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M0503

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, contains NaCl as solubilizer

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About This Item

Empirical Formula (Hill Notation):
C15H18N4O5
CAS Number:
50-07-7
Molecular Weight:
334.33
Beilstein:
7231816
MDL number:
MFCD00078109
UNSPSC Code:
12352207
PubChem Substance ID:
24896555
NACRES:
NA.76
Pricing and availability is not currently available.

biological source

Streptomyces caespitosus

Quality Level

200

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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

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
0000401674
0000401673
0000401672
0000399802
0000361388

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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
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Articles

DNA Damage and Repair

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

1–9 of 9 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. 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?

  4. 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.

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  5. 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.

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

    1 answer

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

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  7. 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.

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

    1 answer

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

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  9. 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.

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