title: Glycosylated star-shaped conjugated oligomers for targeted two-photon fluorescence imaging.
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-NH(2)), is synthesized for two-photon fluorescence imaging. In water, TVFVBN-S-NH(2) 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-NH(2) 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-NH(2) with folic acid to yield TVFVBN-S-NH(2) FA with similar optical and physical properties as those for TVFVBN-S-NH(2). Cellular imaging studies reveal that TVFVBN-S-NH(2) FA has increased uptake by MCF-7 cells relative to that for TVFVBN-S-NH(2), 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.
authors: Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, National University of Singapore, Singapore.
authors: Guan
authors: G
authors: Wang
authors: Xinhai
authors: X
authors: Zhang
authors: Junlong
authors: J
authors: Geng
authors: Kai
authors: K
authors: Li
authors: Dan
authors: D
authors: Ding
authors: Kan-Yi
authors: KY
authors: Pu
authors: Liping
authors: L
authors: Cai
authors: Yee-Hing
authors: YH
authors: Lai
authors: Bin
authors: B
authors: Liu
mesh_terms: D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005260:Female; D005453:Fluorescence; D005492:Folic Acid / Q000737:chemistry*; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006031:Glycosylation; D006801:Humans; D015394:Molecular Structure; D017785:Photons
chemical_list: D005492:Folic Acid; D005947:Glucose