Biological evaluation of two iodine-123-labeled D-glucose acetals prepared as glucose transporter radioligands

Nuclear Medicine and Biology

Volumn 25, Issue 5, 1998, Pages 473-480

  Brunet Desruet, Marie Dominique ^a   Ghezzi, Catherine ^a   Morin, Christophe ^a   Comet, Michel ^a   Fagret, Daniel ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

Glucose transporter; Iodinated glucose acetals; Radioligands; SPECT

Indexed keywords

4,6 O (2' IODOETHYLIDENE) ALPHA,BETA DEXTRO GLUCOSE I 123; 4,6 O (4' IODOBENZYLIDENE) ALPHA,BETA DEXTRO GLUCOSE I 123; ACETAL; DEOXYGLUCOSE; GLUCOSE DERIVATIVE; GLUCOSE TRANSPORTER; IODINATED CONTRAST MEDIUM; IODINE 123; RADIOLIGAND; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; DRUG ACCUMULATION; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ERYTHROCYTE; GLUCOSE TRANSPORT; HEART MUSCLE CELL; HUMAN; HUMAN CELL; LIGAND BINDING; MOUSE; NEWBORN; NONHUMAN; TISSUE DISTRIBUTION;

ACETALS; ANIMALS; ANIMALS, NEWBORN; CELLS, CULTURED; ERYTHROCYTES; GLUCOSE; HUMANS; IODINE RADIOISOTOPES; ISOTOPE LABELING; LIGANDS; MICE; MONOSACCHARIDE TRANSPORT PROTEINS; MYOCARDIUM; RADIOPHARMACEUTICALS; RATS; TISSUE DISTRIBUTION;

EID: 0032127389     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(98)00005-5     Document Type: Article

References (52)

