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Title: Glycosylated star-shaped conjugated oligomers for targeted two-photon fluorescence imaging
Authors: Wang, G.
Zhang, X.
Geng, J.
Li, K.
Ding, D. 
Pu, K.-Y. 
Cai, L. 
Lai, Y.-H. 
Liu, B. 
Keywords: fluorescence
targeted imaging
Issue Date: 27-Jul-2012
Citation: Wang, G., Zhang, X., Geng, J., Li, K., Ding, D., Pu, K.-Y., Cai, L., Lai, Y.-H., Liu, B. (2012-07-27). Glycosylated star-shaped conjugated oligomers for targeted two-photon fluorescence imaging. Chemistry - A European Journal 18 (31) : 9705-9713. ScholarBank@NUS Repository.
Abstract: A glucopyranose functionalized star-shaped oligomer, N-tris{4,4',4"- [(1E)-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)-9H-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. Biological imaging: A star-shaped two-photon absorbing material (see scheme) with folic acid functionalization has been synthesized for targeted two-photon fluorescence imaging of MCF-7 cancer cells. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Chemistry - A European Journal
ISSN: 09476539
DOI: 10.1002/chem.201200849
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