AN ACTIVE SHELTER AGAINST POLLUTION V.16
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1 AN ACTIVE SHELTER AGAINST POLLUTION V.16
2 THE SKIN IS CONSTANTLY EXPOSED The skin is an interface and thus is constantly exposed to environmental agents: Sun radiation Smoke Air pollution Free radicals Reactive chemical species Damage to cells and structural components of the skin. These aggressors induce the generation of free radicals and other highly reactive chemical species that damage skin cells and other components. Reactive species are involved in the development of the extrinsic signs of skin aging and accelerating intrinsic aging.
3 FREE RADICALS AND REACTIVE SPECIES Reactive species: Free radicals: species with unpaired electrons Non-radicals: related nonradical species ROS Reactive oxygen species RNS Reactive nitrogen species RCS Reactive carbonyl species
4 ROS AND RNS EFFECTS ROS RNS Free radicals Superoxide (O 2 -) Hydroxyl (OH ) Nitric oxide (NO ) Nitrogen dioxide (NO 2 ) Non-radicals Ozone (O 3 ) Singlet oxygen (O 21 Δg) Hydrogen peroxide (H 2 O 2 ) Peroxynitrite (ONOO - ) ROS and RNS react with carbohydrates, proteins, glucosaminoglycans, DNA and lipids. Can cause extensive injury and eventually cell death. Can give rise to other reactive species, further amplifying the damage. ROS and RNS can induce numerous harmful effects in cells and other components of the skin.
5 DAMAGE TO BIOMOLECULES BY REACTIVE SPECIES Lipid peroxidation (or autooxidation) Free radicals + lipids lipid peroxides. Causes the leakiness of membranes and an impairment of proteins. Protein nitration Peroxynitrite (RNS) + tyrosine (proteins) 3-nitrotyrosine. Compromises phosphorylation of proteins thus inactivating enzymes and receptors, which are essential for the regulation of cellular mechanisms. O O O H peroxynitrite O 2 N O H H O Tyrosine N H 2 H O N H 2 3-nitrotyrosine
6 REACTIVE SPECIES ORIGINATING FROM THE ENVIRONMENT Air pollution: Originated mainly from fossil fuel combustion, but also from cigarette smoke. Includes SO x and NO x, CO, ozone, heavy metals, organic aerosols Organic aerosols contain polycyclic aromatic hydrocarbons, such as pyrene. Pyrene gets activated by visible/uva light and increases ROS. UV radiation: Generation of ROS in the skin, inducing inflammation, extracellular matrix breakdown and DNA damage. Reactive species originate from air pollution and sun radiation.
7 REACTIVE SPECIES ORIGINATING FROM ENDOGENOUS SOURCES Mitochondria: Major source of endogenous reactive species. ROS are a by-product of the normal aerobic metabolism (oxidative phosphorylation). Other sources: Endoplasmic reticulum (cytochrome). Peroxisomes (oxidative enzymes). ROS RNS ROS RNS And indeed they are necessary At low levels, reactive species have physiological roles (defense from microorganisms, cell signaling ). Reactive species are formed physiologically and play important roles in biological systems at low concentrations.
8 OXIDATIVE IMBALANCE LEADING TO AGING Antioxidants ROS RNS OXIDATIVE STRESS NITROSATIVE STRESS Endogenous antioxidants: Enzymes: catalase, superoxide dismutases. Molecules: vitamins C, E, coenzime Q10. Are reduced with age. Oxidative and nitrosative stress results in damage to skin cells and other components, leading to premature aging. A topical application of antioxidants is an effective preventive strategy. Oxidative imbalances produce stress that damages the skin and cause the appearance of signs of aging.
9 AN ACTIVE SHELTER AGAINST POLLUTION Chromane with a dual scavenging capacity for ROS and RNS to protect the skin from oxidative damage. Scavenger of peroxynitrite and singlet oxygen. Inhibited peroxidation of lipids. Better antioxidative profile compared with other antioxidants. Superior stability in a formulation. Prevented DNA damage induced by UV radiation and by the atmospheric pollutant pyrene. Maintained cell viability in presence of oxidative stress.