1. 125I]-Labeled forskolin analogs with discriminate adenylyl cyclase and a glucose transporter Pharmacological characterization and localization of binding sites in rat brain by in vitro receptor autoradiography . J. Pharmacol. Exp. Ther. 263:1992;1415-1423.
2. Baker G. F., Widdas W. F. The permeation of human red cells by 4,6-O-ethylidene-D-glucopyranose. J. Physiol. 231:1973;129-142.
3. Baldwin S. A. Mammalian passive glucose transporters Members of an ubiquitous family of active and passive transport proteins . Biochim. Biophys. Acta. 1154:1993;17-49.
4. Barnett J. E. G., Holman G. D., Munday K. A. An explanation of the asymmetric binding of sugars to the human erythrocyte sugar-transport system. Biochem. J. 135:1973;539-541.
5. Barnett J. E. G., Holman G. D., Munday K. A. Structural requirements for binding to the sugar-transport system of the human erythrocyte. Biochem. J. 131:1973;211-221.
6. Barnett J. E. G., Holman G. D., Chalkley R. A., Munday K. A. Evidence for two asymmetric conformational states in the human erythrocyte sugar-transport system. Biochem. J. 145:1975;417-429.
7. Baron-Delage S., Mahraoui L., Cadoret A., Veissiere D., Taillemite J. L., Chastre E., et al. Deregulation of hexose transporter expression in Caco-2 cells by ras and polyoma middle T oncogenes. Am. J. Physiol. 270:1996;G314-G323.
8. Basketter D. A., Widdas W. F. Competitive inhibition of hexose transfer in human erythrocytes by cytochalasin B. J. Physiol. 265:1977;39P-41P.
9. Birnbaum M. J., Haspel H. C., Rosen O. M. Transformation of rat fibroblasts by FSV rapidly increases glucose transporter gene transcription. Science. 235:1987;1495-1498.
10. Blondel B., Roijen I., Cheneval J. P. Heart cells in culture A simple method for increasing the proportion of myoblats . Experientia. 27:1971;356-358.
11. Brown R. S., Leung J. Y., Fisher S. J., Frey K. A., Ethier S. P., Wahl R. L. Intratumoral distribution of tritiated-FDG in breast carcinoma Correlation between GLUT-1 expression and FDG uptake . J. Nucl. Med. 37:1996;1042-1047.
12. Brown R. S., Wahl R. L. Overexpression of GLUT-1 glucose transporter in human breast cancer. Cancer. 72:1993;2979-2985.
13. Cornford E. M., Hyman S., Cornford M. E., Caron M. J. Glut1 glucose transporter activity in human brain injury. J. Neurotrauma. 13:1996;523-536.
14. Desruet M.-D., Morin C., Ogier L. Synthesis of iodobenzylidene and iodoethylidene acetals of D-glucose. Carbohydr. Res. 301:1997;225-229.
15. 1-D-glucose (P-1013). Anticancer Drugs. 6:1995;456-464.
16. Flier J. S., Mueckler M. M., Usher P., Lodish H. F. Elevated levels of glucose transport and transporter messenger-RNA are induced by ras or src oncogenes. Science. 235:1987;1492-1495.
17. 18F]2-deoxy-2-fluoro-D-glucose . J. Nucl. Med. 19:1978;1154-1161.
18. Gamberino W. C., Brennan W. A. Glucose transporter isoform expression in Huntington's disease brain. J. Neurochem. 63:1994;1392-1397.
19. Gould G. W., Holman G. D. The glucose transporter family Structure, function and tissue-specific expression . Biochem. J. 295:1993;329-341.
20. Guerre-Millo M. Glucose transporters in obesity. Proc. Nutr. Soc. 55:1996;237-244.
21. Hamant S., Mathieu J.-P., Morin C., Trimcev I., Vidal M. The β-iodoethoxyl group A stable unit for radioiodination . Bioorg. Med. Chem. Lett. 4:1994;1687-1690.
22. Harary I., Farley B. In vitro studies on single beating rat heart cells. Exp. Cell Res. 29:1963;451-465.
23. Hatanaka M. Transport of sugars in tumor cell membranes. Biochim. Biophys. Acta. 355:1974;77-104.
24. Hattner R. S. (1994) Analogs of cytochalasin B as radiopharmaceuticals for nuclear imaging of transmembrane glucose transport. International patent 5,342,926. USA.
25. Henry C., Koumanov F., Ghezzi C., Mathieu J. P., Hamant S., De Leiris J., et al. Experimental models, protocols, and reference values for evaluation of iodinated analogues of glucose. Nucl. Med. Biol. 22:1995;875-885.
26. Holman G. D., Kozka I. J., Clark A. E., Flower C. J., Saltis J., Habberfield A. D., et al. Cell-surface labeling of glucose transporter isoform GLUT4 by bis-mannose photolabel. J. Biol. Chem. 265:1990;18172-18179.
27. Horwood N., Davies D. C. Immunolabelling of hippocampal microvessel glucose transporter protein is reduced in Alzheimer's disease. Virchows Arch. 425:1994;69-72.
