Synthesis and anticancer activity of new azo compounds containing extended π-conjugated systems

Rezaei‐Seresht, Esmail; Mireskandari, Erfan; Kheirabadi, Mitra; Cheshomi, Hamid; Rezaei-Seresht, Hasan; Aldaghi, Leila Sadat

doi:10.1007/s11696-017-0140-9

Cited by 12 publications

(6 citation statements)

References 26 publications

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“…As a result of this analysis, it was determined that GA decreased MCF-7 cell viability. However, the effect of GA on MCF-7 cells at 48 and 72h has been reported to be similar to the study by Rezaei-Seresht et al, (2019) our findings showed that the cytotoxic effect of GA on C6 glioma cells was similar at 48 and 72h. Therefore, our findings indicated that as in other cell lines, GA could efficiently inhibit the proliferation of C6 glioma cells depending on the concentration and/or the duration of treatment.…”

Section: Discussionsupporting

confidence: 91%

Untitled

2023

Pak. J. Pharm. Sci.,

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In our study, the effects of gallic acid (GA), a natural therapeutic agent, on oxidative stress biomarkers and MMP-2 and MMP-9 expressions via the p38/JNK pathway in C6 glioma cells were investigated. The toxicity of GA was determined by the WST-1 method. JNK, p38 and MMP-2/-9 mRNA expressions in the cell line were detected by RT-qPCR. JNK/SAPK, Grap-2/p38 and MMP-2/-9 protein levels were analyzed by using ELISA methods. Biochemical markers were analyzed. GA reduced the cell viability of C6 glioma cells after 24, 48 and 72h of treatment. The expression levels of MMP-2 and MMP-9 mRNA decreased in C6 glioma cells treated with 150µg/ml GA for 24 and 48h compared to the control cells. Unlike SOD activity, GA treatment significantly increased PCO and MDA levels in the cells treated with 150μg/ml GA for 24 and 48h compared to the non-treated cells. According to our results, GA inhibited the proliferation of C6 glioma cells. Also, it reduced MMP-2 and MMP-9 expressions and increase oxidative stress. Therefore, GA may have preventive effects on gliomas progression and/or invasion.

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Section: Discussionsupporting

confidence: 91%

Untitled

2023

Pak. J. Pharm. Sci.,

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“…According to the good biocompatibility of the investigated dyes and the potential for anticancer activity of compounds with similar structure shown in literature, 41 the antiproliferative activity of the investigated dyes against cancer cell lines HCT-116 and MDA-MB-231 has been tested. 40 The assessment of the in vitro antiproliferative activity of the dyes against the human breast cancer MD-MB-231 cell line was performed, and the results are presented in Figure 6.…”

Section: Antiproliferative Activitymentioning

confidence: 99%

Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties

Mijin¹,

Nedeljković²,

Božić³

et al. 2018

Turk J Chem

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New azo dyes bearing 2-pyridone and benzimidazole moieties were prepared using diazotization of 4-(1Hbenzo[d]imidazol-2-yl)aniline and coupling of the obtained diazonium salt with substituted 3-cyano-2-pyridones. Obtained compounds were characterized via UV-Vis, FT-IR, and 1 H and 13 C NMR spectroscopy as well as by elemental analysis data. The UV-Vis spectra of the synthesized dyes were measured in thirteen solvents of different properties at room temperature. Solvatochromism and tautomerism of novel azo dyes were discussed. An MTT (3,4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) test was performed to prove the biocompatibility of the investigated dyes. The investigated dyes exhibited satisfying antiproliferative activities against both tumor cell lines, MDA-MB-231 and HCT-116, demonstrating the potent capacity for treatment of tumors.

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“…Ferulic acid and coumaric acid are low molecular phenolic acids with antioxidant and antimicrobial properties [13]. MCF-7 cells from humans with breast cancer are cytotoxic to gallic acid and caffeic acid, inducing apoptosis [15]. Koetjapic acid, a phenolic acid found in the bark of Sandoricum koetjape, has anticarcinogenic properties [12].…”

Section: Introductionmentioning

confidence: 99%

Seven types of phenolic acid and inhibitory activity for protein tyrosine phosphatase 1B (PTP1B) from the stem of Sandoricum koetjape

Saadah,

Tulandi,

Rohman

2023

IOP Conf. Ser.: Earth Environ. Sci.

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Sandoricum koetjapehas been traditionally used in Indonesian medicine for generations. The stem was used as a remedy for helminthiasis, sneezing, stomachache, indigestion, abdominal pain, leucorrhea, colic, and fever in Indonesia. The purpose of this study was to identify the phenolic acids found in the stem ofS. koetjapeand to test their ability to inhibit the protein tyrosine phosphatase 1B (PTP1B). P-coumaric acid, caffeic acid, ferulic acid, chlorogenic acid, syringic acid, 4-hydroxybenzoic acid, and gallic acid were identified as phenolic acids found in theS. koetjapestem. The interaction of phenolic acids with the PTP1B was predicted using molecular docking. PTP1B has been linked to diabetes, obesity, tumors, and Alzheimer’s. The autodock 4.2 program, which is integrated with the pyrx v.09.8 virtual screening tool, was used to conduct the docking studies. Interacting between p-coumaric acid with PTP1-B on amino acids Glu115, Lys116, Lys120, Cys215, Ala217, Gly218, Ile219, Gly220, and Arg221. P-coumaric acid fulfills Lipinski’s rule and therefore can be taken orally. P-coumaric acid is expected to have a high oral bioavailability in humans, great absorption in the intestine, and an equivalent distribution in blood plasma and intestine. P-coumaric acid’s acute toxicity is also expected to be low. P-coumaric acid is also non-toxic to the liver, immune system, mutagenic, and cytotoxic.Sandoricum koetjapephenolic acids, particularly p-coumaric acid, appeared to be an effective PTP1-B inhibitor based on docking results.

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Synthesis and anticancer activity of new azo compounds containing extended π-conjugated systems

Cited by 12 publications

References 26 publications

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Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties

Seven types of phenolic acid and inhibitory activity for protein tyrosine phosphatase 1B (PTP1B) from the stem of Sandoricum koetjape

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