Two-photon absorption and cell imaging of two multi-branched dyes based on curcumin

•Two multi-branched dyes based on curcumin are synthesized.•The obtained compounds exhibited large TPA cross-section.•The obtained compounds have low toxicities.•The dye 1 could used potentially as biological probe.•The dye 1 could accumulated rapidly in tumor tissues.

Two novel multibranched dyes curcumin-based: 1,7-bis(4′-propyloxy-3′-methyloxy-phenyl)-3-propyloxy-5-carbonyl-1,6-heptadiene (dye 1) and 1,7-bis(4′-acetate ethyloxy-3′-methyloxy-phenyl)-1,6-heptadiene-4,4-diacetate ethyl-3,5-dione (dye 2) were easily prepared. Their one- and two-photon absorption properties have been investigated carefully. The two-photon absorption (TPA) cross sections measured by two-photon excited fluorescence (TPEF) were determined to be 1143 and 842 GM for dye 1 and dye 2, respectively. Cell viability tests revealed the as-prepared compounds possessed low cytotoxicity against MCF-7 cell lines over a period of at least 24 h. In addition, in vitro and in vivo studies demonstrated the dye 1 could enter into tumor cells, and even rapid accumulate in tumor tissues, which makes it an ideal organic material for biomedical imaging.

Graphical abstractTwo novel multi-branched dyes based on curcumin had been synthesized. The experimental results show that the as-prepared compounds bear low toxicity, strong TPEF and large TPA cross-section, which has been used potentially for biological two-photon fluorescent probe.Figure optionsDownload full-size imageDownload as PowerPoint slide