1-(2-chloroethyl)-3-(1-oxyl-2,2,6,6-tetramethylpiperidinyl)-1-nitrosourea

Description

The compound you're describing is **1-(2-chloroethyl)-3-(1-oxyl-2,2,6,6-tetramethylpiperidinyl)-1-nitrosourea**. It's a bit of a mouthful, and you'll often see it referred to by its shorter name, **CCNU**.

**CCNU is an alkylating agent, a type of chemotherapy drug.** Here's a breakdown of its components and their significance:

* **1-Nitrosourea:** This is the core functional group responsible for the drug's cytotoxic (cell-killing) activity. It releases a highly reactive nitrogen-containing species that can damage DNA within cancer cells.
* **1-(2-chloroethyl):** This portion of the molecule is also involved in the alkylating process. It can react with DNA, creating cross-links that interfere with its function.
* **3-(1-oxyl-2,2,6,6-tetramethylpiperidinyl):** This part of the molecule, sometimes referred to as the TEMPO group, is a stable free radical. This allows for CCNU to be studied with techniques like electron paramagnetic resonance (EPR) spectroscopy.

**CCNU's Importance in Research:**

CCNU has been historically important in cancer research, particularly in the treatment of **brain tumors**. However, it is **no longer widely used clinically** due to its severe side effects.

Here's why it remains relevant in research:

* **Understanding Cancer Biology:** CCNU has been instrumental in understanding how alkylating agents work at the molecular level, providing insight into the mechanisms of DNA damage and repair.
* **Development of New Drugs:** The structure of CCNU has served as a basis for the development of newer and safer alkylating agents, such as lomustine, which have fewer side effects.
* **Probing Cell Processes:** The TEMPO group makes CCNU a useful tool for studying various biological processes, including:
* The delivery and uptake of drugs into cells.
* The mechanisms of drug resistance.
* The dynamics of free radical reactions in living systems.

**Overall, while CCNU is not a standard treatment for cancer today, it remains an important research tool for studying cancer biology and for developing new and more effective anti-cancer agents.**

1-(2-chloroethyl)-3-(1-oxyl-2,2,6,6-tetramethylpiperidinyl)-1-nitrosourea: has more antineoplastic activity & less toxicity than CCNU; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]