Peptidomimetics for Cosmetic Applications

Sep 1, 2013 | Contact Author | By: Steven Isaacman, PhD, Nanometics LLC; Michael Isaacman, University of California Santa Barbara; and Sung Bin Y. Shin, PhD, Avon Products
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Title: Peptidomimetics for Cosmetic Applications
peptidomimeticsx peptidex antibioticx penetrationx antimicrobialx peptoidsx
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Keywords: peptidomimetics | peptide | antibiotic | penetration | antimicrobial | peptoids

Abstract: Peptidomimetics, or synthetic bioactive peptides, have been developed that mimic the biological functions of peptides and proteins but overcome many of these challenges and limitations. Further, due to their wide range of activity, synthetic feasibility and ease of handling, they have played a vital part in biological research. This column will discuss the potential application of these short chain oligomers in cosmetics and personal care.

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S Isaacman, M Isaacman, SBY Shin, Peptidomimetics for Cosmetic Applications, Cosm & Toil 128(9) 612 (2013)

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Bioactive peptides are capable of inducing biological responses by stimulating cell surface receptors, inhibiting protein-protein interactions, inducing protein conformational rearrangements, inactivating enzymes, regulating gene expression levels, etc. However, their inherent proteolytic instability, poor transport properties into the bloodstream and across the blood-brain barrier, rapid excretion through the liver and/or kidneys, and reduced efficacy due to inherent structural flexibility make them poor candidates for systemic drug delivery molecules.1

In turn, peptidomimetics, or synthetic bioactive peptides, have been developed that mimic the biological functions of peptides and proteins but overcome many of these challenges and limitations. Further, due to their wide range of activity, synthetic feasibility and ease of handling, they have played a vital part in biological research. This column will discuss the potential application of these short chain oligomers in cosmetics and personal care.

Peptide vs. Peptidomimetic

While the use of bioactive peptides in oral drug delivery applications is still a great challenge, skin-targeted topical applications present unique opportunities. Proteolytic degradation and rapid excretion are less of an issue for the cosmetic application of bioactive peptides. In fact, in the past decade, chemically modified bioactive peptides have been introduced for topical cosmetic applications. Examples include topical palmitoyl pentapeptide, which stimulates collagen production;2 copper tripeptide-1, which promotes wound healing;3 and one synthetic hexapeptide that mimics the action of botulinum neurotoxins (BoNTs).4

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Figure 1. Example peptidomimetic structure schematics

Figure 1. Example peptidomimetic structure schematics

Some examples include azapeptide, beta-peptide, peptoid, vinylogous sulfonopeptide, oligocarbamate and oligourea (see Figure 1).

Footnotes (CT1309 Isaacman)

a Matrixyl (INCI: Glycerin (and) Butylene Glycol (and) Water (aqua) (and) Carbomer (and) Polysorbate-20 (and) Palmitoyl Oligopeptide (and) Palmitoyl Tetrapeptide-3) is a product of Sederma, www.sederma.fr.
b
Argireline (INCI: Acetyl Hexapeptide-3) is a product of Lipotec,www.lipotec.com.

Biography: Steven Isaacman, PhD, Nanometics LLC

Steven Isaacman, PhD, earned a master’s degree in organic chemistry from Stony Brook University, and a Master of Science and doctorate in physical organic chemistry from New York University, where his research involved the design and fabrication of single molecule magnets, chiral molecular switches and self-assembling nano-architectures. In 2006, he founded Nanometics LLC and is the principal investigator on two small business innovation research awards from the National Institutes of Health. In addition, he is a visiting scholar at the Albert Einstein College of Medicine and New York University. As founder and CEO at Nanometics, he leads the research team in designing novel small molecules, polymers and materials for the personal care and pharmaceutical markets.

Biography: Michael Isaacman, PhD, Nanometics, LLC

Michael Isaacman, PhD, graduated from the University of California, Santa Barbara. His research focuses on the synthesis and self-assembling dynamics of silicone-based amphiphilic block copolymers. As an expert in silicone chemistry, he has pioneered novel methodologies for the design and fabrication of silicone polymers for use in drug delivery and personal care. A consultant for the personal care and pharmaceutical industry, he has published in the fields of natural product synthesis, pollutant metal detection and polymer chemistry.

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