Two‐Photon Detection of Organotin Schiff Base Complexes in Cancer Cells

The early detection of cancer cells and their visualization before and after surgery are essential for successful pre‐ and post‐operative disease management. Although fluorescence imaging is a sensitive and versatile tool that is finding increasing use in clinical applications, there is a lack of tumour‐targeting fluorophores. We report here a family of fluorescent Schiff base organotin dyes (1: Et2N−L‐SnPh2, 2: Et2N−L‐SnBu2, 3: MeO−L‐SnPh2, 4: MeO−L‐SnBu2, 5: HO−L‐SnPh2, and 6: HO−L‐SnBu2, where L=2‐hydroxybenzylidene‐4‐hydroxybenzhydrazine). In addition to one‐photon‐excited fluorescence, efficient two‐photon excitation was demonstrated in compounds 1–4. Two of the compounds (5 and 6), both with hydroxyl substituents, were capable of selective accumulation in HeLa cells, allowing differentiation from normal cells (periodontal ligament cells). Compounds 1 and 3 showed excellent cancer cell staining (HeLa) using two‐photon bioimaging, which is promising for biomedicine applications. We report the synthesis of a family of fluorescent organotin Schiff bases and demonstrate bright emission via one‐photon and two‐photon excitation. Two compounds, with hydroxyl substituents, were capable of selective accumulation in HeLa cells, allowing differentiation from normal cells (periodontal ligament cells). We also report a proof‐of‐principle demonstration of cancer cell staining (HeLa) using two‐photon bioimaging, which is promising for biomedicine applications.