AN ACTIVE SHELTER TO PROTECT C ELLS CELLS
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1 AN ACTIVE SHELTER TO PROTECT CELLS v5
2 WHERE IS THE MARKET GOING TO? Niche segments, such as teenagers and men, are growing in the skin care market. They are also following the trends settled by women s skin care. PREVENTION is a rising worry. Teenagers beginning preventive care are in favor of prevention rather than waiting until it s too late! Men More advanced grooming products: mass and premium brands are offering more specific products. Both groups are becoming more interested in retaining a youthful appearance PREVENTIVE COSMETICS is about convincing the society of what science already knows: that acting on your skin TODAY will minimise its damage TOMORROW
3 WHERE IS THE MARKET GOING TO? Big players are more concerned with prevention and how important it is.
4 RADICAL SCAVENGING CLAIM OR REALITY? IN THE SKIN Healthy skin is rich in an intrinsic antioxidative defense system. In old skin or under oxidative stress, this defense system becomes more and more deficient. IN THE MARKET Skin care products with antioxidative claims are one of the most fast growing market for cosmetics worldwide. * Gematria Test Lab GmbH AP method (HPC Today, n 1/2009) BUT 73% of products thatt claim antioxidative id properties showed no or very low antioxidative activity! * Adding SPF and UVA protection is a major trend in the skin care market, but not the only one We are finding more and more products in the skin care market with radical scavengers claims: SPF is necessary but not enough
5 RADICAL SCAVENGING CLAIM OR REALITY? REQUIREMENTS FOR ANTIOXIDANTS AND FORMULATIONS * High antioxidative capacity and reactivity in order to neutralize the very short time living ROS in the skin. Antioxidants used in formulations should not be converted into reactive radical species themselves. Antioxidants should be sufficiently stable inside a cosmetic formulation. The lipophilic or hydrophilic character of antioxidants determines the distribution inside the skin tissues and makes them more or less accessible to free radicals. The cosmetic formulation may enhance or hinder the penetration ability of actives inside the skin. * Gematria Test Lab GmbH
6 REACTIVE SPECIES Antioxidant is an old, limited concept. New research requires NEW TERMINOLOGY: ROS Reactive Oxygen Species RNS Reactive Nitrogen Species RCS Reactive Carbonyl Species
7 REACTIVE SPECIES External Factors RCS Lipid Peroxidation ROS RNS Protein Crosslinking DNA damage Cellular necrosis Internal Factors
8 ROS AND RNS ROS (REACTIVE OXYGEN SPECIES) AND OXIDATIVE STRESS Under normal conditions, i ROS are cleared from the cell by endogenous antioxidant enzymes. Imbalance between the rate of ROS induced oxidative damage and the rate that antioxidants repair the damage and remove ROS is the level of oxidative stress. Skin is a major target of oxidative stress due to ROS originated in the environment and in the skin itself, which causes aging signs such as wrinkles, lost of elasticity, and age spots. RNS (REACTIVE NITROGEN SPECIES) Nitrosative stress occurs when the generation of RNS in a system exceeds the system s s ability to neutralize and eliminate them. Nitrosative stress may lead to nitrosylation reactions (with NO ) that can alter protein structure thus inhibiting normal function. NITRIC OXIDE (NO ) NITRIC DIOXIDE (NO 2 ) NITRITE (NO 2- ) PEROXYNITRITE (ONOO - ) NITROXYL ANION (NO - )
9 LIPOCHROMAN-6: VERSATILITY Lipochroman-6, due to its two reactive centers, has a double action: ROS scavenger RNS scavenger CH 3 O 8 1 O 7 2 Lipochroman-6 HO
10 IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (I) 1. RNS Capture The nitration of tyrosine residues of proteins is an irreversible reaction which compromises cyclic interconversion between phosphorylated/non-phosphorylated tyrosine, necessary in activation/deactivation of enzymes and receptors. Evaluation of reactivity between tyrosine and peroxynitrite at different concentrations of Lipochroman-6, determined by HPLC. RNS O O OH peroxynitrite O 2 N OH HO Tyrosine NH 2 HO NH 2 3-Nitrotyrosine Lipochroman-6 protects enzymes from inactivation Inhibits the reaction between tyrosine and peroxynitrite in a dose-dependent dependent manner.
