Phosphonium betaines derived from hexafluoro-1,4-naphthoquinone: Synthesis and cytotoxic and antioxidant activities

Zhivetyeva, Svetlana I.; Zakharova, Olga D.; Ovchinnikova, L.P.; Baev, Dmitry S.; Bagryanskaya, I. Yu.; Shteingarts, V. D.; Толстикова, Т. Г.; Nevinsky, Georgy A.; Tretyakov, Evgeny V.

doi:10.1016/j.jfluchem.2016.10.014

Cited by 8 publications

(3 citation statements)

References 31 publications

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“…Naphthoquinones are a kind of common natural compounds, which have bactericidal, anti-oxidant and antiviral effects (Zhivetyeva et al, 2016;Novais et al, 2018). Some studies have shown that naphthoquinone derivatives have anti-tumor and apoptosis-inducing effects (Li et al, 2017;Liu et al, 2018).…”

Section: Discussionmentioning

confidence: 99%

A potential estrogen receptor inhibitor compound 34 induces apoptosis via ROS-independent intrinsic apoptosis in MCF-7 cells

Ding

Zhu

Teng

et al. 2019

Bangladesh J Pharmacol

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This study aimed to investigate the anti-tumor effects of compound 34 on MCF-7 cells in vitro, and explore its mechanisms. MTT results showed that compound 34 selectively inhibited estrogen receptor-positive cells proliferation. Hoechst 33342 staining showed nuclear pyknosis, nuclear debris associated with apoptotic bodies. JC-1 staining showed the loss of mitochondrial membrane potential. Although compound 34 increased intracellular reactive oxygen species (ROS), compound 34-induced apoptosis was not prevented by pretreatment with ROS scavengers. Western blotting showed apoptosis-related protein like cytochrome c and cleaved PARP protein increased. Furthermore, docking studies exhibited that compound 34 could bind into ERα. In summary, compound 34 selectively inhibited estrogen receptor positive cells proliferation and induced apoptosis in MCF-7 cells via ROS-independent intrinsic apoptosis in MCF-7 cells. It may be a potential targeted drug of estrogen receptor for therapeutic application of breast cancer. Video Clip of Methodology: Assay of Cell Proliferation: 5 min 5 sec Full Screen Alternate

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Section: Discussionmentioning

confidence: 99%

A potential estrogen receptor inhibitor compound 34 induces apoptosis via ROS-independent intrinsic apoptosis in MCF-7 cells

Ding

Zhu

Teng

et al. 2019

Bangladesh J Pharmacol

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“…As, for example, in the reaction of fluoronaphthoquinone (1) with triphenyl-phosphine (Ph 3 P), derivatives of phosphonium betaines derived from hexafluoro-1,4-naphthoquinone: (triphenyl- [5,6,7,8-tetrafluoro-1-oxido-4-oxo-3-(phenylimino)-3,4-dihydro-naphthalen-2-yl]phosphonium) 3 (Scheme 1), were obtained. 4 The reaction was explained as due to the formation of intermediate 2 (Scheme 1). Depending upon reaction conditions, it was reported that Ph 3 P reacted with p-chloranil (4) to produce either Zwitter salts 5 or 6 5 (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…The reactions of 1,4-naphthoquinone with triphenylphosphine (Ph 3 P) have been previously described. As, for example, in the reaction of fluoronaphthoquinone ( 1 ) with triphenylphosphine (Ph 3 P), derivatives of phosphonium betaines derived from hexafluoro-1,4-naphthoquinone: (triphenyl[5,6,7,8-tetrafluoro-1-oxido-4-oxo-3-(phenylimino)-3,4-dihydro-naphthalen-2-yl]phosphonium) 3 (Scheme ), were obtained . The reaction was explained as due to the formation of intermediate 2 (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Copper Complexes of 1,4-Naphthoquinone Containing Thiosemicarbazide and Triphenylphosphine Oxide Moieties; Synthesis and Identification by NMR, IR, Mass, UV Spectra, and DFT Calculations

et al. 2022

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New 1,4-naphthoquinone derived by triphenylphosphaneylidene (Ph 3 P) and N -substituted-hydrazine-1-carbothioamides were obtained during a one-pot reaction of 2,3-dichloro-1,4-naphthoquinone with thiosemicarbazides, Ph 3 P and in the presence of triethyl amine (Et 3 N) as a catalyst. The structure of the ligands was established by ESI, IR, and NMR spectra, in addition to elemental analyses and X-ray structure analysis. On subjecting the newly prepared ligands with CuCl 2 and Ph 3 P, autoxidation occurs, and ( E )-(2-(1,4-dioxo-3-(triphenyl phosphanylidene)-3,4-dihydronaphthalen-2(1 H )-ylidene)carbamothioyl)hydrazinyl)-((triphenylphosphanyl)oxy)copper derivatives were formed in very good yields. The structure of the obtained complexes was proved by ESI, IR, NMR, and UV spectra, in addition to elemental analyses and theoretical calculations.

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C−F Bond Activation Mediated by Phosphorus Compounds

Bayne

Stephan

2019

Chemistry A European J

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The activation and functionalization of CÀFb onds has garnered significant attention in the scientificc ommunity as as trategy to mitigate toxicitya nd environmental concerns, as well as provide new pathways to agro-and pharmaceuticalc hemicals and materials. Although severalt ransition-metal-based systemsh ave been developed for this transformation,t he use of main-group compoundsr emains less explored. In recent years, several strategies for CÀF bond activation have focused on the use of phosphorusbased reagents. In this Minireview,a no verview of strategies is provided that exploits P V andP III -based Lewis acids as well as P III Lewis bases in frustrated Lewis pair (FLP) protocols for hydrodefluorination, CÀCc ouplings andC ÀFd erivatizations.

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Phosphonium betaines derived from hexafluoro-1,4-naphthoquinone: Synthesis and cytotoxic and antioxidant activities

Cited by 8 publications

References 31 publications

A potential estrogen receptor inhibitor compound 34 induces apoptosis via ROS-independent intrinsic apoptosis in MCF-7 cells

A potential estrogen receptor inhibitor compound 34 induces apoptosis via ROS-independent intrinsic apoptosis in MCF-7 cells

Copper Complexes of 1,4-Naphthoquinone Containing Thiosemicarbazide and Triphenylphosphine Oxide Moieties; Synthesis and Identification by NMR, IR, Mass, UV Spectra, and DFT Calculations

C−F Bond Activation Mediated by Phosphorus Compounds

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