28. Jagust W. J., Seab J. P., Huesman R. H., Valk P. E., Mathis C. A., Reed B. R., et al. Diminished glucose transport in Alzheimer's disease Dynamic PET studies . J. Cereb. Blood Flow Metab. 11:1991;323-330.
29. Koumanov F., Henry C., Ghezzi C., Bignan G., Morin C., Mathieu J. P., et al. Biological studies of analogues of glucose iodinated in positions 1, 2, or 3. Nucl. Med. Biol. 23:1996;53-60.
30. LeFevre P. G. Sugar transport in the red blood cell Structure-activity relationships in substrates and antagonists . Pharmacol. Rev. 13:1961;39-70.
31. Leo A., Hansch C., Elkins D. Partition coefficients and their uses. Chem. Rev. 71:1971;525-616.
32. Levine M., Levine S., Jones M. N. The effect of temperature on the competitive inhibition of sorbose transfer in human erythrocytes by glucose. Biochim. Biophys. Acta. 225:1971;291-300.
33. Livingstone C., Dominiczak A. F., Campbell I. W., Gould G. W. Insulin resistance, hypertension and the insulin-responsive glucose transporter, GLUT4. Clin. Sci. 89:1995;109-116.
34. Lowry O. H., Rosebrough N. J., Lewis Farr A., Randall R. J. Protein measurement with the Folin phenol reagents. J. Biol. Chem. 193:1951;265-275.
35. Magata Y., Saji H., Arano Y., Horiuchi K., Torizuka K., Yokoyama A. Procurement of radioiodinated glucose derivative and its biological character. Nucl. Med. Biol. 14:1987;7-13.
36. Mathieu J.-P., Riche F., Coornaert S., Bardy A., Busquet G., Godart J., et al. Marquage d'acides gras en position ω par les isotopes de l'iode. J. Biophys. Méd. Nucl. 6:1982;233-237.
37. Mellanen P., Minn H., Grénman R., Härkönen P. Expression of glucose transporters in head-and-neck tumors. Int. J. Cancer. 56:1994;622-629.
38. 18F-FDG . J. Nucl. Med. 37:1993;158-159.
39. Mueckler M. Facilitative glucose transporters. Eur. J. Biochem. 219:1994;713-725.
40. Mueckler M., Kruse M., Strube M., Riggs A. C., Chiu K. C., Permutt M. A. A mutation in the GLUT2 glucose transporter gene of a diabetic patient abolishes transport activity. J. Biol. Chem. 269:1994;17765-17767.
41. Nelson C. A., Czerniak P., Crane P. D. Direct binding of H3-cytochalasin B to glucose transport proteins from normal tissues and tumors. J. Nucl. Med. 35:1994;225P.
42. Nelson C. A., Wang J. Q., Leav I., Crane P. D. The interaction among glucose transport, hexokinase, and glucose-6-phosphatase with respect to 3H-2-deoxyglucose retention in murine tumor models. Nucl. Med. Biol. 23:1996;533-541.
43. Nelson C. A., Wang Q. J., Bourque J. P., Crane P. D. Targeting of glucose transport proteins for tumor imaging Is it feasible? J. Nucl. Med. 37:1996;1031-1037.
44. Nishioka T., Oda Y., Seino Y., Yamamoto T., Inagaki N., Yano H., et al. Distribution of the glucose transporters in human brain tumors. Cancer Res. 52:1992;3972-3979.
45. Novak R. A., LeFevre P. G. Interaction of sugar acetals with the human erythrocyte glucose transport system. J. Membr. Biol. 17:1974;383-390.
46. Simpson I. A., Chundu K. R., Davies-Hill T., Honer W. G., Davies P. Decreased concentrations of GLUT1 and GLUT3 glucose transporters in the brains of patients with Alzheimer's disease. Ann. Neurol. 35:1994;546-551.
47. Takata K., Kasahara M., Oka Y., Hirano H. Review Mammalian sugar transporters: their localization and link to cellular functions . Acta Histochem. Cytochem. 26:1993;165-178.
48. Valera A., Solanes G., Fernandez-Alvarez J., Pujol A., Ferrer J., Asins G., et al. Expression of GLUT-2 antisense RNA in β cells of transgenic mice leads to diabetes. J. Biol. Chem. 269:1994;28543-28546.
49. Wadzinski B. E., Shanahan M. F., Ruoho A. E. Derivatization of the human erythrocyte glucose transporter using a novel forskolin photoaffinity label. J. Biol. Chem. 262:1987;17683-17689.
50. Wahl R. L. Targeting glucose transporters for tumour imaging Sweet idea, sour result . J. Nucl. Med. 37:1996;1038-1041.
51. Yamamoto T., Seino Y., Fukumoto H., Koh G., Yano H., Inagaki N., et al. Over-expression of facilitative glucose transporter genes in human cancer. Biochem. Biophys. Res. Commun. 170:1990;223-230.
52. Zierath J. R., Houseknecht K. L., Kahn B. B. Glucose transporters and diabetes. Semin. Cell. Dev. Biol. 7:1996;295-307.