):
  • the organic silicon derivatives according to the invention are under the form of monomers, dimers or trimers, mainly monomers or dimers, or a mixture of monomers, dimers and trimers, mainly a mixture of monomers and dimers, with a state in solution which can be represented by the following formula (II):
  • T0, T1 and T2 have respectively the formulas:
  • R is such as above defined for compounds (I), X represents a hydroxyl group or a radical R such as above defined, and r, s and t are such as that 1 ⁇ r+s+t ⁇ 3.
  • C 1 -C 4 alkyl group a hydrocarbon chain having from 1 to 4 atoms of carbon, linear, ramified, or even cyclic.
  • a group is notably a methyl, ethyl, propyl, butyl, 1-methylethyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl and cyclopropylmethyl group.
  • fragments of hyaluronic acid it is meant fragments resulting from native HA as such or from one of any of its salts, especially from sodium hyaluronate fragments.
  • the organic silicon derivative of formula (I) is chosen among the monomethylsilanetriol or the dimethylsilanediol. It is especially chosen the monomethylsilanetriol, and even more particularly the monomethylsilanetriol combined with one or several hyaluronic acid fragments of molecular weight between 150 and 600 kDa (hereafter “MSH” complex) or between 250 and 600 kDa.
  • MSH hyaluronic acid fragments of molecular weight between 150 and 600 kDa
  • the present invention also spreads to a cosmetic composition for topical application including, in association with any physiologically compatible excipient with skin, as main active ingredient, the complex such as previously defined, particularly the monomethylsilanetriol, and even more particularly the monomethylsilanetriol combined with one or several hyaluronic acid fragments of molecular weight between 150 and 600 kDa or between 250 and 600 kDa, said composition being intended for preventing or repairing the cutaneous damages related to aging for which it is necessary to boost the epidermal cell activity while limiting the catabolic action of the cutaneous tissue.
  • the complex such as previously defined, particularly the monomethylsilanetriol, and even more particularly the monomethylsilanetriol combined with one or several hyaluronic acid fragments of molecular weight between 150 and 600 kDa or between 250 and 600 kDa
  • the quantity of complex of formula (I) in the above composition is between 1 and 10% in weight in relation to the total weight of the composition, preferably between 2 and 5% in weight.
  • physiologically compatible excipient with skin a tensioactive, a preservative, body fat, a dye, an emulsifier, a gelling agent, an emollient, a moisturizer, a pigment, an antioxidant or all other adjuvant usually used in cosmetics.
  • compositions according to the invention are adapted to an administration through cutaneous topical way, presented under all forms usually used for such an administration.
  • they are formulated for instance under the form of cream, milk, gel, lotion, emulsion, etc.
  • the invention also concerns the use of a complex such as previously defined as a cytostimulating agent intended for boosting the epidermal cell (keratinocytes) activity while limiting the catabolic action of the cutaneous tissue.
  • a complex such as previously defined as a cytostimulating agent intended for boosting the epidermal cell (keratinocytes) activity while limiting the catabolic action of the cutaneous tissue.
  • a complex such as previously defined as a cytostimulating agent intended for boosting the epidermal cell (keratinocytes) activity while limiting the catabolic action of the cutaneous tissue.
  • a complex such as previously defined as a cytostimulating agent intended for boosting the epidermal cell (keratinocytes) activity while limiting the catabolic action of the cutaneous tissue.
  • the monomethylsilanetriol and even more particularly the monomethylsilanetriol combined with one or several hyaluronic acid fragments of molecular weight between 150 and 600 kDa or between 250 and
  • the present invention concerns a cosmetic care process intended for preventing or repairing cutaneous damages related to aging and for which it is necessary to boost the epidermal cell activity.
  • the process is achieved by applying on skin the composition such as previously defined, particularly based on the monomethylsilanetriol and even more particularly based on the monomethylsilanetriol combined with one or several hyaluronic acid fragments of molecular weight between 150 and 600 kDa or between 250 and 600 kDa.
  • Formula B (gel) Complex (dimethylsilanediol/HA 5% fragments 250-600 kDa) Carbomer (acrylate copolymer/acrylamide 1.5% & mineral oil) Sodium benzoate 0.2% Sorbic acid 1% 1,3-butanediol 10% Glycerine 5% Sodium carbonate 0.13% Phenoxyethanol 0.9% Water qsp 100%
  • test 4 the invention is hereafter illustrated by the following tests above described in the specification (tests 1 to 3), and a comparative study (test 4).
  • tests 1, 2 and 4 the experimental studies have been carried out on a reconstructed human epidermis model (RHE, supplier: SkinEthic®) whose interest is a strong homology with human epidermis.
  • RHE human epidermis model
  • Test 1 Evidence of the Cytostimulating Effect of the MSH Complex on Reconstructed Epidermis with Human Origin.
  • the culture of RHE consisted in placing them in a “MCDB 153 ” growth medium (supplier: SkinEthic®) containing 5 mg/mL of insulin, 1.5 mM of CaCl 2 and 25 mg/ml of gentamycine, for 24 hours at 37° C. and 5% CO 2 .
  • the culture of RHE is identical to the one of the herebefore test 1.
  • the dosage of the IL1 and IL8 pro-inflammatory interleukines is achieved on a supernatant resulting from culture medium after 24 hours of treatment, with the help of ELISA dosage kits (R&D System Quantikine Immunoassay, D800C, DTA00C and DLA50), and for identical configurations to those of the above test 1.
  • Test 3 Evidence of a Slowed Down Catabolism on Agarose Gel for the MSH Complex
  • the experimental study consisted in measuring the deterioration kinetic of the MSH complex according to the invention submitted in vitro to bovine hyaluronidases, by electrophoresis on agarose gel. 10 l of 1 mg/ml hyaluronidases are mixed to 50 l of complex in a PBS buffer solution during 30 minutes at 37° C.
  • the electrophoresis displays, for the three times of sampling and reaction, a more important distribution of HA with a high molecular weight for the MSH complex according to the invention, compared to fragmented HA non combined.
  • Test 4 Comparison of Cytostimulant Effects of the MSH Complex and of the Dimethylsilanediol Hyaluronate of High Molecular Weight

