M0440

Mitomicina C from Streptomyces caespitosus

meets USP testing specifications

• Sinónimos: Mitomycin
• Fórmula empírica (notación de Hill): C₁₅H₁₈N₄O₅
• Número de CAS: 50-07-7
• Peso molecular: 334.33
• Beilstein/REAXYS Number: 7231816
• EC Number: 200-008-6
• MDL number: MFCD00078109
• UNSPSC Code: 12352203
• PubChem Substance ID: 24896554
• NACRES: NA.76

Propiedades

• biological source: Streptomyces caespitosus
• 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

Descripción

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

Modo de acción: Este producto es un agente alquilante dirigido específicamente a la secuencia del nucleósido de guanina 5′-CpG-3′. Inhibe la síntesis de ADN mediante reacción covalente con el ADN al establecer enlaces transversales entre las cadenas complementarias del ADN. Esta interacción evita la separación de las cadenas de ADN complementarias, inhibiendo así la replicación del ADN.

Espectro antimicrobiano: La mitomicina C tiene una fuerte actividad antitumoral, en especial contra las células tumorales de la ascitis de Ehrlich, y una fuerte acción bactericida contra las bacterias grampositivas y gramnegativas.

Caution

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.

Información de seguridad

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H351
• pcodes: P201 - P301 + P310 + P330
• Hazard Classifications: Acute Tox. 2 Oral - Carc. 2
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges