WO2015105407A1 - Procédé de production d'une formulation nanolipidique pour les soins et/ou la réparation de la peau et formulation nanolipidique ainsi obtenue - Google Patents

Procédé de production d'une formulation nanolipidique pour les soins et/ou la réparation de la peau et formulation nanolipidique ainsi obtenue Download PDF

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Publication number
WO2015105407A1
WO2015105407A1 PCT/MY2015/000001 MY2015000001W WO2015105407A1 WO 2015105407 A1 WO2015105407 A1 WO 2015105407A1 MY 2015000001 W MY2015000001 W MY 2015000001W WO 2015105407 A1 WO2015105407 A1 WO 2015105407A1
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WIPO (PCT)
Prior art keywords
lipid
formula
nano
formulation
solid
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PCT/MY2015/000001
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English (en)
Inventor
Zanariah UJANG
Ahmad Hazri AB RASHID
Siti Kasmarizawaty SUBOH
Zuliana AHMAD
Maizatul Nadiah OTHMAN
Mazita MOHD DIAH
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Sirim Berhad
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Publication of WO2015105407A1 publication Critical patent/WO2015105407A1/fr

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/927—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of insects, e.g. shellac
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

  • the present invention relates generally to the field of pharmaceutical and especially to formulation for skin care and/or treatment. More particularly, the present invention relates to a method for producing a nano lipid carrier system encapsulating Supercritical Fluid Extraction (SFE) extracts of Curcuma
  • SFE Supercritical Fluid Extraction
  • the present invention also relates to a nanolipid formulation for skin repair and/or treatment produced from such method and use of the same.
  • Nanostructured lipid carriers have been developed as the new generation of lipid nanoparticles and has major attention as novel colloidal drug carriers for topical use. It has been said that NLC differs from Solid Lipid Nanoparticles (SLN) mainly in their matrix composition resulting in distinct morphological structures, have received a great deal of investigation for cutaneous administration and as carrier systems for many applications (e.g., cosmetic, drug delivery) . NLC have a higher drug loading capacity for a number of active compounds and the solubility of liquid lipid is higher than that of the solid lipid which enhances drug-loading capacity Muller 2002) .
  • SSN Solid Lipid Nanoparticles
  • the preparation of NLC is mainly conducted by melt emulsification, low temperature solidification and high speed homogenization methods.
  • the different lipid molecules ar>e mixed with solid lipids and liquid lipids (oils) .
  • the production method and different composition of the solid and liquid lipids produces different types of NLC. (Muller 2002) .
  • As for the characterization of the NLC s produced are mainly carried out by particle size analysis, scanning electron microscopy (SEM) , differential scanning microscopy (DSC), polydispersity index, zeta potential, encapsulation efficiency and the slow release profile study mainly by Franz cell study methodology.
  • aqueous SLN and NLC dispersions for the topical route have been described, such as occlusive effects leading to an enhancement of drug penetration, UV-blocking effects and sustained release properties ( issing and Muller 2002). To achieve a desired consistency for topical/dermalogical administration, these aqueous dispersions should be incorporated into creams or hydrogels.
  • the degree of penetration of actives depends strongly on the physicochemical properties of the active compound and of the nature of the vehicle in which the topical formulation is applied (e.g., polarity of the solvent, particle size, type of vehicle) (Benech et al., 2000), (C.Fernandez et.al., 2000).
  • new colloidal carrier systems have been utilized to increase the availability of active ingredients. Controlling the particle size of these carriers is critical to the successful delivery of the active agent. Since these are cutaneous applications lipid-based are the most suitable.
  • Ginger Ginger (Zingiber officinale
  • Roscoe is a plant that belongs to the Zingiberaceae family. It is indigenous to the Asia Southeast. Ginger products, such as essential oil and oleoresin, are internationally commercialized for use in food and pharmaceutical processing. Past studies on the antioxidant properties of ginger species were confined to rhizomes (Habsah et al., 2000; Jitoe et al., 1992; Zaeoung, Plubrukarn, & Keawpradub, 2005) .
  • Skin- lightening cosmeceutical products were recently developed from rhizomes of the ginger species zingiber zerumbet and curcuma xanthorrhiza (Rozanida, Nurul Izza, Mohd Helme, & Zanariah, 2006) .
  • Skin whitening products are commercially available for cosmetic purposes in order to obtain a lighter skin appearance. They are also utilized for clinical treatment of pigmentary disorders such as melasma or post inflammatory hyper pigmentation (Nico et al., 2009).
