- Shanghai Nianxing Industrial Co., Ltd
- China
- Product Name: MG-132
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- ShangHai DC Chemicals Co.,Ltd
- China
- Product Name: MG-132
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- Purity: 98.9%
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- DC Chemicals Limited
- China
- Product Name: MG-132
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- Dayang Chem (Hangzhou) Co., Ltd.
- China
- Product Name: Calpain Inhibitor IV
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- Taiwan Oyi peptide Co. Ltd
- China
- Product Name: MG-132
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133407-82-6
133407-82-6 structure
- Name: MG-132
- Chemical Name: N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal
- CAS Number: 133407-82-6
- Molecular Formula: C26H41N3O5
- Molecular Weight: 475.621
- Catalog: Biochemical Inhibitor Proteases Proteasome inhibitor
- Create Date: 2018-02-08 08:00:00
- Modify Date: 2024-01-02 15:33:44
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MG-132 is a potent, reversible, and cell-permeable 20S proteasome inhibitor which inhibits proteasomal chymotrypsin-like peptidase activity with an IC50 of 24.2 nM.
| Name | N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal |
|---|---|
| Synonyms |
benzyloxycarbonyl-Leu-Leu-Leu-aldehyde
L-Leucinamide, N-((phenylmethoxy)carbonyl)-L-leucyl-N-((1S)-1-formyl-3-methylbutyl)- Z-LLL-CHO benzyl N-[(2S)-4-methyl-1-[[(2S)-4-methyl-1-[[(2S)-4-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamate MG132 zLLL Z-Leu-Leu-Leu-CHO Cbz-Leu-Leu-Leu-H L-Leucinamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-formyl-3-methylbutyl]- N-[(Benzyloxy)carbonyl]-L-leucyl-N-[(2S)-4-methyl-1-oxopentan-2-yl]-L-leucinamide Z-Leu-Leu-Leu-H benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonyl-leucyl-leucyl-leucinal Z-Leu-Leu-leucinal N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal MFCD00674886 Carbobenzoxy-L-leucyl-L-leucyl-L-leucinal Cbz-Leu-Leu-Leu-CHO N-[(Benzyloxy)carbonyl]-L-leucyl-N-[(2S)-4-methyl-1-oxo-2-pentanyl]-L-leucinamide MG-132 |
| Description | MG-132 is a potent, reversible, and cell-permeable 20S proteasome inhibitor which inhibits proteasomal chymotrypsin-like peptidase activity with an IC50 of 24.2 nM. |
|---|---|
| Related Catalog | |
| Target |
IC50: 24.2 nM (chymotrypsin-like activity)[1] |
| In Vitro | Dose-dependent inhibition of cell growth is observed in HeLa cells with an IC50 of approximately 5 μM MG132 for 24 h. MG132 inhibits the growth of HeLa cells via inducing the cell cycle arrest as well as triggering apoptosis[2]. MG-132 inhibits C6 glioma cell proliferation in a time- and dose-dependent manner (the IC50 value at 24 h is 18.5 μM). MG-132 (18.5 μM) suppresses the proteasome activity by about 70% at 3 h. MG-132 induces apoptosis via down-regulation of antiapoptotic proteins Bcl-2 and XIAP, up-regulation of pro-apoptotic protein Bax and caspase-3, and production of cleaved C-terminal 85 kDa PARP. MG-132 also causes a more than 5-fold increase of reactive oxygen species[3]. The IC50 of MG-132 against HeLa, CaSki, and C33A cervical cancer cells viability after 48 h of incubation is 2.1, 3.2, and 5.2 μM, respectively[4]. |
| In Vivo | The in vivo antitumor activity of MG-132 against cervical cancer is examined using s.c. xenograft models. MG-132 is injected at 1 mg/kg using the following schedule: days 1, 4, 8, 12, 15 18, 23, and 26 for mice bearing HeLa tumors. The growth inhibition rates of MG132 compared to control is 49%[4]. MG-132 (i.p., 0.1 mg/kg/day) attenuates pressure-overload-induced cardiac hypertrophy and improves cardiac function in abdominal aortic banding (AAB) rats through regulation of ERK1/2 and JNK1 signaling pathways[5]. |
