Crystal structure, optical properties and biological imaging of two curcumin derivatives

• Two novel curcumin derivative was synthesized.
• The comounds exhibited obvious TPA in the range from 700–900 nm in high polar solvents.
• Cytotoxicity tests showed that the low concentrations of the compounds did not cause reduction in cell viability at 24 h.
• TPM imaging and photostability revealed the compounds are suitable for cell imaging.

Two new curcumin derivatives, 1,7-bis(4-ethyloxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione and 1,7-bis(4-butyloxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione, are conveniently synthesized. Single and two-photon fluorescence of two compounds have been investigated. The two-photon absorption cross-sections (σ) of the two compounds were calculated by quantum chemical method, which are as high as 386 and 418 × 10−50 cm4 s photon−1 in dimethyl formamide (DMF), as well as up to 475 and 563 × 10−50 cm4 s photon−1 in dichloromethane, respectively. Furthermore, cellular imaging results demonstrate that the as-prepared compounds have high photostability, strong fluorescence in the red region and are nontoxic up to 40 μmol/L, which are suitable for long-term and high-specificity immunofluorescent cellular labeling.

Two curcumin derivatives were synthesized. Cell imaging of MCF-7 cells labeled with the as-prepared compounds revealed the potential applications as a biological probe.Figure optionsDownload as PowerPoint slide