  • ginger species appear to have great potential for topical applications in cosmetics and pharmaceuticals.
  • the use of these actives in any known carrier system still suffers from various limitations such as poor physical and chemical stability and poor delivery of actives to the skin.
  • the present invention details out the method use to incorporate supercritical fluid extract into a nano lipid carrier system that is then suitable for use as a nanolipid formula for skin care application .
  • SCX Skin repair formulation
  • the present invention provides a method for producing a nano lipid formula utilizing a combination of solid and liquid lipid processed through a determined set of process parameters and incorporating a supercritical fluid extract of Curcuma Xanthorrhiza into the said formula.
  • the resulting nano lipid formula is stable and provides a mechanism for control release of the active fraction.
  • the nano lipid formulation is targeted for use in cosmetics and pharmaceuticals for skin repair such as dry and coarse skin conditions.
  • Figure 1 shows a graphical representation of release profile of xanthorrhizol using polysulfone membrane from NLC 22 (BW) and NLC 25 (CA) formulation (SCX 0.5 % w/w) embodied in the present invention.
  • the present invention provides a method for producing nano structured lipid formulation containing supercritical fluid extract of Curcuma Xanthorrhiza for skin care and repair application.
  • High pressure homogenization technique was used to produce the nanolipid formula which contains the supercritical extract of Curcuma Xanthorrhiza as its active ingredient .
  • the selected solid and liquid lipids were heated above their melting point and then mixed at a certain percentage.
  • the supercritical fluid extract of Curcuma Xanthorrhiza then added to the lipid phase and mixed thoroughly.
  • the lipid solution was then mixed with a hot aqueous phase consisting of distilled water and a surfactant.
  • the mixture was then passed through several cycles of high pressure homogenization process to yield the nano lipid particles.
  • the resulting nano lipid formula was further characterized to ascertain its properties and benefits for dermal application.
  • nanolipid formula In the present invention, tests were carried out to examine the physical properties of the nanolipid formula such as its particle size, polydispersity index and zeta potential.
  • the particle size formed is in the range of 200 to 300 nm and its zeta potential values range in between -30 to -40 mV indicating the formation of stable nano particles system.
  • nanolipid formula was subj ected to the encapsulation efficiency study and Franz Diffusion study.
  • the encapsulation test showed that the nanolipid formula is able to retain 98.5% of the active ingredient within its nanostructured configuration.
  • the Franz Diffusion study has indicated a control release profile feature being exhibited by the nano lipid formula.
  • the hydration effect of the formula was also studied on human volunteers and a long term sustained effect of increased skin hydration was observed among the volunteers.
  • the method of producing the nanolipid formula as presented in this invention has resulted in a formula that is in the nano size range, stable, able to effectively encapsulate the active ingredient and exhibit a control release profile.
  • the nanolipid formula derived from this invention may be used for cosmetic and pharmaceutical applications, particularly for the purpose of skin protection and repair, particularly for dry and coarse skin.
  • the nano lipid formula can be admixed into existing formulations such as emulsion, gel, cream, lotion, serum, toner, mask, water-in-oil , oil-in-water, microemulsion, nanoemulsion, etc in varying proportion.
  • Fresh unpeeled rhizomes of C. xanthorrhiza were washed, sliced, air dried at ambient temperature and ground. 200 g of the ground rhizomes were placed in the SFE extraction vessel and extraction was done using SFE 500 instrument at 450 bars, temperature at
  • the high pressure homogenization (HPH) technique was used to prepare NLC dispersions.
  • the lipid compounds were heated at a temperature of 5°C above the melting point of the solid lipid, the Supercritical Fluid
  • Test Example 1 Characterization of NLC 1.1. Particle size analysis The mean particle size (z-ave) and the polydispersity index (PI) were determined by photon correlation spectroscopy (PCS) with a Malvern Zetasizer IV (Malvern Instrument, UK). The z-ave and PI values of NLC cream were obtained by the average of 10 measurements. 20 mg of sample was dispersed in 5 ml deionised water and sonicated at 5°C for 15 minutes. Zetasizer Nano.
  • the zeta potential is a measure of the electric charge at the surface of the particles indicating the physical stability of colloidal systems.
  • the ZP values higher than [30mV] indicate electrostatic long-term stability of aqueous dispersions (Muller et al . 2000; Mehnert and ader
