Merck
All Photos(1)

M4287

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, BioReagent, suitable for cell culture

Synonym(s):
Mitomycin
Empirical Formula (Hill Notation):
C15H18N4O5
CAS Number:
Molecular Weight:
334.33
Beilstein:
7231816
Numéro MDL:
ID de substance PubChem:
NACRES:
NA.76

Source biologique

Streptomyces caespitosus

Niveau de qualité

200

Gamme de produits

BioReagent

Forme

powder

technique(s)

cell culture | mammalian: suitable

Couleur

gray
purple/blue

 

(1) 3.2, (2) 6.5

Solubilité

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.)

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

DNA synthesis | interferes

Temp. de stockage

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

Description générale

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.

Actions biochimiques/physiologiques

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.

Attention

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.

Notes préparatoires

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

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral - Carc. 2

Code de la classe de stockage

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Point d'éclair 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).

More Documents

SDS

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service