Self-Assembled Nanorods of Phenylboronic Acid Functionalized Pyrene for In Situ Two-Photon Imaging of Cell Surface Sialic Acids and Photodynamic Therapy.

Sialic acid (SA) plays important roles in various biological and pathological processes. Methods for monitoring and detection of SA are of great significance in terms of fundamental research, cancer diagnostics, and therapeutics, which are still limited until now. Here, a phenylboronic acid (PBA)-functionalized pyrene derivative, 4-(4-(pyren-1-yl)butyramido)phenylboronic acid (Py-PBA), was synthesized and used as a building block for self-assembling into hydrophilic nanorods. The Py-PBA nanorods (Py-PBA NRs) featured highly specific and efficient imaging of SA on living cells with the advantages of excellent fluorescence stability, good biocompatibility, and unique two-photon fluorescence properties. Meanwhile, the assembled Py-PBA NRs could efficiently generate 1O2 under two-photon irradiation, making it an excellent candidate for photodynamic therapy. This nanoplatform realized in situ recognition and two-photon imaging of SA on the cell surface as well as effective cancer cell therapy, providing a potential method for simple and selective analysis of SA in living cells and a new prospect for image-guided therapy.