  • Table 4 Mean particle size (z-ave), polydispersity index (PI) and zeta potential (ZP) value of SCX extract - free and SCX extract - loaded NLC formulations .
  • SCX extract in NLC was determined by ultrafiltration technique. Because of the high viscosity of NLC cream, the samples were diluted with water at the ratio 1: 5 and mixed by the vortex mixer (Janke and Kunkel) , IKA ® - Laorthechnik) for 10 min and shaken with a horizontal shaker (Janke and Kunkel, IKA ® - Labortechnik, HS 501 digital) at 200rpm for 15 min. Subsequently, the mixture was filled in the ultrafiltartion tube (Amicon Ultra-4, Milipore, Ireland) with the molecule weight cut-off of 30 kDa and centrifuged at 4500 rpm for -30 min. The amount of SCX extract in the NLC and the ultrafiltrate (free SCX extract) was analysed by HPLC.
  • 0.2 mL of formulation was diluted to 5 mL with chloroform/methanol (1:1). The solution was mixed with 5ml of acetonitrile/water (1:1) solution to make up a final solution of 10ml.
  • HPLC high performance liquid chromatography
  • Ultracentrifugation was performed using a Amicon Ultra-4 (4500 rpm for 30 minutes), which consists of a filter membrane (molecular weight cutoff 30 000 Da) at the base of a sample recovery chamber to separate the dispersion medium.
  • the entrapment efficiency of the system was determined by measuring the concentration of total amount of SCX extract (Xanthorrhizol ) and SCX free extract in the dispersion medium by HPLC, as mentioned below.
  • the chromatographic system consisted of a Shimadzu LC-20AD low pressure gradient pump, 7SIL-20A autosampler. CTO-20AC Oven , D2 & W, SPD-M2 OA PDA detector and in line vacuum degasser. The eluate was monitored at 275 nm (maximum for xantho as verified by scanning spectrophotometry)
  • Chromatographic separation was accomplished by injecting the sample onto a Supelco Ascentis 250 x4.6mm, 5- ⁇ Ci 8 column. Using a column oven set at 40 °C with a flow rate of 0.8mL/min. A gradient elution was carried out as follows. 0 min, 50% B; 30 min, 70% B ; 4 min 100% B 5 min 50% B then reequilibrating prior to the next injection. Data were recorded using LC Solutions software Preparation of Xanthorrhizol standard
  • Xantho (Sigma) was used as a standard in this evaluation, lmg of xantho was dissolved in 500uL of Ethanol to give a concentration of 2000ug/mL stock solution. Various concentrations were generated from this stock by further dilution with Ethanol solution. Xantho calibration curve was plotted in a defined concentration range of 1- 400ug/ml.
  • % E.E. (Total amount of SCX extract - Free amount of SCX extract)
  • the Franz diffusion cell were made of glass with a contact area of 1.81 cm 2 and pretreated with 70% denatured alcohol.
  • the Franz diffusion cell consisted of a donor and receptor compartment.
  • the membrane was mounted between the cell compartment and an O-ring was used to position the membrane and covered with the glass to prevent evaporation of the sample.
  • the receptor chamber volume varied from 6.7 to 7.2 mL and was filled with 0.8 % SDS solution. It was kept at 32.5°C by circulating water through an external water jacket. After 30 minutes of equilibration of the membrane with the receptor solution, the O-ring was filled with about lg of NLC product and covered with the glass. The chamber was held together with a clamp.
  • the receptor solution was continuously stirred by means of a spinning bar magnet at 700 rpm. Receptor solution samples, 0.5 ml aliquots, were withdrawn through the sampling port of the receptor chamber at various time interval; 0, 1, 2, 4, 6, 8, 24, 48 and 72 hours. The cells were refilled with receptor solution to keep the volume of receptor solution constant during the experiment. The receptor' s solution was sampling into HPLC vials and further analyze using HPLC system. Now with reference to Figure 1, NLC formulation using beeswax as the solid lipid shows no release at early time (until 8 hours) but increasing rapidly from 24 to 72 hours.
  • the active permeated through polysulfone membrane ranged from about 173.76 ug/cm 2 after 24 hours to 776.23 ug/cm 2 at the end of test. It release profile increase 5 folds comparing with cetyl alcohol (NLC 25) at 72 hours. From the literature, the release profile can be modified by particle size, type and concentration of surfactant, temperature and production procedure (zur Muhlen et al., 1998, Muller et al . , 2000, 2002). NLC formulation using beeswax, increase rapidly due to the smallest particle size (246.33 nm) comparing to the formulation using cetyl alcohol as lipid. Sanna et.
  • the skin hydration effect was measured on 33 volunteers who used the product on the forearm twice daily. The volunteers was divided into two groups with one group using the nano lipid formula containing the extract (product A) and the other group using the the formula without the extract (product B) . The skin hydration is measured using a corneometer .
  • Zancan K.C et al Extraction of ginger (Zingiber officinale Roscoe) oleoresin with C02 and co-solvents: a study of the antioxidant action of the extracts, J. of Supercritical Fluids 21 (2002) 57-76.

