Efficacy of 2-halogen substituted D-glucose analogs in blocking glycolysis and killing "hypoxic tumor cells"

Cancer Chemotherapy and Pharmacology

Volumn 58, Issue 6, 2006, Pages 725-734

  Lampidis, Theodore J ^a   Kurtoglu, Metin ^a   Maher, Johnathan C ^a   Liu, Huaping ^a   Krishan, Awtar ^a   Sheft, Valerie ^a   Szymanski, Slawomir ^b   Fokt, Izabela ^b   Rudnicki, Witold R ^c   Ginalski, Krzysztof ^c   Lesyng, Bogdan ^c,d   Priebe, Waldemar ^b  

^a UNIVERSITY OF MIAMI   (United States)

^b UNIVERSITY OF TEXAS   (United States)

^c UNIVERSITY OF WARSAW   (Poland)

^d UNIVERSITY OF WARSAW   (Poland)

Author keywords

2 Deoxy D glucose; 2 Fluoro 2 deoxy D glucose; Antitumor activity; Glycolysis; Hypoxia

Indexed keywords

2 BROMO 2 DEOXY ALPHA BETA DEXTRO GLUCOSE; 2 CHLORO 2 DEOXY ALPHA BETA DEXTRO GLUCOSE; 2 DEOXY 2 FLUORO ALPHA BETA DEXTRO GLUCOSE; DEOXYGLUCOSE; FLUORODEOXYGLUCOSE; GLUCOSE DERIVATIVE; HALOGEN; HEXOKINASE; TRYPAN BLUE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CANCER GROWTH; CANCER INHIBITION; CELL HYPOXIA; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG BINDING; DRUG EFFICACY; DRUG SYNTHESIS; FLOW CYTOMETRY; GLYCOLYSIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL; TUMOR CELL;

CELL HYPOXIA; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DEOXYGLUCOSE; DRUG DESIGN; FLUORODEOXYGLUCOSE F18; GLUCOSE-6-PHOSPHATE; GLYCOLYSIS; HALOGENS; HEXOKINASE; HUMANS; LACTIC ACID; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 33748473375     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-006-0207-8     Document Type: Article

References (42)

