Chemicals
MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide), rotenone (Rot), 4-2-hydroxyethyl-1-piperazineethanesulfonic acid (HEPES), dimethyl sulfoxide (DMSO), cyclosporin A (Cs.A), D-mannitol, dithiobis-2-nitrobenzoic acid (DTNB), thiobarbituric acid (TBA), 2′,7′-dichlorofluorescein diacetate (DCFH-DA), tetramethoxypropane (TEP), reduced glutathione (GSH), sodium succinate, malondialdehyde (MDA), Tris–HCl, n-butanol, sulfuric acid, pyruvate, malate, sucrose, ethylene glycol-bis (2-aminoethylether)- N,N,N′,N′-tetraacetic acid (EGTA), KCl, Na2HPO4, collagenase, MgCl2, potassium phosphate, butylated hydroxytoluene (BHT), ethylene ediamine tetra acetic acid (EDTA), rhodamine 123 (Rh 123), Bovine serum albumin (BSA), and coomassie blue were purchased from Sigma Chemical Co. (St. Louis, MO, USA).
Chemistry
The synthesis of target compound 1-Ferrocenyl-3-(dimethylamino)-3-(4-methylsulfonylphenyl) propan-1-one was accomplished by our previously published method (
19). In our previous study, this compound having ferrocene motif and methyl sulfonyl COX-2 pharmacophore showed high potency for COX-2 inhibitory and cytotoxicity effects.
Experimental data
1-Ferrocenyl-3-(dimethylamino)-3-(4-methylsulfonylphenyl) propan-1-one
The mixture of α, β-unsaturated carbonyl compound (2 mmol) and dimethylamine (2 mmol) was added to a flask immersed in the water bath of an ultrasonic cleaner room temperature controlled by circulated water for 6 hours. After completing the reaction, the crude product was washed with petroleum ether to remove the excess of amines, and a few unreacted α, β -unsaturated carbonyl compounds, and the final product was purified by crystallization (10% EtOAc in light petroleum ether).
Red solid; decomp: 153 °C; IR (KBr): 1652 (C=O), 1311, 1152 (SO2); LC-MS (ESI) m/z: 440 (M+ + 1); H1NMR (CDCl3): 2.23 (s, 6H, N-CH3), 2.99 (s, 3H, SO2CH3), 3.15 (m, 1H, CH2), 3.33 (m, 1H, CH2), 4.02 (s, 5H, Fc), 4.15 (bs, 1H, CH), 4.48 (s, 2H, Fc), 4.72 (s, 2H, Fc), 7.58 (d, 2H, 4-methylsulfonylphenyl H3 & H5, J = 7.9 Hz), 7.91 (d, 2H, 4-methylsulfonyl phenyl H2 & H6, J = 7.9 Hz); C13 (CDCl3): 42.9, 43.4, 44.5, 65.1 (aliphatic), 69.2, 69.2 (ortho – C5H4), 69.7 (C5H5), 72.4, 72.4 (meta – C5H4), 78.8 (ipso – C5H4), 127.3, 129.4, 139.4, 147.3 (aromatic), 201.4 (C=O); Anal. Calculated for C22H25FeNO3S: C, 60.14; H, 5.74; N, 3.19. Found: C, 60.34; H, 5.96; N, 3.01.
Melanoma Tumor Preparation
Melanoma was inoculated intra dermally in NMRI adult mice with F10 melanoma cells. Briefly, the mice were anesthetized by a combination of xylazine and ketamine administered via intraperitoneal (i.p.) injections and then using a scalpel. The cells were placed underneath the skin, and after all these parts were sutured. The tumor size was measured every 3 days with a digital caliper. Their volume calculated based on O’reilly
et al. (1997) as follows: 52 v= (tumor weights) 2 (tumor length) 0.52. In the posterolateral part of the body, a small incision was done, and a part of the tumor was extracted and divided into small parts (about 2 mm each). The melanoma and tissues were immediately put into ice-cold RPMI-1640 supplemented with 100 U/mL penicillin G and 100 µg/mL streptomycin. Then, the samples were rinsed with sterile phosphate-buffered saline (PBS) twice and cut into small fragments. Then, the fragments were incubated with a collagenase of 1% in a gently shaking water bath for one h at 37 °C. After passed through a 38 µm mesh sieve, the resulting cell suspension was washed twice and centrifugated at a speed of 300 g × 10 min. Then the pellet was diluted to 1 × 10
6 cells/mL and incubated in RPMI 1640 containing supplemented with 10% FBS, in 37 °C with 5% CO
2 (
20).
