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(2E)-2-Benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401), a novel arylidene indanone derivative, scavenges free radicals and exhibits antiproliferative activity of Jurkat cells

Prasanna Rajagopalan
Prasanna Rajagopalan
 y 
Harish C. Chandramoorthy
Harish C. Chandramoorthy
   | 31 mar 2020
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Article Category: Original article
Publicado en línea: 31 mar 2020
Páginas: 131 - 139
DOI: https://doi.org/10.1515/abm-2019-0052
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© 2019 Prasanna Rajagopalan et al., published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Figure 1

Chemical structure of (2E)-2-benzylidene-4,7-dimethyl-2,3-di-hydro-1H-inden-1-one (MLT-401) (C18H16O), molecular weight 248.32
Chemical structure of (2E)-2-benzylidene-4,7-dimethyl-2,3-di-hydro-1H-inden-1-one (MLT-401) (C18H16O), molecular weight 248.32

Figure 2

Antioxidant profile of (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401). IC50 values of the compound for antioxidant properties by (A) DPPH assay 1611 nM, (B) ABTS assay 2115 nM, and (C) FRAP assay 1586 nM
Antioxidant profile of (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401). IC50 values of the compound for antioxidant properties by (A) DPPH assay 1611 nM, (B) ABTS assay 2115 nM, and (C) FRAP assay 1586 nM

Figure 3

(A) GI50 of (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401) in Jurkat cells (341.4 nM), primary lymphocytes (4126 nM), and Vero cells (3185 nM) showing antiproliferative effects by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. (B) Fold difference in antiproliferative efficacy by MLT-401 between cancer and normal cells was tested. **P < 0.01
(A) GI50 of (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401) in Jurkat cells (341.4 nM), primary lymphocytes (4126 nM), and Vero cells (3185 nM) showing antiproliferative effects by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. (B) Fold difference in antiproliferative efficacy by MLT-401 between cancer and normal cells was tested. **P < 0.01

Figure 4

Cellular profile after treatment with 350 nM (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401). (A) Agarose (1.6%) gel electrophoresis reflecting the presence of DNA fragments on treatment for 0, 24, and 48 h. DNA Molecular Weight Marker III (0.12–21.2 kbp) (Roche, Cat. No. 10 528 552 001) was used in the fragmentation assay. Base pair sizes (ML or marker ladder) are indicated in the Figure. DNA was stained with 0.5 μg/mL of ethidium bromide, and visualized at 302 nm (B) Cell cycle changes in Jurkat cells at different times after MLT-401 treatment. Jurkat cells were treated with MLT-401 for 24, 48, and 72 h, and untreated controls were incubated for the same times. Cells were collected after the incubation period, stained with Guava Cell Cycle analysis reagent, and analyzed in a Guava easyCyte flow cytometer to determine the percentage of cells in different phases of the cell cycle. An increase of cells in the sub-G0/G1 phase was observed with the increase in time of MLT-401 treatment
Cellular profile after treatment with 350 nM (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401). (A) Agarose (1.6%) gel electrophoresis reflecting the presence of DNA fragments on treatment for 0, 24, and 48 h. DNA Molecular Weight Marker III (0.12–21.2 kbp) (Roche, Cat. No. 10 528 552 001) was used in the fragmentation assay. Base pair sizes (ML or marker ladder) are indicated in the Figure. DNA was stained with 0.5 μg/mL of ethidium bromide, and visualized at 302 nm (B) Cell cycle changes in Jurkat cells at different times after MLT-401 treatment. Jurkat cells were treated with MLT-401 for 24, 48, and 72 h, and untreated controls were incubated for the same times. Cells were collected after the incubation period, stained with Guava Cell Cycle analysis reagent, and analyzed in a Guava easyCyte flow cytometer to determine the percentage of cells in different phases of the cell cycle. An increase of cells in the sub-G0/G1 phase was observed with the increase in time of MLT-401 treatment

Figure 5

The levels of mitochondrial membrane-bound enzyme activities in Jurkat cells treated with 350 nM (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401) at end of 24, 48, and 72 h treatment. (A) Na+/K+ ATPase activity, (B) Ca2+ ATPase activity, and (C) Mg2+ ATPase activity. Data represent mean ± standard deviation of 3 individual experiments performed in triplicate. *P < 0.05
The levels of mitochondrial membrane-bound enzyme activities in Jurkat cells treated with 350 nM (2E)-2-benzylidene-4,7-dimethyl-2,3-dihydro-1H-inden-1-one (MLT-401) at end of 24, 48, and 72 h treatment. (A) Na+/K+ ATPase activity, (B) Ca2+ ATPase activity, and (C) Mg2+ ATPase activity. Data represent mean ± standard deviation of 3 individual experiments performed in triplicate. *P < 0.05
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