A potent DNA crosslinker
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Mitomycin C

Item No. 11435

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1aS,2,8S,8aR,8bS-hexahydro-8a-methoxy-5-methyl-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
CAS Number
50-07-7
Synonyms
  • Ametycine
  • MitoExtra
  • Mitonco
  • Mitoplus
  • MMC
  • NSC 26980
Molecular Formula
C15H18N4O5
Formula Weight
334.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 0.1 mg/mlPBS (pH 7.2): 0.5 mg/ml
λmax
216, 359 nm
SMILES
NC1=C(C)C(C(N(C[C@H]2[C@@H]3N2)[C@@]3(OC)[C@@H]4COC(N)=O)=C4C1=O)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $72

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    10 mg

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    25 mg

    $251

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    50 mg

    $394

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    Cayman Chemical
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    Product Description

    Mitomycin C (MMC) is an antitumor antibiotic that was discovered as a fermentation product of S. caespitosus.1 As an alkylating agent, its activity depends on reductive activation either through low pH or DT-diaphorase or NADH cytochrome c reductase.2 Activated MMC crosslinks double stranded DNA and is widely used as a tool to selectively inhibit DNA synthesis and mutagenensis, to stimulate genetic recombination, chromosome breakage and sister chromatid exchange, and to induce DNA repair.3,4 MMC has clinical significance in combination cancer chemotherapy of solid tumors as well as for modulating wound healing after ophthalmological surgeries and in the management of various corneal disorders.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Philips, F.S., Schwartz, H.S., and Sternberg, S.S. Pharmacology of mitomycin C: I. Toxicity and pathologic effects. Cancer Res. 20, 1354-1361 (1960).

    2. Mao, Y., Varoglu, M., and Sherman, D.H. Molecular characterization and analysis of the biosynthetic gene cluster for the antitumor antibiotic mitomycin C from Streptomyces lavendulae NRRL 2564. Chem. Biol. 6(4), 251-263 (1999).

    3. Tomasz, M. Mitomycin C: Small, fast and deadly (but very selective). Chem. Biol. 2, 575-579 (1995).

    4. Iyer, V.N., and Szybalski, W. A molecular mechanism of mitomycin action: Linking of complementary DNA strands. Proc. Natl. Acad. Sci. USA 50, 355-362 (1963).

    5. Kato, Y., Onishi, H., and Machida, Y. Contribution of chitosan and its derivatives to cancer chemotherapy. In Vivo 19, 301-310 (2005).

    6. Shao, T., Li, X., and Ge, J. Target drug delivery system as a new scarring modulation after glaucoma filtration surgery. Diagn.Pathol. 6(64), 1-5 (2011).