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2.1. Chemicals and reagents

Butein (B-178), Hoechst 33258, Cy3-labeled mouse anti--tubulin (c-4585),

propidium iodide, 3-(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), and the Cy3-labeled mouse anti--tubulin were purchased from Sigma

Chemical (St. Louis, MO). Butein was dissolved in DMSO, and the concentration of

DMSO was < 1 % in the control and drug-containing medium.

2.2. Antibodies

Anti-CDC2, anti-phospho-CDC2 (Tyr15), anti-phospho-CDC2 (Thr14),

anti-phospho-CDC2 (Thr161), anti-phospho-histone H3 (Ser10), anti-phospho-p53

(Ser15), and anti-poly (ADP-ribose) polymerase (PARP) was purchased from Cell

Signaling Technology, Inc. (Beverly, MA, USA). Anti-caspase-3 antibody was

purchased from BioVision (BioVision, Inc., USA). Anti-cyclin B1 (Ab-2) antibody

was purchased from Oncogene Sciences (Cambridge, MA). Anti-actin (I-19) antibody,

goat anti-rabbit IgG horseradish peoxidase, and goat anti-mouse IgG horseradish

peoxidase were purchased from Santa Cruz Biotechnology, Inc. (Santa Cruz, CA).

Antibody Source Molecular Weight Brand Catalog

Actin mouse 42 Santa Cruz sc-1616

CDC2 rabbit 34 Oncogene PC-25

Cyclin B1 mouse 60 Oncogene CC03

Caspase-3 mouse 32 Biovision 3004-100

PARP rabbit 17 Cell Signaling Tech #9542

Phospho-CDC2 (Thr161) rabbit 34 Cell Signaling Tech #9114

Phospho-CDC2 (Tyr15) rabbit 34 Cell Signaling Tech #4539

Phospho-CDC2 (Thr14) rabbit 34 Cell Signaling Tech #2543

Phospho-p53 (Ser15) rabbit 53 Cell Signaling Tech #9284

Phospho-histone H3 (Ser10) rabbit 17 Cell Signaling Tech #9701

Securin mouse 22 Abcam ab3305

Anti-rabbit IgG-HRP goat secondary antibody Santa Cruz sc-2004 Anti-mouse IgG-HRP goat secondary antibody Santa Cruz sc-2005 Anti-rabbit IgG-Hylite 488 goat secondary antibody Jackson 115-485-003

2.3. Cell culture

The wild type, securin (-/-), and p53 (-/-) HCT116 colorectal carcinoma cell lines

were kindly provided by Dr. B. Vogelstein of Johns Hopkins University (Baltimore, MD). These cell lines were cultured in complete McCoy‟s 5A medium (Sigma

Chemical) supplemented with 10% fetal bovine serum (FBS), 100 units/ml penicillin, 100 μg/ml streptomycin and sodium bicarbonate. These cells were maintained at 37°C

and 5% CO2 in a humidified incubator (310/Thermo, Forma Scientific, Inc., Marietta,

OH).

2.4. Cytotoxicity assay

The cells were plated in 96-well plates at a density of 1 × 104 cells/well for 16-20

h. Thereafter, the cells were treated with various concentrations of butein for 24 h,

and then the cells were washed with phosphate-buffered saline (PBS) and were

replaced fresh complete McCoy‟s 5A medium for cultured 2 days. Subsequently, the cells were incubated with 0.5 mg/ml of MTT in fresh complete McCoy‟s 5A medium

for 4 h. The surviving cells converted MTT to formazan by forming a blue-purple

color when dissolved in dimethyl sulfoxide. The intensity of formazan was measured

at 565 nm using a microplate reader (VERSAmax, Molecular Devices Inc., CA). The

relative percentage of cell viability was calculated by dividing the absorbance of

treated cells by that of the control in each experiment.

2.5. Time-lapse observation of cell death

HCT116 colon cancer cells were plated at a density of 2 × 105 cells per 35-mm

Petri dish in complete medium for 16-20 h. Then the cells were treated with or

without 40 μM butein by time-lapse observation under an optical phase contrast

microscope with an incubator system (OLYMPUS IX71, Japan). The pictures were

edited by DP manager software (Ver. 3.3.1, OLYMPUS)

2.6. Cell cycle analysis

The cell cycle progression after treatment with butein was measured by flow

cytometer. The cells were plated at a density of 1 × 106 cells per 60-mm Petri dish in

complete medium for 16-20 h. After treatment, the cells were collected and fixed with

ice-cold 70% ethanol overnight at -20 °C. After centrifugation, the cell pellets were

treated with 4 μg/ml PI solution containing 1% Triton X-100 and 100 μg/ml RNase at

37 °C for 30 min. After re-centrifugation, the cells resuspended in 1 ml ice-cold PBS.

To avoid cell aggregation, the cell solutions were filtrated through nylon mesh

membrane. Subsequently, the samples were analyzed by CellQuest software in flow

cytometer (BD Biosciences, San Jose, CA). A minimum of ten thousand cells was

analyzed for DNA content, and the percentage of cell cycle phases was quantified by

ModFit LT software (Ver. 2.0, Becton-Dickinson).

