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M4287

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, BioReagent, suitable for cell culture

Synonym(s):

Mitomycin

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About This Item

Empirical Formula (Hill Notation):
C15H18N4O5
CAS Number:
Molecular Weight:
334.33
Beilstein/REAXYS Number:
7231816
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.76

biological source

Streptomyces caespitosus

Quality Level

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

Exclamation markHealth hazard

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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