RonaCare Cyclopeptide-5
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1 RonaCare Cyclopeptide-5 Ringing in a unique, new peptide generation March 2010
2 Smart molecule design Merck researchers achieved a break-through in designing the first cyclic and homodetic* peptide for cosmetic applications RonaCare Cyclopeptide-5 *all of the covalent linkages between the amino acids are natural peptide bonds January 2010 PC-SCA Page 2
3 RonaCare Cyclopeptide-5 RonaCare Cyclopeptide-5 stands out from all commercially available peptides being used in cosmetic applications due to its unique structure as a cyclic shaped agent. Providing Anti-aging benefits Wrinkle reduction Firmness Elasticity January 2010 PC-SCA Page 3
4 The lock-and-key-model In essence, different peptides produce different biological effects by signalling cells to perform various functions by attaching to receptors found on the surface of each cell. You think of the peptides as key and the skin cell-surface receptors as locks. This is the lock-and-key-model. January 2010 PC-SCA Page 4
5 What makes Cyclopeptide-5 different? Its cyclic structure Receptor outside Linear Peptide Receptor Cyclopeptide-5 R G D The best fit of lock and key inside Signaling starts January 2010 PC-SCA Page 5
6 What is the biological target of Cyclopeptide-5? This revolutionary peptide shows high selectivity to certain receptors like αvβ5 and αvβ6 integrins R G D Cyclopeptide-5 Skin Cell outside inside membrane C. Brakebusch, R. Fässler (2003) The integrin-actin connection, an external love affair, The EMBO Journal, 22(10), January 2010 PC-SCA Page 6
7 How Cyclopeptide-5 works With such integrins as lock and RonaCare Cyclopeptide-5 as key, it is shown that it is possible to mimic natural processes of skin communication and repair. Skin turns more elastic and firmer and appears to have fewer wrinkles January 2010 PC-SCA Page 7
8 RonaCare Cyclopeptide-5 the first of a new peptide generation for cosmetics Equipped with the outstanding edge of RonaCare Cyclopeptide-5, you can create cosmetic products that work with the ultimate in precision. Welcome to a new dimension in effective anti-aging January 2010 PC-SCA Page 8
9 RonaCare Cyclopeptide-5 the first of a new peptide generation for cosmetics Find out more about this exciting peptide story January 2010 PC-SCA Page 9
10 Smart molecule design RonaCare Cyclopeptide-5 was designed with three smart features A cyclic structure A crgd motif Special amino acids increasing its activity, selectivity and stability January 2010 PC-SCA Page 10
11 Smart molecule design the cyclic structure The cyclic form of the peptide provides a high rigidity and makes it highly selective to the desired biological target the integrin RGD binding site The cyclic conformation enhances its stability January 2010 PC-SCA Page 11
12 Smart molecule design - the crgd motif Cyclopeptide-5 consists of Arginine (R) R ARG ACHA Glycine (G) Aspartate (D) G GLY D-PHE D-Phenylalanine ASP Aminocyclohexane carboxylic acid (ACHA) D January 2010 PC-SCA Page 12
13 Smart molecule design - the crgd motif The crgd motif stands for the cyclic structure of the following amino acid sequence: arginine-glycine-aspartate The crgd motif is the best configuration to mimic natural processes at the chosen biological target site the integrins January 2010 PC-SCA Page 13
14 Smart molecule design special amino acids Why did we use D-Phenylalanine? D-amino acids stabilize the peptide against proteases additionally the aromatic D-amino acids adjust in that position of a crgd peptide a defined conformation hereby increasing the ligand-receptor interaction (activity and selectivity) January 2010 PC-SCA Page 14
15 Smart molecule design special amino acids Why did we use Aminocyclohexane carboxylic acid (ACHA)? ACHA is a symmetric non-natural amino acid (optically inactive) which achieves a high solubility With ACHA an optimum shape of the crgd could be designed January 2010 PC-SCA Page 15
16 Cyclopeptide-5 its biological target What are Integrins? Integrins are cell surface receptors (the lock in the lock-and-key-model) Integrins bind to cell surface and ECM components such as fibronectin, vitronectin, collagen and laminin (the keys in the lock-and-key-model). Cyclopeptide-5 takes over the role as a key January 2010 PC-SCA Page 16
17 Cyclopeptide-5 its biological target Integrins have two main functions: Attachment of the cell to the ECM Signal transduction from the ECM to the cell January 2010 PC-SCA Page 17
18 Cyclopeptide-5 its biological target Attachment of the cell to the ECM Integrins couple the ECM outside the cell to the cytoskeleton inside the cell The connection between the cell and the ECM may help the cell to endure pulling forces without being ripped out of the ECM January 2010 PC-SCA Page 18
19 Cyclopeptide-5 its biological target Signal transduction Integrins are responsible for transmitting signals between skin cells and the extracellular milieu by doing outside-in signalling and inside-out signalling Integrins and their signaling pathways David A. Barron: Rice University January 2010 PC-SCA Page 19
20 Cyclopeptide-5 its biological target Keratinocyte Integrins Keratinocytes express a number of integrins being essential for their anchorage and migration Some of them are constitutively expressed Some are expressed or up-regulated upon stimulation like wound healing January 2010 PC-SCA Page 20
21 Cyclopeptide-5 its biological target RonaCare Cyclopeptide-5 shows high selectivity respectively is a ligand for integrins like αvβ5 and αvβ6 αvβ5 is a constitutively expressed epidermal integrin but also being expressed during the wound healing process αvβ6 is an expressed epidermal integrin being induced during the wound healing process January 2010 PC-SCA Page 21
