Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group

Popiół, Justyna; Gunia‐Krzyżak, Agnieszka; Piska, Kamil; Żelaszczyk, Dorota; Koczurkiewicz, Paulina; Słoczyńska, Karolina; Wójcik-Pszczoła, Katarzyna; Krupa, Anna; Kryczyk-Poprawa, Agata; Żesławska, Ewa; Nitek, Wojciech; Żmudzki, Paweł; Marona, Henryk; Pękala, Elżbieta

doi:10.3390/molecules24122321

Cited by 11 publications

(14 citation statements)

References 68 publications

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“…As octocrylene is considered to be a photostable UV filter [ 33 ], the comparable results obtained for (+)-usnic acid is satisfactory. Moreover, the photostability of (+)-usnic acid is higher in comparison with OMC [ 13 , 34 ]. The results obtained for the formulation containing the combination of (+)-usnic acid and octocrylene are of great importance, as the observed decrease in SPF in vitro was only 2.35%, which indicates the high photostability of the mixture.…”

Section: Discussionmentioning

confidence: 99%

(+)-Usnic Acid as a Promising Candidate for a Safe and Stable Topical Photoprotective Agent

Galanty

Popiół

Paczkowska-Walendowska

et al. 2021

Molecules

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The study aimed to examine whether usnic acid—a lichen compound with UV-absorbing properties—can be considered as a prospective photoprotective agent in cosmetic products. Moreover, a comparison of two usnic acid enantiomers was performed to preselect the more effective compound. To meet this aim, an in vitro model was created, comprising the determination of skin-penetrating properties via skin-PAMPA assay, safety assessment to normal human skin cells (keratinocytes, melanocytes, fibroblasts), and examination of photostability and photoprotective properties. Both enantiomers revealed comparable good skin-penetrating properties. Left-handed usnic acid was slightly more toxic to keratinocytes (IC50 80.82 and 40.12 µg/mL, after 48 and 72 h, respectively) than its right-handed counterpart. The latter enantiomer, in a cosmetic formulation, was characterized by good photoprotective properties and photostability, comparable to the UV filter octocrylene. Perhaps most interestingly, (+)-usnic acid combined with octocrylene in one formulation revealed enhanced photoprotection and photostability. Thus, the strategy can be considered for the potential use of (+)-usnic acid as a UV filter in cosmetic products. Moreover, the proposed model may be useful for the evaluation of candidates for UV filters.

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Section: Discussionmentioning

confidence: 99%

(+)-Usnic Acid as a Promising Candidate for a Safe and Stable Topical Photoprotective Agent

Galanty

Popiół

Paczkowska-Walendowska

et al. 2021

Molecules

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“…To evaluate functional photostability of compounds 8 and 9 PMMA plates with tested compounds was irradiated with solar light simulator (Suntest CPS+, Atlas, Linsengericht, Germany) equipped with an optical filter cutting off wavelengths shorter than 290 nm and IR-block filter to neutralize thermal effects. The light source emission was maintained at 500 W/m 2 and irradiation procedure was conducted for 1 h which corresponds to cumulative dose of ultraviolet radiation 218 kJ/m 2 and is consistent with previous studies [10,54]. The UV absorption spectrum of the samples and photoprotective activity parameters were analysed post-irradiation and compared with pre-irradiation results.…”

Section: Photostability Studymentioning

confidence: 91%

“…The decrease of SPFin vitro was comparable to that showed by EHMC. In previous study, formulation containing EHMC was irradiated in the same conditions and % of Initial SPFin vitro was 80.83 [10]. Results are presented as means from two independent experiments, at each determination six scans were performed.…”

Section: Photostability Studiesmentioning

confidence: 99%

“…In our recent study, we designed new UV filters based on the structure of 3-benzylidene camphor. In our compounds, the camphor fragment was replaced with the imidazolidine-2,4-dione moiety with the aim of improving safety, the incorporation of allyl group contributed to the extension of the UV absorption, whereas 2-ethoxy-2-oxoethyl substituents in the imidazolidine ring improved the solubility of molecules [10].…”

Section: Introductionmentioning

confidence: 99%

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The Involvement of Xanthone and (E)-Cinnamoyl Chromophores for the Design and Synthesis of Novel Sunscreening Agents