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Abstract

Cette invention concerne un procédé de production d'un système de transport nanolipidique encapsulant des extraits de Curcuma Xanthorriza obtenus par extraction par fluide supercritique (SFE) à l'aide d'une technique d'homogénéisation à haute pression (HPH) pour les soins et/ou la réparation de la peau. Le procédé utilise un lipide solide et un lipide liquide pour encapsuler l'extrait de Curcuma xanthorrhiza obtenu par extraction par fluide supercritique, le lipide solide comprenant de l'acide cétylique et de la cire d'abeilles et le lipide liquide, de l'huile de noyaux d'abricots. La formule nanolipidique est produite par le procédé d'homogénéisation à haute pression en utilisant une pression dans la plage d'environ 305 à 815 kg/cm (300-800 bar). Cette invention concerne également une formulation nanolipidique pour les soins et/ou la réparation de la peau produite par ledit procédé et son utilisation.
PCT/MY2015/000001 2014-01-07 2015-01-06 Procédé de production d'une formulation nanolipidique pour les soins et/ou la réparation de la peau et formulation nanolipidique ainsi obtenue WO2015105407A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
MYPI2014700029 2014-01-07
MYPI2014700029A MY176528A (en) 2014-01-07 2014-01-07 A method for producing nanolipid formulation for skin care and/or repair and a nanolipid formulation of the same

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017185147A1 (fr) * 2016-04-25 2017-11-02 L'oreal Transporteurs lipidiques nanostructurés et leurs procédés de fabrication et d'utilisation
FR3119989A1 (fr) * 2021-02-19 2022-08-26 Le Rouge Français Matière première colorante issue de plantes selon un procédé mettant en œuvre une extraction particulière et un enrobage particulier.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0920635A (ja) * 1995-07-04 1997-01-21 Shiseido Co Ltd 美白用皮膚外用剤
US20060134059A1 (en) * 2004-12-22 2006-06-22 Laurence Dryer Compositions and methods of their use for improving the condition and appearance of skin
US20120148669A1 (en) * 2009-03-31 2012-06-14 Ins. Nat. De La Sante Et De La Recher Med (Inserm) Method for preparing functionalized lipid capsules
US20120195957A1 (en) * 2009-04-30 2012-08-02 Mandip Singh Sachdeva Novel nanoparticle formulations for skin delivery
US20130017239A1 (en) * 2010-03-24 2013-01-17 Lipotec S.A. Lipid nanoparticle capsules

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0920635A (ja) * 1995-07-04 1997-01-21 Shiseido Co Ltd 美白用皮膚外用剤
US20060134059A1 (en) * 2004-12-22 2006-06-22 Laurence Dryer Compositions and methods of their use for improving the condition and appearance of skin
US20120148669A1 (en) * 2009-03-31 2012-06-14 Ins. Nat. De La Sante Et De La Recher Med (Inserm) Method for preparing functionalized lipid capsules
US20120195957A1 (en) * 2009-04-30 2012-08-02 Mandip Singh Sachdeva Novel nanoparticle formulations for skin delivery
US20130017239A1 (en) * 2010-03-24 2013-01-17 Lipotec S.A. Lipid nanoparticle capsules

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017185147A1 (fr) * 2016-04-25 2017-11-02 L'oreal Transporteurs lipidiques nanostructurés et leurs procédés de fabrication et d'utilisation
WO2017185155A1 (fr) * 2016-04-25 2017-11-02 L'oreal Transporteurs lipidiques nanostructurés et leurs procédés de production et d'utilisation
FR3119989A1 (fr) * 2021-02-19 2022-08-26 Le Rouge Français Matière première colorante issue de plantes selon un procédé mettant en œuvre une extraction particulière et un enrobage particulier.
EP4056165A3 (fr) * 2021-02-19 2022-10-05 Le Rouge Français Matière première colorante issue de plantes selon un procédé mettant en oeuvre une extraction particulière et un enrobage particulier

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