Novel 3,5-bis(arylidiene)-4-piperidone based monocarbonyl analogs of curcumin: anticancer activity evaluation and mode of action study

Thakur, Anuj; Manohar, Sunny; Gerena, Christian E. Vélez; Zayas, Beatriz; Kumar, Vineet; Malhotra, Sanjay V.; Rawat, Diwan S.

doi:10.1039/c3md00399j

Cited by 34 publications

(12 citation statements)

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“…Recently, structural modification of curcumin has offered a potential approach for optimizing new leads for anticancer drug development [30]. Structural modification studies of curcumin have suggested β-diketone moiety as the position leading to chemical instability, while modification to mono-ketone moiety improved stability as well as cytotoxicity [31]. Accordingly, curcuminoid analogs exerting mono-ketone moiety such as trienones could be used as curcuminbased leads for anticancer drug development.…”

Section: Discussionmentioning

confidence: 99%

A trienone analog of curcumin, 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one, possesses ROS- and caspase-mediated apoptosis in human oral squamous cell carcinoma cells in vitro

et al. 2020

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The leading causes of oral cancer treatment failure are cancer metastasis and chemotherapeutic resistance. Thus, developing novel anticancer agents that are effective against those aggressive cancer cells would be important for complementary or alternative treatments. The objective of this study was to investigate cytotoxicity and anticancer mechanisms of a synthetic trienone analog of curcumin, 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one (trienone 11), against human oral squamous cell carcinoma (OSCC) cells exhibiting multidrug resistance (CLS-354/DX). The study of cytotoxicity showed that trienone 11 exerted threefold stronger cytotoxicity to CLS-354/DX cells than curcumin. Trienone 11 (15-30 μM) markedly induced intracellular reactive oxygen species (ROS) resulting in apoptotic cell death within 24 h, through activation of caspase-3/7 and caspase-9. A ROS inhibitor, N-acetylcysteine (NAC) prevented apoptotic cell death via decreasing caspase activation. Thus, the cytotoxicity of trienone 11 against CLS-354/DX cells was ROS-mediated intrinsic apoptosis. Overall, trienone 11 could be an interesting lead for developing anti-cancer agents against multidrug resistant OSCC cells.

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Section: Discussionmentioning

confidence: 99%

A trienone analog of curcumin, 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one, possesses ROS- and caspase-mediated apoptosis in human oral squamous cell carcinoma cells in vitro

et al. 2020

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“…The molecule looks like an "organic clip" [13,14]. The dihedral angles between N-phenylsulfonyl group and piperidone ring is 22.8(2)°.…”

Section: Commentmentioning

confidence: 99%

Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C₂₄H₁₈F₂N₂O₃S

Sun

Liu

et al. 2019

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Penelitian yang telah dilakukan oleh Thakur et al, (2014) menemukan bahwa senyawa kurkumin 3,5 bis (arilidiene)-4-piperidon monocarbonil memiliki aktivitas biologis, sebagai anti kanker. Selain itu juga telah ditemukan bahwa analog kurkumin N-acriloil/Ncinnamoil 3,5-bis(piridin-4-il) metilene-4piperidon memiliki aktivitas sebagai agen anti kanker (Paul et al, 2014) dan renoprotective (Trujillo, et al, 2013).…”

Section: Pendahuluanunclassified

Sintesis Dan Uji Toksisitas Senyawa Analog Kurkumin 3,5 Bis((e)-Metoksi Benziliden)-1-(2-Etil Asetat)-Piperidin-4-On

Aisyah¹,

Zamri²,

Teruna³

2018

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Curcumin analogs are secondary metabolites and belong to the phenolic group. These compounds have biological activities, such as anti-inflammatory, anticancer and antioxidant. This studies has successfully synthesized 3,5-bis ((E)-metoxy benzylidene) -1-(- 2-ethyl acetate) piperidine 4-one analog compound from 4-piperidone with 4-methoxy benzaldehyde by using reflux method. Compounds obtained in the form of yellow solids with yield 83.01%. The melting point was measured, identified by TLC then elucidated with UV-Vis, FT-IR, LC-MS, 1H NMR obtained results showed that the curcumin compound had a structure in accordance with the target molecule. The toxicity test using the BSLT method showed that the two compounds had LC50 values = 1.061μg / mL.

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Novel 3,5-bis(arylidiene)-4-piperidone based monocarbonyl analogs of curcumin: anticancer activity evaluation and mode of action study

Abstract: Piperidone-sulphonamide and curcumin based molecular hybrids were synthesised, which showed anti-cancer activity on 60 human tumor cell line panels and their inhibitory effect due to apoptosis.

Cited by 34 publications

References 43 publications

A trienone analog of curcumin, 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one, possesses ROS- and caspase-mediated apoptosis in human oral squamous cell carcinoma cells in vitro

A trienone analog of curcumin, 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one, possesses ROS- and caspase-mediated apoptosis in human oral squamous cell carcinoma cells in vitro

Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C₂₄H₁₈F₂N₂O₃S

Sintesis Dan Uji Toksisitas Senyawa Analog Kurkumin 3,5 Bis((e)-Metoksi Benziliden)-1-(2-Etil Asetat)-Piperidin-4-On

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Novel 3,5-bis(arylidiene)-4-piperidone based monocarbonyl analogs of curcumin: anticancer activity evaluation and mode of action study

Abstract: Piperidone-sulphonamide and curcumin based molecular hybrids were synthesised, which showed anti-cancer activity on 60 human tumor cell line panels and their inhibitory effect due to apoptosis.

Cited by 34 publications

References 43 publications

A trienone analog of curcumin, 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one, possesses ROS- and caspase-mediated apoptosis in human oral squamous cell carcinoma cells in vitro

A trienone analog of curcumin, 1,7-bis(3-hydroxyphenyl)-1,4,6-heptatrien-3-one, possesses ROS- and caspase-mediated apoptosis in human oral squamous cell carcinoma cells in vitro

Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S

Sintesis Dan Uji Toksisitas Senyawa Analog Kurkumin 3,5 Bis((e)-Metoksi Benziliden)-1-(2-Etil Asetat)-Piperidin-4-On

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Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C₂₄H₁₈F₂N₂O₃S