Glycosyl-modified diporphyrins for in vitro and in vivo fluorescence imaging
- Authors
- Wu, M., Yu, Z.W., Liu, Y., Feng, D.F., Yang, J.J., Yin, X.B., Zhang, T., Chen, D.Y., Liu, T.J., and Feng, X.Z.
- ID
- ZDB-PUB-130607-10
- Date
- 2013
- Source
- Chembiochem : a European journal of chemical biology 14(8): 979-986 (Journal)
- Registered Authors
- Feng, Xi
- Keywords
- fluorescent probes, glycosylation, imaging agents, porphyrin dimers
- MeSH Terms
-
- Fluorescent Dyes/analysis*
- Fluorescent Dyes/toxicity
- Glucose/analogs & derivatives*
- Glucose/toxicity
- Zebrafish/embryology
- 3T3 Cells
- Dimerization
- Optical Imaging/methods*
- Patch-Clamp Techniques
- Glycosylation
- Lactose/analogs & derivatives*
- Lactose/toxicity
- Porphyrins/analysis*
- Porphyrins/toxicity
- Mice
- Animals
- Humans
- HeLa Cells
- PubMed
- 23649900 Full text @ Chembiochem
The application of probes for optical imaging is becoming popular as they have high safety and good biocompatibility. We prepared two kinds of glycosyl-modified diporphyrins, and their potentials as fluorescent probes were tested for the first time. After preparation of the glycosyl-modified porphyrin monomers, Ag-promoted coupling of the monomers was used to obtain glucose-modified porphyrin dimer (GPD) and lactose-modified porphyrin dimer (LPD). The strong interaction between the two porphyrin rings achieves red-shifted emission, and thus circumvents autofluorescence and light-scattering in biological samples. Although the glycosylation improves solubility, it also yielded selective attachment to cell membranes, and to chorions of early developmental-stage zebrafish. Patch-clamp experiments revealed the biocompatibility and low toxicity of GPD and LPD. Moreover, an in vivo imaging experiment provided direct evidence that zebrafish chorion contains sugar-binding proteins. The modification and derivatization make porphyrins potential bioimaging probes for specific optical imaging.