M0440

Mitomycin C aus Streptomyces caespitosus

meets USP testing specifications

• Synonym(e): Mitomycin
• Empirische Formel (Hill-System): C₁₅H₁₈N₄O₅
• CAS-Nummer: 50-07-7
• Molekulargewicht: 334.33
• UNSPSC Code: 12352203
• NACRES: NA.76
• PubChem Substance ID: 24896554
• EC Number: 200-008-6
• Beilstein/REAXYS Number: 7231816
• MDL number: MFCD00078109

Eigenschaften

• biological source: Streptomyces caespitosus
• Quality Segment: 200
• color: blue-violet
• solubility: H₂O: 40 mg/mL, clear to very slightly hazy, colorless, H₂O: soluble
• 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

Beschreibung

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

Wirkungsmechanismus: Dieses Produkt ist ein Alkylierungsmittel, das spezifisch auf die Guaninnukleosidsequenz 5′-CpG-3′ abzielt. Es hemmt die DNA-Synthese, indem es kovalent mit der DNA reagiert und Vernetzungen zwischen komplementären DNA-Strängen bildet. Diese Wechselwirkung verhindert die Trennung der komplementären DNA-Stränge und hemmt somit die DNA-Replikation.

Antimikrobielles Spektrum: Mitomycin C weist eine starke Antitumorwirkung, insbesondere gegen Ehrlich-Aszites-Tumorzellen, sowie eine starke bakterizide Wirkung gegen grampositive und gramnegative Bakterien auf.

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

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.

Sicherheitshinweise

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H351
• Hazard Classifications: Acute Tox. 2 Oral - Carc. 2
• Lagerklasse: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
• pcodes: P202 - P264 - P280 - P301 + P310 - P405 - P501