22 Scenes of aging - How Cyclopeptide-5 comes in here Histological changes of the skin due to the ageing process can be found in The epidermis thinning The dermis reduced compacting The basement membrane loss in the distinctive wave structure January 2010 PC-SCA Page 22
23 Scenes of aging The basement membrane is, together with other components, responsible for the connection between the dermis and epidermis, the socalled dermo-epidermal-junction (DEJ). January 2010 PC-SCA Page 23
24 Scenes of aging The aging of the basement membrane This typical change in the DEJ is related to a reduction of protein expression and an increase in the destruction of supporting DEJ fibres. The main consequences are the flattening of the basement membrane and multiple functional und structural changes of its components Histological difference of young (A, 28 years old) and intrinsically aged skin (B, 69 years old). O. Holtkötter (2005) Unveiling the molecular basis of intrinsic skin ageing, International Journal of Cosmetic Science, 27, January 2010 PC-SCA Page 24
25 Scenes of aging Functional changes of the basement membrane can be Migration of keratinocytes Liberation of enzymes Defective communication between dermis and epidermis January 2010 PC-SCA Page 25
26 Scenes of aging The changes of the basement membrane due to the aging process lead to. less elasticity and firmness of the skin January 2010 PC-SCA Page 26
27 RonaCare Cyclopeptide-5 A unique peptide of a new generation comes in here mimicking natural processes of skin communication and repair reviving the communication process between dermis and epidermis stimulating the production of important proteins of the basement membrane protecting ECM-structures against enzymatic degradation with high selective activity January 2010 PC-SCA Page 27
28 Anti-Aging efficacy in vitro: cdna-microarray study up-regulation of genes stimulating important basement membrane proteins and growth factors, e.g. laminin IV, collagen IV. A full thickness skin equivalent consisting of dermis and epidermis has been used as testing model with 0,3 ppm Cyclopeptide-5 January 2010 PC-SCA Page 28
29 Anti-Aging efficacy in vitro: Example down of Collagenase 3: ~ - 47% down of Elastase A2: ~ - 23% down regulation Cyclopeptide-5 protects ECM-structures against enzymatic degradation Inhibition vs Placebo 0% -5% -10% -15% -20% -25% -30% -35% -40% -45% -50% 1 2 Collagenase 3 Collagenase 3 Elastase A2 January 2010 PC-SCA Page 29
30 Anti-Aging efficacy in vitro: Example Activation vs Placebo 70% 60% 50% 40% 30% 20% 10% 0% up-regulation Collagen4 LamininA4 4 A4 up of Collagen-4: ~ + 50% up of Laminin A4: ~ + 60% Cyclopeptide-5 stimulates the production of important basement membrane proteins January 2010 PC-SCA Page 30
31 Anti-Aging efficacy in vitro: Laminin is a glycoprotein and part of the ECM is forming the basement membrane together with Collagen type IV and other components binds to cell surface receptors and thereby tightly connects the basement membrane to the adjacent cell layer. This ensures the stabilization of cellular structures. January 2010 PC-SCA Page 31
32 Anti-Aging efficacy in vitro: Collagen type IV is the netforming type of all collagen types it is found primarily in the basement membrane January 2010 PC-SCA Page 32
33 Anti-Aging efficacy in vivo Design clinical study I (Crows feet) Surface evaluation by means of Primos at day 0 and volunteers (n = 20, f) with normal skin Female, Age range: years (average: 44,8) Test area: Crows` feet application of test products twice daily for 28 days Testproducts (verum vs. untreated, 2 mg/cm 2 ) Phase shifting rapid in vivo measurement of skin (Primos) January 2010 PC-SCA Page 33
34 Anti-aging efficacy in vivo: Crows feet reduction A. A. B. B. Surface at crows feet area before treatment (t = 0) Surface after treatment with verum after 28 days Verum = Formulation containing 0,2% Ectoin and 40 ppm Cyclopeptide-5 encapsulated in a liposome January 2010 PC-SCA Page 34
35 Anti-Aging efficacy in vivo Design of clinical study II (Skin Smoothness) Surface evaluation by means of Primos at day 0, 14 and volunteers (n = 20, f) with normal skin Female, Age range: years (average: 44,8) Test area: inner forearm application of test products twice daily for 28 days Testproducts (verum vs. placebo, 2 mg/cm 2 ) Phase shifting rapid in vivo measurement of skin (Primos) January 2010 PC-SCA Page 35
36 Anti-aging efficacy in vivo: skin smoothness Improvement of Smoothness relative to initial untreated conditions [%] d 28 d 1 = Placebo: Formulation without RonaCare Cyclopeptide-5 2 = Verum: Formulation with 4% RonaCare Cyclopeptide-5 RonaCare Cyclopeptide-5 improves skin smoothness and leads to wrinkle reduction January 2010 PC-SCA Page 36
37 RonaCare Cyclopeptide-5 From a formulators point of view due to the flexible cyclohexyl-side-chain of Aminocyclohexane carboxylic acid no crystallization of Cyclopeptide-5 was detected.cyclopeptide-5 is an inner salt of high stability. Meaning that this kind of peptide has no need for a counter-ion. January 2010 PC-SCA Page 37
38 RonaCare Cyclopeptide-5 INCI: Water (for EU: Aqua), Ethanol, Lecithin, (5 %) Ectoin, (100 ppm) Cyclopeptide-5 (INCI applied for) Appearance: Opaque, slightly yellowish Use-level: 2-5% Formulation hints: No technical limitations Applications: Anti-aging in daily skin care Article-No: Pack Sizes: 50 g sample (brown glass bottle) 1 kg (brown glass bottle) Patent(application)s: WO 2009/124754, US 6,127,335, EP B1 Improved availability via liposomal technology January 2010 PC-SCA Page 38
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