Chrysin-piperazine conjugates as antioxidant and anticancer agents

Patel, Rahul V.; Mistry, Bhupendra M.; Syed, Rabbani; Rathi, Anuj K.; Lee, Yoo-Jung; Sung, Jung‐Suk; Shinf, Han-Seung; Keum, Young‐Soo

doi:10.1016/j.ejps.2016.02.011

Cited by 38 publications

(31 citation statements)

References 32 publications

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“…Further, it seems that compounds bearing electron withdrawing substituents such as methoxy or trifluoromethoxy functionalities as well as unsubstituted derivatives exerted best antioxidant potencies against DPPH and ABTS. In addition, IC 50 levels of sulfonyl piperazines were found to be lowered significantly against DPPH radical when compared with previously studied chrysin‐piperazine derivatives, which showed 20.30 ± 0.476 to 34.06 ± 0.913 μg/ml of IC 50s . However, activity against ABTS radical looked similar as previously studied.…”

Section: Resultssupporting

confidence: 71%

“…In addition, it is affirmed that OH group of the chrysin is crucial to furnish anticipated biological potencies as it interacts with ROS and protects against oxidative stress as well as DNA damage . In a light of aformentioned facts, we have designed chrysin‐based piperazine molecules, which includes the presence of one OH group in chyrsin core as well as substituting another OH group by desired active pharmacophores and these analogues appeared to have significant antioxidant and anticancer effects. Moreover, organic and inorganic precursors holding sulfone entity were found to have promising potential as biological active agents, whereas piperazine analgoues have been proposed to be a key factor enhancing biological effects of the bearing molecules.…”

Section: Introductionsupporting

confidence: 66%

“…From the bioassay data obtained in this study, it can be observed that modifying previously studied chrysin‐piperazine conjugates to their sulfonylpiperazine precursors, which lead to the substantially enhanced biological efficacies. Our previous research for the similar molecular systems involving chrysin‐piperazine analogues revealed 20.30 ± 0.476 to 34.06 ± 0.913 μg/ml and 5.569 ± 0.025 to 8.971 ± 0.881 μg/ml of IC 50 values in DPPH and ABTS bioassay, respectively, as well as 5.044 ± 0.423 to 9.914 ± 0.445 μg/ml and 12.876 ± 0.411 to 63.210 ± 0.158 μg/ml of IC 50 values against HeLa and SK‐OV‐3 cell lines, respectively …”

Section: Resultsmentioning

confidence: 99%

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Sulfonylpiperazines based on a flavone as antioxidant and cytotoxic agents

Patel

Mistry

Syed

et al. 2019

Archiv der Pharmazie

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Chrysin-based sulfonylpiperazines 7a-k were synthesized and investigated for their in vitro free radical scavenging potential as well as cytotoxic efficacies against selected cancer cell lines. Cytotoxicity of the new compounds toward noncancer cells was confirmed using the SRB assay against Madin-Darby Canine Kidney cells.Reaction of piperazine with different substituted benzenesulfonyl chlorides in triethylamine furnished sulfonylpiperazines (3a-k), which were then allowed to react with 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one (6) prepared reacting chrysin with 1,4-dibromobutane to give the final derivatives 7a-k. The results concluded that chrysin-sulfonylpiperazines exerted better antioxidant and anticancer efficacies than previously studied chrysin-piperazine precursors. For example, compounds 7h, 7j, and 7k with 4-OCF 3 , 4-OCH 3 , and 2,4-diOCH 3 groups exhibited the best antioxidant potential against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radicals. Moreover, halogenated analogues (7b, 7c, 7g, and 7h) demonstrated promising anticancer potential against SK-OV3, HeLa, and HT-29 cell lines, whereas those bearing a methoxy functional group (7j and 7k) had beneficial effects against the cell lines A-549 and HT-29. Thus, it can be confirmed from the bioassay results that the overall structural design as well as proper substitution is crucial to deliver the anticipated biological effects. Spectroscopic techniques such as FT-IR, 1 H NMR, 13 C NMR, mass and elemental analysis (CHN) were carried out to confirm the final structures.

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Section: Resultssupporting

confidence: 71%

Section: Introductionsupporting

confidence: 66%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Sulfonylpiperazines based on a flavone as antioxidant and cytotoxic agents

Patel

Mistry

Syed

et al. 2019

Archiv der Pharmazie

Self Cite

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“…Various flavonoid derivatives modified at C‐7 position have been reported and these derivatives compared with their parent compound, displayed significant biological activity against several anticancer cell lines and several microorganisms . Especially in literature, to increase the anticancer properties of flavonoids, several derivatives of flavonoids have been prepared, in which flavonoid ring system linked to the different amines separated by two carbon spacers at C‐7 position .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Cancer‐Selective Antiproliferative and Apoptotic Effects of Some (±)‐Naringenin Cycloaminoethyl Derivatives

Zaim

Doğanlar

Zreigh

et al. 2018

Chemistry & Biodiversity

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Naringenin is a naturally occurring flavonoid and due to its broad spectrum of biological activities, including anticancer properties, has attracted scientific attention in recent years. To contribute to these studies, we synthesized some new (±)-naringenin cyclic aminoethyl derivatives, analyzed the cytotoxic and anti-proliferative properties of them via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, and mitochondrial apoptosis signaling response and gene expressions belong to caspase-3 depended apoptosis as biomarkers in both healthy and cancer cell lines. Our results suggest that some of our naringenin derivatives are potential anticancer agents with a selective death potential and targeting properties for mitochondrial apoptosis signaling against at least human cervix and breast cancer.

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“…The fruit of this plant is commonly used in Thailand and other East Asian countries as food and herbal medicine. Chrysin possesses several biological activities including, anti-cancer (3,4), anti-inflammation (5,6), and antioxidant properties (7,8) and is reported to cause an increase of testosterone production via suppression of aromatase, an enzyme that converts androgen to estrogen (9). However, biological actions are only facilitated given the stable structure and low molecular weights of the active compounds that can be soluble and pass through cell membranes (10).…”

Section: Introductionmentioning

confidence: 99%