| Chemical & Physical Properties | |
|---|---|
| CAS Number | 50-07-7 |
| Catalog No. | 2A-9011469 |
| Chinese Name | 丝裂霉素C |
| Synonyms | MFCD00078109; Mitomycin C(Ametycine); EINECS 200-008-6 |
| Molecular Formula | C15H18N4O5 |
| Molecular Weight | 334.327 |
| Purity | ≥98 (HPLC) |
| Density | 1.9±0.1 g/cm3 |
| Boiling Point | 532.0±60.0 °C at 760 mmHg |
| Melting Point | 360 °C |
| Appearance | liquid |
| Water Solubility | soluble |
| Storage Condition | This product should be sealed and stored in a cool |
| Packaging | II |
| Application | Mitomycin C is an anti-tumor drug and antibiotic that can effectively inhibit DNA synthesis. |
| SMILES | COC12C(COC(N)=O)C3=C(C(=O)C(C)=C(N)C3=O)N1CC1NC12 |
| InChI | InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1 |
| InChI Key | NWIBSHFKIJFRCO-WUDYKRTCSA-N |
| NACRES Code | NA.76 |
| UNSPSC | 12352207 |
| Hazard Symbols | 6.1(a) |
| MSDS | msds/11469_1_50_07_7.pdf |
| Bioactivity | Mitomycin C is an antitumor drug and antibiotic that shows extraordinary ability to inhibit DNA synthesis. Related Catalog Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> DNA Alkylator/Crosslinker Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Research Areas >> Cancer Natural Products >> Others Target DNA synthesis[1] In Vitro The HCT116 (p53-/-) cells are minimally sensitive to either Mitomycin C or TRAIL alone. However, surprisingly, combination treatment with MMC and TRAIL decreases cell viability significantly. Although Mitomycin C and TRAIL alone are moderately effective, Mitomycin C substantially enhances the effect of TRAIL on suppression of the cell proliferation. Mitomycin C and TRAIL treatment alone induces 9.5% and 35.0% apoptosis, respectively. However, combination treatment with Mitomycin C and TRAIL enhances apoptosis to 66.6%[1]. Mitomycin C is a cytotoxic chemotherapeutic agent that causes DNA damage in the form of DNA cross-links as well as a variety of DNA monoadducts and is known to induce p53[2]. In Vivo Mice bearing xenografted HCT116 (p53-/-) colon tumors and HT-29 colon tumors are treated with Mitomycin C (i.p., 1 mg/kg) and TRAIL (i.v., 100 μg) every other day. Animals are treated with 10 consecutive cycles of the combination therapy regimen. The combination therapy suppresses tumor growth significantly and does not impact the weight of the mice, indicating that the therapeutic combination of Mitomycin C and TRAIL is well-tolerated and has anti-tumor activity in vivo[1]. Intravesical Mitomycin C instillations has an effect on body weight that is not observed in normal, NaCl instilled or Epirubicin instilled rats. After 3 consecutive weekly instillations of 1 mg/mL Mitomycin C there is almost no weight gain, whereas rats in the other 3 groups has a statistically significant weight gain compared with MMC treated rats[3]. Cell Assay Colon adenocarcinoma HCT116 and HT-29 human colon cancer cells are used. The CellTiter-Glo Luminescent Cell Viability Assay is used to measure cell viability, which use a unique, stable form of luciferase to measure ATP as an indicator of viable cells, and the luminescent signal produced is proportional to the number of viable cells present in culture. Cells are pretreated with Mitomycin C (5 μM) for 12 h or 24 h, and then exposed to different concentrations of TRAIL for 12 h. An equal volume (100 μL) of CellTiter-GloTM reagent is added and the solution is mixed gently for 2 min on an orbital shaker. Mixture is incubated at room temperature for 10 min to allow luminescent signal to stabilize, and then imaging is performed using the Xenogen IVIS system to quantify the cell viability[1]. Animal Admin Mice[1] Four- to 6-wk-old NCr nude mice are treated with Mitomycin C (1 mg/kg) by intraperitoneal injection for 24 h, followed by one intravenous dose of purified