1. Adamson J, Foster AB (1969) 2-Chloro-2-deoxy-D-glucose and 2,2-dichloro-2-deoxy-D-arabino-hexose. Carb Res 10:517-523
2. Albert M, Dax K, Ortner J (1998) A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives. Tetrahedron 54:4839-4848
3. Aleshin AE, Kirby C, Liu XF et al (2000) Crystal structures of mutant monomeric hexokinase I reveal multiple ADP binding sites and conformational changes relevant to allosteric regulation. J Mol Biol 296:1001-1015
4. Bessell EM, Foster AB, Westwood JH (1972) The use of deoxyfluoro-D- glucopyranoses and related compounds in a study of yeast hexokinase specificity. Biochem J 128:199-204
5. Brown J (1962) Effects of 2-deoxyglucose on carbohydrate metabolism: review of the literature and studies in the rat. Metabolism 11:1098
6. Crane RK, Sols A (1954) The non-competitive inhibition of brain hexokinase by glucose-6-phosphate and related compounds. J Biol Chem 210:597-606
7. Di Raddo P, Diksic M (1986) Fluorination of 3,4,6-tri-O-acetyl-1,5- anhydro-2-deoxy-D-arabino-hex-1-enitol in water. Carb Res 153:141-145
8. Gordon RK, Ginalski K, Rudnicki WR et al (2003) Anti-HIV-1 activity of 3-deaza-adenosine analogs - Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem 270:3507-3517
9. Greijer AE, van der Wall E (2004) The role of hypoxia inducible factor 1 (HIF-1) in hypoxia induced apoptosis. J Clin Pathol 57:1009-1014
10. Hoekstra C, Paglianiti I, Hoekstra O (2000) Monitoring response to therapy in cancer using [18F]-2-fluoro-2-deoxy-D-glucose and positron emission tomography: an overview of different analytical methods. Eur J Nucl Med 27:731-743
11. Hwang M-J, Stockfisch TP, Hagler AT (1994) Derivation of class II force fields. II. Derivation and characterization of a class II force field, CFF93, for the alkyl functional group and alkane molecules. J Am Chem Soc 116:2515-2525
12. Kalir T, Wang BY, Goldfischer M, Haber RS et al (2002) Immunohistochemical staining of GLUT1 in benign, borderline, and malignant ovarian epithelia. Cancer 94:1078-1082
13. Kamata K, Mitsuya M, Nishimura T et al (2004) Structural basis for allosteric regulation of the monomeric allosteric enzyme human glucokinase. Structure 12:429-438
14. King MP, Attardi G (1989) Human cells lacking mtDNA: repopulation with exogenous mitochondria by complementation. Science 246:500-503
15. Krishan A, Paika K, Frei E (1975) Cytofluorometric studies on the action of podophyllotoxin and epipodophyllotoxins (VM-26, VP-16-213) on the cell cycle traverse of human lymphoblasts. J Cell Biol 66:52
16. Lampidis TJ, Priebe W (2003) Cancer chemotherapy with 2-deoxy-D-glucose. US Patent 6,670,330,B1, 30 Dec 2003
17. 14C-2-deoxyglucose. Radiology 134:771-773
18. Liu H, Hu YP, Savaraj N, Priebe W, Lampidis TJ (2001) Hypersensitization of tumor cells to glycolytic inhibitors. Biochemistry 40:5542-5547
19. Liu X, Kim CS, Kurbanov FT et al (1999) Dual mechanisms for glucose 6-phosphate inhibition of human brain hexokinase. J Biol Chem 274:31155-1159
20. Liu H, Savaraj N, Priebe W, Lampidis TJ (2002) Hypoxia increases tumor cell sensitivity to glycolytic inhibitors a strategy for solid tumor therapy (Model C). Biochem Pharmacol 64:1746-1751
21. Maher JC, Krishan A, Lampidis TJ (2004) Greater cell cycle inhibition and cytotoxicity induced by 2-deoxy-D-glucose in tumor cells treated under hypoxic versus aerobic conditions. Cancer Chemother Pharmacol 53:116-122
22. McKeehan WL (1982) Glycolysis, glutaminolysis, and cell proliferation. Cell Biol Int Rep 6:635-650
23. Maple JR, Hwang M-J, Stockfisch TP et al (1994) Derivation of class II force fields. I. Methodology and quantum force field for the alkyl functional group and alkane molecules. J Comput Chem 15:162-182
24. Maschek G, Savaraj N, Priebe W (2004) 2-Deoxy-D-Glucose increases the efficacy of adriamycin and paclitaxel in human osteosarcoma and non-small cell lung cancers in vivo. Cancer Res 64:31-34
25. Mazurek S, Boschek CB, Eigenbrodt E (1997) The role of phosphometabolites in cell proliferation, energy metabolism, and tumor therapy. J Bioenerg Biomembr 29:315-327
26. Nirenberg MW, Hogg JF (1958) Inhibition of anaerobic glycolysis in Ehrlich ascites tumor cells by 2-deoxy-D-glucose. Cancer Res 18:518
27. Noguchi Y, Marat D, Saito A et al (1999) Expression of facilitative glucose transporters in gastric tumors. Hepatogastroenterology 46:2683-2689
28. Ortner J, Albert M, Weber H, Dax K (1999) Studies on the reaction of D-glucal and its derivatives with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2. 2.2]octane salts. J Carb Chem 18:297-316
29. Rappe AK, Goddard WAI (1991) Charge equilibration for molecular dynamics simulations. J Phys Chem 95:3358-3363
30. Reitzer LJ, Wice BM, Kennell D (1979) Evidence that glutamine, not sugar, is the major energy source for cultured HeLa cells. J Biol Chem 254:2669-2676
31. Reitzer LJ, Wice BM, Kennell D (1980) The pentose cycle: control and essential function in HeLa cell nucleic acid synthesis. J Biol Chem 255:5616-5626
32. Rohren EM, Turkington TG, Coleman RE (2004) Clinical applications of PET in oncology. Radiology 231:305-332
33. Rudlowski C, Becker AJ, Schroder W et al (2003) GLUT1 messenger RNA and protein induction relates to the malignant transformation of cervical cancer. Am J Clin Pathol 120:691-698
34. Rudnicki WR, Kurzepa M, Szczepanik T et al (2000) A simple model for predicting the free energy of binding between anthracycline antibiotics and DNA. Acta Biochim Pol 47:1-9
35. Schmidt MF, Biely P, Kratky Z, Schwarz RT (1978) Metabolism of 2-deoxy-2-fluoro-D-[3H]glucose and 2-deoxy-2-fluoro-D-[3H]mannose in yeast and chick-embryo cells. Eur J Biochem 87:55-68
36. Semenza GL (2003) Targeting HIF-1 for cancer therapy. Nat Rev Cancer 10:721-732
37. Sharma V, Luker GD, Piwnica-Worms D (2002) Molecular imaging of gene expression and protein function in vivo with PET and SPECT. J Magn Reson Imaging 16: 336-351
38. Wachsberger PR, Gressen EL, Bhala A et al (2002) Variability in glucose transporter-1 levels and hexokinase activity in human melanoma. Melanoma Res 12:35-43
39. Teichman M, Descotes G, Lafont D (1993) Bromination of 1,5-anhydrohex-1-enitols (glycals) using quarternary ammonium tribromides as bromine donors: synthesis of α-1,2-trans-2-bromo-2-deoxyglycopyranosyl bromides and fluorides. Synthesis 889-894
40. Wahl R, Hutchins G, Buchsbaum D (1991) 18F-2-deoxy-2-fluoro-D-glucose (FDG) uptake into human tumor xenografts: feasibility studies for cancer imaging with PET. Cancer 67:1544-1550
41. Wick AN, Drury DR, Nakada HI, Wolfe JB (1957) Localization of the primary metabolic block produced by 2-deoxyglucose. J Biol Chem 224:963
42. Zingone A, Seidel J, Aloj L et al (2002) Monitoring the correction of glycogen storage disease type 1a in a mouse model using [(18) F] FDG and a dedicated animal scanner. Life Sci 71:1293-1301