| Fluorescent fructose derivatives for imaging breast cancer cells. | |
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MedLine Citation:
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PMID: 17444608 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Jelena Levi; Zhen Cheng; Olivier Gheysens; Manish Patel; Carmel T Chan; Yingbing Wang; Mohammad Namavari; Sanjiv Sam Gambhir |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2007-04-20 |
Journal Detail:
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Title: Bioconjugate chemistry Volume: 18 ISSN: 1043-1802 ISO Abbreviation: Bioconjug. Chem. Publication Date: 2007 May-Jun |
Date Detail:
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Created Date: 2007-05-16 Completed Date: 2007-08-29 Revised Date: 2007-12-03 |
Medline Journal Info:
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Nlm Unique ID: 9010319 Medline TA: Bioconjug Chem Country: United States |
Other Details:
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Languages: eng Pagination: 628-34 Citation Subset: IM |
Affiliation:
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Molecular Imaging Program at Stanford, Department of Radiology, Stanford University, Stanford, California 94305, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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4-Chloro-7-nitrobenzofurazan
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analogs & derivatives*,
analysis,
chemical synthesis,
metabolism Azoles / chemistry Biological Transport Breast Neoplasms / diagnosis, metabolism*, ultrastructure Carbocyanines / analysis*, chemical synthesis, chemistry, metabolism Female Fluorescent Dyes / analysis*, chemical synthesis, metabolism Fructose / analogs & derivatives*, analysis, chemical synthesis, metabolism Glucose Transporter Type 5 / metabolism* Humans Microscopy, Fluorescence Nitrobenzenes / chemistry Tumor Cells, Cultured |
| Grant Support | |
ID/Acronym/Agency:
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P50 CA114747/CA/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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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; 10199-89-0/4-Chloro-7-nitrobenzofurazan; 30237-26-4/Fructose |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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