Photolysis and cellular toxicities of the organic ultraviolet filter chemical octyl methoxycinnamate and its photoproducts

Stein, Hannah V.; Berg, Courtney; Maung, Jessica N.; O’Connor, Lauren; Pagano, Alexandra E.; MacManus-Spencer, Laura A.; Paulick, Margot G.

doi:10.1039/c7em00059f

Cited by 31 publications

(15 citation statements)

References 37 publications

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“… Stein et al isolated and characterized the cellular toxicities of the major products of UV‐induced photolysis of octinoxate. They reported that the parent compound and two cyclodimer photoproducts are toxic to cells (NIH/3T3). Danovaro et al conducted several independent in situ studies on several species of coral in different areas of the world.…”

Section: Commentarymentioning

confidence: 99%

Sunscreen bans: Coral reefs and skin cancer

et al. 2018

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Summary What is known and objective Hawaii will ban two major ingredients of sunscreens. This article reviews the reasons and future directions. Hawaii recently enacted legislation that will ban the use of two major ingredients of the majority of commonly used sunscreens. The reason for the ban is the ingredients’ putative deleterious impact on marine ecosystems, particularly coral reefs. But sunscreens also save lives by decreasing the risk of UV‐induced skin cancers. We review both sides of the issue and potential implications for the healthcare system. Comment Coral reefs consist of organisms in delicate equilibria that are susceptible to small changes in their surroundings. Recent natural and man‐made disruptions, direct or indirect, such as changes in ocean temperature and chemistry, ingress of invasive species, pathogens, pollution and deleterious fishing practices, have been blamed for the poor health, or even the outright destruction, of some coral reefs. The most popular sunscreen products contain two ingredients—oxybenzone and octinoxate—that have also been implicated in coral toxicity and will be banned. This creates a healthcare dilemma: Will the protection of coral reefs result in an increase in human skin cancers? What is new and conclusion Concentration estimates and mechanism studies support an association—direct or indirect (via promotion of viral infection)—of sunscreens with bleaching of coral reefs. A ban on the two most common sunscreen ingredients goes into effect in Hawaii on January 1, 2021. Proponents suggest that this is a trend, just the first of many such bans worldwide; opponents warn of a dire increase in human skin cancers. As a result, alternative sunscreen compounds are being sought.

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Section: Commentarymentioning

confidence: 99%

Sunscreen bans: Coral reefs and skin cancer

et al. 2018

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“…Previous neutral red cell cytotoxicity assay using NIH/3T3 cells showed that trans-EHMC, cis-EHMC, 4-MBA, and the two cyclodimers produced are toxic to cells, reducing cellular viabilities to 8-69%, depending on the concentrations used (Stein et al, 2017). In contrast, the 2-EH photodegradation product is not harmful to cells, demonstrating that different photoproducts contribute differently to the overall toxicity of EHMC photolysate (Stein et al, 2017).…”

Section: Ethylhexyl Methoxycinnamatementioning

confidence: 99%

Ethylhexyl methoxycinnamate and butyl methoxydibenzoylmethane: Toxicological effects on marine biota and human concerns

Silva

Santos

Castro

et al. 2021

J of Applied Toxicology

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Ethylhexyl methoxycinnamate (EHMC) (CAS number: 5466-77-3) and butyl methoxydibenzoylmethane (BMDM) (CAS number: 70356-09-1) are important sunscreens. However, frequent application of large amounts of these compounds may reflect serious environmental impact, once it enters the environment through indirect release via wastewater treatment or immediate release during water activities. In this article, we reviewed the toxicological effects of EHMC and BMDM on aquatic ecosystems and the human consequences. According to the literature, EHMC and BMDM have been detected in water samples and sediments worldwide.Consequently, these compounds are also present in several marine organisms like fish, invertebrates, coral reefs, marine mammals, and other species, due to its bioaccumulation potential. Studies show that these chemicals are capable of damaging the aquatic beings in different ways. Further, bioaccumulation studies have shown that EHMC biomagnifies through trophic levels, which makes human seafood consumption a concern because the higher position in the trophic chain, the more elevate levels of ultraviolet (UV) filters are detected, and it is established that EHMC present adverse effects on the human organism. In contrast, there are no studies on the BMDM bioaccumulation and biomagnification potential. Different strategies can be adopted to avoid the damage caused by sunscreens in the environment and human organism. Two of them include the use of natural photoprotectors, such as polyphenols, in association with UV filters in sunscreens and the development of new and safer UV filters. Overall, this review shows the importance of studying the impacts of sunscreens in nature and developing safer sunscreens and formulations to safeguard marine fauna, ecosystems, and humans.

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“…When exposed to sunlight, both OMC isomers form photoproducts (4-methoxybenzaldehyde (4-MBA) and 2-ethylhexanol (2-EH)) that can further may dimerize in various cyclodimers (MacManus-Spencer et al 2011). These photoproducts, including cyclodimers, have different levels of cellular toxicity and may even be more toxic than OMC itself (Duale et al 2010;Stein et al 2017). They can sensitize singlet oxygen ( 1 O 2 ) and lead to ROS formation, but this mechanism needs to be explored (Hanson et al 2006;Hanson et al 2015).…”

Section: Uv-b Filter Octylmethoxycinnamate Photoinstabilitymentioning

confidence: 99%

Antioxidants as stabilizers of UV filters: an example for the UV-B filter octylmethoxycinnamate

Lorigo

2019

biomed dermatol

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Background: Sunlight is one of the main harmful exogenous factors that induce the reactive oxygen species formation. The human skin is the first line of photoprotection against harmful exogenous factors, such as UV radiations. The topical application of sunscreens, containing UV-B filters, is widely used to protect against UV-induced damage. Octylmethoxycinnamate is the world's most widely used UV-B filter in sunscreens. However, recent studies have demonstrated that this substance is an endocrine disruptor compound and with potential to damage DNA. Thus, the safety of this organic filter is a current concern for human health, and it was urgent to develop new photoprotective strategies. In this sense, due to the potential to neutralize the UV-induced free radicals, the use of antioxidants as UV filter stabilizers presented as a novel promising strategy. Research: The purpose of this review was to assess the use of antioxidants as stabilizers for UV-B filter octylmethoxycinnamate. For this, we discuss the chemical and physical characteristics of UV-B filter octylmethoxycinnamate, emphasizing the stability, photostability, and reactivity of this UV filter. The use of antioxidants in sunscreens will also be addressed, from a perspective of the main characteristics that allowed their use in sunscreen formulations. Then, the concomitant use of both was described from a historical and physical chemical perspective, always emphasizing the advantages and disadvantages of this association. Conclusions: The combination of antioxidants with UV-B filter octylmethoxycinnamate in appropriated formulations represents a viable strategy to protect the human skin against UV-induced damage.

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Photolysis and cellular toxicities of the organic ultraviolet filter chemical octyl methoxycinnamate and its photoproducts

Cited by 31 publications

References 37 publications

Sunscreen bans: Coral reefs and skin cancer

Sunscreen bans: Coral reefs and skin cancer

Ethylhexyl methoxycinnamate and butyl methoxydibenzoylmethane: Toxicological effects on marine biota and human concerns

Antioxidants as stabilizers of UV filters: an example for the UV-B filter octylmethoxycinnamate

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