2.7. Annexin V and PI assays

The cells were plated at a density of 7 × 105 cells per 60-mm Petri dish in

complete medium for 16-20 h. Thereafter, the cells were treated with 0-40 μM butein

for 24 h. Apoptotic cells was performed using an annexin-V-FITC Apoptosis Detection Kit (BioVision, Mountain View, CA) according to the manufacturer‟s

instructions. Then cells were collected and resuspended in 500 μl of binding buffer,

added 5 μl of annexin-V-fluorescein isothiocyanate (FITC) and 5 μl of propidium

iodide (PI). Finally, the samples were analyzed by flow cytometer using CellQuest

software (FACScan, Becton–Dickinson, San Jose, CA). The cells showed annexin V(+)/PI(−) and annexin V(+)/PI(+), which indicated at early and late apoptosis,

respectively.

2.8. Western blot

After the end of drug treatment, the cells were lysed in the ice-cold whole cell

extract buffer containing the protease inhibitors. The lysate was vibrated for 30 min at

4 ℃ and centrifuged at 10,000 rpm for 10 minutes. Protein concentration was

measured by BCA protein assay kit (Pierce, Rockford, IL). Equal amounts of proteins

were subjected to electrophoresis using 12 % sodium dodecyl sulfate-polyacrylamide

gels. To verify equal protein loading and transfer, proteins were then transferred to

polyvinylidene difluoride membranes and the membranes were blocked overnight at 4

℃ using blocking buffer (5 % non-fat dried milk in solution containing 50 mM

Tris/HCl (pH 8.0), 2 mM CaCl2, 80 mM sodium chloride, 0.05 % Tween 20 and 0.02

% sodium azide). The membranes were then incubated for 2 h at 25℃ with specific

primary antibody followed by anti-rabbit or anti-mouse immunoglobulin

G-horseradish peroxidase conjugated secondary antibodies. The membranes were

washed three times for 10 min with washing solution. Finally, the protein bands were

visualized on the X-ray film using the enhanced chemiluminescence detection system

(PerkinElmer Life and Analytical Sciences, Boston, MA). A gel-digitizing software,

Un-Scan-It gel (ver. 5.1; Silk Scientific, Inc.), was used to analyze the intensity of

bands on X-ray film by semi-quantification.

2.9. Immunofluorescence staining and confocal microscopy

The cells were cultured on coverslips, which were kept in 35-mm Petri dish at a

density of 5 × 105 per well for 16-20 h. After treatment with or without 40 μM butein

for 24 h, the cells were washed with PBS. Then fixation with 4% paraformaldehyde

solution overnight at 4 °C, the cells were washed three times with PBS, and

non-specific binding sites were blocked in PBS containing 10 % FBS and 0.3 %

Triton X-100 for 1 h at 37 °C. Thereafter, the cells were separately incubated with

rabbit anti-phospho-histone H3 (1:100) antibody in PBS containing 10 % FBS

overnight at 4°C, and washed three times with 0.3 % Triton X-100 in PBS. Then the

cells were incubated with anti-rabbit IgG-Hylite 488 (1:100) in PBS containing 10 %

FBS for 1 h at 37 °C, and washed three times with 0.3 % Triton X-100 in PBS. The

samples incubated with mouse anti-securin (1:100) antibody in PBS containing 10 %

FBS overnight at 4°C, and washed three times with 0.3 % Triton X-100 in PBS. Then

the cells were incubated with anti-mouse IgG-Cy3 (1:100) in PBS containing 10 %

FBS for 1 h at 37 °C. The β-tubulin and nuclei were stained with the Cy3-labeled

anti-β-tubulin and Hoechst 33258, respectively. After staining, the samples were

immediately examined under Olympus confocal microscope (Olympus, Tokyo,

Japan).

2.11. Mitotic index analysis

The cells were cultured on coverslips in a 35-mm Petri dish at a density of 5 ×

105 for 16-20 h. After treatment with or without 40 μM butein for 24 h, the cells were

carefully and gently washed with PBS (pH 7.4) and then fixed with 4%

paraformaldehyde solution in PBS for one hour at 37 ºC. The cells were incubated

with rabbit anti-phosphorylated histone H3 (Ser10) antibody. Then the cells were

incubated with goat anti-rabbit IgG-Hylite 488. The -tubulin was stained with the Cy3-labeled mouse anti--tubulin (1:50) for 30 min at 37 ºC. Finally, the nuclei were

stained with 2.5 g/mL Hoechst 33258 for 30 min. Mitotic index indicated the

percentage of mitotic cell number/total counted cells that was counted under a

fluorescence microscope in each treatment. The prophase, metaphase, anaphases, and

telophase in total mitotic phases were counted under fluorescence microscope.

2.12. Analysis of phospho-histone H3 by flow cytometer

After treatment with butein for 24 h, HCT116 cells were harvested and fixation

with 75% alcohol in -20℃ overnight. Subsequently, the samples were incubated with

10 % bovine serum albumin in PBS for 1 hour at 4 °C. After that, the samples were

incubated with rabbit anti-phospho-histone H3 antibody (1:100), and following

incubated with anti-rabbit IgG-Hylite 488 (1:100) for 2 hours at 4 °C in dark. At the

end of incubation, the cells were resuspended in 1 × PBS and immediately analyzed

by a flow cytometer (FACS Calibur, BD Biosciences). The fluorescence intensities of

phospho-histone H3 were quantified the green fluorescence using CellQuest software

(BD Biosciences).

2.13. Statistical analysis

Each experiment was repeated at least three times. Data from the population of cells treated with different conditions were analyzed using paired Student‟s t-test. In a

comparison of multiple groups, data were analyzed by one-way or two-way analysis of variance (ANOVA), and further post Tukey‟s tests using the statistic software of

GraphPad Prism 5 (GraphPad software, Inc. San Diego, CA). A p value of < 0.05 was

considered as statistically significant in each experiment.

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