| Kinase Assay | After growing on six-well plates (3×105 cells/well) for 24 h, C6 glioma cells are treated with either PBS (control) or 18.5 μM MG-132 for 3, 6, 12, or 24 h at 37°C. Cells are thoroughly scraped from the culture dishes with a cell scraper and washed with cold PBS. After centrifugation for 10 min at 800×g, the cell pellets are suspended in ice-cold buffer (50 mM Tris-HCl, pH 7.5, 20 μM ATP, 5 mM MgCl2, 1 mM dithiothreitol, and 20% glycerol) and homogenized with a Pyrex glass microhomogenizer (20 strokes). The homogenate is centrifuged at 15 000×g for 10 min at 4°C to obtain supernatant. Protein concentration is determined using protein assay kits. A total of 10 μL (1 μg/μL) of each freshly made supernatant is incubated in a 96-well plate at 37°C for 30 min with 10 μL of 300 μM of Succinyl-LLVY-AMC and 85 μL of assay buffer (20 mM Tris-HCl, pH 7.5, and 20% glycerol). Release of fluorescent AMC is measured with a spectrofluorometer at 440 nm with an excitation wavelength of 380 nm[3]. |
| Cell Assay | C6 glioma cells are seeded onto 96-well microplates (3×104 cells/well) and cultured for 24 h. The cells are treated with PBS or MG-132 final concentrations of 10, 20, 30, and 40 μM, respectively. Cell viability is assessed using an MTT assay at 3, 6, 12, and 24 h after MG-132 treatment. The absorbance value at 570 nm is read using an automatic multi-well spectrophotometer. C6 glioma cells (3×105 cells/well) are allowed to grow on coverslips in 6-well culture plates for 24 h. The cells are then treated with either PBS (control) or 18.5 μM MG-132 at 37°C for 24 h. Cells growing on glass coverslips are fixed in methanol for 5 min at room temperature. The fixed cells are washed twice with PBS and then incubated with Hoechst 33342 for 5 min at room temperature and observed under a fluorescence microscope. Fragmented or condensed nuclei are scored as apoptotic[3]. |
| Animal Admin | Mice[4] C.B-17/lcr-scid/scidJcl mice are inoculated s.c. with HeLa, CaSki, or C33A (1×107 cells). Tumors are allowed to grow for 1 week. Mice are killed and tumors are removed. Tumors are then cut into 2-mm diameter pieces and s.c. transplanted in C.B-17/lcr-scid/scidJcl mice (n=6 per group). One week after inoculation, mice are treated with i.v. injection of saline (control), MG-132 (1 mg/kg/dose) twice a week for 4 weeks. The volume (V) of tumors is measured before every injection, as estimated using equation V=a×b2/2 where a and b are major and minor axes of the tumor measured by a caliper, respectively. Rats[5] Male Sprague-Dawley rats (8 weeks old, 180-230 g) are used to establish pressure-overload model. All animals are separated into four groups (10 rats per group): (i) vehicle-treated sham group; (ii) MG-132-treated sham group; (iii) vehicle-treated abdominal aortic banding (AAB) group; and (iv) MG-132-treated AAB group. Under intraperitoneal pentobarbital (50 mg/kg) anesthesia, AAB is created using a 5-0 suture tied twice around the abdominal aorta in which a 21-gauge needle is inserted. The needle is then retracted yielding a 70-80% constriction with an outer aortic diameter of ~0.8 mm. In the sham surgery rats, the same surgery is performed except the aorta is constricted. At Day 3 after the surgery, MG-132-treated rats are intraperitoneally injected with 0.1 mg/kg/day of MG-132 for 8 weeks. All control animals are injected with a corresponding volume of vehicle only (0.1% DMSO). |
| References |
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 682.0±55.0 °C at 760 mmHg |
| Melting Point | 80-84℃ (DEC.) |
| Molecular Formula | C26H41N3O5 |
| Molecular Weight | 475.621 |
| Flash Point | 366.3±31.5 °C |
| Exact Mass | 475.304626 |
| PSA | 113.60000 |
| LogP | 5.75 |
| Vapour Pressure | 0.0±2.1 mmHg at 25°C |
| Index of Refraction | 1.506 |
| Storage condition | −20°C |
| Water Solubility | methanol: 1 mg/mL | Soluble in ethanol, chloroform, methanol, water. |