Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.201200849
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
glucopyranose
oligomers
self-assembly
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. https://doi.org/10.1002/chem.201200849
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
URI: http://scholarbank.nus.edu.sg/handle/10635/89017
ISSN: 09476539
DOI: 10.1002/chem.201200849
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

16
checked on Sep 20, 2018

WEB OF SCIENCETM
Citations

17
checked on Sep 10, 2018

Page view(s)

53
checked on Jul 27, 2018

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.