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M4287

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, suitable for cell culture, BioReagent

Synonym(s):

Mitomycin

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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:
24896917
NACRES:
NA.76

Product Name

Mitomycin C from Streptomyces caespitosus, powder, BioReagent, suitable for cell culture

biological source

Streptomyces caespitosus

Quality Level

200

product line

BioReagent

form

powder

technique(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.)

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

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.

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Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

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

Regulatory Information

新产品

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000403871
0000403871
SLCJ2007
SLCC9585
SLBP4042V

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  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. What is the difference between Mitomycin C products M4287 and M0503?

    M4287 has been cell culture tested; M0503 has not been cell culture tested.

  4. 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.

  5. How should the product be dissolved?

    Mitomycin C is soluble at 0.5 mg/mL in water, yielding a clear blue solution.

  6. 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.

  7. What is the recommended concentration of Mitomycin C, Product M4287, should I use for eukaryote cell culture?

    A concentration between 10-50 micrograms/mL is typically used.

  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.

Mitomycin derivatives. 1. Preparation of mitosane and mitosene compounds and their biological activities.
S Kinoshita et al.
Journal of medicinal chemistry, 14(2), 103-109 (1971-02-01)
Y Mao et al.
Chemistry & biology, 6(4), 251-263 (1999-04-01)
The mitomycins are natural products that contain a variety of functional groups, including aminobenzoquinone- and aziridine-ring systems. Mitomycin C (MC) was the first recognized bioreductive alkylating agent, and has been widely used clinically for antitumor therapy. Precursor-feeding studies showed that
EFFECTS OF MITOMYCIN C ON HUMAN CHROMOSOMES.
M M COHEN et al.
The Journal of cell biology, 23, 386-395 (1964-11-01)
Akshay Gopinathan Nair et al.
Indian journal of ophthalmology, 63(4), 335-339 (2015-06-06)
Dacryocystorhinostomy (DCR) is the procedure of choice in patients with epiphora due to primary acquired nasolacrimal duct obstruction. The evolution of surgical tools, fiber-optic endoscopes, effective anesthesia techniques, and the adjunct use of antimetabolites intraoperatively; namely mitomycin-C (MMC) have significantly
Mavi Camarasa et al.
Cloning and stem cells, 11(3), 453-462 (2009-07-15)
Human embryonic stem cell (hESC) growth is dependent on various factors released by feeder cells. Some of them have already been elucidated, although much research is still needed to understand the biology of stem cell maintenance in culture. Traditionally, primary
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