MitomycinCisproducedbyastrainofactinomyces, Streptomycescaespitosus.Itcontainsthreeanticancermoieties,quinine,urethane,andaziridinegroups.Itisusedtogeneratemitoticallyinactivefeedercellsincellculturesystems,suchasthemitoticallyinactivefibroblastsusedinembryonicstemcellsystems.
Thisproductisan alkylatingagent thatspecificallytargetstheguaninenucleosidesequence5′-CpG-3′.ItinhibitsDNAsynthesisbycovalentlyreactingwithDNA,formingcrosslinksbetweencomplementarystrandsofDNA.ThisinteractionpreventsseparationofcomplementaryDNAstrands,inhibitingDNAreplication.
MitomycinChasstrong antitumoractivity,especiallyagainstEhrlichascitestumorcells,andstrongbactericidalactionagainstgram-positiveandgram-negativebacteria. MitomycincroleinpluripotentstemcellsresearchexpandsintotheCRISPR/Cas9revolutiontopermitefficientgenecorrection.
AdditionalInformation
| Synonyms | MMC,Mutamycin,Ametycin,Mitocin-C |
|---|---|
| Product# | M-1108 |
| CAS# | 50-07-7 |
| ChemicalName | [(1AS,8S,8AR,8BS)-6-AMINO-8A-METHOXY-5-METHYL-4,7-DIOXO-1,1A,2,4,7,8,8A,8B-OCTAHYDROAZIRENO[2",3":3,4]PYRROLO[1,2-A]INDOL-8-YL]METHYLCARBAMATE |
| Formula | C15H18N4O5 |
| MW | 334.3 |
| Appearance | Blue-VioletCrystals |
| Purity | 98% |
| Solubility | Solubleinwater(100mg/mlat25°C),ethanol(50mM),methanol(5mg/ml),DMSO(100mM),andDMF |
| BoilingPoint | 581.8±50.0°Cat760mmHg |
| StorageTemp | -20°C |
| TherapeuticArea | OncologicalDisorders |
| Use | ADNAcrosslinkingagentthatinhibitsDNAsynthesisandinducesapoptosisinavarietyofcellsuseincancer |
| MerckIndex | 13.6236[p.2001 |
|---|---|
| MDLNumber | MFCD00078109 |
| ChemACX | X1004059-0 |
| InChI | 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 |
| SMILES | CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4)N |
