Just Click It: New Chemical Reactions for Cosmetic Applications

Oct 1, 2012 | Contact Author | By: Steven Isaacman, PhD, Nanometics LLC; and Michael Isaacman, University of California Santa Barbara
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Title: Just Click It: New Chemical Reactions for Cosmetic Applications
click chemistryx polymer synthesisx materials sciencex
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Keywords: click chemistry | polymer synthesis | materials science

Abstract: In the past decade, the chemistry community has seen the resurgence of several classical chemical reactions that once lay dormant in the depths of outdated organic chemistry textbooks. Well-established since the late 19th century, these reactions were largely ignored as synthetic chemists devoted their time to the development of new synthetic methodologies to keep up with the flourishing field of natural product synthesis. Recently, a resurgence in interest surrounding these classic reactions has led to amazing discoveries in chemical biology, polymer chemistry and materials science.

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In the past decade, the chemistry community has seen the resurgence of several classical chemical reactions that once lay dormant in the depths of outdated organic chemistry textbooks. Well-established since the late 19th century, these reactions were largely ignored as synthetic chemists devoted their time to the development of new synthetic methodologies to keep up with the flourishing field of natural product synthesis. Recently, a resurgence in interest surrounding these classic reactions has led to amazing discoveries in chemical biology, polymer chemistry and materials science.1 Commonly referred to as “click chemistry,” a term coined by Sharpless in 2001,2 these reactions are characterized by their robust and rapid production of highly pure products. While a daunting number of options are available in the synthetic chemist’s toolbox, click reactions are particularly useful for the cosmetic chemist as they can be performed in benign solvents, including water; they tolerate the presence of a variety of functional groups; they produce products in exceptionally high yields; and they require minimal purification.2Starting materials are “spring-loaded” to react quickly and selectively with each other to produce single products (see Figure 1). Click reactions are widely popular in academia and are actively being exploited in drug discovery, polymer synthesis, materials science and chemical biology, but their use in cosmetic chemistry remains largely unexploited as the industry remains slow to assimilate new synthetic innovations.

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Figure 1. The click approach

Figure 1. The click approach allows for the rapid and selective conjugation of two clickable partners, shown in orange and blue.

Figure 2. In CuAAC, an azide-containing moiety (red) is reacted with an alkyne-containing moiety (blue)

Figure 2. In CuAAC, an azide-containing moiety (red) is reacted with an alkyne-containing moiety (blue) in the presence of a catalytic amount of copper (I) to produce a highly stable triazole ring. The triazole ring can be produced in near quantitative yields.

Figure 3. Schematic of the synthesis of block copolymers using click chemistry

Figure 3. Schematic of the synthesis of block copolymers using click chemistry; two alkyne-bearing pseudo-polypeptide blocks (blue) are clicked with an azide-bearing silicone block (red) to produce an amphiphillic polymer.

Figure 4. Self-assembly of clickable amphiphilic block copolymers

Figure 4. Self-assembly of clickable amphiphilic block copolymers: a) polymers with minimal aggregation, b) solvent-directed self-assembly leads to a vesicle structure, c) transmission electron microscope image of vesicles, demonstrating a diameter of ~150 nm; scale bar = 50 nm

Figure 5. In a metal-free, strain-promoted click reaction, an azide-containing moiety (red) is reacted with a cyclooctyne-containing moiety (blue)

Figure 5. In a metal-free, strain-promoted click reaction, an azide-containing moiety (red) is reacted with a cyclooctyne-containing moiety (blue) to produce a triazole ring. No catalyst is required and release of ring-strain from the cyclooctyne provides the driving force for the reaction.

Figure 6. Live cell imaging using a bioorthogonal click approach

Figure 6. Live cell imaging using a bioorthogonal click approach; a) a normal live cell with no fluorescence; b) an azide-functionalized sugar is incorporated into the cellular membrane via an enzymatic pathway; c) a cyclooctyne functionalized with a fluorophore is clicked with the cell, which is now fluorescent and can be imaged; and d) bioorthogonal fluorescent labeling of live animals.

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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