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

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 disruptio...

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Veröffentlicht in:Molecules (Basel, Switzerland) Jg. 24; H. 12; S. 2321
Hauptverfasser: 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
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Switzerland MDPI AG 24.06.2019
MDPI
Schlagworte:
5-arylidenehydantoin derivatives
Acids
Animals
Atoms & subatomic particles
Cell Line, Tumor
Cell Proliferation - drug effects
Cell Proliferation - radiation effects
Cosmetics
Drug Stability
Humans
Hydantoins - chemistry
Hydantoins - pharmacology
Hydantoins - radiation effects
Mice
Models, Molecular
Molecular Structure
photoprotection
Radiation-Protective Agents - chemistry
Radiation-Protective Agents - pharmacology
Radiation-Protective Agents - radiation effects
safety evaluation
Spectrum Analysis
Structure-Activity Relationship
Sunscreen
Sunscreening Agents - chemistry
Sunscreening Agents - radiation effects
Ultraviolet radiation
Ultraviolet Rays
UV radiation
UV-filters
UV radiation
photoprotection
UV-filters
safety evaluation
5-arylidenehydantoin derivatives
ISSN:1420-3049, 1420-3049
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Zusammenfassung: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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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24122321