1,4,7-triazacyclononane-n,n',n''-tris(methylenephosphonate monoethyl ester)

Description

**1,4,7-triazacyclononane-N,N',N''-tris(methylenephosphonate monoethyl ester)**, also known as **TCTP**, is a complex organic molecule with a triazacyclononane (TACN) ring structure and three pendant methylenephosphonate monoethyl ester groups.

**Structure and Properties:**

* **TACN Ring:** The triazacyclononane ring is a nine-membered ring containing three nitrogen atoms. This ring structure provides rigidity and coordination sites for metal ions.
* **Phosphonate Groups:** The three methylenephosphonate monoethyl ester groups are attached to the nitrogen atoms of the TACN ring. These groups are negatively charged and can act as strong chelating ligands.
* **Ethyl Ester:** The monoethyl ester functionality provides a degree of lipophilicity, which can enhance membrane permeability.

**Importance in Research:**

TCTP is a valuable tool in a range of research areas, including:

* **Metal Ion Complexation:** Due to its multiple coordination sites and negatively charged phosphonate groups, TCTP is an excellent chelator for various metal ions, such as copper, zinc, and iron. This property makes it useful in studies involving metal-mediated reactions, catalysis, and bioinorganic chemistry.
* **Bioinorganic Chemistry:** TCTP can serve as a model for understanding the coordination chemistry of metal ions in biological systems. Its ability to mimic the binding sites of metalloenzymes has applications in studying enzyme activity, metal transport, and metal detoxification.
* **Drug Delivery:** The lipophilicity of the ethyl ester groups can enhance the membrane permeability of TCTP, making it a potential carrier for drug delivery systems. This property allows for targeted delivery of therapeutic agents to specific cells or tissues.
* **Bioimaging:** The phosphonate groups can be modified with fluorescent probes, enabling TCTP to be used as a fluorescent sensor for metal ions. This application has potential in bioimaging and diagnostics.
* **Materials Science:** TCTP can act as a building block for the synthesis of novel materials with tailored properties. Its ability to form coordination complexes with metal ions can lead to the development of new catalysts, sensors, and nanomaterials.

**Research Applications:**

TCTP has been employed in various research studies, including:

* Investigating the role of metal ions in biological processes
* Developing new metal-based catalysts
* Creating fluorescent probes for bioimaging
* Designing novel drug delivery systems
* Synthesizing functional materials with unique properties

**Conclusion:**

1,4,7-triazacyclononane-N,N',N''-tris(methylenephosphonate monoethyl ester) (TCTP) is a versatile and valuable molecule in diverse research fields. Its ability to chelate metal ions, enhance membrane permeability, and serve as a building block for new materials makes it a crucial tool in advancing our understanding of various scientific disciplines.

1,4,7-triazacyclononane-N,N',N''-tris(methylenephosphonate monoethyl ester): a (31)P NMR probe for measurement of divalent cations in biological systems; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]