engleski

Stokes shifted styryl Dyes – interactions with DNA/RNA, cytotoxicity and application as fluorescent probes

The excellent optical properties of styryl dyes (photostability and ease of synthesis) gave rise to applications, such as in optical devices or as biosensors and cellular or tissue staining agents. In this work, nine novel styryl dyes were designed and prepared as the continuation of previous work, to further study the relation of the structure of styryl dye to photophysical properties and binding to biomolecules. Various N-quaternary heterocyclics, ranging from the smallest aromatic structure of pyridine (P-PY, O-PY) to the largest, benzo[e]indole (BZ-IND), were employed. The dyes fluorescence spectra showed remarkable Stokes' shifts dependent on the heterocyclic moiety. All the studied dyes showed a strong fluorescence increase upon binding to DNA/RNA with micromolar affinity. Joined results of several methods supported the binding of dyes into the DNA minor or RNA major groove, with no significant selectivity between various types of ds-DNA or ds- RNA. The most of dyes showed no cytotoxic effect on human cells, except for BZ-IND which was toxic even at 1μM concentrations. Intracellular localization studies showed that most dyes localize in the mitochondria, again except for BZ- IND which distributes equally between mitochondria and lysosome, and benzo[d]selenazole (BZ-Se) which accumulates preferably in the lysosome. Here presented results show excellent properties of these novel dyes for use as intracellular staining agents or, in the case of the bioactive BZ-IND derivative, possible application as a theranostic agent.

styryl dyes ; stokes shift ; DNA/RNA binding ; theranostic agent

nije evidentirano