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      Mitomycin C (Ametycine)
      Mitomycin C (Ametycine)

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      This product is for research use only, not for human use. We do not sell to patients.
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      InvivoChem Cat #: V1426
      CAS #: 50-07-7Purity ≥98%

      Description: Mitomycin C (Mitozytrex; Mutamycin; Ametycine) is an antineoplastic antibiotic drug that acts by inhibiting DNA synthesis, and has been approved to treat different cancers. Mitomycine C is a methylazirinopyrroloindoledione analog isolated from the bacterium Streptomyces caespitosus and other Streptomyces bacterial species. Bioreduced mitomycin C generates oxygen radicals, alkylates DNA, and produces interstrand DNA cross-links, thereby inhibiting DNA synthesis.

      References: Mol Cell. 2009 Sep 11;35(5):704-15; Cell Cycle. 2012 Sep 1;11(17):3312-23.

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      Molecular Weight (MW)334.37
      FormulaC15H18N4O5
      CAS No.50-07-7
      Storage-20℃ for 3 years in powder form
      -80℃ for 2 years in solvent
      Solubility (In vitro)DMSO: 67 mg/mL (200.4 mM)
      Water: <1 mg/mL
      Ethanol:<1 mg/mL
      Solubility (In vivo)

      Chemical Name: ((1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate

      InChi Key: NWIBSHFKIJFRCO-WUDYKRTCSA-N

      InChi Code: NC(OCC[4:S=I]H()C[5:S=N]()(OC)C[6:S=N]()(H)NC[S=N]([email protected][16]()[email protected](C(N)=C([email protected]=O)C)=O)@7-H)=O

      SMILES Code: NC(OC[[email protected]]1[[email protected]]([[email protected]](N2)([H])[[email protected]]2([H])C3)(OC)N3C4=C1C(C(N)=C(C)C4=O)=O)=O

      Synonyms

      Ametycine; mitomycine C; mitomycinX. US trade names: Mitozytrex; Mutamycin. Foreign brand names: Ametycine; MitocinC; Mitolem; MitoMedac; Mutamycine. Abbreviations: MITC; MITO; MITOC; MTC; NCIC04706


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      In Vitro

      In vitro activity: Mitomycin C, by inducing DNA interstrand crosslinks, physically blocks DNA replication, recombination, and RNA transcription. Mitomycin C potentiates TRAIL-induced apoptosis in HCT116 (p53-/-) colon cancer cells and sensitizes TRAIL-resistant colon cancer cells HT-29 to the cytokine by through JNK-independent upregulation of death receptors. In different human cancer cell lines, such OVCAR-5 (ovary), HT-29 (colon), SK-N-MC (neuroblastoma), HEP-2 (liver), COLO-205 (colon), NIH-OVCAR-3 (ovary) and A-549 (lung) cells, Mitomycin C shows cytotoxic activity.

      Cell Assay: Mitomycin-C enhanced TRAIL (TNF-related apoptosis-inducing ligand)-induced apoptosis in p53 deficient colon cancer HCT116 cells. In the cell viability assay, pretreated with 5M with mitomycin C for 24h and then exposure to 25ng/ml TRAIL  and 5M mitomycin C for 12h in HCT116 cells showed surprisingly decreased cell viability. In the crystal violet staining assay showed 5M mitomycin C combinated 25ng/ml TRAIL can substantially enhanced suppression effects of HCT116 cells. Pretreatment with 5M mitomycin C can enhanced TRAIL initiated processing of caspase-8, -9, -3 and cleavage of RARP (poly-ADP-ribose polymerase, substrate of caspase-3).  The western blot assay showed in both HCT116 and HT29 cells, mitomycin C suppressed the expression anti apoptotic proteins Mcl-1, Bcl-2, Bcl-XL, and downregulated caspase-inhibitor c-IAP-1, XIAP, while upregulated expression of pro-apoptotic proteins Bax and Bim.

      In VivoThe NMRI-Fox1nu nude mice was inoculated subcutaneously and then randomized to several groups: treated with electrochemotherapy and administrated 5mM mitomycin C or electrochemotherapy only or 5mM mitomycin C only. Results showed that tumor volume reduced in electrochemotherapy plus mitomycin C group, and mice survival rates were greater in electrochemotherapy plus mitomycin C group and mitomycin C group only, compared controls(p＜0.001). The tumor response rate was 53% for mitomycin C alone
      Animal modelRat bladder tumor model
      Formulation & DosageDissolved in saline; 400 μM; Intravesical injection
      References

      Mol Cell. 2009 Sep 11;35(5):704-15; Cell Cycle. 2012 Sep 1;11(17):3312-23; Int J Oncol. 2014 Jan;44(1):147-52.

      These protocols are for reference only. InvivoChem does not independently validate these methods.

       

      Mitomycin C

      MMC (Mitomycin C) potentiates TRAIL-induced apoptosis of HCT116 (p53−/−) cells. Cell Cycle. 2012 Sep 1;11(17):3312-23.
      		 

      Mitomycin C

      Cell Cycle. 2012 Sep 1;11(17):3312-23.
      		 

      Mitomycin C

      Effects of MMC on JNK kinase expression, which mediates DR4 and DR5 expression. Cell Cycle. 2012 Sep 1;11(17):3312-23.

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