Anticancer effects of O-aminoalkyl derivatives of alloxanthoxyletin and seselin

Ostrowska, Kinga; Olejarz, Wioletta; Wrzosek, Małgorzata; Głuszko, Alicja; Nowicka, Grażyna; Szczepański, Mirosław J.; Materek, Ilona B.; Kozioł, Anna E.; Struga, Marta

doi:10.1016/j.biopha.2017.09.050

Cited by 10 publications

(7 citation statements)

References 25 publications

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“…Small molecules for this purpose frequently originated from natural sources. In this regard, naturally occurring chromenes (mammea A/BB), pyranocoumarins (alloxanthoxyletin, seselin) and their synthetic analogs were described as antitumoral and antiprotozoal agents . Therefore, parallels in differentiation existing between cancer cells and protozoan parasites prompted us to prepare chromenes derivatives which are potentially cytotoxic and antiparasitic agents.…”

Section: Introductionmentioning

confidence: 99%

Prospecting for cytotoxic and antiprotozoal 4‐aryl‐4H‐chromenes and 10‐aryldihydropyrano[2,3‐f]chromenes

Martin

Mbaveng

Moraes

et al. 2018

Archiv der Pharmazie

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Different studies reported that genetic predisposition or metabolic dysfunction are the risk factors for cancer. Infectious parasitic diseases were listed among factors that predispose to cancer. Because of the resemblance between the life cycle of cancer cells and some parasites, this study aimed to prepare pyran derivatives with cytotoxic and antiprotozoal potencies. Therefore, 7 chromenes, 10 pyranocoumarins, and an unexpected intermediate were obtained from a multi-reagent one-pot reaction. These compounds were evaluated for their cytotoxicity on sensitive and resistant leukemia cancer cells lines and against two protozoan parasites, namely Trypanosoma cruzi and Leishmania amazonensis amastigote. Promising cytotoxicity (IC values of less than 1 µM) was obtained for two of the synthetic products (12 and 15). Compound 12 induced apoptosis and cell cycle arrest in CCRF-CEM leukemia cells in G0/G1 while compound 15 and doxorubicin induced apoptosis and arrest in the S and G2/M phases. Ten of these products showed trypanocidal activity, while only five of them were weakly active on L. amazonensis. Three of the obtained pyrans showed significant cytotoxicity and antitrypanocidal activity, simultaneously. Nevertheless, all antiparasitic compounds revealed potency with low selectivity toward THP-1 cells used as host.

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Section: Introductionmentioning

confidence: 99%

Prospecting for cytotoxic and antiprotozoal 4‐aryl‐4H‐chromenes and 10‐aryldihydropyrano[2,3‐f]chromenes

Martin

Mbaveng

Moraes

et al. 2018

Archiv der Pharmazie

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“…Despite the need to use column chromatography such approach allowed us to obtain the products much faster. Synthesis and characteristic of the alloxanthoxyletin derivative was described before (Ostrowska et al 2017). Alpha lipoic acid (±1,2-Dithiolane-3-pentanoic acid) was used as a second substrate for synthesis and it was supplied from Sigma Aldrich.…”

Section: Synthesis Of Ester Of α-Lipoic Acid and Derivative Of Alloxamentioning

confidence: 99%

“…Moreover, 7-hydroxy-5′,5a′,9-trimethylpyrano[2′,3′-f]-(2 H)-chromen-2-one) served as a starting compound in the synthesis of LAA exhibited lower cytotoxicity than LAA against both tumor cell lines, with IC 50 values 43.97 toward the HTB-140 cell lines, and with IC 50 values 57.82 toward the A549 cell lines (For rev. see: Ostrowska et al 2017).…”

Section: Biological Studiesmentioning

confidence: 99%

“…On the basis of recent studies concerning the biological and pharmacological properties of both coumarins and αlipoic acid, our research are focused on yielding a novel molecular combinations received by joining the two biologically active compounds to obtain a more active substance. Our previous study demonstrated that some alloxanthoxyletin derivatives revealed a high cytotoxic potential against human melanoma cells (HTB-140) and human epithelial lung carcinoma cells (A549) (Ostrowska et al 2017), therefore, we decided to investigate a novel derivative of alloxanthoxyletin. In the present study new ester of α-lipoic acid and derivative of alloxanthoxyletin (LAA) was synthesized and evaluated for its anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and anticancer effects of α-lipoic ester of alloxanthoxyletin

et al. 2019

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Upon analyzing the structure-activity relationship, it was found that coumarin-based derivatives exerted cytotoxic and antitumor activity. In the present study a new ester of α-lipoic acid and derivative of alloxanthoxyletin (LAA) was synthesized and evaluated for its anticancer activity. The structure of this new compound was confirmed by 1 H NMR, 13 C NMR, and HRMS spectroscopic analyses. Both, the cytotoxicity and the migration tests showed that human melanoma cells (HTB-140) and human lung cancer cells (A549) were more sensitive to LAA exposure than human normal keratinocytes (HaCaT). Moreover, LAA induced significant HTB-140 and A549 apoptosis, as evidenced by V-FITC/7-AAD flow cytometry analysis. Preincubation of the HTB-140 and A549 cells with LAA increased a sensitivity of tumor cells to a druginduced cell death. Significantly lower expression of IL-6 mRNA was observed in A549 and HTB-140 cells which were preincubated with LAA and then treated with doxorubicin as compared to the cells pre-incubated with LAA and then treated with cisplatin. The results suggest that the newly synthetized LAA is compound with anticancer activity promising for potential applications, but further studies are needed to gain more insight into the mechanism of action of tested derivative.

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“…Seselin ( 4 ) is an example of an angular pyranocoumarin found in various plants, e.g., from the family of Rutaceae [17]. Among other bioactivities, the compound itself and some natural and non-natural derivatives induce apoptosis in melanoma HTB-140 cells [18].…”

Section: Introductionmentioning

confidence: 99%

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

Schultze

Schmidt

2018

Beilstein J. Org. Chem.

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8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing olefin metathesis (RCM). Furano-, pyrano-, oxepino- and azepinocoumarins were synthesized from the same set of precursors using Ru-catalyzed double bond isomerizations and RCM in a defined order. One class of products, pyrano[2,3-f]chromene-2,8-diones, were inaccessible through direct RCM of an acrylate, but became available from the analogous allyl ether via an assisted tandem catalytic RCM/allylic oxidation sequence.

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Anticancer effects of O-aminoalkyl derivatives of alloxanthoxyletin and seselin

Cited by 10 publications

References 25 publications

Prospecting for cytotoxic and antiprotozoal 4‐aryl‐4H‐chromenes and 10‐aryldihydropyrano[2,3‐f]chromenes

Prospecting for cytotoxic and antiprotozoal 4‐aryl‐4H‐chromenes and 10‐aryldihydropyrano[2,3‐f]chromenes

Synthesis and anticancer effects of α-lipoic ester of alloxanthoxyletin

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

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