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Glycosyl‐Modified Diporphyrins for in Vitro and in Vivo Fluorescence Imaging
Author(s) -
Wu Ming,
Yu ZuoWei,
Liu Yang,
Feng DaoFu,
Yang JiaJia,
Yin XueBo,
Zhang Tao,
Chen DongYan,
Liu TianJun,
Feng XiZeng
Publication year - 2013
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201300065
Subject(s) - biocompatibility , glycosyl , porphyrin , chemistry , fluorescence , preclinical imaging , derivatization , in vivo , biophysics , dimer , autofluorescence , combinatorial chemistry , biochemistry , chromatography , organic chemistry , biology , physics , high performance liquid chromatography , microbiology and biotechnology , quantum mechanics
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.