4698157
| Question | Answer |
| Name two drugs that are enediyne | Chalicheamicin and esperamycin are drugs which are enediynes |
| Mode of action | Formation of a benzenedyl diradical which cleaves a H off central C of DNA and causing eventual DNA cutting and death |
| Mechanism 1st part | Cellular nucleophile attacks the trigger (trisulphide moiety) 's-sME' bond and forms internal sulphur nucleophile. Then s- undergoes conjugate addition to enone. New bond formed. ketone is reformed as dB takes a H from surrounding. The new bond that formed causes the alkyne bonds to come closer 3.35-3.16A. Allowing Bergmann cyclo aromatisation. |
| Bergmann cyclo aromatisation | Radical arrows open up the alkyne and formation of a sigma bond formed a 6 MEMBERED cyclo diradical. |
| DNA Cleavage | Diradical cleaves H Central C radical formed O2 +h radical sees formation of peroxide on central C Reduction sees formation of alcohol The DNA is cleaved forming an aldehyde DNA has successfully been cut and cell dies |
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