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US12/572,658 2008-10-03 2009-10-02 Complex combining an organic silicon derivative with hyaluronic acid calibrated fragments, for preventive and repairing action of cutaneous damages Abandoned US20100113385A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/649,640 US8822433B2 (en) 2008-10-03 2012-10-11 Complex combining an organic silicon derivative with hyaluronic and acid calibrated fragments, for preventive and repairing action of cutaneous damages

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FRFR08/05479 2008-10-03
FR0805479A FR2936708B1 (fr) 2008-10-03 2008-10-03 Complexe associant un derive organique du silicium avec des fragments calibres d'acide hyaluronique, a action preventive et reparatrice des degradations cutanees.

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US13/649,640 Active US8822433B2 (en) 2008-10-03 2012-10-11 Complex combining an organic silicon derivative with hyaluronic and acid calibrated fragments, for preventive and repairing action of cutaneous damages

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US (2) US20100113385A1 (pl)
EP (1) EP2172186B1 (pl)
ES (1) ES2615360T3 (pl)
FR (1) FR2936708B1 (pl)
PL (1) PL2172186T3 (pl)
PT (1) PT2172186T (pl)
SI (1) SI2172186T1 (pl)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230181444A1 (en) * 2020-05-20 2023-06-15 Exsymol Sam Compositions comprising organo-silanol compounds, and applications

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3051672B1 (fr) * 2016-05-30 2020-04-24 Exsymol Composition cosmetique ou dermocosmetique comprenant un extrait de sureau et un derive organique de silicium
BE1026018B1 (fr) * 2018-02-19 2019-09-16 Soles Mundi Sprl Composition comprenant du monométhylsilanetriol
FR3094211B1 (fr) * 2019-04-01 2023-11-17 Exsymol Sa utilisation cosmétique de composés organo-siliciés
EP4385486A1 (en) 2022-12-16 2024-06-19 Laboratoires Fill-Med Manufacturing Combination of an organosilicon compound with a crosslinked glycosaminoglucan for preventing and repairing cutaneous ageing

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5037803A (en) * 1987-03-04 1991-08-06 Jean Gueyne Product comprising a silicon organic compound combined with a cosmetically active substance
US20070172442A1 (en) * 2004-01-29 2007-07-26 Pierre Fabre Dermo-Cosmetique Topical compositions associating sodium hyaluronate fragments and retinoid useful for cosmetic and medical dermatology

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60204708A (ja) 1984-03-30 1985-10-16 Lion Corp 化粧料用保湿剤
FR2761074B1 (fr) 1997-03-24 1999-05-28 Exsymol Sa Composes a base de silicium biologiquement actifs sous forme solide
FR2865935B1 (fr) * 2004-02-05 2006-06-23 Exsymol Sa Utilisation de composes organo-silicies pour contraindre des tissus conjonctifs leses par l'intermediaire d'une action mecanique

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5037803A (en) * 1987-03-04 1991-08-06 Jean Gueyne Product comprising a silicon organic compound combined with a cosmetically active substance
US20070172442A1 (en) * 2004-01-29 2007-07-26 Pierre Fabre Dermo-Cosmetique Topical compositions associating sodium hyaluronate fragments and retinoid useful for cosmetic and medical dermatology

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Brown., Chem. Soc. Rev., 1978,7, 359-376. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230181444A1 (en) * 2020-05-20 2023-06-15 Exsymol Sam Compositions comprising organo-silanol compounds, and applications

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PL2172186T3 (pl) 2017-06-30
ES2615360T3 (es) 2017-06-06
EP2172186B1 (fr) 2016-11-30
FR2936708A1 (fr) 2010-04-09
SI2172186T1 (sl) 2017-04-26
US8822433B2 (en) 2014-09-02
FR2936708B1 (fr) 2012-08-17
US20130035308A1 (en) 2013-02-07
EP2172186A1 (fr) 2010-04-07
PT2172186T (pt) 2017-02-08

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Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:SEGUIN, MARIE CHRISTINE;REEL/FRAME:024408/0826

Effective date: 20100511

STCB Information on status: application discontinuation

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