Mitomycin C from Streptomyces caespitosus

Empirical Formula (Hill Notation):	C15H18N4O5
CAS Number:	50-07-7
Molecular Weight:	334.33
Beilstein/REAXYS Number:	7231816
MDL number:	MFCD00078109
PubChem Substance ID:	24896917
NACRES:	NA.76

Кат. номер

M4287-2MG-PW

M4287-5X2MG

M4287-2MG

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
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.
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.
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.
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.
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.

Quality Level	200
biological source	Streptomyces caespitosus
product line	BioReagent
form	powder
application(s)	cell culture | mammalian: suitable
color	gray, purple/blue
A	(1) 3.2, (2) 6.5
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.)
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

Pictograms	GHS07,GHS08
Signal Word	Warning
Hazard Statements	H302 - H351
Precautionary Statements	P201 - P301 + P312 + P330 - P308 + P313
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable