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M4287 Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, BioReagent, suitable for cell culture

  • CAS Number 50-07-7

  • Empirical Formula (Hill Notation) C15H18N4O5

  • Molecular Weight 334.33

  •  Beilstein/REAXYS Number 7231816

  •  MDL number MFCD00078109

  •  PubChem Substance ID 24896917

  •  NACRES NA.76

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application, Antibiotics by Mechanism of Action,
Quality Level   200
biological source   Streptomyces caespitosus
product line   BioReagent
form   powder
application(s)   cell culture | mammalian: suitable
color   gray
  purple/blue
    (1) 3.2, (2) 6.5
solubility   H2O: 4 mL/vial, clear to slightly hazy, blue to purple (Stock solutions should be filter sterilized and stored at 2-8 °C in the dark.)
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
storage temp.   2-8°C
SMILES string   [H][C@]12CN3C4=C([C@@H](COC(N)=O)[C@@]3(OC)[C@@]1([H])N2)C(=O)C(N)=C(C)C4=O
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

Description

General description

Mitomycin C is a systemic chemotherapy compound and an antibiotic obtained from Streptomyces caespitosus. It is the first bioreductive alkylating agent to be identified and is a derivative of 3-amino-5-hydroxybenzoic acid (AHBA), D-glucosamine, L-methionine and carbamoyl phosphate.
Chemical structure: Aziridine

Application

Mitomycin C from Streptomyces caespitosus has been used for the treatment of feeder layers such as, PMEF (primary mouse embryonic fibroblasts) and CD1 mouse embryonic fibroblasts (MEFs) for the culture of hESCs (human embryonic stem cells). It has also been used for the treatment of BLC (basal-like cancer) cell line.

Biochem/physiol Actions

Mitomycin C causes the cross-linking of double-stranded DNA, which results in mutagenesis, inhibition of DNA synthesis, initiation of DNA repair events, and activation of apoptosis. The capability to inhibit DNA synthesis is attributable to the aminoquinone group present in mitomcyin C. This compound does not affect the synthesis of RNA and protein. In tissue culture, this compound decreases cell viability and suppresses mitosis, and causes disorganization of nucleus and the production of giant cells. Mitomycin C has potent anti-Gram negative and anti-Gram positive activities. It contains three moieties, quinine, urethane, and aziridine groups. It is used to generate mitotically inactive feeder cells in cell culture systems, such as the mitotically inactive fibroblasts used in embryonic stem cell systems.

Mode of Action: This product is an alkylating agent that specifically targets the guanine nucleoside sequence 5′-CpG-3′. It inhibits DNA synthesis by covalently reacting with DNA, forming crosslinks between complementary strands of DNA. This interaction prevents separation of complementary DNA strands, inhibiting DNA replication.

Antimicrobial Spectrum: Mitomycin C has strong antitumor activity, especially against Ehrlich ascites tumor cells, and strong bactericidal action against gram-positive and gram-negative bacteria.

Caution

This vial contains 2 mg Mitomycin C and 48 mg NaCl. Stock solutions should be filter sterilized and stored at 2-8°C in the dark. Solutions at pH 6-9 can be stored at 0-5°C for up to a week, but if a precipitate forms, a fresh solution should be prepared - the precipitated solution has been proven toxic to cells.

Preparation Note

Mitomycin C is soluble in water at .5 mg/mL, with a pH of 6.0-7.5. It undergoes rapid degradation in acidic solutions with pH<6, and is mostly likely to retain activity in solutions with a pH between 6-9.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What is the difference between Mitomycin C products M4287 and M0503?
M4287 has been cell culture tested; M0503 has not been cell culture tested.
How should solutions of Mitomycin C, Product M4287,be stored?
Solutions of this product should not be stored frozen. Solutions can be stored at 2-8°C, and should be used within 1-2 weeks. Solutions are light sensitive, but the powder is not.
How should the product be dissolved?
Mitomycin C is soluble at 0.5 mg/mL in water, yielding a clear blue solution.
At what concentration can Mitomycin C, Product M4287,be used with embryonic stem (ES) cells?
Treatment of the feeder layer with media containing 100 micrograms/mL mitomycin at 37°C for 30 minutes blocked replication of ES cells.
What is the recommended concentration of Mitomycin C, Product M4287, should I usefor eukaryote cell culture?
A concentration between 10-50 micrograms/mL is typically used.
How do I find price and availability?
There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 or view local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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Peer-Reviewed Papers
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References

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