Review and Modern Advances of Retinoids for Cosmetics

May 1, 2014 | Contact Author | By: Steven Isaacman, PhD, and Michael Isaacman, PhD, Nanometics LLC, Great Neck, NY, USA; Peter Smith, New York University, New York City, USA
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Title: Review and Modern Advances of Retinoids for Cosmetics
retinoidsx cancerx agingx acnex vitamin Ax
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Keywords: retinoids | cancer | aging | acne | vitamin A

Abstract: For skin cancer, skin aging and acne, retinoids have proven both preventive and therapeutic. Successful efforts toward more bioavailable vitamin A derivatives and retinoid formulations have increased their use for cosmetic benefits. Recent work to further optimize retinoids and reduce their side effects has yielded a new generation of promising molecules, described here.

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S Isaacman, M Isaacman and P Smith, Review and Modern Advances of Retinoids for Cosmetics, Cosm & Toil 129(4) 46-50 (May 2014)

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The vitamin A metabolite retinol is essential for life, and has been shown to exhibit a diverse range of biological functions. Natural as well as synthetic molecules that are structurally related to vitamin A are referred to as retinoids, and typically consist of a polyene chain linking a cyclic end group to a polar end group. Within the cell, retinoids function as signaling molecules, and play important roles in vision, embryonic development, cell proliferation, cell differentiation and immune functions. Vitamin A is stored intracellularly as retinyl esters, which after conversion to retinol, are oxidized to more bioactive retinaldehydes or retinoic acids. The structural abundance of retinoids and subsequent bioactivity allow for a variety of therapeutic applications within the pharmaceutical and cosmetic space.

Chemotherapy and Cancer Prevention

In carcinogenesis, the intracellular levels of retinyl esters are greatly reduced, compromising retinoid signaling. In relation, extensive work has been conducted to examine the efficacy of retinoids to restore signaling for cancer therapy. These studies show retinoids are both chemopreventive and chemotherapeutic, with their activity attributed to abilities to induce cell differentiation, arrest cell proliferation and promote apoptosis in cancer cells.

All-trans retinoic acid, or tretinoin, is the most extensively studied retinoid for cancer therapies, and has been evaluated in clinical trials for the treatment of lymphoma, melanoma, lung cancer, neuroblastoma and leukemia. Retinoids have shown efficacy at preventing the onset and development of cancer, especially precancerous skin lesions. UV irradiation can cause a deficiency of vitamin A; as such, retinoid treatment can prevent aberrant signaling and skin cancer development.

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Figure 1. Chemical structure of vitamin A (retinol)

Figure 1. Chemical structure of vitamin A (retinol)

Chemical structure of vitamin A, retinol, showing the characteristics of retinoids; cyclic end group (green), polyene linker (black), and polar end group (blue)

Figure 2. Various retinoids currently utilized in the treatment and prevention of certain cancers, skin aging and acne

Figure 2. Various retinoids currently utilized in the treatment and prevention of certain cancers, skin aging and acne

The structural abundance of retinoids and subsequent bioactivity allow for a variety of therapeutic applications within the pharmaceutical and cosmetic space.

Figure 3. Synthetic retinoid derivatives that exhibit enhanced properties

Figure 3. Synthetic retinoid derivatives that exhibit enhanced properties

New synthetic esters, such as hydroxypinacolone retinoate, are proving to be viable alternative.

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.

Biography: Peter Smith

Peter Smith

Peter Smith is currently (2014) a fourth-year undergraduate student at New York University, where his research is focused on the design and synthesis of bioactive peptidomimetics. He has developed new methods to utilize these functionalized oligomers as both antimicrobial agents and inhibitors of crystal growth. Smith is the recipient of multiple New York University undergraduate research grants, and his work has extended into personal care with research at Nanometics LLC.

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