Function of dipeptide diaminobutyroyl benzylamide diacetate in skin

2018-08-18

Dipeptide diaminobutyroyl benzylamide diacetate, often marketed under the name Syn-Ake, is a synthetic peptide that mimics the effects of Waglerin-1, a neurotoxin found in the venom of the Temple Viper. This peptide has gained significant attention in the field of dermatological research due to its purported ability to reduce muscle contractions and, consequently, the appearance of fine lines and wrinkles. The development of this peptide highlights the innovative approach of utilizing biomimetic compounds to achieve desired therapeutic effects in skin care.

Chemical structure and properties

The molecular structure of dipeptide diaminobutyroyl benzylamide diacetate comprises two amino acids: diaminobutyric acid and phenylalanine, which are modified to enhance stability and bioactivity. The inclusion of diacetate groups increases its solubility and facilitates its incorporation into various cosmetic formulations. The peptide's structure is designed to interact with the neuromuscular junction, modulating the release of acetylcholine and thereby reducing muscle activity.

The molecular structure of Dipeptide diaminobutyroyl benzylamide diacetateFig 1. The molecular structure of Dipeptide diaminobutyroyl benzylamide diacetate.

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Dipeptide diaminobutyroyl benzylamide diacetate mechanism of action

Interaction with neuromuscular junction

Dipeptide diaminobutyroyl benzylamide diacetate primarily functions by inhibiting the neuronal signals that trigger muscle contraction. It achieves this by blocking the acetylcholine receptors on the muscle cells. Acetylcholine is a neurotransmitter responsible for transmitting signals from nerve cells to muscles, leading to muscle contraction. By competitively inhibiting these receptors, the peptide reduces the frequency and intensity of muscle contractions, which can smooth out dynamic wrinkles formed due to repetitive facial expressions.

Recent advancements in computational chemistry have allowed for detailed molecular docking studies of dipeptide diaminobutyroyl benzylamide diacetate. These studies provide insights into the peptide's binding affinity and interaction dynamics with acetylcholine receptors. The findings have confirmed that the peptide's structural conformation is optimized for high-affinity binding, which is crucial for its inhibitory action on muscle contractions.

Modulation of signaling pathways

On a cellular level, dipeptide diaminobutyroyl benzylamide diacetate has been shown to influence various signaling pathways that contribute to its anti-wrinkle effects. Research indicates that this peptide can modulate the activity of genes involved in muscle contraction and cell adhesion. Furthermore, it has been observed to affect the intracellular calcium levels, which play a crucial role in muscle contraction. By reducing calcium influx into muscle cells, the peptide further diminishes the contractile activity.

Function of dipeptide diaminobutyroyl benzylamide diacetate in skin

Anti-wrinkle effects

The anti-wrinkle effects of dipeptide diaminobutyroyl benzylamide diacetate are among its most notable biological activities. The peptide functions primarily by mimicking the action of waglerin-1, a compound derived from the venom of the Temple Viper. Waglerin-1 is known to inhibit the nicotinic acetylcholine receptor (nAChR) at the neuromuscular junction, thereby reducing muscle contractions. Dipeptide diaminobutyroyl benzylamide diacetate achieves a similar effect by selectively binding to these receptors, preventing acetylcholine from triggering muscle contractions that lead to wrinkle formation. This mechanism results in a relaxation of facial muscles, which smooths out expression lines and reduces the depth and appearance of wrinkles over time.

Clinical studies and in vitro experiments have demonstrated that this peptide can significantly reduce the depth and appearance of wrinkles, particularly those caused by repetitive facial movements. In vitro assays using cultured human skin cells have shown that the peptide effectively inhibits acetylcholine-induced contractions. In vivo studies involving topical application of peptide-containing formulations on human volunteers have demonstrated significant reductions in wrinkle depth and skin roughness over a period of several weeks.

Skin barrier function

Beyond its role in reducing wrinkles, dipeptide diaminobutyroyl benzylamide diacetate has been shown to enhance the skin's barrier function. The peptide interacts with keratinocytes, the predominant cell type in the epidermis, promoting cell cohesion and strengthening the skin barrier. This improvement in barrier integrity is crucial for maintaining skin hydration and protecting against external environmental aggressors, such as pollutants and pathogens. By reinforcing the skin's natural defense mechanisms, the peptide helps preserve skin health and appearance.