Popiół

Gunia‐Krzyżak

Słoczyńska

et al. 2020

IJMS

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Excessive UV exposure contributes to several pathological conditions like skin burns, erythema, premature skin aging, photodermatoses, immunosuppression, and skin carcinogenesis. Effective protection from UV radiation may be achieved with the use of sunscreens containing UV filters. Currently used UV filters are characterized by some limitations including systemic absorption, endocrine disruption, skin allergy induction, and cytotoxicity. In the research centers all over the world new molecules are developed to improve the safety, photostability, solubility, and absorption profile of new derivatives. In our study, we designed and synthesized seventeen novel molecules by combining in the structures two chromophores: xanthone and (E)-cinnamoyl moiety. The ultraviolet spectroscopic properties of the tested compounds were confirmed in chloroform solutions. They acted as UVB or UVA/UVB absorbers. The most promising compound 9 (6-methoxy-9-oxo-9H-xanthen-2-yl)methyl (E)-3-(2,4-dimethoxyphenyl)acrylate) absorbed UV radiation in the range 290–369 nm. Its photoprotective activity and functional photostability were further evaluated after wet milling and incorporation in the cream base. This tested formulation with compound 9 possessed very beneficial UV protection parameters (SPFin vitro of 19.69 ± 0.46 and UVA PF of 12.64 ± 0.32) which were similar as broad-spectrum UV filter tris-biphenyl triazine. Additionally, compound 9 was characterized by high values of critical wavelength (381 nm) and UVA/UVB ratio (0.830) thus it was a good candidate for broad-spectrum UV filter and it might protect skin against UVA-induced photoaging. Compound 9 were also shown to be photostable, non-cytotoxic at concentrations up to 50 µM when tested on five cell lines, and non-mutagenic in Ames test. It also possessed no estrogenic activity, according to the results of MCF-7 breast cancer model. Additionally, its favorable lipophilicity (miLogP = 5.62) does not predispose it to penetrate across the skin after topical application.

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“…Nevertheless, AVO is known to be photounstable, and its photodegradation is based on the keto‐enol tautomerization, where the enol‐form absorbs in the UVA range, and the diketo‐form absorbs in the UVC range (10). Photoallergic reactions to AVO have been reported in the literature, which may be correlated with its photoinstability due to its main photodegradation products, arylglyoxals and benzyls, which are highly sensitizing compounds (11–13).…”

Section: Introductionmentioning

confidence: 99%

Effects of UV‐filter Photostabilizers in the Photostability and Phototoxicity of Vitamin A Palmitate Combined with Avobenzone and Octyl Methoxycinnamate

Scarpin

Kawakami

Rangel

et al. 2021

Photochem & Photobiology

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A challenge for cosmetic and dermatologic products is to develop new high‐performance and safer anti‐aging products based on new compounds to enhance the stability of retinyl palmitate combined with broad‐spectrum UV‐filters. Consequently, the aim of this work was to evaluate the effects of three often used avobenzone photostabilizers—ethylhexyl methoxycrylene (EHMCR), tris(tetramethylhydroxypiperidinol) citrate (TTMHP) and tris‐biphenyl triazine (TBPT)—on the photostability and phototoxicity of the combination of avobenzone (AVO), octyl methoxycinnamate (OMC) and retinyl palmitate (RP). The photostability studies were performed by the exposure of formulations to UVA radiation. The phototoxicity was evaluated by the 3T3 neutral red uptake phototoxic assay (OECD TG 432). The addition of EHMCR, TBPT, and TTMHP in the formulations, with/or without RP, improved the photostability of AVO and RP, but EHMCR was the most effective in stabilizing RP. In the phototoxicity assay, the combinations AVO‐OMC containing or not RP showed phototoxic potential. EHMCR and TTMHP reduced the phototoxicity of the combination AVO‐OMC, whereas EHMCR also decreased the phototoxicity of the combination containing RP. Therefore, EHMCR might be used to the photostabilization of formulations of AVO‐OMC with/or not RP, while TTMHP can be added to this photounstable UV‐filter combination.

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Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group

Cited by 11 publications

References 68 publications

(+)-Usnic Acid as a Promising Candidate for a Safe and Stable Topical Photoprotective Agent

(+)-Usnic Acid as a Promising Candidate for a Safe and Stable Topical Photoprotective Agent

The Involvement of Xanthone and (E)-Cinnamoyl Chromophores for the Design and Synthesis of Novel Sunscreening Agents

Effects of UV‐filter Photostabilizers in the Photostability and Phototoxicity of Vitamin A Palmitate Combined with Avobenzone and Octyl Methoxycinnamate

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