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M0440 Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

≥970 μg/mg (USP XXIV)

  • CAS Number 50-07-7

  • Empirical Formula (Hill Notation) C15H18N4O5

  • Molecular Weight 334.33

  •  Beilstein/REAXYS Number 7231816

  •  EC Number 200-008-6

  •  MDL number MFCD00078109

  •  PubChem Substance ID 24896554

  •  NACRES NA.76

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application, Antibiotics by Mechanism of Action,
Quality Level   100
biological source   Streptomyces caespitosus
assay   ≥970 μg/mg (USP XXIV)
color   blue-violet
solubility   H2O: 40 mg/mL, clear to very slightly hazy, colorless
  H2O: soluble
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
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

Packaging

5, 25 mg in glass bottle

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 & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
WGK 3
RTECS 
CN0700000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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