Cell treatments
Melanoma cells and normal fibroblast (106 cells) were cultured in RPMI 1640 medium supplemented with 10% FBS at 37 °C with 5% CO2 in a humidified atmosphere for 12 h. FDMPO was freshly prepared before use and dissolved in DMSO 0.05%. Melanoma cells and normal fibroblast were incubated with or without the treatment of FDMPO (0, 5, 10, 25, 50 and 100 µM) and DMSO 0.05% as control, and all toxicity parameters were evaluated after 12 h.
Cytotoxicity Assay
Melanoma cells and normal fibroblast (10
4 cells/well) were exposed to various concentrations of FDMPO (0, 5, 10, 25, 50, and 100 µM). Cell viability at 12 h was determined by MTT with final concentration of 0.5 mg/mL. After 4 h of exposure by adding 100 µL DMSO, the purple-blue MTT formazan precipitate was dissolved, and the absorbance was measured at 570 nm using an enzyme-linked immunosorbent assay (ELISA) reader (Tecan, Rainbow hermo, Austria) (
21).
Caspase 3 Activity
Caspase-3 colorimetric assay kit (R&D Systems Inc., Minneapolis, MN, United States) was used to measure the caspase activity in the cell lysates. Melanoma cells and normal fibroblast were exposed to IC50 12 h of FDMPO (50 µM). After treatment, the cells were lysed in a buffer mixture (50 mM Tris-HCl (pH 7.4), 2 mM DTT, 1 mM EDTA, 10 mM digitonin, and 10 mM EGTA). The activation of caspase 3 was estimated by the hydrolysis of substrate peptide, Ac-DEVD-pNA to p-nitroaniline, by caspase 3. p-nitroaniline has a high absorbance at 405 nm. The absorbance was p-nitroaniline measured using an ELISA reader (Tecan, Rainbow hermo, Austria) at 405 nm. Three independent experiments were run for caspase-3 activity determination (
21).
Apoptosis versus Necrosis
Apoptosis was identified using Annexin V-FITC Apoptosis Kit (K101 BioVision, USA). Briefly, cells were treated with IC50 of FDMPO. After 12 h, the cells were re-suspended in the 500 μL binding buffer. FITC-conjugated annexin V and PI were added, and after 5 min incubation, samples were analyzed on a flow cytometer (Cyflow Space-Partec, Germany).
Preparation of Mitochondria
The melanoma and normal tissues were dissected and cut into slices (1 mm) using surgical scissors and cleared from blood vessels, and homogenized with a glass homogenizer in a 10-fold volume of the isolation buffer (225 mM D-mannitol, 75 mM sucrose, and 0.2 mM EDTA, pH 7.4) in an ice-cold bath. The homogenate was centrifuged at 1000 ×g for 10 min, and the pellet was removed. The supernatant containing mitochondria was centrifuged at 10000 ×g for 10 min at 4 °C. The protein content in mitochondria was determined using the Bradford assay was determined (22). Protein concentration in the suspension was 1000 µg/mL. The number of mitochondria for each test was 1000 µg/mL. The isolated mitochondria from both groups were treated with various concentrations of FDMPO (0, 5, 10, 25, 50, and 100 µM) for the assessment of succinate dehydrogenases activity, and for the other testes were exposed with ½ IC50, IC50, and 2IC50 at 37 °C for 1 h.
Succinate Dehydrogenases Activity
The activity of succinate dehydrogenases or SDH (mitochondrial complex II) was measured by the reduction of MTT. Briefly, 100 µL of mitochondrial suspensions (containing 100 µg protein mitochondria, 70 mM sucrose, 230 mM mannitol, 3 mM HEPES, 2 mM Tris-phosphate, 5 mM succinate, and 1 µM of rotenone with pH 7.4.) was incubated with various concentrations of FDMPO (0, 5, 10, 25, 50 and 100 µM) at 37 °C for 1hr. Then, 25 µL of 0.4% MTT was added to the medium at 37 °C for 30 min. The product of formazan crystals was dissolved in 100 µL DMSO, and the absorbance at 570 nm was measured with an ELISA reader (Tecan, Rainbow hermo, Austria (
23).
Mitochondrial Swelling Assay
Mitochondrial swelling was monitored as the changes in absorbance at 540 nm. Incubations with various concentrations of FDMPO (25, 50, and 100 µM) were carried out at 37 °C with 100 µg of mitochondrial protein/mL in the swelling buffer containing 70 mM sucrose, 230 mM mannitol, 3 mM HEPES, 2 mM Tris-phosphate, 5 mM succinate and 1 µM of rotenone with pH 7.4. Mitochondrial swelling was measured spectrophotometrically in 60 min (15, 30, 45, and 60 min). Mitochondrial swelling results in a decrease in absorbance monitored at 540 nm (
23).
Mitochondrial ROS Formation Assay
Briefly, purified mitochondria (1000 µg protein/mL) were isolated and were placed in respiration buffer (0.32 mM sucrose, 10 mM Tris, 20 mM Mops, 50 μM EGTA, 0.5 mM MgCl
2, 0.1 mM KH
2PO
4 and 5 mM sodium succinate 10 µM DCFH-DA with pH 7.4) with various concentrations of FDMPO (25, 50 and 100 µM). Fluorescence intensity of DCFH-DA was measured using fluorescence spectrofluorometer at an excitation/emission wavelength 488 nm and 527 nm in duration 60 min (15, 30, 45, and 60 min) (
23).
Mitochondrial MMP Collapse Assay
Briefly, the mitochondrial fractions (1000 µg protein/mL) were incubated with various concentrations of FDMPO (25, 50, and 100 µM) in MMP assay buffer (220 mM sucrose, 68 mM D-mannitol, 10 mM KCl, 5mM KH
2PO
4, 2 mM MgCl
2, 50 μM EGTA, 5 mM sodium succinate, 10 mM HEPES, 2 μM Rotenone, 10 µM rhodamine 123), at 37 ºC for an hour. The fluorescence was monitored using spectrofluorometer at the excitation and emission wavelength of 490 nm and 535 nm, respectively, in 60 min (15, 30, 45 and 60 min) (
23).
Cytochrome c Release Assay
Isolated mitochondria were incubated in 1.5-mL Eppendorf tubes within buffer assay (140 mM KCl, 10 mM NaCl, 2 mM MgCl
2, 0.5 mM KH
2PO
4, 20 mM HEPES, 0.5 mM EGTA; pH 7.2). Inhibitor of MPT pore, cyclosporine A at the final concentration 5 µM and anti-oxidant BHT at the final concentration 5 µM were added 15 min before the addition of FDMPO (IC50). After an hour, the tubes were centrifuged at 10,000 g × 10 min. The supernatant contained the cytochrome c released from the mitochondria (cytosolic fraction), and the pellet consisted of the mitochondrial fraction. The concentration of cytochrome c was determined by using the Quantikine Rat/Moue Cytochrome c Immunoassay kit (Minneapolis, Minn) according to the manufacturer’s instructions (
24).
Statistical Analysis
The results were analyzed using Graph Pad Prism (version 5, Graph Pad Software Inc., La Jolla, CA, USA). Results are presented as mean ± SD. Assays were performed in triplicate, and the mean was used for statistical analysis. Statistical significance was determined using the one-way ANOVA test, followed by the post-hoc Tukey posttest, and two-way ANOVA followed by the posttest Bonferonie. Statistical significance was set at p < 0.05.