Skip to Content
Merck
All Photos(1)

Key Documents

M0503

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, contains NaCl as solubilizer

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C15H18N4O5
CAS Number:
Molecular Weight:
334.33
Beilstein:
7231816
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.76
Pricing and availability is not currently available.

biological source

Streptomyces caespitosus

Quality Level

form

powder

contains

NaCl as solubilizer

color

gray
purple/blue

 

(1) 3.2, (2) 6.5

solubility

H2O: 1 vial + 4 mL, clear to slightly hazy, blue to purple

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

DNA synthesis | interferes

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

Looking for similar products? Visit Product Comparison Guide

General description

Chemical structure: aziridine

Application

Mitomycin C is produced by a strain of actinomyces, Streptomyces caespitosus. It contains three anticancer 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.

Biochem/physiol Actions

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.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Xin Wang et al.
Nature medicine, 19(4), 473-480 (2013-03-26)
Sorting nexin 27 (SNX27), a brain-enriched PDZ domain protein, regulates endocytic sorting and trafficking. Here we show that Snx27(-/-) mice have severe neuronal deficits in the hippocampus and cortex. Although Snx27(+/-) mice have grossly normal neuroanatomy, we found defects in
Ali Fathi et al.
Proteomics, 9(21), 4859-4870 (2009-10-29)
Gene expression analyses of embryonic stem cells (ESCs) will help to uncover or further define signaling pathways and molecular mechanisms involved in the maintenance of self-renewal and pluripotency. We employed a 2-DE-based proteomics approach to analyze human ESC line, Royan
D Hompes et al.
Journal of surgical oncology, 109(6), 527-532 (2014-01-01)
Oxaliplatin and Mitomycin C (MMC) are both suitable as intraperitoneal chemotherapy agents in HIPEC for peritoneal carcinomatosis (PC) of colorectal cancer (CRC). Patient cohorts from two different HIPEC-centers underwent cytoreductive surgery and HIPEC with Oxaliplatin (39 patients) and MMC (56
Masaki Hikida et al.
The Journal of experimental medicine, 206(3), 681-689 (2009-03-11)
Resting antigen-experienced memory B cells are thought to be responsible for the more rapid and robust antibody responses after antigen reencounter, which are the hallmark of memory humoral responses. The molecular basis for the development and survival of memory B
Sayuri Yamazaki et al.
Journal of immunology (Baltimore, Md. : 1950), 193(11), 5488-5497 (2014-10-29)
Accumulating evidence shows that immunological tolerance induced by Ag administration together with UVB irradiation is dependent on Foxp3(+) CD4(+) regulatory T (Treg) cells. However, the mechanisms by which UVB controls Treg cells in the skin are currently unclear. In this

Articles

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Questions

1–7 of 7 Questions  
  1. Is Mitomycin C, Product M0503, soluble in PBS?

    1 answer
    1. According to literature resources, the solubility of Mitomycin C in phosphate-buffered saline (PBS) is between 0.5 to 1.0 mg/mL depending on the exact ambient temperature.

      Helpful?

  2. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

      Helpful?

  3. How do I store a stock solution of Mitomycin C, Product M0503?

    1 answer
    1. Generally, solutions at pH 6-9 can be stored at 0-5 °C for up to a week, and possibly much longer. If a precipitate forms, a fresh solution should be prepared. The precipitated solution has proven to be toxic to cells. A stock solution should also be stored in the dark since mitomycin C is readily decomposed by light. Solutions should not be frozen, since a precipitate is likely to form.

      Helpful?

  4. Why does Mitomycin C, Product M0503, contain  NaCl?

    1 answer
    1. Sodium chloride is added to mitomycin C to increase solubility and solution stability.

      Helpful?

  5. What is the difference between Mitomycin C Product No. M0503 and M4287?

    1 answer
    1. The difference between Product Nos. M0503 and M4287 is that Product No. M4287 has been tested on cells. A feeder layer is treated with media containing 10 μg/mL mitomycin C for 3 hours at 37°C to block replication.

      Helpful?

  6. Is Mitomycin C, Product M0503, light sensitive?

    1 answer
    1. Mitomycin C is light sensitive only when in solution and not as a powder.

      Helpful?

  7. How do I use Mitomycin C, Product M0503, to block replication?

    1 answer
    1. Cell functions that require cellular division are abolished by treatment with mitomycin C (causes DNA crosslinking). This can be used to treat cells for feeder layers, for mixed lymphocyte reactions and for removal of fibroblasts from mixed cell cultures. Mitomycin is used at 25 μg/mL to treat cells at 1 - 6 × 107 cells/mL. Cells are treated for 25 minutes at 37 °C. Selected Methods in Cellular Immunology, Michell, BB, and Shiigi, SM, Eds., WH Freeman and Co., New York, 1980, p. 240.

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service