I was reading Wikipedia and come across a class of antitumor antibiotic that has an interesting mode of action. An example is calicheamicin γ1:

The molecule consists of two main parts. The part circled in red:

is the “warhead” of the molecule. The rest of the molecule is the targeting system that binds with DNA in the minor groove, delivering the “warhead” to the deoxyribose (sugar) backbone of DNA, which ultimately leads to strand scission.

The interesting part is the “warhead” which is an enediyne moiety. This undergoes a Bergman cyclization, generating a 1,4-didehydrobenzene diradical that abstracts hydrogen atoms from the deoxyribose (sugar) backbone.

thanks, i hadn’t seen that structure before

SCIENCE said:

thanks, i hadn’t seen that structure before

Ditto. I haven’t seen anything remotely like it. I’d love a copy of the software that was used to design it in the first place (to fit in the groove and deliver the active component). It looks quite deadly to DNA, but how the heck does it get into cancer cells in the first place?

mollwollfumble said:

SCIENCE said:

thanks, i hadn’t seen that structure before

Ditto. I haven’t seen anything remotely like it. I’d love a copy of the software that was used to design it in the first place (to fit in the groove and deliver the active component). It looks quite deadly to DNA, but how the heck does it get into cancer cells in the first place?

It gets into all the cells, but cancer cells divide quicker and effects those cells more, hopefully…

mollwollfumble said:

I’d love a copy of the software that was used to design it in the first place (to fit in the groove and deliver the active component).

It’s a natural product from the bacterium Micromonospora echinospora.

KJW said:

mollwollfumble said:

I’d love a copy of the software that was used to design it in the first place (to fit in the groove and deliver the active component).

It’s a natural product from the bacterium Micromonospora echinospora.

That, I didn’t expect.