Document Detail

Fluorescent fructose derivatives for imaging breast cancer cells.
MedLine Citation:
PMID:  17444608     Owner:  NLM     Status:  MEDLINE    
Breast cancer cells are known to overexpress Glut5, a sugar transporter responsible for the transfer of fructose across the cell membrane. Since Glut5 transporter is not significantly expressed in normal breast cells, fructose uptake can potentially be used to differentiate between normal and cancerous cells. Fructose was labeled with two fluorophores at the C-1 position: 7-nitro-1,2,3-benzadiazole (NBD) and Cy5.5. The labeling site was chosen on the basis of the presence and substrate specificity of the key proteins involved in the first steps of fructose metabolism. Using fluorescence microscopy, the uptake of the probes was studied in three breast cancer cell lines: MCF 7, MDA-MB-435, and MDA-MB-231. Both fluorescent fructose derivatives showed a very good uptake in all tested cell lines. The level of uptake was comparable to that of the corresponding glucose analogs, 2-NBDG and Cy5.5-DG. Significant uptake of 1-NBDF derivative was not observed in cells lacking Glut5 transporter, while the uptake of the 1-Cy5.5-DF derivative was independent of the presence of a fructose-specific transporter. While 1-NBDF showed Glut5-specific accumulation, the coupling of a large fluorophore such as Cy5.5 likely introduces big structural and electronic changes, leading to a fructose derivative that does not accurately describe the uptake of fructose in cells.
Jelena Levi; Zhen Cheng; Olivier Gheysens; Manish Patel; Carmel T Chan; Yingbing Wang; Mohammad Namavari; Sanjiv Sam Gambhir
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2007-04-20
Journal Detail:
Title:  Bioconjugate chemistry     Volume:  18     ISSN:  1043-1802     ISO Abbreviation:  Bioconjug. Chem.     Publication Date:    2007 May-Jun
Date Detail:
Created Date:  2007-05-16     Completed Date:  2007-08-29     Revised Date:  2014-09-07    
Medline Journal Info:
Nlm Unique ID:  9010319     Medline TA:  Bioconjug Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  628-34     Citation Subset:  IM    
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MeSH Terms
4-Chloro-7-nitrobenzofurazan / analogs & derivatives*,  analysis,  chemical synthesis,  metabolism
Azoles / chemistry
Biological Transport
Breast Neoplasms / diagnosis,  metabolism*,  ultrastructure
Carbocyanines / analysis*,  chemical synthesis,  chemistry,  metabolism
Fluorescent Dyes / analysis*,  chemical synthesis,  metabolism
Fructose / analogs & derivatives*,  analysis,  chemical synthesis,  metabolism
Glucose Transporter Type 5 / metabolism*
Microscopy, Fluorescence
Nitrobenzenes / chemistry
Tumor Cells, Cultured
Grant Support
P50 CA114747/CA/NCI NIH HHS; P50 CA114747/CA/NCI NIH HHS
Reg. No./Substance:
0/1-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-1-deoxyfructose; 0/1-Cy5.5-1-deoxyfructose; 0/7-nitrobenz-2-oxa-1,3-diazol-4-yl; 0/Azoles; 0/CY5.5 cyanine dye; 0/Carbocyanines; 0/Fluorescent Dyes; 0/Glucose Transporter Type 5; 0/Nitrobenzenes; 30237-26-4/Fructose; EQF2794IRE/4-Chloro-7-nitrobenzofurazan

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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