While this material is soluble in DMSO, stability studies of solutions prepared in this solvent have not been conducted. Historical data indicates the freeze/thaw process may result in a precipitate that cannot be dissolved. Please see the link below to review additional information available in the product datasheet:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/266/701/m4287pis.pdf
M4287
Mitomycin C from Streptomyces caespitosus
powder, suitable for cell culture, BioReagent
Synonym(s):
Mitomycin
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| Pack Size | SKU | Availability | Price |
|---|---|---|---|
| 2 mg | Available to ship TODAYfromMILWAUKEE | $192.00 | |
| 5 x 2 mg | Check Cart for Availability | $751.00 |
About This Item
Empirical Formula (Hill Notation):
C15H18N4O5
CAS Number:
Molecular Weight:
334.33
NACRES:
NA.76
PubChem Substance ID:
UNSPSC Code:
12352207
MDL number:
Beilstein/REAXYS Number:
7231816
Product Name
Mitomycin C from Streptomyces caespitosus, powder, BioReagent, suitable for cell culture
biological source
Streptomyces caespitosus
Quality Segment
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
General description
Mitomycin C is a systemic chemotherapy compound and an antibiotic obtained from Streptomyces caespitosus.[1][2] 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.[3]
Chemical structure: Aziridine
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).[4][5][6] It has also been used for the treatment of BLC (basal-like cancer) cell line.[7]
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.[3][8] 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.[2] Mitomycin C has potent anti-Gram negative and anti-Gram positive activities.[8] 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.
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.
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.
Disclaimer
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.
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This Item | |||
|---|---|---|---|
| mode of action DNA synthesis | interferes | mode of action DNA synthesis | interferes | mode of action DNA synthesis | interferes | mode of action - |
| antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria | antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria | antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria | antibiotic activity spectrum - |
| technique(s) cell culture | mammalian: suitable | technique(s) - | technique(s) - | technique(s) - |
| product line BioReagent | product line - | product line - | product line - |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level - |
| form powder | form powder | form - | form - |
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
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Protocols
This page covers the indirect co-culture of embryonic stem cells with embryonic fibroblasts.
Articles
Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic
Related Content
Instructions
Global Trade Item Number
| SKU | GTIN |
|---|---|
| M4287-5X2MG | 04061835568826 |
| M4287-2MG | 04061835514205 |
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Why dissolve the powder in water when it seems to be more soluble and stable in DMSO?
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What is the main difference between M4287 and M0503? And are both of them suitable for cell culture?
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The main difference between M4287 and M0503 is that M4287 is specifically recommended for cell culture and is cell culture tested with a recommended concentration for use in eukaryotic cell culture.
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Where can I find out the expiry date of the product (powder form, not dissolved yet)?
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This product is not assigned an expiration date. It is assigned a recommended retest date of approximately 4 years after the quality release date. A recommended retest date is the time during which the product is expected to remain within established stability specifications, provided that it has been stored under defined conditions. After the Retest Date, product samples should be examined to ensure that the product is still in compliance with the established specifications.
For more information, you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/US/en/life-science/quality-and-regulatory-management/quality-services.
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What concentration of Mitomycin C (Product M4287) for use with mesenchymal stem cells MSC?
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The use of Mitomycin C (Product M4287) with mesenchymal stem cells (MSC) has not been investigated. This is an application that will need to be validated by the end user.
However, certain publications indicate the use of 1 mg/mL of mitomycin C stock solution in stromal cell culture.
This concentration may be suitable: https://www.sciencedirect.com/science/article/pii/S0014483520304590Helpful?
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How long can it be stored at 4 degrees when dissolved in water? How should I store it to keep it active for a longer period of time?
1 answer-
As mentioned in product information sheet, generally, solutions at pH 6–9 can be stored at 0–5 °C
for up to a week. For more information please see https://www.sigmaaldrich.com/product/sigma/m4287Helpful?
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How should solutions of Mitomycin C, Product M4287, be stored?
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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.
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At what concentration can Mitomycin C, Product M4287, be used with embryonic stem (ES) cells?
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Treatment of the feeder layer with media containing 100 micrograms/mL mitomycin at 37°C for 30 minutes blocked replication of ES cells.
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What is the recommended concentration of Mitomycin C, Product M4287, should I use for eukaryote cell culture?
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A concentration between 10-50 micrograms/mL is typically used.
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What is the difference between Mitomycin C products M4287 and M0503?
1 answer-
M4287 has been cell culture tested; M0503 has not been cell culture tested.
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How should the product be dissolved?
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Mitomycin C is soluble at 0.5 mg/mL in water, yielding a clear blue solution.
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