Photochemical studies of 4-tert-butyl-4′-methoxydibenzoylmethane (BM-DBM)

Cantrell, Ann; McGarvey, David J.

doi:10.1016/s1011-1344(01)00226-3

Cited by 88 publications

(65 citation statements)

References 9 publications

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“…4, whereas a substantial decrease in absorbance of BMDBM is observed. This loss in photostability is in accordance with previous reports on this UV filter present in certain sunscreen formulations [35], [36], and is due to the well known keto-enol isomerisation upon UV exposure which is followed by photo-cleavage and generation of free radicals [9], [37], [38].…”

Section: Resultssupporting

confidence: 92%

Prevention of UVA-Induced Oxidative Damage in Human Dermal Fibroblasts by New UV Filters, Assessed Using a Novel In Vitro Experimental System

et al. 2014

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BackgroundUVA rays present in sunlight are able to reach the dermal skin layer generating reactive oxygen species (ROS) responsible for oxidative damage, alterations in gene expression, DNA damage, leading to cell inflammation, photo-ageing/-carcinogenesis. Sunscreens contain UV filters as active ingredients that absorb/reflect/dissipate UV radiation: their efficiency depends on their spectral profile and photostability which should then be reflected in biological protection of underlying skin.MethodsA set of new UV filters was synthesized, and the most photostable one was compared to BMDBM, a widely used UVA filter. Cultured human dermal fibroblasts were exposed to UVA radiation which was filtered by a base cream containing or not UV filters placed above cell culture wells. The endpoints measured were: cell viability (MTT assay), ROS generation (DCFH-DA assay), mitochondrial function (JC-1 assay), DNA integrity (Comet assay) and gene expression (MMP-1, COL1A1) by RT-qPCR.ResultsThe new UV filter resulted more efficient than BMDBM in preserving cell viability, mitochondrial functionality and oxidative DNA damage, despite similar inhibition levels of intracellular ROS. Moreover, expression of genes involved in dermal photoageing were positively affected by the filtering action of the tested molecules.ConclusionsThe experimental model proposed was able to validate the efficacy of the new UV filter, taking into account important cellular events related to UV-induced intracellular oxidative stress, often underestimated in the assessments of these compounds.General SignificanceThe model may be used to compare the actual biological protection of commercial sunscreens and suncare products aside from their SPF and UVA-PF values.

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Section: Resultssupporting

confidence: 92%

Prevention of UVA-Induced Oxidative Damage in Human Dermal Fibroblasts by New UV Filters, Assessed Using a Novel In Vitro Experimental System

et al. 2014

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“…The obtained transient was tentatively assigned to the triplet state ( 3 BM‐DBM‐Me*) by comparison with the spectrum reported in the literature for a preirradiated solution of BM‐DBM (absorption in the range 300–500 nm, τ ∼500 ns) (7). This assignment was confirmed by quenching experiments.…”

Section: Resultsmentioning

confidence: 72%

“…As stated above, the photoactive form of avobenzone is the diketo tautomer. Its excited triplet state has been previously detected by laser flash photolysis of preirradiated samples (7). Nevertheless, the results obtained with photomixtures can be misleading due to the presence of varying amounts of the enol form and other photoproducts that can act as triplet quenchers.…”

Section: Resultsmentioning

confidence: 99%

A Blocked Diketo Form of Avobenzone: Photostability, Photosensitizing Properties and Triplet Quenching by a Triazine‐derived UVB‐filter

Paris

Lhiaubet‐Vallet

Jiménez

et al. 2009

Photochem & Photobiology

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Novel sunscreens are required providing active protection in the UVA and UVB regions. On the other hand, there is an increasing concern about the photosafety of UV filters, as some of them are not sufficiently photostable. Avobenzone is one of the most frequently employed sunscreen ingredients, but it has been reported to partially decompose after irradiation. In the present work, photophysical and photochemical studies on a methylated avobenzone-derivative have shown that the diketo form is responsible for photodegradation. A transient absorption was observed at 380 nm after laser flash photolysis excitation at 308 nm. It was assigned to the triplet excited state of the diketo form, as inferred from quenching by oxygen and b-carotene. This transient also interacted with key building blocks of biomolecules by triplet-triplet energy transfer (in the case of thymidine) or electron transfer processes (for 2¢-deoxyguanosine, tryptophan and tyrosine). Irradiation of the avobenzone derivative in the presence of a triazine UV-B filter (E-35852) diminished the undesirable effects of the compound by an efficient quenching of the triplet excited state. Thus, sunscreen formulations including triplet quenchers could provide effective protection from the potential phototoxic and photoallergic effects derived from poor photostability of avobenzone.

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“…In particular, photodegradation of AVO, the most widely utilized FDA approved UVA filter, has been well documented . AVO degradation has been attributed to excitation from the triplet state of its keto form to generate numerous photoproducts …”

Section: Resultsmentioning

confidence: 99%

Biodegradable bioadhesive nanoparticle incorporation of broad‐spectrum organic sunscreen agents

Suh

Lewis

Fong

et al. 2018

Bioengineering & Transla Med

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Conventional emulsion‐based sunscreen formulations are limited by postapplication epicutaneous penetration that increases the risk of allergic dermatitis, cellular damage, and filter photodegradation upon ultraviolet radiation (UVR) exposure. Encapsulation of the UVB filter padimate O within bioadhesive biodegradable nanoparticles (BNPs) composed of poly(d,l‐lactic acid)‐hyperbranched polyglycerol was previously shown to enhance UVR protection while preventing skin absorption. Herein, we assess the capacity of BNP co‐incorporation of avobenzone and octocrylene to provide broad‐spectrum UVR protection. The ratio of UV filters within nanoparticles (NPs) was optimized for filter–filter stabilization upon UV irradiation and maximum drug loading. In vitro water‐resistance test showed significant particle retention at 85% over 3 hr. In a pilot clinical study, protection against UVR‐induced erythema of BNPs was found to be comparable to the FDA standard P2. Thus, sunscreen formulations utilizing BNP incorporation of a combination of organic filters may offer key safety and performance advantages.

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Photochemical studies of 4-tert-butyl-4′-methoxydibenzoylmethane (BM-DBM)

Cited by 88 publications

References 9 publications

Prevention of UVA-Induced Oxidative Damage in Human Dermal Fibroblasts by New UV Filters, Assessed Using a Novel In Vitro Experimental System

Prevention of UVA-Induced Oxidative Damage in Human Dermal Fibroblasts by New UV Filters, Assessed Using a Novel In Vitro Experimental System

A Blocked Diketo Form of Avobenzone: Photostability, Photosensitizing Properties and Triplet Quenching by a Triazine‐derived UVB‐filter

Biodegradable bioadhesive nanoparticle incorporation of broad‐spectrum organic sunscreen agents

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