Undergoes biological reduction and DOUBLE alkylation
Mitomycin C
Fundamentals:
- Quinone
- Undergoes biological reduction
- Blocks DNA replication
- Targets C-G units Mustard gases
- Aziride
- -O-Me
- -OCONH2
LOC:
- Minor Groove DNA
Mechanism:
- N lone pair forms imine
- Glycoside (-O-Me) leaves LG
- Hydroquinone forms
- Ring opens Aziride
- Bioreduction
- DNA attacks opened ring where Leaving group was
- N lone pair forms imine
- Amide leavs LG
- DNA attacks alkene