11 IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (II) 2. ROS Capture (I) The ability of Lipochroman-6 to inhibit lipid peroxidation was evaluated in incubations of sprague dowley rat microsomes throug a TBARS test. ROS TBARS assay COMPOUND IC 50 (µm) LIPOCHROMAN ± 0.13 IDEBENONE ± 0.65 KINETIN >1000 LIPOIC ACID >1000 Lipochroman-6 proved to inhibit lipid peroxidation at lower concentrations, compared to other anti-ros
12 IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (III) 2. ROS Capture (II) The antioxidant activity of Lipochroman-6 was evaluated as a part of a study for an interlaboratory comparison to assess the antioxidant potential of several compounds 1. ROS TBA assay (2-Thiobarbituric acid) Rank Substance Mean 1 LIPOCHROMAN BHT Trolox Tocopherol MBC 0.38 Protection of lipid structures was the best of five antioxidants in the interlaboratory comparison. 1 J. Buenger et al, International Journal of Cosmetic Science, 2006, 28,
13 IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (IV) 3. Determination of the Antioxidative Power (AP) AP method: the reducing activity against the stable test radical DPPH (diphenylpicryl-hydrazyl) is monitored by ESR (Electron Spin Ressonance) spectroscopy. The signal intesity decay is recorded at different times until saturation, when all the Lipochroman-6 molecules have reacted with DPPH. AP parameter: allows to quantify both the reaction capacity and speed of antioxidants. AP and t r (reaction time) are typical values for each antioxidant. with an excellent long term stability is a powerful antioxidant After being stored, Lipochroman-6 enhanced its AP up to 1,470,000, and reaction time values ranged from 0.20 (at 0h) to 0.17 (at 48h).
14 IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (V) 4. Determination of the Antioxidative AP method: the reducing activity against the stable test radical DPPH (diphenyl-picryl-hydrazyl) is Power (AP) vs BHT in final formulations (I) monitored by ESR (Electron Spin Ressonance) spectroscopy. The signal intesity decay is recorded at different times until saturation, when all the Lipochroman-6 molecules have reacted with DPPH. AP parameter: allows to quantify both the reaction capacity and speed of antioxidants. AP and t r (reaction time) are typical values for each antioxidant. Sample AP (AU) tr (min) LIPOCHROMAN-6 995, BHT 12, showed an antioxidative power 82-fold higher than BHT
15 IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (VI) 4. Determination of the Antioxidative Power (AP) vs BHT in final formulations (II) Long-term stability of two antioxidants (Lipochroman-6 or BHT) incorporated in final cosmetic creams at 0.05% 05% was determined by measuring AP and tr. Measurements were performed over 3 months at different storage conditions (RT and 40 ºC). showed a folds higher AP compared to the cream containing BHT, at RT and folds higher than BHT, at 40 ºC
16 IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (VII) 5. Singlet oxygen quenching ability Among ROS, there is an exceptionally reactive form known as singlet oxygen (0 2 (a 1 g )). Singlet oxygen decay vs Lipochroman-6 concentration Lifetime of O 2 (a 1 g ) decay is affected by Lipochroman-6 The near-infrared emission of 0 2 (a 1 g ) was detected at 1275nm by a NIR photomultiplier module working in photon counting mode. Test solutions were prepared by mixing 2.5ml of methanol-d 4, 100µl of stock 1H-phenalen-1-one 1 solution (photosensitiser) and a known volume of a Lipochroman-6 solution in methanol-d 4. is a potent t singlet oxygen scavenger Its activity is remarkably close to tocopherols, which rank among the most effective molecules.
