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Reagent: 2-NBDG Monitoring Glucose Uptake into Single, Living, & Malignant Cells A fluorescent glucose derivative was first developed for measurement of glucose uptake activity in E. coli and for rapid determination of non-culture counts of bacteria.1 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2deoxyD-glucose (2-NBDG), accumulates in living but not dead cells and allows for analysis of glucose uptake into cells in real time. Discovery that 2-NBDG uptake into E.coli and C. albicans was blocked by d- but not lglucose, indicated the involvement of glucose transporters (GLUTS) for entry into cells. This was later confirmed in studies where 2-NBDG treatment of cells overexpressed with GLUT2 led to significant increase in fluorescence compared to mock-transfected cells.2 OH O HO HO CODE CKG-23003-v Over time, 2-NBDG is metabolized to a phosphorylated fluorescent derivative and decomposed to a non-florescent one in NO2 cells.9 Therefore, fluorescent intensity is a representation of equilibrium of generation and decomposition of 2-NBDG and the fluorescent N N metabolite.10 The intracellular fate of 2-NBDG O could limit its application, and studies should be carefully performed and interpreted. Despite this limitation, recent studies indicate the fluorescent analog can be useful in studies involving mammalian as well as cancer cells, and may help to further understanding of the role glucose in various diseases. OH HN The use of this fluorescent analog for 2-NBDG quantifying glucose uptake was further expanded to mammalian cells and focused on understanding glucose metabolism, insulin signaling events, and role of glucose on tumor growth. Lanner, et al., utilized 2-NBDG to determine the role of calcium in insulinmediated glucose uptake in skeletal muscles.3 Also 2-NBDG has been most recently used to study glucose uptake and consumption by malignant cancer cells. Cancer cells change metabolism by CKG-23002-v altering glycolysis, which causes an increase glucose consumption and glucose conversion to lactic acid during this process. Lactic acid build-up contributes to invasion and metastasis while suppressing adequate immune response, further contributing to ideal conditions for tumor growth .4-6 O’Neil recently demonstrated uptake of 2-NBDG into malignant cells could be used to monitor glucose in cells, and others have used this method to monitor glucose uptake in order to study the effects of diet on tumor growth.7,8 PRODUCT QTY 2-NBDG 2-[N-(7-Nitrobenz-2-Oxa-1,3-Diazol-4-yl)Amino]-2- Deoxy-d-Glucose (M.W. 342.26) C12H14N4O8 Reagent for Monitoring Glucose Uptake into Single, Living Cells 0.5 mg vial 2-NBDLG 0.5 mg vial 2-[N-(7-Nitrobenz-2-Oxa-1,3-Diazol-4-yl)Amino]-2-Deoxy-l-Glucose (M.W. 342.26) C12H14N4O8 Control Substrate for 2-NBDG T. Yamamoto, Y. Nishiuchi, T. Teshima, H. Matsuoka, and K. Yamada, Tetrahedron Lett., 49, 6876 (2008). (Original) K. Yamada, M. Saito, H. Matsuoka, and N. Inagaki, Nature Protocols, 2, 753 (2007). (Protocols for Measurement) • This compound is distributed through Peptide Institute, Inc. under the license of Hirosaki University Graduate School of Medicine, Tokyo University of Agriculture and Technology, and the Peptide Institute, Inc 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. K. Yoshioka, et al., Biochem. Biophys. Acta, 1289, 5 (1996). K. Yamada, et al., J. Biol. Chem., 75, 22278 (2000). J.T. Lanner, et al., Diabetes, 55, 2077 (2006). R. Stern, S. Shuster, B.A. Neudecker, and B. Formby, Exp. Cell. Res., 276, 24 (2002). S. Walenta, et al., Cancer Res., 60, 916 (2000). K. Fischer, et al., Blood, 109, 3812 (2007). R.G. O’Neil, L. Wu, and N. Mullani, Mol. Imaging Biol., 7, 388 (2005). C. Otto, et al., BMC Cancer, 8, 122 (2008). K. Yoshioka, et al., Biosci. Biotechnol. Biochem., 60, 1899 (1996). K. Yamada, et al., Nature Protocols, 2, 753 (2007). Peptides International, Inc. P.O. Box 99703 Louisville, KY 40269-0703 USA Phone: 502-266-8787 Fax: 502-267-1329 1-800-777-4779 E-mail: [email protected]