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- Title
Glycosylated Star-Shaped Conjugated Oligomers for Targeted Two-Photon Fluorescence Imaging.
- Authors
Wang, Guan; Zhang, Xinhai; Geng, Junlong; Li, Kai; Ding, Dan; Pu, Kan-Yi; Cai, Liping; Lai, Yee-Hing; Liu, Bin
- Abstract
A glucopyranose functionalized star-shaped oligomer, N-tris{4,4′,4′′-[(1 E)-2-(2-{( E)-2-[4-(benzo[ d]thiazol-2-yl)phenyl]vinyl}-9,9-bis(6-2-amido-2-deoxy-1-thio-β- D-glucopyranose-hexyl)-9 H-fluoren-7-yl)vinyl]phenyl}phenylamine (TVFVBN-S-NH2), is synthesized for two-photon fluorescence imaging. In water, TVFVBN-S-NH2 self-assembles into nanoparticles with an average diameter of ∼49 nm and shows a fluorescence quantum yield of 0.21. Two-photon fluorescence measurements reveal that TVFVBN-S-NH2 has a two-photon absorption cross-section of ∼1100 GM at 780 nm in water. The active amine group on the glucopyranose moiety allows further functionalization of TVFVBN-S-NH2 with folic acid to yield TVFVBN-S-NH2FA with similar optical and physical properties as those for TVFVBN-S-NH2. Cellular imaging studies reveal that TVFVBN-S-NH2FA has increased uptake by MCF-7 cells relative to that for TVFVBN-S-NH2, due to specific interactions between folic acid and folate receptors on the MCF-7 cell membrane. This study demonstrates the effectiveness of glycosylation as a molecular engineering strategy to yield water-soluble materials with a large two-photon absorption (TPA) cross-section for targeted cancer-cell imaging.
- Publication
Chemistry - A European Journal, 2012, Vol 18, Issue 31, p9705
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201200849