10 LIPOCHROMAN synthetic molecule EFFICACY IN VITRO MOLECULAR-LEVEL EFFICACY Scavenging of RNS Singlet oxygen quenching Inhibition of peroxidation of membrane lipids Protection of essential oils from lipid peroxidation Antioxidative power IN VITRO CELLULAR-LEVEL EFFICACY Shield against cellular oxidative stress Defense against photo-oxidative damage Protection against pollution components
11 3-nitrotyrosine formation (%) SCAVENGING OF RNS Tyrosine and peroxynitrite were incubated with LIPOCHROMAN synthetic molecule. The ability to scavenge peroxynitrite was monitored by measuring the formation of 3-nitrotyrosine by HPLC. The active ingredient was able to block 3-nitrotyrosine formation by up to 94.4%. LIPOCHROMAN synthetic molecule prevented tyrosine nitration.
12 SINGLET OXYGEN QUENCHING Singlet oxygen was generated in the presence of different concentrations of LIPOCHROMAN synthetic molecule. The amount of singlet oxygen was measured by its near-ir emission to assess the kinetics of its decay and calculate the quenching rate constant (k q ). The active ingredient reduced the lifetime of singlet oxygen. Its k q was of (1.21 ± 0.08) x 10 8 M -1 s -1, close to α tocopherol k q of 1.22 x 10 8 M -1 s -1. LIPOCHROMAN synthetic molecule showed scavenging properties toward singlet oxygen.
13 INHIBITION OF LIPID PEROXIDATION Microsomal membranes were incubated with LIPOCHROMAN synthetic molecule or other antioxidants. Lipid peroxidation was induced by FeSO 4 and ascorbic acid. The formation of lipid peroxides was assessed by using the thiobarbituric acid reactive substances (TBARS) test. COMPOUND IC 50 (µm) LIPOCHROMAN synthetic molecule 1.04 ± 0.13 Idebenone 11.5 ± 0.65 Kinetin > 1000 Lipoic acid > 1000 LIPOCHROMAN synthetic molecule inhibited lipid peroxidation at lower concentrations than other antioxidants. LIPOCHROMAN synthetic molecule efficiently reduced lipid peroxidation.
14 PROTECTION OF ESSENTIAL OILS FROM PEROXIDATION Peroxide value (meq/kg) Peroxide value (meq/kg) Essential oils were mixed with potassium iodide and 0.01% LIPOCHROMAN synthetic molecule and kept at 60 ºC for 2 weeks. The amount of iodine liberated by the peroxidation of the oils was measured by titration and the peroxide values were calculated. The ingredient blocked peroxide formation in both essential oils, maintaining the initial levels along 2 weeks. LIPOCHROMAN synthetic molecule protected essential oils with time.
15 ANTIOXIDATIVE POWER (I) The antioxidative power (AP) method was used to compare LIPOCHROMAN synthetic molecule with other antioxidants while also assessing its stability in solution. AP (AU) at t 0 AP t r 0 h 1,130, h 1,310, h 1,147, The active ingredient showed a higher AP compared with that of other common antioxidants. When stored in solution for 24 and 48 h it maintained its antioxidative properties.
16 AP (AU) at RT ANTIOXIDATIVE POWER (II) The AP method was used to compare the properties of LIPOCHROMAN synthetic molecule with BHT alone or in a formulation. LIPOCHROMAN synthetic molecule showed a 82-fold higher AP and 24-fold greater reactivity compared with BHT. In a formulation it had a higher AP with time, even if stored at 40 ºC. LIPOCHROMAN synthetic molecule showed better antioxidative properties than BHT and remained stable in a formulation.
17 SHIELD AGAINST CELLULAR OXIDATIVE STRESS (I) Cell viability (%) Human dermal fibroblasts (HDFa) were exposed to oxidative stress by the addition of hydrogen peroxide (H 2 O 2 ). Cell viability was assessed by the calcein-am and the neutral red uptake methods. Non-treated non-exposed Non-treated H 2 O 2 -exposed ₂ ₂ ₂ ₂ ₂ ₂ LIPOCHROMAN synthetic molecule (1µg/ml) + H 2 O 2 Pretreatment with the ingredient preserved cell viability in a dose-dependent manner.
