M0440

Mitomycin C from Streptomyces caespitosus

meets USP testing specifications

• Synonym(s): Mitomycin
• Empirical Formula (Hill Notation): C₁₅H₁₈N₄O₅
• CAS Number: 50-07-7
• Molecular Weight: 334.33
• Beilstein: 7231816
• EC Number: 200-008-6
• MDL number: MFCD00078109
• UNSPSC Code: 12352203
• PubChem Substance ID: 24896554
• NACRES: NA.76

Properties

• 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

Description

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

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.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300,H351
• Precautionary Statements: P201 - P301 + P310 + P330
• Hazard Classifications: Acute Tox. 2 Oral - Carc. 2
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves