Mitomycin C from Streptomyces caespitosus
SIGMA/M4287 - powder, BioReagent, suitable for cell culture
Synonym: Mitomycin
CAS Number: 50-07-7
Empirical Formula (Hill Notation): C15H18N4O5
Molecular Weight: 334.33
MDL Number: MFCD00078109
Linear Formula: C15H18N4O5
Product Type: Chemical
| (1) 3.2, (2) 6.5 | |
| antibiotic activity spectrum | Gram-negative bacteria |
| Gram-positive bacteria | |
| biological source | Streptomyces caespitosus |
| color | gray |
| purple/blue | |
| form | powder |
| InChI | 1S/C15H18N4O5/c1-5-9(16)1 |
| InChI key | NWIBSHFKIJFRCO-WUDYKRTCSA |
| mode of action | DNA synthesis | interferes |
| product line | BioReagent |
| Quality Level | 200  |
| SMILES string | [H][C@]12CN3C4=C([C@@H](C |
| solubility | H2O: 4 mL/vial, clear to slightly hazy, blue to purple (Stock solutions should be filter sterilized and stored at 2-8 °C in the dark.) |
| storage temp. | 2-8°C |
| technique(s) | cell culture | mammalian: suitable |
| Application: | Mitomycin C from Streptomyces caespitosus has been used for the treatment of feeder layers such as, PMEF (primary mouse embryonic fibroblasts) and CD1 mouse embryonic fibroblasts (MEFs) for the culture of hESCs (human embryonic stem cells). It has also been used for the treatment of BLC (basal-like cancer) cell line. |
| Biochem/physiol Actions: | Mitomycin C causes the cross-linking of double-stranded DNA, which results in mutagenesis, inhibition of DNA synthesis, initiation of DNA repair events, and activation of apoptosis. The capability to inhibit DNA synthesis is attributable to the aminoquinone group present in mitomcyin C. This compound does not affect the synthesis of RNA and protein. In tissue culture, this compound decreases cell viability and suppresses mitosis, and causes disorganization of nucleus and the production of giant cells. Mitomycin C has potent anti-Gram negative and anti-Gram positive activities. It contains three 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. |
| Disclaimer: | 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. |
| General description: | Mitomycin C is a systemic chemotherapy compound and an antibiotic obtained from Streptomyces caespitosus. It is the first bioreductive alkylating agent to be identified and is a derivative of 3-amino-5-hydroxybenzoic acid (AHBA), D-glucosamine, L-methionine and carbamoyl phosphate. Chemical structure: Aziridine |
| 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. |
| Symbol |   GHS07,GHS08 |
| Signal word | Warning |
| Hazard statements | H302 - H351 |
| Precautionary statements | P201 - P301 + P312 + P330 - P308 + P313 |
| Hazard Codes | Xn |
| Risk Statements | 22-40 |
| Safety Statements | 22-36/37-60 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352207 |