18 SHIELD AGAINST CELLULAR OXIDATIVE STRESS (II) Cell viability (%) HDFa were pretreated with different antioxidants and exposed to oxidative stress by the addition of H 2 O 2. Cell viability was assessed by the calcein-am test. LIPOCHROMAN synthetic molecule was more effective than resveratrol, vitamin E and ferulic acid against oxidative stress.
19 DEFENSE AGAINST PHOTO-OXIDATIVE DAMAGE (I) DNA damage (χ2 OTM) Human melanocytes were incubated with LIPOCHROMAN synthetic molecule for 2 h and irradiated with UVA (1.0 J/cm 2 ) at 4 ºC. The DNA breaks induced were analyzed by the alkaline comet assay. ***p<0.001
20 DEFENSE AGAINST PHOTO-OXIDATIVE DAMAGE (II) Non-treated non-irradiated Non-treated UVA-irradiated LIPOCHROMAN synthetic molecule (1 µg/ml) + UVA LIPOCHROMAN synthetic molecule (10 µg/ml) + UVA LIPOCHROMAN synthetic molecule (50 µg/ml) + UVA LIPOCHROMAN synthetic molecule showed a photoprotective capacity against DNA damage induced by UVA radiation.
21 PROTECTION AGAINST POLLUTION COMPONENTS DNA damage (χ2 OTM) Human keratinocytes were incubated with LIPOCHROMAN synthetic molecule in the presence of 4 µm pyrene and irradiated with UVA/visible light to photoactivate pyrene. The DNA breaks induced were analyzed by the alkaline comet assay. Non-treated + pyrene + light LIPOCHROMAN synthetic molecule (30 µg/ml) + pyrene + light ***p<0.001 The ingredient reduced DNA damage by -99.3%, representing significant protection. LIPOCHROMAN synthetic molecule protected skin cells from the genotoxic effect of pollutants.
22 CONCLUSIONS has a dual scavenging capacity: for ROS and for RNS. inhibited tyrosine nitration up to -94.4% and showed a potent singlet oxygen scavenging activity. reduced peroxidation of membrane lipids and of essential oils. presented a better antioxidative power compared with other well-known antioxidants, such as BHT, even in a final formulation. protected dermal fibroblasts against oxidative stress induced by ROS, increasing cell viability up to 173.2% with respect to H 2 O 2 -exposed cells. provided shelter from the ROS induced by UV irradiation or by air pollutants, reducing DNA damage by up to -72.2% (UVA) and -99.3% (pyrene), in skin cells.
23 TECHNICAL INFORMATION DESCRIPTION Chromane that protects biomolecules and cellular functions from the damage caused by the reactive species generated from air pollution or UV radiation, as well as from endogenous sources, consequently preventing the premature signs of aging. APPEARANCE Powder. INCI Dimethylmethoxy Chromanol. Preservative free. PROPERTIES LIPOCHROMAN synthetic molecule is a scavenger of ROS and RNS that inhibits protein inactivation and DNA damage and prevents cell death due to oxidative stress. APPLICATIONS LIPOCHROMAN synthetic molecule can be incorporated into lipophilic-based cosmetic formulations to avoid deterioration of skin. DOSAGE %. ph Not applicable.
24 AN ACTIVE SHELTER AGAINST POLLUTION AIMTEC and LIPOCHROMAN are owned by The Lubrizol Corporation. The other tradenames and trademarks used herein belong to their respective and lawful owners. Note: Graphs and photographs of efficacy tests are available for customer use provided that the final product contains the same concentration of active as the formulations in our tests. Customers must request written permission for use of the graphic material and/or ingredient tradenames to Lipotec. Customers are responsible for compliance with local and international advertising regulations. The specific situation of the trademark in each country may vary and we recommend that you contact us for updated information. 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 made as to its accuracy, suitability for particular applications, how the product(s) will perform in combination with other substance or in the user s process or the results obtained. All expressed and implied warranties are disclaimed. Lipotec MAKES NO WARRANTIES, EXPRESS OR IMPLIED, INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE. The recipient is solely responsible for ensuring that products marketed to consumers comply with all relevant laws and regulations and assumes all risk and liability of any use or handling of any materials. Recipient of this publication agrees to indemnify and hold harmless each entity of the LIPOTEC organization for any and all actions 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. Nothing contained herein is to be considered as permission, recommendation, nor as an inducement to practice any patented invention without permission of the patent owner.
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