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Chapter 6: Problem 3

What properties would you incorporate into the design of DNA intercalating agents?

Short Answer

Expert verified
To design effective DNA intercalating agents, one should incorporate properties such as the correct size and planar shape, distribution of charge, specificity for DNA sequences, and resistance to metabolic degradation.

Step by step solution

01

Recognize the process

DNA intercalation is a process where a molecule inserts itself between DNA base pairs. This process is often utilized by DNA intercalating agents, which are usually planar polycylic aromatic molecules.
02

Consider the agent properties

In designing such agents, several key properties need to be considered. First, the planarity and size of the molecule are essential for it to fit between the DNA base pairs. Secondly, the molecule also needs to have the correct distribution of charge to interact electrostatically with the DNA.
03

Understand the interaction with DNA

The specific interaction with the DNA sequence and structure is also important. For instance, some agents are more likely to interact with AT rich regions. Furthermore, the ability of the agent to withstand metabolic degradation is particularly crucial, as premature degradation could limit its DNA-interacting potential.

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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.

Draw a mechanism for the intrastrand cross linkage of two guanines by busulfan \((6.33, n=4)\).

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