Method of preparation and use of derivatives of perylene-diimide (PDI) in different applications such as bioimaging or biomarkers.

New and innovative aspects

The large versatility of the developed methodology permits to obtain compounds with two positions of functionalization, in the imide positions allowing to interact with different targets and, in this way, to control the biological specificity (what will be detected and to what parts of the cell it will go), and in the bay positions choosing the emission colour for the modulation of the fluorescent emission.

The bioconjugation, chemical strategy to form stable links between different biomolecules, presents some disadvantages, solved using this new proposed methodology. In addition, it avoids having to develop specific systems for each application, which suppose a great cost saving and increases its field of action in multiple sectors.

Main advantages of its use

The available market alternatives show low photostabilities, are very sensitive to pH or to ionic strength and their fluorescent emission intensities are low. In addition, they usually have low emission wavelengths, so no desirable phenomena such as energy self-absorption or scattering may take place.

The perylene-diimide (PDI) obtained by this invention have many desirable characteristics that solve the market deficiencies, such as: high fluorescence, high chemical and optical stability, stability against radiation, different wavelengths of fluorescent emission depending on the substituents in that positions and the possibility of an easy functionalization in N and N' positions. In addition, they exhibit high quantum yields, which can even reach one unit.

Specifications

The modifications made in the substituents of organic molecules known as perylene-diimide (PDI) or perylene bisimides (PBI) modify their solubility, making them versatile in different media, both organic and aqueous. Variations in the substituents of the imide positions do not significantly affect to their fluorescent properties, allowing the inclusion of bioconjugate biomolecules, while in the substituents of the bay positions, they modify their luminescent properties, allowing to modulate the emission wavelengths of the resultant fluorophore.

Thanks to the bioconjugation, novel systems with unique characteristics are obtained, such as fluorescent emission. In this case, the possibility of its use as a specific biomarker in fields such as bioimage, therapy and diagnosis is considered

Applications

The potential market is relatively wide due to the versatility of this technology. Its possible applications are in multiple sectors, such as: medicine, material science and agrofood industry. More specific applications can be mentioned, such as:

• Development of individual kits for bioconjugation, specifically fluorescent markers in medicine field that allow the realization of diagnoses and monitoring of specific treatments.
• Detection of biological contaminating species of high interest in agrofood industry such as enterotoxins or avidin (PDI-Biotin systems).
• Study of epithelial cells (PDI-Mupirocin systems).
• Marking, monitoring or determination of protein biodistribution.
• Monitoring of cell events such as drug administration to target cells and the study of enzymatic functions among others.

Intellectual property status

Protected by patent P201830029

Current development status

The technology related to the synthesis method is developed.

Desired business relationship

Commercial agreement; License agreement; Technical cooperation: further development; Technical cooperation: testing new applications; Technical cooperation: adaptation to specific needs.