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Chapter 6: Problem 14

Draw a mechanism for how kedarcidin (6) might act as an antitumor agent (a reducing agent is required).

Short Answer

Expert verified
The antitumor action of kedarcidin can be explained by the Bergman cyclization process in presence of a reducing agent, forming a highly reactive 1,4-didehydrobenzene diradical that can cause DNA damage. This leads to cell death especially in rapidly dividing cells, displaying kedarcidin's antitumor activity.

Step by step solution

01

Understanding Kedarcidin structure

Firstly, familiarize yourself with the structure of kedarcidin (6). It is an enediyne compound with two acetylenic groups (carbon-carbon triple bonds) and a double bond located in the same cyclic structure (an enediyne core).
02

Initiating Bergman Cyclization

The mechanism for how kedarcidin might act as an antitumor agent revolves around a chemical reaction known as 'Bergman cyclization'. The cyclization process in this context refers to the formation or conversion of a molecule into a more cyclic form. In the presence of a reducing agent, the triple bond acetylenic groups in the enediyne core undergoes a transformation to form a cyclic structure with 1,4-didehydrobenzene diradical intermediate.
03

Damage to DNA

The 1,4-didehydrobenzene diradical thus formed is highly reactive and can cause DNA strand scission, leading to damage of the DNA molecule. This damage to the DNA molecule leads to cell death, especially in rapidly dividing cells like cancer cells, thereby displaying kedarcidin's antitumor activity.
04

Completing the reaction

Finally, the diradical undergoes rapid reactions with molecular oxygen, leading to stable end products. It is this series of reactions that is hypothesized to be the reason for the antitumor action of kedarcidin.

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Most popular questions from this chapter

\(N, N\)-Diethylnitrosoamine (4) is carcinogenic, resulting in ethylation of DNA. Two other products formed are acetaldehyde and \(\mathrm{N}_{2}\). Under anaerobic conditions or in the absence of NADPH no carcinogenicity is observed. Draw a mechanism for DNA ethylation by this compound.

Amino-seco-CBI-TMI (3) is a minor groove alkylating agent. Show a mechanism for alkylation of DNA that does not involve direct \(\mathrm{S}_{\mathrm{N}} 2\) displacement of the chloride by DNA.

Alkylating agents are used in cancer chemotherapy to interfere with DNA biosynthesis or replication. Why can these be useful considering that normal cells also need DNA?

Draw a mechanism for the formation of a 1,4 -benzene diradical from an activated enediyne (Bergman rearrangement).

Show how isoguanosine (1) could form a Watson-Crick base pair with isocytidine (2).
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