17 6. Inhibition of peroxide formation in essential oils IN VITRO EFFICACY MOLECULAR-LEVEL STUDIES (VIII) Peroxidation is a very frequent chain reaction = lipid molecules + oxygen (ROS). Essential oils are susceptible of autoxidation when in contact with oxygen due to their high lipid content. Essential oils were dissolved in isohexadecane and 0.01% Lipochroman-6 was added. Samples were kept at 60 ºC for 2 weeks. Rosemary (Rosmarinus Officinalis) Leaf Oil Oleic Acid Control 0.01% completely inhibited peroxide formation in both oils
18 1. Cellular photoprotection (Comet Assay) Non treated cell (negative control) No DNA migration UVA treated cell (positive control) The broken DNA migrates from the cell IN VITRO EFFICACY CELLULAR-LEVEL STUDIES (I) Melanocytes were incubated with three different concentrations of Lipochroman-6 (1.0µg/ml, 10.0 µg/ml and 50.0 µg/ml) for 2 hours at 37 ºC. After this contact period, cells were irradiated with UVA. UV-induced DNA breaks were analyzed by the alkaline Comet Assay. Negative controls included non-irradiated untreated cells and non-irradiated cells treated with Lipochroman-6. UVA irradiated cells without Lipochroman-6 were used as positive controls. Cells + UVA+ 1.0 µg/ml LIPOCHROMAN-6 Small DNA migration 19.3% PROTECTION Cells + UVA µg/ml LIPOCHROMAN-6 Small DNA migration 57.7% PROTECTION Cells + UVA µg/ml LIPOCHROMAN-6 Small DNA migration 72.2% PROTECTION prevents skin from photoaging Protects cellular DNA from ROS oxidation, induced by UVA radiation.
19 IN VITRO EFFICACY CELLULAR-LEVEL STUDIES (II) 2. Inhibition of oxidative stress on human dermal fibroblasts Oxidative stress is the imbalance between cellular production of free radical species and the ability of cells to eliminate them employing endogenous antioxidant defence mechanisms. This stress damage cells irreversibly. In skin cell cultures, oxidative stress was generated by the addition of H 2 O 2 to the culture medium. The protecting effects of the tested compounds (Lipochroman-6, Resveratrol, Vitamin E and Ferulic Acid) were measured by a cell viability assay (Calcein-AM assay). is more effective than Resveratrol, Vitamin E and Ferulic Acid against oxidative stress
20 COSMETIC BENEFITS COMPLETE PROTECTION from Photoaging Anti-ROS & Anti-RNS Cell viability increase against oxidative stress Cellular photoprotection Ideal ingredient for skin-care formulations Double activity It has a very strong antioxidative capacity according to AP method (Gematria Test Lab GmbH) More effective than Resveratrol Not only protects the skin, but also formulations from oxidation
21 TECHNICAL INFORMATION DESCRIPTION Chromane that protects cells from several damages such as structural alteration of proteins, inhibition of enzymatic activity and interferences of the regulatory cellular function. APPEARANCE Powder. INCI Dimethylmethoxy chromanol. PROPERTIES Protects cells from reactive species, preventing skin from premature aging. APPLICATIONS Lipochroman-6 can be incorporated in lipophilic based cosmetic formulations to avoid deterioration of skin. DOSAGE %
22 AN ACTIVE SHELTER TO PROTECT CELLS Disclaimer: While the claims and supporting data provided in this publication are believed to be reliable and they are presented free and for guidance only, there are no warranties of any kind. All expressed and implied warranties are disclaimed. The recipient is solely responsible for ensuring that products marketed to consumers comply with all relevant laws and regulations. LIPOTEC is the exclusive holder of the both industrial and intellectual property rights identified herein. Recipient of this publication agrees to indemnify and hold harmless each entity of the LIPOTEC organization for any and all regulatory action arising from recipient s use of any claims or information in this publication, including, but not limited to, use in advertising and finished product label claims, and not present this publication as evidence of finished product claim substantiation to any regulatory authority. All tradenames, trademarks, copyrights and images used herein belong to their respective and lawful owners
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