Anti-inflammatory properties

Dipeptide diaminobutyroyl benzylamide diacetate possesses significant anti-inflammatory properties. Inflammation is a key driver of skin aging and various dermatological conditions, leading to the breakdown of collagen and elastin fibers. The peptide has been shown to modulate inflammatory pathways, reducing the production of pro-inflammatory cytokines such as interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α). This anti-inflammatory activity helps mitigate inflammation-induced damage, thereby supporting overall skin health and potentially slowing the aging process.

Antioxidant activity

Oxidative stress is another major factor in skin aging, contributing to the degradation of collagen and elastin and the formation of wrinkles. Dipeptide diaminobutyroyl benzylamide diacetate has been found to exhibit antioxidant properties, neutralizing reactive oxygen species (ROS) that cause oxidative damage. By reducing ROS levels, the peptide helps protect skin cells from oxidative stress, thereby preserving the skin's structural integrity and preventing premature aging.

Stimulation of collagen and elastin production

Dipeptide diaminobutyroyl benzylamide diacetate may stimulate the production of collagen and elastin, the primary structural proteins in the skin. Collagen provides the skin with strength and resilience, while elastin allows it to return to its original shape after stretching or contracting. By promoting the synthesis of these proteins, the peptide helps maintain skin elasticity and firmness, contributing to a more youthful appearance.

Cellular communication and homeostasis

Dipeptide diaminobutyroyl benzylamide diacetate also plays a role in enhancing cellular communication and homeostasis. It influences the signaling pathways that regulate cell growth, differentiation, and repair. By modulating these pathways, the peptide ensures that skin cells function optimally, maintaining the skin's overall health and resilience. This activity is particularly important in repairing damaged skin and maintaining a balanced, healthy skin environment.

Synthesis and stability of dipeptide diaminobutyroyl benzylamide diacetate

Chemical synthesis

The synthesis of dipeptide diaminobutyroyl benzylamide diacetate involves solid-phase peptide synthesis (SPPS), a widely used method for creating peptides in the lab. This technique allows for precise control over the sequence and chemical modifications of the peptide, ensuring high purity and consistency. The process begins with the attachment of the first amino acid to a solid resin, followed by sequential addition of protected amino acids to elongate the peptide chain. After the desired sequence is assembled, the peptide is cleaved from the resin and purified using high-performance liquid chromatography (HPLC).

Stability and formulation

Stability is a critical factor in the development of peptide-based therapeutics. Dipeptide diaminobutyroyl benzylamide diacetate is chemically stable, which facilitates its incorporation into various cosmetic and dermatological formulations. The presence of diacetate groups enhances its solubility and stability in aqueous solutions, making it suitable for use in creams, gels, and serums. Furthermore, the peptide can be stabilized through encapsulation techniques such as liposomes and nanoparticles, which protect it from degradation and enhance its penetration into the skin.

Application of dipeptide diaminobutyroyl benzylamide diacetate in dermatological research

Biomimetic approaches

The development of dipeptide diaminobutyroyl benzylamide diacetate represents a significant advancement in biomimetic approaches to skin care. By mimicking the natural mechanisms of neurotoxins, this peptide offers a novel and targeted method for addressing signs of aging. Its ability to modulate muscle contractions without invasive procedures makes it a promising candidate for non-surgical anti-aging treatments.

Synergistic formulations

Researchers are also investigating the potential of combining dipeptide diaminobutyroyl benzylamide diacetate with other bioactive compounds to enhance its efficacy. Synergistic formulations that include peptides, antioxidants, and growth factors aim to provide comprehensive anti-aging benefits. For instance, combining this peptide with hyaluronic acid, a powerful hydrating agent, can enhance skin moisture levels while reducing the appearance of wrinkles.

References

  1. Gorouhi, F.; et al. Immediate and long-term clinical benefits of a topical treatment for facial lines and wrinkles. The Journal of Clinical and Aesthetic Dermatology. 2009, 2(3): 38-43.
  2. Debono, J.; et al. Viper venom botox: the molecular origin and evolution of the waglerin peptides used in anti-wrinkle skin cream. Journal of Molecular Evolution. 2017, 84(1): 1-4.

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