M0440

Mitomycine C from Streptomyces caespitosus

meets USP testing specifications

• Synonyme(s) : Mitomycin
• Formule empirique (notation de Hill) : C₁₅H₁₈N₄O₅
• Numéro CAS: 50-07-7
• Poids moléculaire : 334.33
• UNSPSC Code: 12352203
• NACRES: NA.76
• PubChem Substance ID: 24896554
• EC Number: 200-008-6
• Beilstein/REAXYS Number: 7231816
• MDL number: MFCD00078109

Propriétés

• 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

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 d′action : Ce produit est un agent alkylant qui cible spécifiquement la guanine dans la séquence nucléosidique 5′-CpG-3′. Il inhibe la synthèse de l′ADN en réagissant de façon covalente et en formant des liaisons croisées entre les brins complémentaires d′ADN. Ceci empêche la séparation des brins complémentaires d′ADN, ce qui inhibe la réplication de l′ADN.

Spectre antimicrobien : La mitomycine C présente une activité antitumorale puissante, particulièrement envers les cellules du carcinome ascitique d′Ehrlich, et une forte activité bactéricide envers les bactéries à Gram négatif et à Gram positif.

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.

Informations sur la sécurité

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H351
• Hazard Classifications: Acute Tox. 2 Oral - Carc. 2
• Classe de stockage: 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