rhTRAIL (100 μg). As a negative control, a subset of the mice are injected (i.p. and i.v.) with saline (vehicle) at the same frequency of treatment. Animals are treated for 3 consecutive weeks. The tumor size is monitored every week using caliper measurements of the tumor volume. Rats[3] Young adult female Wistar rats at age 13 weeks with a median weight of 217 g (range 187 to 255) are randomized into 4 groups of 10 each, namely a normal group with no instillations, an NaCl 0.9% or placebo group that received instillations with the solvent of the chemotherapeutic agents, an Mitomycin C (1 mg/mL) group and an Epirubicin (1 mg/mL) group. References [1]. Cheng H, et al. Mitomycin C potentiates TRAIL-induced apoptosis through p53-independent upregulation of death receptors: Evidence for the role of c-Jun N-terminal kinase activation. Cell Cycle. 2012 Sep 1;11(17): 3312-23. [2]. Abbas T, et al. Differential activation of p53 by the various adducts of mitomycin C. J Biol Chem. 2002 Oct 25;277(43):40513-9. [3]. Michielsen D, et al. Mitomycin C and epirubicin: functional bladder damage in rats after repeat intravesical instillations. J Urol. 2005 Jun;173(6):2166-70. Chemical & Physical Properties Density 1.9±0.1 g/cm3 Boiling Point 532.0±60.0 °C at 760 mmHg Melting Point 360 °C Molecular Formula C15H18N4O5 Molecular Weight 334.327 Flash Point 275.5±32.9 °C Exact Mass 334.127716 PSA 146.89000 LogP -0.27 Vapour Pressure 0.0±3.2 mmHg at 25°C Index of Refraction 1.828 InChIKey NWIBSHFKIJFRCO-WUDYKRTCSA-N SMILES COC12C(COC(N)=O)C3=C(C(=O)C(C)=C(N)C3=O)N1CC1NC12 Stability Stable. Incompatible with strong acids, strong bases, strong oxidizing agents. Water Solubility soluble |
| Use of | Mitomycin C is an antitumor drug and antibiotic that shows extraordinary ability to inhibit DNA synthesis. Properties Articles543 Name mitomycin C Synonym More Synonyms Mitomycin C Biological Activity Description Mitomycin C is an antitumor drug and antibiotic that shows extraordinary ability to inhibit DNA synthesis. Related Catalog Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> DNA Alkylator/Crosslinker Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Research Areas >> Cancer Natural Products >> Others DNA synthesis[1] In Vitro The HCT116 (p53-/-) cells are minimally sensitive to either Mitomycin C or TRAIL alone. However, surprisingly, combination treatment with MMC and TRAIL decreases cell viability significantly. Although Mitomycin C and TRAIL alone are moderately effective, Mitomycin C substantially enhances the effect of TRAIL on suppression of the cell proliferation. Mitomycin C and TRAIL treatment alone induces 9.5% and 35.0% apoptosis, respectively. However, combination treatment with Mitomycin C and TRAIL enhances apoptosis to 66.6%[1]. Mitomycin C is a cytotoxic chemotherapeutic agent that causes DNA damage in the form of DNA cross-links as well as a variety of DNA monoadducts and is known to induce p53[2]. References [1]. Cheng H, et al. Mitomycin C potentiates TRAIL-induced apoptosis through p53-independent upregulation of death receptors: Evidence for the role of c-Jun N-terminal kinase activation. Cell Cycle. 2012 Sep 1;11(17): 3312-23. [2]. Abbas T, et al. Differential activation of p53 by the various adducts of mitomycin C. J Biol Chem. 2002 Oct 25;277(43):40513-9. [3]. Michielsen D, et al. Mitomycin C and epirubicin: functional bladder damage in rats after repeat intravesical instillations. J Urol. 2005 Jun;173(6):2166-70. Chemical & Physical Properties Molecular Formula C15H18N4O5 Exact Mass 334.127716 PSA 146.89000 LogP -0.27 Index of Refraction 1.828 InChIKey NWIBSHFKIJFRCO-WUDYKRTCSA-N Stability Stable. Incompatible with strong acids, strong bases, strong oxidizing agents. Water Solubility soluble |
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