title: Glycosyl-modified diporphyrins for in vitro and in vivo fluorescence imaging.
abstract: 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.
authors: State Key Laboratory of Medicinal Chemical Biology, College of Life Science and College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300071, China.
authors: Ming
authors: M
authors: Wu
authors: Zuo-Wei
authors: ZW
authors: Yu
authors: Yang
authors: Y
authors: Liu
authors: Dao-Fu
authors: DF
authors: Feng
authors: Jia-Jia
authors: JJ
authors: Yang
authors: Xue-Bo
authors: XB
authors: Yin
authors: Tao
authors: T
authors: Zhang
authors: Dong-Yan
authors: DY
authors: Chen
authors: Tian-Jun
authors: TJ
authors: Liu
authors: Xi-Zeng
authors: XZ
authors: Feng
mesh_terms: D016475:3T3 Cells; D000818:Animals; D019281:Dimerization; D005456:Fluorescent Dyes / Q000032:analysis* / Q000633:toxicity; D005947:Glucose / Q000031:analogs & derivatives* / Q000633:toxicity; D006031:Glycosylation; D006367:HeLa Cells; D006801:Humans; D007785:Lactose / Q000031:analogs & derivatives* / Q000633:toxicity; D051379:Mice; D061848:Optical Imaging / Q000379:methods*; D018408:Patch-Clamp Techniques; D011166:Porphyrins / Q000032:analysis* / Q000633:toxicity; D015027:Zebrafish / Q000196:embryology
chemical_list: D005456:Fluorescent Dyes; D011166:Porphyrins; D005947:Glucose; D007785:Lactose