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

Publisher: MDPI Country of Publication: Switzerland NLM ID: 101092791 Publication Model: Electronic Cited Medium: Internet ISSN: 1422-0067 (Electronic) Linking ISSN: 14220067 NLM ISO Abbreviation: Int J Mol Sci Subsets: MEDLINE

Original Publication: Basel, Switzerland : MDPI, [2000-

Ultraviolet Rays*; Cinnamomum zeylanicum/*chemistry ; Sunscreening Agents/*chemistry ; Xanthones/*chemistry; Humans ; Molecular Structure ; Mutagenicity Tests ; Skin/drug effects ; Skin/radiation effects ; Skin Aging/drug effects ; Skin Aging/radiation effects ; Spectrophotometry, Ultraviolet ; Structure-Activity Relationship ; Sunburn/prevention & control ; Sunscreening Agents/chemical synthesis ; Sunscreening Agents/pharmacology ; Xanthones/pharmacology

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-9 H -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 (SPF in 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.
Competing Interests: The authors declare no conflict of interest.

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2016/21/B/NZ7/01756 Narodowe Centrum Nauki

Keywords: (E)-cinnamoyl; UV absorption; UV filters; UV radiation; photoprotective activity; xanthone

0 (Sunscreening Agents)
0 (Xanthones)

Date Created: 20201230 Date Completed: 20210329 Latest Revision: 20240330

20240330

PMC7792956

10.3390/ijms22010034

33375127