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Key Documents

M0503

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

powder, contains NaCl as solubilizer

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen


About This Item

Empirický vzorec (Hillův zápis):
C15H18N4O5
Číslo CAS:
Molekulová hmotnost:
334.33
Beilstein/REAXYS Number:
7231816
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.76

biological source

Streptomyces caespitosus

Quality Level

form

powder

contains

NaCl as solubilizer

color

gray
purple/blue

 

(1) 3.2, (2) 6.5

solubility

H2O: 1 vial + 4 mL, clear to slightly hazy, blue to purple

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

Chemical structure: aziridine

Application

Mitomycin C is produced by a strain of actinomyces, Streptomyces caespitosus. It contains three anticancer 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.

Biochem/physiol Actions

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.

pictograms

Health hazardExclamation mark

signalword

Warning

hcodes

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


Osvědčení o analýze (COA)

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Sortimentní položky

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

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