Anti-cancer and anti-hepatitis C virus NS5B polymerase activity of etodolac 1,2,4-triazoles

Çıkla-Süzgün, Pelin; Kaushik‐Basu, Neerja; Basu, Amartya; Arora, Payal; Talele, Tanaji T.; Durmaz, İrem; Çetin-Atalay, Rengül; Küçükgüzel, Ş. Güniz

doi:10.3109/14756366.2014.971780

Cited by 27 publications

(15 citation statements)

References 26 publications

(36 reference statements)

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“…In order to determine the potential anticancer activity of the obtained diflunisal hydrazide hydrazone 3b and diflunisal, we evaluated their cytotoxic activity on liver cancer cell lines (Huh7, HepG2, Hep3B, Mahlavu, FOCUS and SNU-475) with the sulforhodamine B assay (2.5e40 mM) for 72 h as described before [25] Table 1 Anti-HCV activity of diflunisal hydrazideehydrazones (3a-t).…”

Section: Anticancer Activity Of Compound 3b Against Liver Cancer Cellmentioning

confidence: 99%

Synthesis of novel diflunisal hydrazide–hydrazones as anti-hepatitis C virus agents and hepatocellular carcinoma inhibitors

Şenkardeş

Kaushik‐Basu

Durmaz

et al. 2016

European Journal of Medicinal Chemistry

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a b s t r a c tHepatitis C virus (HCV) infection is a main cause of chronic liver disease, leading to liver cirrhosis and hepatocellular carcinoma (HCC). The objective of our research was to develop effective agents against viral replication. We have previously identified the hydrazideehydrazone scaffold as a promising hepatitis C virus (HCV) and hepatocelluler inhibitor. Herein we describe the design a number of 2 0 ,4 0 -difluoro-4-hydroxy-N'-(arylmethylidene) biphenyl-3-carbohydrazide (3a-t) as anti-HCV and anticancer agents. Results from evaluation of anti-HCV activity indicated that most of the synthesized hydrazone derivatives inhibited viral replication in the Huh7/Rep-Feo1b and Huh 7.5-FGR-JCI-Rluc2A reporter systems. Antiproliferative activities of increasing concentrations of 2 0 ,4 0 -difluoro-4-hydroxy-N'-(2-pyridyl methylidene)biphenyl-3-carbohydrazide 3b and diflunisal (2.5e40 mM) were assessed in liver cancer cell lines (Huh7, HepG2, Hep3B, Mahlavu, FOCUS and SNU-475) with sulforhodamine B assay for 72 h. Compound 3b with 2-pyridinyl group in the hydrazone part exhibited promising cytotoxic activity against all cell lines with IC 50 values of 10, 10.34 16.21 4.74, 9.29 and 8.33 mM for Huh7, HepG2, Hep3B, Mahlavu, FOCUS and SNU-475 cells, respectively, and produced dramatic cell cycle arrest at SubG1/G0 phase as an indicator of apoptotic cell death induction.

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Section: Anticancer Activity Of Compound 3b Against Liver Cancer Cellmentioning

confidence: 99%

Synthesis of novel diflunisal hydrazide–hydrazones as anti-hepatitis C virus agents and hepatocellular carcinoma inhibitors

Şenkardeş

Kaushik‐Basu

Durmaz

et al. 2016

European Journal of Medicinal Chemistry

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“…As well as other NSAIDs, naproxen was reported to be efficient in the prevention of many cancers [3][4][5]. Hydrazide-hydrazones [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and 1,2,4-triazole rings [22][23][24][25][26] have diverse biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Han¹,

Bekçi²,

Cumaoğlu³

et al. 2018

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How to cite this article: Han M, Bekçi H, Cumaoğlu A, Küçükgüzel ŞG. Synthesis and characterization of 1,2,4-triazole containing hydrazidehydrazones derived from (S)-Naproxen as anticancer agents. Marmara Pharm J. 2018; 22 (4): 559-569. ABSTRACT: A novel series of new naproxen derivativeswere synthesized, in this study. The structures of compounds 5, 6 and 7a-m were defined by spectral ( 1 H-NMR, 13 C-NMR, HR-MS and FT-IR) methods and their purity was proven by elemental analysis, thin layer chromatography and high pressure liquid chromatography. These compounds were evaluated for in vitro anticancer activity by using MTS method against PC-3 and DU-143 (androgen-independent human prostate cancer cell lines) and LNCaP (androgen-sensitive human prostate adenocarcinoma) prostate cancer cell lines. Cisplatin was used as the positive sensitivity reference standard. Compounds (7a-m) exhibited anticancer activity with IC50 values of 87.2-400 µM against prostate cancer cell lines.

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“…This was dissolved in water and acidified with hydrochloric acid (HCl) solution (10%). The precipitate was washed with water and recrystallized from ethanol …”

Section: Methodsmentioning

confidence: 99%

“…Etodolac, ( R , S )‐2‐[1,8‐diethyl‐1,3,4‐tetrahydropyrano[3,4‐ b ]indole‐1‐yl]acetic acid, is a non‐steroidal anti‐inflammatory drug which has anticancer activities reported in the literature . In addition, etodolac hydrazones, thiosemicarbazides, 1,2,4‐triazoles, 1,2,3‐triazoles, and 4‐thiazolidinones have been reported to have anticancer effect and to be hepatitis C NS5B polymerase inhibitors. Etodolac have tetrahydropyrano group.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, anticancer activity, and molecular modeling of etodolac‐thioether derivatives as potent methionine aminopeptidase (type II) inhibitors

Çoruh

Çevik

Yelekçi

et al. 2018

Archiv der Pharmazie

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A series of (R,S)-1-{[5-(substituted)sulfanyl-4-substituted-4H-1,2,4-triazole-3-yl]methyl}-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indoles (5a-v) were designed and synthesized using a five-step synthetic protocol that involves substituted benzyl chlorides and (R,S)-5-[(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-yl)methyl]-4-substituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones in the final step. The synthesized derivatives were evaluated for cytotoxicity and anticancer activity in vitro using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) colorimetric method against VERO, HEPG2 (human hepatocellular liver carcinoma), SKOV3 (ovarian carcinoma), MCF7 (human breast adenocarcinoma), PC3 and DU145 (prostate carcinoma) cells at 10 M (10 μM) for 24 h. Compounds 5d and 5h showed the best biological potency against the SKOV3 cancer cell line (IC = 7.22 and 5.10 μM, respectively) and did not display cytotoxicity toward VERO cells compared to etodolac. Compounds 5k, 5s, and 5v showed the most potent biological activity against the PC3 cancer cell line (IC = 8.18, 3.10, and 4.00 μM, respectively) and did not display cytotoxicity. Moreover, these compounds were evaluated for caspase-3, -9, and -8 protein expression and activation in the apoptosis pathway for 6, 12, and 24 h, which play a key role in the treatment of cancer. In this study, we also investigated the apoptotic mechanism and molecular modeling of compounds 5k and 5v on the methionine aminopeptidase (type II) enzyme active site in order to get insights into the binding mode and energy.

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Anti-cancer and anti-hepatitis C virus NS5B polymerase activity of etodolac 1,2,4-triazoles

Cited by 27 publications

References 26 publications

Synthesis of novel diflunisal hydrazide–hydrazones as anti-hepatitis C virus agents and hepatocellular carcinoma inhibitors

Synthesis of novel diflunisal hydrazide–hydrazones as anti-hepatitis C virus agents and hepatocellular carcinoma inhibitors

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Synthesis, anticancer activity, and molecular modeling of etodolac‐thioether derivatives as potent methionine aminopeptidase (type II) inhibitors

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