2-(n-(7-nitrobenz-2-oxa-1-3-diazol-4-yl)amino)-2-deoxyglucose and Neoplasms

2-(n-(7-nitrobenz-2-oxa-1-3-diazol-4-yl)amino)-2-deoxyglucose has been researched along with Neoplasms* in 3 studies

Reviews

1 review(s) available for 2-(n-(7-nitrobenz-2-oxa-1-3-diazol-4-yl)amino)-2-deoxyglucose and Neoplasms

ArticleYear
Aberrant Uptake of a Fluorescent L-Glucose Analogue (fLG) into Tumor Cells Expressing Malignant Phenotypes.
    Biological & pharmaceutical bulletin, 2018, Volume: 41, Issue:10

    Glucose, one of the most fundamental sugar elements, has either D- or L-conformation. Of these, most cells preferentially take up D-glucose as an essential energy/carbon source. Such stereoselective uptake of glucose has been explored by fluorophore-bearing D- and L-glucose analogues. 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-D-glucose (2-NBDG), the most widely used fluorescent D-glucose analogue, was abundantly taken up into living Escherichia coli cells, whereas no detectable uptake was obtained for 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-L-glucose (2-NBDLG), the antipode of 2-NBDG developed as a fluorescent L-glucose analogue (fLG). Interestingly, we found three-dimensionally accumulating tumor cell aggregates taking up 2-NBDLG when they expressed nuclear heterogeneity, one of the major cytological criteria for cells suspected of high-grade malignancy in clinical diagnosis. 2-NBDLG uptake was not detected in aggregates consisting of homogeneous cells and was specifically abolished by phloretin, a broad-spectrum inhibitor against transporters/channels. Preliminary studies have suggested that a combined use of 2-NBDLG, which emits green fluorescence, with 13-[4-[(2-deoxy-D-glucopyranose-2-yl)aminosulfonyl]-2-sulfonatophenyl]-4,5-trimethylene-7,8-trimethylene-1,2,3,4,6,9,10,11-octahydro-4-aza-6-oxa-8-azoniapentacene (2-TRLG), a membrane-impermeable fLG bearing a large red fluorophore, is effective for discriminating malignant tumor from benign cells both in living biopsy specimens endoscopically dissected from patients with early-stage gastric cancer and in ascites fluid of patients with gynecological cancers. Confocal endomicroscopic imaging of a carcinogen-induced cancer in bile duct of hamsters indicated that the fLG uptake pattern well correlated with pathological diagnosis for carcinoma. Safety tests according to Good Laboratory Practice regulations have been successfully completed so far. fLGs are unique fluorescent glucose analogues for identifying and characterizing living cancer cells based on derangements in their transport function.

    Topics: 4-Chloro-7-nitrobenzofurazan; Animals; Deoxyglucose; Diagnostic Imaging; Filaggrin Proteins; Fluorescence; Fluorescent Dyes; Glucose; Humans; Neoplasms; Stereoisomerism

2018

Other Studies

2 other study(ies) available for 2-(n-(7-nitrobenz-2-oxa-1-3-diazol-4-yl)amino)-2-deoxyglucose and Neoplasms

ArticleYear
A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake.
    PloS one, 2019, Volume: 14, Issue:7

    Glycoconjugation to target the Warburg effect provides the potential to enhance selective uptake of anticancer or imaging agents by cancer cells. A Warburg effect targeting group, rationally designed to facilitate uptake by glucose transporters and promote cellular accumulation due to phosphorylation by hexokinase (HK), has been synthesised. This targeting group, the C2 modified glucose analogue 2-(2-[2-(2-aminoethoxy)ethoxy]ethoxy)-D-glucose, has been conjugated to the fluorophore nitrobenzoxadiazole to evaluate its effect on uptake and accumulation in cancer cells. The targeting vector has demonstrated inhibition of glucose phosphorylation by HK, indicating its interaction with the enzyme and thereby confirming the potential to facilitate an intracellular trapping mechanism for compounds it is conjugated with. The cellular uptake of the fluorescent analogue is dependent on the glucose concentration and is so to a greater extent than is that of the widely used fluorescent glucose analogue, 2-NBDG. It also demonstrates selective uptake in the hypoxic regions of 3D spheroid tumour models whereas 2-NBDG is distributed primarily through the normoxic regions of the spheroid. The increased selectivity is consistent with the blocking of alternative uptake pathways.

    Topics: 4-Chloro-7-nitrobenzofurazan; Cell Hypoxia; Cell Line, Tumor; Deoxyglucose; Drug Delivery Systems; Glucose; Glucose Transport Proteins, Facilitative; Hexokinase; Humans; Models, Biological; Neoplasm Proteins; Neoplasms

2019
Optical molecular imaging approach for rapid assessment of response of individual cancer cells to chemotherapy.
    Journal of biomedical optics, 2012, Volume: 17, Issue:10

    Predicting the response of individual patients to cytotoxic chemotherapy drugs is critical for developing individualized therapies. With this motivation, an optical molecular imaging approach was developed to detect cisplatin induced changes in the uptake and intracellular retention of choline. Intracellular uptake of choline was characterized using a click chemistry reaction between propargyl choline and Alexa-488 azide. Cisplatin induced changes in the uptake of propargyl choline in cells and tumor spheroids were compared with similar measurements using a fluorescent analogue of deoxyglucose and conventional cell viability assays. Uptake and intracellular retention of propargyl choline decreased with an increase in concentration of cisplatin. Intracellular uptake of propargyl choline was significantly reduced within 3 h of incubation with a sub-lethal dose of cisplatin. Results demonstrate that the imaging approach based on propargyl choline was more sensitive in detecting the early response of cancer cells to cisplatin as compared to the imaging based on fluorescent analogue of deoxyglucose and cell viability assays. Imaging measurements in tumor spheroids show a significant decrease in the uptake of propargyl choline following treatment with cisplatin. Overall, the results demonstrate a novel optical molecular imaging approach for rapid measurement of the response of individual cancer cells to cisplatin treatment.

    Topics: 4-Chloro-7-nitrobenzofurazan; Analysis of Variance; Antineoplastic Agents; Apoptosis; Cell Survival; Choline; Cisplatin; Deoxyglucose; Fluorescent Dyes; HeLa Cells; Humans; Hydrazines; Microscopy, Fluorescence; Molecular Imaging; Neoplasms; Spheroids, Cellular

2012