Strained Alkyne-Cycloparaphenylenes: a New Class of Clickable Fluorophores

Presenter(s): Anna Garrison — Biochemistry

Faculty Mentor(s): Julia Fehr

Session: (Virtual) Poster Presentation

Looking inside the human body is a critical tool researchers and physicians need in order to explore the human species, navigate and discover new diseases, or even begin to look at cures or treatment plans for illnesses. What most don’t know, is that the human body is dark and examining its intricate details is impossible without some sort of tagging method. Fluorophores are fluorescent chemical markers that can be used to illuminate and strategically fluoresce certain aspects of biological systems. [n]cycloparaphenylenes or “CPPs” are a unique class of macrocycles made of radially oriented pi systems. CPPs can be synthesized with various techniques to manipulate molecules with different electronic properties that yield varying size-dependent fluorescence. CPPs foster the potential to be used for biological imaging due to their tunable optical properties and reactivity. In this study, the use of macrocyclic angle-strained alkyne-containing CPPs is explored as their unique moiety can serve as the means of attachment to biological molecules through copper-free click chemistry. This study reports the first account of a strained-alkyne CPP clicked to a biological molecule. Additionally, it is demonstrated that strained-alkyne CPPs are not only nontoxic to living cells, but can also be used to fluoresce the cell surface of living human Jurkat cells utilizing a metabolic labelling approach. This is a less invasive cell labelling procedure that can be used to image live cells.

Leave a Reply

Your email address will not be published. Required fields are marked *