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5-anhydro-2-deoxy-d-arabino-hex-1-enitol 2-dichloro-2-deoxy-d-arabino-hexose [18f]-2-fluoro-2-deoxy-d-glucose 18f-2-deoxy-2-fluoro-d-glucose 2-deoxy-2-fluoro-d-[3h]glucose 2-deoxy-2-fluoro-d-[3h]mannose 2-fluoro-2-deoxy-d-glucose month download article/chapter 2-chloro-2-deoxy-d-glucose 2-deoxy-d-glucose increases 2-halogenated d-glucose analogs 2-deoxy-d-glucose 2-trans-2-bromo-2-deoxyglycopyranosyl bromides 2-deoxy-2-fluoro-aldoses article cancer chemotherapy 3-deaza-adenosine analogs—inhibition hypoxic tumor cells full article pdf aerobic cells increases increasing halogen size cultured hela cells hypoxia induced apoptosis tumor cells treated protein induction relates privacy choices/manage cookies anti-hiv-1 activity deoxyfluoro-d-glucopyranoses check access facilitative glucose transporters glucose transporter-1 levels instant access chick-embryo cells sylvester cancer center anderson cancer center related subjects cell cycle traverse quantum force field human tumor xenografts d-glucose selective tumor concentration glucose 6-phosphate inhibition positron emission tomography conditions privacy policy mutant monomeric hexokinase european economic area preferentially inhibiting growth standard chemotherapeutic protocols 6-tri-o-acetyl-1 s-adenosylhomocysteine hydrolase van der wall

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         headline:Efficacy of 2-halogen substituted d-glucose analogs in blocking glycolysis and killing “hypoxic tumor cells”
         description: Purpose: Since 2-deoxy-D-glucose (2-DG) is currently in phase I clinical trials to selectively target slow-growing hypoxic tumor cells, 2-halogenated D-glucose analogs were synthesized for improved activity. Given the fact that 2-DG competes with D-glucose for binding to hexokinase, in silico modeling of molecular interactions between hexokinase I and these new analogs was used to determine whether binding energies correlate with biological effects, i.e. inhibition of glycolysis and subsequent toxicity in hypoxic tumor cells. Methods and Results: Using a QSAR-like approach along with a flexible docking strategy, it was determined that the binding affinities of the analogs to hexokinase I decrease as a function of increasing halogen size as follows: 2-fluoro-2-deoxy-D-glucose (2-FG) > 2-chloro-2-deoxy-D-glucose (2-CG) > 2-bromo-2-deoxy-D-glucose (2-BG). Furthermore, D-glucose was found to have the highest affinity followed by 2-FG and 2-DG, respectively. Similarly, flow cytometry and trypan blue exclusion assays showed that the efficacy of the halogenated analogs in preferentially inhibiting growth and killing hypoxic vs. aerobic cells increases as a function of their relative binding affinities. These results correlate with the inhibition of glycolysis as measured by lactate inhibition, i.e. ID50 1 mM for 2-FG, 6 mM for 2-CG and > 6 mM for 2-BG. Moreover, 2-FG was found to be more potent than 2-DG for both glycolytic inhibition and cytotoxicity. Conclusions: Overall, our in vitro results suggest that 2-FG is more potent than 2-DG in killing hypoxic tumor cells, and therefore may be more clinically effective when combined with standard chemotherapeutic protocols.
         datePublished:2006-03-23T00:00:00Z
         dateModified:2006-03-23T00:00:00Z
         pageStart:725
         pageEnd:734
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            2-Deoxy-d-glucose
            2-Fluoro-2-deoxy-d-glucose
            Hypoxia
            Glycolysis
            Antitumor activity
            Oncology
            Pharmacology/Toxicology
            Cancer Research
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      headline:Efficacy of 2-halogen substituted d-glucose analogs in blocking glycolysis and killing “hypoxic tumor cells”
      description: Purpose: Since 2-deoxy-D-glucose (2-DG) is currently in phase I clinical trials to selectively target slow-growing hypoxic tumor cells, 2-halogenated D-glucose analogs were synthesized for improved activity. Given the fact that 2-DG competes with D-glucose for binding to hexokinase, in silico modeling of molecular interactions between hexokinase I and these new analogs was used to determine whether binding energies correlate with biological effects, i.e. inhibition of glycolysis and subsequent toxicity in hypoxic tumor cells. Methods and Results: Using a QSAR-like approach along with a flexible docking strategy, it was determined that the binding affinities of the analogs to hexokinase I decrease as a function of increasing halogen size as follows: 2-fluoro-2-deoxy-D-glucose (2-FG) > 2-chloro-2-deoxy-D-glucose (2-CG) > 2-bromo-2-deoxy-D-glucose (2-BG). Furthermore, D-glucose was found to have the highest affinity followed by 2-FG and 2-DG, respectively. Similarly, flow cytometry and trypan blue exclusion assays showed that the efficacy of the halogenated analogs in preferentially inhibiting growth and killing hypoxic vs. aerobic cells increases as a function of their relative binding affinities. These results correlate with the inhibition of glycolysis as measured by lactate inhibition, i.e. ID50 1 mM for 2-FG, 6 mM for 2-CG and > 6 mM for 2-BG. Moreover, 2-FG was found to be more potent than 2-DG for both glycolytic inhibition and cytotoxicity. Conclusions: Overall, our in vitro results suggest that 2-FG is more potent than 2-DG in killing hypoxic tumor cells, and therefore may be more clinically effective when combined with standard chemotherapeutic protocols.
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      dateModified:2006-03-23T00:00:00Z
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      pageEnd:734
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         2-Deoxy-d-glucose
         2-Fluoro-2-deoxy-d-glucose
         Hypoxia
         Glycolysis
         Antitumor activity
         Oncology
         Pharmacology/Toxicology
         Cancer Research
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