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Cited by 15Skin Protection and AgingPhotochromic and Fluorescence ChemistryPhotopolymerization techniques and applications

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

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Popiół, Justyna, Gunia-Krzyżak, Agnieszka, Piska, Kamil, Żelaszczyk, Dorota, Koczurkiewicz, Paulina, Słoczyńska, Karolina, Wójcik-Pszczoła, Katarzyna, Krupa, Anna +6 more·2019·Molecules
DOI 10.3390/molecules24122321PMC PMC6630718
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Abstract

Effective protection from the harmful effects of UV radiation may be achieved by using sunscreens containing organic or inorganic UV filters. The number of currently available UV filters is limited and some of the allowed molecules possess limitations such as systemic absorption, endocrine disruption properties, contact and photocontact allergy induction, and low photostability. In the search for new organic UV filters we designed and synthesized a series consisting of 5-benzylidene and 5-(3-phenylprop-2-en-1-ylidene)imidazolidine-2,4-dione (hydantoin) derivatives. The photoprotective activity of the tested compounds was confirmed in methanol solutions and macrogol formulations. The most promising compounds possessed similar UV protection parameter values as selected commercially available UV filters. The compound diethyl 2,2′-((Z)-4-((E)-3-(4-methoxyphenyl)allylidene)-2,5-dioxoimidazolidine-1,3-diyl)diacetate (4g) was characterized as an especially efficient UVA photoprotective agent with a UVA PF of 6.83 ± 0.05 and favorable photostability. Diethyl 2,2′-((Z)-4-(4-methoxybenzylidene)-2,5-dioxo- imidazolidine-1,3-diyl)diacetate (3b) was the most promising UVB-filter, with a SPFin vitro of 3.07 ± 0.04 and very good solubility and photostability. The main photodegradation products were geometric isomers of the parent compounds. These compounds were also shown to be non-cytotoxic at concentrations up to 50 µM when tested on three types of human skin cells and possess no estrogenic activity, according to the results of a MCF-7 breast cancer model.

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  • The synthesised hydantoin derivatives (98-110) revealed moderate SPF values but demonstrated the ability to absorb both UVA and UVB radiation (λc between 339 and 391 nm).

    “Although the synthesised compounds revealed moderate SPF values, they demonstrated the ability to absorb both UVA and UVB radiation (λc between 339 and 391 nm) [136].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [136]

    Section 2.4 (page unavailable) reports modest in vitro SPF values for some derivatives and UVA absorption alongside UVB-related SPF; Section 2.3 describes the tested series as containing both UVA and UVB absorbers. The available text does not give the claimed critical-wavelength range of 339–391 nm, and it distinguishes UVA from UVB filters rather than establishing that every compound absorbs both. (LLM, conf=0.85)

    Experimental — accuracy not yet measured

  • Compounds 104 and 109 were the least toxic against HaCaT keratinocytes and human fibroblasts cell lines, and compound 99 revealed the best UVB photoprotective properties within the tested series, with SPF = 4.7.

    “Compounds 104 and 109 were considered the less toxic against HaCaT keratinocytes and human fibroblasts cell lines, and compound 99 revealed the best UVB photoprotective properties within the tested series, with a SPF = 4.7.”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [136]

    The Conclusions (p. unavailable) identify compound 2a as having the best UVB photoprotection in the tested series, with an in vitro SPF of 4.79 ± 0.02—close to, but not exactly, 4.7. Section 2.6.1 (p. unavailable) reports no cytotoxicity in HaCaT keratinocytes or BJ fibroblasts for the tested derivatives, but does not identify compounds 104 and 109 as the least toxic. The source uses labels such as 2a rather than 99, so the numbered compounds cannot be matched from these passages. (LLM, conf=0.85)

    Experimental — accuracy not yet measured

  • For hydantoin derivatives, presence of alkoxy groups at positions 4- (compounds 99, 104, and 109) and 3,4- (compounds 102 and 107) is associated with the highest values of critical wavelength, unlike non-substituted benzene rings.

    “In addition, the presence of alkoxy groups at positions 4- (compounds 99, 104, and 109) and 3,4- (compounds 102 and 107) is associated with the highest values of critical wavelength, contrarily to what is observed with non-substituted benzene rings [136].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [136]

    Section 2.4 (Photoprotective Activity) reports that compounds with 4- and 3,4-alkoxy substitution have higher critical wavelengths than unsubstituted analogues. It says the highest values occur with 2,4-substitution, however, not the 4- and 3,4-substituted compounds. The source also uses different compound numbers from those in the citing sentence. (LLM, conf=0.88)

    Experimental — accuracy not yet measured

  • For hydantoin derivatives, methoxy substituents at the aromatic ring are associated with photoprotection against UVA radiation, while absence of methoxy groups is associated with UVB filter properties.

    “For instance, methoxy substituents at the aromatic ring are associated with photoprotection against UVA radiation; in contrast, the absence of methoxy groups in the aromatic ring is associated with interesting UVB filter properties [136].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [136]

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References 74 · Cited by 15

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Authors
Popiół, J., Gunia-Krzyżak, A., Piska, K., Żelaszczyk, D., Koczurkiewicz, P., Słoczyńska, K., Wójcik-Pszczoła, K., Krupa, A., Kryczyk-Poprawa, A., Żesławska, E., Nitek, W., Żmudzki, P., Marona, H., & Pękala, E.
Affiliations
  • Jagiellonian University (PL)
  • Department of Bioorganic Chemistry, Chair of Organic Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Krakow, Poland
  • Department of Pharmaceutical Biochemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Krakow, Poland
  • Department of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Krakow, Poland
  • Uniwersytet Komisji Edukacji Narodowej w Krakowie (PL)
ORCID
Venue
Molecules
Publisher
MDPI AG
Published
2019-06-24
Volume
24
Issue
12
Pages
2321
ISSN
1420-3049 (ISSN-L)
DOI
10.3390/molecules24122321
PMC
PMC6630718
OpenAlex
W2950486751
Cited by
15
References
74
Citations by year
2026: 2 · 2025: 2 · 2024: 3 · 2022: 2 · 2021: 4 · 2020: 2
FWCI
2.02
Type
journal article
Language
en
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Locations
  • Molecules (publishedVersion, cc-by)
  • Europe PMC (PubMed Central) (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • Jagiellonian University Repository (Jagiellonian University) (submittedVersion, cc-by-nc-nd)
  • Homo Politicus (Academy of Humanities and Economics in Lodz) (submittedVersion, cc-by-nc-nd)
  • Jagiellonian University Repository (Jagiellonian University) (submittedVersion, other-oa)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Funders
Narodowe Centrum Nauki (2016/21/B/NZ7/01756)
Topics
  • Health Sciences › Medicine › Dermatology › Skin Protection and Aging
  • Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
  • Physical Sciences › Chemistry › Organic Chemistry › Photopolymerization techniques and applications
Keywords
UV filters, hydantoin derivatives, sunscreen ingredients, photoprotection, UVA protection factor, photostability, photodegradation, cis-trans isomers, cytotoxicity, estrogenic activity, MCF-7 cells, skin cells, endocrine disruption, contact allergy
MeSH terms
Animals, Drug Stability, Humans, Hydantoins, Models, Molecular, Radiation-Protective Agents, Spectrum Analysis, Structure-Activity Relationship, Sunscreening Agents, Ultraviolet Rays, Molecular Structure, Cell Line, Tumor, Cell Proliferation, Mice

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

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