Peptides in Cosmetics

Peptides have become very important ingredients in cosmetic products. According to their mode of action, they have been divided into three main groups: signal peptides, neurotransmitter-affecting peptides, and carrier peptides. The first group mainly consists of peptides which are able to increase collagen synthesis, or alternatively, inhibit the breakdown of collagen by collagenase. The second group includes peptides mimicking the effects of botulinum neurotoxins whereas the third group, the carrier peptides, acts by delivering trace elements required for enzymatic processes.

Signal peptides

Aged skin is, amongst others, characterized by reduced levels of collagen and elastin. Increasing the number of fibroblasts or their collagen production and/or inhibiting further collagen hydrolysis are therefore considered effective means to halt or slow the aging process of the skin. Many of the peptides used in cosmetic preparations are compounds which act on fibroblasts. One of the peptides described to act in this way is H-Val- Gly-Val-Ala-Pro-Gly-OH (VGVAPG) (Product: H-2390 Chemotactic Domain of Elastin). H-2390 is an elastin-derived peptide sequence repeated several times in tropoelastin. It was found to stimulate the proliferation of human skin fibroblasts presumably via the elastin receptor. The N-terminally palmitoylated peptide is marketed under the name of palmitoyl-oligopeptide and is supposed to penetrate more efficiently through the epidermis than the parent compound. H-Lys-Thr-Thr-Lys-Ser-OH (KTTKS) (Product: H-1592 Procollagen Type I (212-216)) is a subfragment of the carboxy-terminal propeptide of type I collagen (residues 197-241) and represents the minimal sequence shown to stimulate extracellular matrix biosynthesis in fibroblasts. It augments type I and II collagen and fibronectin production in a dose- and time-dependent manner with no effect on total protein synthesis or on the ratio of secreted proteins to cell-associated proteins. The N-terminally palmitoylated peptide is marketed as a cosmetic ingredient under the designation palmitoyl pentapeptide-3.

Neurotransmitter-affecting peptides

Many of the peptides used in cosmetic preparations belong to the group of neurotransmitter-affecting peptides. These peptides act in a similar way as botulinum toxin (Botox). By inhibiting signal transduction pathways at neuromuscular junctions they attenuate the formation of wrinkles and fine lines which appear over time due to the repetitive contraction of the intrinsic muscles of facial expression. A well-known mimic of botulinum toxin used in cosmetic preparations is Acetyl-Glu-Glu-Met-Gln-Arg-Arg-NH₂. It is a synthetic peptide corresponding to a sequence within the N-terminal region of SNAP-25 (amino acids 12-17) and competes with SNAP-25 for a position in the SNARE complex, thereby modulating its formation. The resulting destabilization of the SNARE complex leads to an inhibition of neurotransmitter release and a subsequent attenuation of muscle contraction. Another class of potentially interesting substances in the cosmetic industry includes peptides derived from snake venoms. Waglerin-1 (H-Gly-Gly-Lys-Pro-Asp-Leu- Arg-Pro-Cys-His-Pro-Pro-Cys-His-Tyr-Ile-Pro-Arg-Pro-Lys-Pro-Arg-OH), for example, is a peptide isolated from the venom of the temple viper, Tropidolaemus wagleri. It consists of 22 amino acids and selectively blocks the epsilon form of the muscular nicotinic acetylcholine receptor (mnAChR) thereby keeping the affected muscles in a relaxed state.

Carrier peptides

The tripeptide H-Gly-His-Lys-OH (GHK) (Product: H-3510 Liver Cell Growth Factor) was originally identified in human plasma and has a high affinity for copper²⁺ (Cu²⁺). It acts as a signaling peptide and a carrier molecule for copper which is a co-factor for several enzymes involved in collagen and elastin formation. The copper peptide was shown to stimulate wound healing but also to reduce fine lines and wrinkles and to improve elasticity and firmness of aged skin. A wide variety of effects have been ascribed to GHK-Cu. The peptide exhibits anti-inflammatory actions by suppressing the expression of pro-inflammatory cytokines. It also chemoattracts capillary cells, macrophages and mast cells, increases the synthesis of collagen and elastin, and stimulates the proliferation of fibroblasts and keratinocytes.

Other mechanisms

Many peptides used in cosmetic preparations act by other mechanisms to improve skin appearance or delay skin aging. These include ROS scavengers, collagen fiber organizing compounds, and anti-inflammatory peptides: Peptides such as carnosine (Product: G-1250), anserine (Product: G-4555 L-Anserine · nitrate) and carcinine (Product: G-4425) are histidine dipepeptides with antioxidant activity.

Conclusions

Synthetic peptides have become important for the cosmetic industry. Due to demographic changes and the aging population wishing to maintain a young lifestyle and appearance, cosmetic industry research has focused on anti-aging skin therapy. Today, more than 30 peptides are used in anti-aging skin care products and there are many more in development. Bachem is the market leader in the production of synthetic peptides and has long standing partnerships with major firms in the pharmaceutical and cosmetic industry. We are well-equipped for small to industrial scale synthesis of peptides of any complexity. Bachem is therefore the ideal partner in the development and production of cosmetic peptides. Together with our customers, we accomplish each of the demanding steps in a development project, finally leading to the successful cosmetic product.

References

Product Monograph Peptides in Cosmetics

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Peptides are emerging as new therapeutic tools for a wide range of applications in the field of dermatology. Some peptides affect various cellular and molecular processes within the skin through modulation of collagen, elastin and melanin. In particular, the ability of some synthetic peptides to increase or maintain production of dermal extracellular matrix proteins such as collagen is of interest for anti-aging applications (1). Furthermore, researchers have shown that several peptides have the ability to promote wound healing, cell migration and angiogenesis. As shown in Table 1, there are many peptides in various clinical phases of development for the treatment of a variety of dermatologic conditions such as acne, dermatitis, ulcers and psoriasis.