Synthesis of Tolmetin Hydrazide–Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Cells

Küçükgüzel, Ş. Güniz; Koç, Derya; Çıkla-Süzgün, Pelin; Özsavcı, Derya; Özakpınar, Özlem Bingöl; Mega-Tiber, Pınar; Orun, Oya; Erzincan, Pınar; Sağ-Erdem, Safiye; Şahın, Fikrettin

doi:10.1002/ardp.201500178

Cited by 43 publications

(36 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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

jrp

View full text Add to dashboard Cite

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.

show abstract

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

jrp

View full text Add to dashboard Cite

show abstract

“…13 C-NMR spectrum data of compound 4d 16 C-NMR spectrum data of compound 4d The results revealed that tolmetin hydrazone showed anticancer activity againts HT-29 colon cancer cell line (dose depended) with IC 50 value of 76 µM. Tolmetin hydrazone was then used in further tests to investigate the apoptotic effect on HT-29 cancer cell line.…”

Section: Figmentioning

confidence: 99%

“…Metastat (Col-3), minocyclin and doxycycline are the examples of these inhibitors (34). Küçükgüzel and co-workers (16) synthesized N'-[(2,6-dichlorophenyl)methyliden]-2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetohydrazide and found activity againts HT-29 colon cancer cell line with IC 50 value of 76 µM. This information showed, against colon cancer cell line anticancer activiy of tolmetin maintains whereas the thiosemicarbazide molecule from the same compound have no activity againts colon cancer, instead, it shows activity againts prostate cancer cells.…”

Section: Figmentioning

confidence: 99%

Synthesis and Anticancer Activity of Tolmetin Thiosemicarbazides

Dadas¹,

Coşkun²,

Bingöl-Ozakpinar³

et al. 2015

Marmara Pharm J

Self Cite

View full text Add to dashboard Cite

show abstract

“…Briely, cells were seeded into 96-well plates (10 4 cells/well) and incubated at 37°C in CO 2 incubator for 24 h. The next day, appropriate doses of drug were added and cells were further incubated for 24 or 48 h. MTT of 10 μL was added to each well for an additional 4 h. The precipitated formazan was dissolved in 100 μL of 10% SDS, and the absorbance was taken at 570 nm [38].…”

Section: Cell Viability Assaymentioning

confidence: 99%

Apoptotic Effects of Etodolac in Breast Cancer Cell Cultures

Orun¹,

Tiber²,

Sevinç³

2017

Nonsteroidal Anti-Inflammatory Drugs

Self Cite

View full text Add to dashboard Cite

Nonsteroidal anti-inlammatory drugs (NSAIDs) are commonly used as anti-inlammatory and analgesic agents. This family of drugs suppresses prostaglandin synthesis through inhibition of cyclooxygenase (COX) enzymes. Recent studies displayed that anti-carcinogenic actions of these drugs are mediated by COX-2 enzyme. Currently, there is intense research on COX-2 inhibitors as therapeutic targets. Etodolac is not perfectly selective but shows 'preferential selectivity' for COX-2. Here, in this study, we wanted to take gene expression snapshots of several apoptotic proteins under diferent conditions of drug exposure. The aim, therefore, focused to determine diferential efects of etodolac on the regulation of apoptotic genes in hormone-responsive MCF-7 and triple-negative MDA-MB-231 cancer cell lines. Our data suggest that MDA-MB-231 is more responsive to etodolac exposure. Cell proliferation and apoptosis consistently regulated upon drug addiction. Furthermore, COX-2/HER2 was explicitly an up-regulated, phosphorylated form of Bad accumulated and anti-apoptotic proteins SAG and survivin increased in both transcriptional and translational levels. Changes in mitochondrial Bcl-2 family proteins were moderate and pro-and anti-apoptotic proteins showed similar levels of regulation in both cell lines. We believe that these indings would be supportive for future studies targeting etodolac-based therapies, as it reveals apoptotic factors diferentially regulated in hormone-responsive and invasive cell lines.Keywords: apoptosis, MCF-7, MDA-MB-231, MTT, Bad, SAG © 2017 The Author(s). Licensee InTech. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. IntroductionNonsteroidal anti-inlammatory drugs (NSAIDs), regularly used for their anti-inlammatory and analgesic efects, were shown to have potency for cancer prevention as well [1,2]. This family of drugs suppresses prostaglandin synthesis through inhibition of cyclooxygenase (COX) enzymes. COX enzymes have two isoforms COX-1 and COX-2, with a recent addition of a splice variant of COX-1, COX-3, which is not functional in humans. COX-1 is commonly expressed in body, showing constitutive activation. COX-2, on the other hand, is hardly detectable in normal conditions but is induced upon stimulation by mitogenic agents, cytokines, growth factors, and so on. Later reports, however, demonstrated that COX-2 is also constitutively expressed in basal levels at several tissues including gastric mucosa, developing brain or kidney [3][4][5].COX isoforms catalyse prostaglandin G/H (PGG2/PGH2) synthesis from arachidonic acid, and these prostaglandins are then converted to stable forms like PGD2, PGE2, PGF2, prostacyclin (PGI2) or thromboxane A2 (TXA2) depending on the cell type. Inhibition of COX enzymes, therefore, could result in improper prostaglandin activity, which in turn may ca...

show abstract

Synthesis of Tolmetin Hydrazide–Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Cells

Cited by 43 publications

References 47 publications

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

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

Synthesis and Anticancer Activity of Tolmetin Thiosemicarbazides

Apoptotic Effects of Etodolac in Breast Cancer Cell Cultures

Contact Info

Product

Resources

About