Synthesis, characterization, antioxidant, and anticancer studies of 6-[3-(4-chlorophenyl)-1H-pyrazol-4-yl]-3-[(2-naphthyloxy) methyl][1,2,4] triazolo[3,4-b][1,3,4]thiadiazole in HepG2 cell lines

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Abstract

Triazolo- thiadiazoles exhibit a variety of pharmacological properties, due to their cytotoxicity. In continuation of a previous study on triazolo-thiadiazoles, the authors have synthesized a new thiadiazole, 6-[3-(4-chlorophenyl)- 1-H-pyrazol-4-yl]-3-[(2-naphthyloxy)methyl] [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (CPNT), which was further characterized by advanced spectral techniques and elemental analysis. The compound exhibited a dose-dependent cytotoxic effect on hepatocellular carcinoma cell line, HepG2 with very low IC50 value of 0.8 μg/ml in 24 h when compared with standard drug, doxorubicin. Incorporation of [3H] thymidine in conjunction with cell cycle analysis suggested that CPNT inhibited the growth of HepG2 cells. Flow cytometric studies revealed more percentage of cells in subG1 phase, indicating apoptosis, which was further confirmed through chromatin condensation studies by Hoechst staining. In vitro antioxidant activity of CPNT was determined by DPPH and ABTS free radical scavenging assays which revealed increasing scavenging activity with increasing concentration of the compound when compared with reference ascorbic acid.

Original languageEnglish
Pages (from-to)1074-1080
Number of pages7
JournalMedicinal Chemistry Research
Volume20
Issue number7
DOIs
Publication statusPublished - 09-2011

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Thiadiazoles
Hep G2 Cells
Antioxidants
Scavenging
Cells
Cell Line
Cytotoxicity
Doxorubicin
Thymidine
Ascorbic Acid
Inhibitory Concentration 50
Chromatin
Free Radicals
Condensation
Hepatocellular Carcinoma
Assays
Cell Cycle
Pharmacology
Apoptosis
Staining and Labeling

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

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title = "Synthesis, characterization, antioxidant, and anticancer studies of 6-[3-(4-chlorophenyl)-1H-pyrazol-4-yl]-3-[(2-naphthyloxy) methyl][1,2,4] triazolo[3,4-b][1,3,4]thiadiazole in HepG2 cell lines",
abstract = "Triazolo- thiadiazoles exhibit a variety of pharmacological properties, due to their cytotoxicity. In continuation of a previous study on triazolo-thiadiazoles, the authors have synthesized a new thiadiazole, 6-[3-(4-chlorophenyl)- 1-H-pyrazol-4-yl]-3-[(2-naphthyloxy)methyl] [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (CPNT), which was further characterized by advanced spectral techniques and elemental analysis. The compound exhibited a dose-dependent cytotoxic effect on hepatocellular carcinoma cell line, HepG2 with very low IC50 value of 0.8 μg/ml in 24 h when compared with standard drug, doxorubicin. Incorporation of [3H] thymidine in conjunction with cell cycle analysis suggested that CPNT inhibited the growth of HepG2 cells. Flow cytometric studies revealed more percentage of cells in subG1 phase, indicating apoptosis, which was further confirmed through chromatin condensation studies by Hoechst staining. In vitro antioxidant activity of CPNT was determined by DPPH and ABTS free radical scavenging assays which revealed increasing scavenging activity with increasing concentration of the compound when compared with reference ascorbic acid.",
author = "Dhanya Sunil and Isloor, {Arun M.} and Prakash Shetty and K. Satyamoorthy and Prasad, {A. S Bharath}",
year = "2011",
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T1 - Synthesis, characterization, antioxidant, and anticancer studies of 6-[3-(4-chlorophenyl)-1H-pyrazol-4-yl]-3-[(2-naphthyloxy) methyl][1,2,4] triazolo[3,4-b][1,3,4]thiadiazole in HepG2 cell lines

AU - Sunil, Dhanya

AU - Isloor, Arun M.

AU - Shetty, Prakash

AU - Satyamoorthy, K.

AU - Prasad, A. S Bharath

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AB - Triazolo- thiadiazoles exhibit a variety of pharmacological properties, due to their cytotoxicity. In continuation of a previous study on triazolo-thiadiazoles, the authors have synthesized a new thiadiazole, 6-[3-(4-chlorophenyl)- 1-H-pyrazol-4-yl]-3-[(2-naphthyloxy)methyl] [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (CPNT), which was further characterized by advanced spectral techniques and elemental analysis. The compound exhibited a dose-dependent cytotoxic effect on hepatocellular carcinoma cell line, HepG2 with very low IC50 value of 0.8 μg/ml in 24 h when compared with standard drug, doxorubicin. Incorporation of [3H] thymidine in conjunction with cell cycle analysis suggested that CPNT inhibited the growth of HepG2 cells. Flow cytometric studies revealed more percentage of cells in subG1 phase, indicating apoptosis, which was further confirmed through chromatin condensation studies by Hoechst staining. In vitro antioxidant activity of CPNT was determined by DPPH and ABTS free radical scavenging assays which revealed increasing scavenging activity with increasing concentration of the compound when compared with reference ascorbic acid.

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