Simple 2(5H)-furanone derivatives with selective cytotoxicity towards non-small cell lung cancer cell line A549 – Synthesis, structure-activity relationship and biological evaluation

Byczek-Wyrostek, Anna; Kitel, Radosław; Rumak, Klaudia; Skonieczna, Magdalena; Kasprzycka, Anna; Walczak, Krzysztof

doi:10.1016/j.ejmech.2018.03.021

Cited by 24 publications

(18 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furan and its derivatives, which are often found in fruity and sweet flavors, are associated with damage to nasal mucosa and the lamia propia in rats (Arts et al, 2004). These compounds also exhibited anti-cancer properties in a lung adenocarcinoma cancer line (Yuan et al, 2006;Byczek-Wyrostek et al, 2018). The presence of silicon oils (siloxanes) is also a cause for concern.…”

Section: Discussionmentioning

confidence: 99%

E-Liquid Containing a Mixture of Coconut, Vanilla, and Cookie Flavors Causes Cellular Senescence and Dysregulated Repair in Pulmonary Fibroblasts: Implications on Premature Aging

et al. 2020

View full text Add to dashboard Cite

Electronic cigarette (e-cig) usage has risen dramatically worldwide over the past decade. While they are touted as a safe alternative to cigarettes, recent studies indicate that high levels of nicotine and flavoring chemicals present in e-cigs may still cause adverse health effects. We hypothesized that an e-liquid containing a mixture of tobacco, coconut, vanilla, and cookie flavors would induce senescence and disrupt wound healing processes in pulmonary fibroblasts. To test this hypothesis, we exposed pulmonary fibroblasts (HFL-1) to e-liquid at varying doses and assessed cytotoxicity, inflammation, senescence, and myofibroblast differentiation. We found that e-liquid exposure caused cytotoxicity, which was accompanied by an increase in IL-8 release in the conditioned media. E-liquid exposure resulted in elevated senescence-associated beta-galactosidase (SA-β-gal) activity. Transforming growth factor-β1 (TGF-β1) induced myofibroblast differentiation was inhibited by e-liquid exposure, resulting in decreased α-smooth muscle actin and fibronectin protein levels. Together, our data suggest that an e-liquid containing a mixture of flavors induces inflammation, senescence and dysregulated wound healing responses.

show abstract

Section: Discussionmentioning

confidence: 99%

E-Liquid Containing a Mixture of Coconut, Vanilla, and Cookie Flavors Causes Cellular Senescence and Dysregulated Repair in Pulmonary Fibroblasts: Implications on Premature Aging

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Briefly, 1 H-NMR (500 MHz) and 13 C-NMR (500 MHz) spectra were recorded on a Bruker AC 500 spectrometer (Bruker, Karlsruhe, Germany) in an appropriate solvent with tetramethylsilane (TMS) as an internal reference. High resolution mass spectrometry (HRMS) data were recorded on UPLC/Q-TOF, equipped with an ESI source (Agilent Technologies, Santa Clara, CA, USA).…”

Section: Nuclear Magnetic Resonance (Nmr) Spectroscopy and Mass Spectrometry (Ms) For Blsmentioning

confidence: 99%

“…The metabolites display antibacterial, antiviral, antitumor and other activities [ 9 , 10 , 11 ]. Butenolide, a collective name for α,β-unsaturated lactones with four carbon heterocyclic rings produced by a variety of marine organisms, is drawing increasing attention in drug discovery [ 12 , 13 , 14 , 15 , 16 ]. Butenolide derivatives display an impressive range of pharmacological properties, including anti-inflammatory [ 17 , 18 ], antibacterial [ 19 ], antiviral [ 20 ], and antitumor activities [ 21 , 22 ], while aromatic butenolides were found to have α- and β-glucosidase inhibitory activities [ 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

“…) 13. C NMR (126 MHz, DMSO-d6) δ 169.79, 158.16, 153.49, 136.96, 131.88, 129.59, 129.52, 129.48, 129.13, 126.03, 122.05, 121.80, 121.58, 116.58, 115.81, 79.87, 76.92, 28.29, 28.27.…”

mentioning

confidence: 99%

“…) 13. C NMR (126 MHz, DMSO-d6) δ 169.85, 158.12, 137.53, 136.87, 132.42, 130.28, 129.61, 129.49, 129.30, 129.11, 128.87, 128.24, 127.91, 127.29, 122.56, 122.13, 115.75, 112.43, 79.94, 69.75, 28.90, 25.94, 18.01.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Biological Evaluation of Analogues of Butyrolactone I as PTP1B Inhibitors

Hong

Fan

et al. 2020

Marine Drugs

View full text Add to dashboard Cite

In recent years, a large number of pharmacologically active compounds containing a butenolide functional group have been isolated from secondary metabolites of marine microorganisms. Butyrolactone I was found to be produced by Aspergillus terreus isolated from several marine-derived samples. The hypoglycemic activity of butyrolactone I has aroused our great interest. In this study, we synthesized six racemic butenolide derivatives (namely BL-1–BL-6) by modifying the C-4 side chain of butyrolactone I. Among them, BL-3 and BL-5 improved the insulin resistance of HepG2 cells and did not affect the proliferation of RIN-m5f cell line, which indicated the efficacy and safety of BL-3 and BL-5. Furthermore, BL-3, BL-4, BL-5, and BL-6 displayed a significant protein tyrosine phosphatase 1B (PTP1B) inhibitory effect, while the enantiomers of BL-3 displayed different 50% percentage inhibition concentration (IC50) values against PTP1B. The results of molecular docking simulation of the BLs and PTP1B explained the differences of biological consequences observed between the enantiomers of BL-3, which supported BLs as PTP1B inhibitors, and also indicated that the chirality of C-4 might influence the inhibitory effect of the BLs. Our findings provide a novel strategy for the development of butyrolactone derivatives as potential PTP1B inhibitors for the treatment of type 2 diabetes mellitus.

show abstract

Multicomponent Selective Thioetherification of KSAc: Easy Access to Symmetrical/Unsymmetrical 4‐Alkylthio‐3‐halo‐2(5H)‐furanones

et al. 2023

View full text Add to dashboard Cite

An easy two‐/three‐component selective thioetherification of KSAc for the synthesis of a series of symmetrical/unsymmetrical 4‐alkylthio‐3‐halo‐2(5H)‐furanones has been described. The reaction without any metal catalyst or additive is carried out in air atmosphere at room temperature for 5 h, only using potassium thioacetate as an odourless sulfur source and a base simultaneously. The broad substrate scope and high yield make it important for the studies on both constructing C−S bond based on non‐aryl Csp2−X bond and synthesizing new 2(5H)‐furanone functional molecules.

show abstract

Simple 2(5H)-furanone derivatives with selective cytotoxicity towards non-small cell lung cancer cell line A549 – Synthesis, structure-activity relationship and biological evaluation

Cited by 24 publications

References 28 publications

E-Liquid Containing a Mixture of Coconut, Vanilla, and Cookie Flavors Causes Cellular Senescence and Dysregulated Repair in Pulmonary Fibroblasts: Implications on Premature Aging

E-Liquid Containing a Mixture of Coconut, Vanilla, and Cookie Flavors Causes Cellular Senescence and Dysregulated Repair in Pulmonary Fibroblasts: Implications on Premature Aging

Synthesis and Biological Evaluation of Analogues of Butyrolactone I as PTP1B Inhibitors

Multicomponent Selective Thioetherification of KSAc: Easy Access to Symmetrical/Unsymmetrical 4‐Alkylthio‐3‐halo‐2(5H)‐furanones

Contact Info

Product

Resources

About