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M0503

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, contains NaCl as solubilizer

Empirical Formula (Hill Notation):
C15H18N4O5
CAS Number:
Molecular Weight:
334.33
Beilstein:
7231816
MDL number:
PubChem Substance ID:
NACRES:
NA.76

Quality Level

biological source

Streptomyces caespitosus

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

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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

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Product Information Sheet

More Documents

Quotes and Ordering

  1. 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.

  2. 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.

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

    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.

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

    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.  

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

    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.

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

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

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

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

  8. 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.

  9. 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. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Lars Petter Jordheim et al.
Molecular pharmacology, 84(1), 12-24 (2013-04-13)
The benefit of cancer chemotherapy based on alkylating agents is limited because of the action of DNA repair enzymes, which mitigate the damage induced by these agents. The interaction between the proteins ERCC1 and XPF involves two major components of
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

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