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Merck

M4287

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
NACRES:
NA.76
PubChem Substance ID:
24896917
UNSPSC Code:
12352207
MDL number:
MFCD00078109
Beilstein/REAXYS Number:
7231816

Key Documents

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Product Name

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

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

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 key

NWIBSHFKIJFRCO-WUDYKRTCSA-N

biological source

Streptomyces caespitosus

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

Quality Level

200

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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.

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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

hcodes

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Storage Class

11 - Combustible Solids

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Certificates of Analysis (COA)

Lot/Batch Number
SLCJ2007
SLCC9585
SLBP4042V
SLCB4710
SLBX4310

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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
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)
Katja Schenke-Layland et al.
Biomaterials, 32(11), 2748-2756 (2011-01-25)
Stem or progenitor cell populations are often established in unique niche microenvironments that regulate cell fate decisions. Although niches have been shown to be critical for the normal development of several tissues, their role in the cardiovascular system is poorly
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
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
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