Influence of New Synthetic Xanthones on the Proliferation and Migration Potential of Cancer Cell Lines In Vitro

Szkaradek, Natalia; Sypniewski, Daniel; Żelaszczyk, Dorota; Gałka, Sabina; Borzdziłowska, Paulina; Marona, Henryk; Bednarek, Ilona

doi:10.2174/1871520619666190405113519

Cited by 3 publications

(2 citation statements)

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“…Xanthone derivatives have been subject of multidirectional research for many years. A lot of them have a favorable biological and pharmacological activity profile, including among other antioxidant [17], antimicrobial [18], anticancer [19,20], and anti-inflammatory effect [21]. Moreover, xanthone derivatives have also recently been of interest in the field of cosmetics chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…Xanthone (dibenzo-γ-pyrone) possesses conjugated double b potential substitution positions. Coupling with an appropriate a additional chromophores gives the opportunity to select substan tended photoprotectiveness in a wide UV range but also with a sa Xanthone derivatives have been subject of multidirectional resear of them have a favorable biological and pharmacological activity p other antioxidant [17], antimicrobial [18], anticancer [19,20], and a [21]. Moreover, xanthone derivatives have also recently been of in metics chemistry.…”

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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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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Xanthones: A Class of Heterocyclic Compounds with Anticancer Potential

Rauf

Thiruvengadam

Gul

et al. 2022

CTMC

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Xanthones (9H xanthen-9-one) are an important class of heterocyclic compounds containing oxygen and moiety of gamma-pirone, dense with a two-benzene ring structured, distributed widely in nature. Naturally occurring xanthones are found in micro-organisms and higher plants as secondary metabolites in fungi and lichens. Compounds of the family Calophyllaceae, Guttiferae and Gentianaceae are the most common natural source of xanthones. The structure of xanthones nucleus, coupled with its biogenetic source, imposes that the carbons are numbered according to the biosynthetic pact. The characteristics oxygenation pattern of xanthones earlier is mixed shikimate-acetate biogenesis. The major class of xanthones includes simple oxygenated, non-oxygenated, xanthonolignoids, bisxanthones, prenylated and related xanthones, as well as miscellaneous xanthones. Their great pharmacological importance and interesting scaffolds were highly encouraged by scientists to investigate either the synthesis design or natural products for cancer treatment. Because currently used antitumor drugs possess high toxicity and low selectivity, efficacious treatment may be compromised. This review is limited to the antitumor activity of xanthones and the chemistry of xanthone core, which may help provide fundamental knowledge to the medicinal chemist for new and advanced research in drug development.

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Hyperthermia Intensifies α-Mangostin and Synthetic Xanthones’ Antimalignancy Properties

Rech,

Żelaszczyk,

Marona

et al. 2024

IJMS

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In order to improve naturally occurring xanthones’ anticancer properties, chemical synthesis is proposed. In this study, from eight novel xanthone derivatives coupled to morpholine or aminoalkyl morpholine, only the two most active ones were chosen. For additional enhancement of the anticancer activity of our tested compounds, we combined chemotherapy with hyperthermia in the range of 39–41 °C, from which the mild conditions of 39 °C were the most influencing. This approach had a profound impact on the anticancer properties of the tested compounds. TOV-21G and SC-OV-3 ovarian cell line motility and metastasis behavior were tested in native and hyperthermia conditions, indicating decreased wound healing properties and clonogenic activity. Similarly, the expression of genes involved in metastasis was hampered. The expression of heat shock proteins involved in cancer progression (Hsc70, HSP90A, and HSP90B) was significantly influenced by xanthone derivatives. Chemotherapy in mild hyperthermia conditions had also an impact on decreasing mitochondria potential, visualized with JC-1. Synthetic xanthone ring modifications may increase the anticancer activity of the obtained substances. Additional improvement of their activity can be achieved by applying mild hyperthermia conditions. Further development of a combined anticancer therapy approach may result in increasing currently known chemotherapeutics, resulting in a greater recovery rate and diminishment of the cytotoxicity of drugs.

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Influence of New Synthetic Xanthones on the Proliferation and Migration Potential of Cancer Cell Lines In Vitro

Cited by 3 publications

References 46 publications

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

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

Xanthones: A Class of Heterocyclic Compounds with Anticancer Potential

Hyperthermia Intensifies α-Mangostin and Synthetic Xanthones’ Antimalignancy Properties

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