Biological studies of analogues of glucose iodinated in positions 1, 2, or 3

Nuclear Medicine and Biology

Volumn 23, Issue 1, 1996, Pages 53-60

  Koumanov, F ^a,c   Henry, C ^a   Ghezzi, C ^a   Bignan, G ^b   Morin, C ^b   Mathieu, J P ^a   Hamant, S ^a   Vidal, M ^b   De Leiris, J ^a   Comet, M ^a  

^a Grp Physiol Physiopathol C   (France)

^b UNIVERSITÉ JOSEPH FOURIER   (France)

^c UNIV GRENOBLE ALPES   (France)

Author keywords

Cellular uptake of glucose; Iodinated analogues of glucose; Radiopharmaceuticals

Indexed keywords

GLUCOSE; GLUCOSE DERIVATIVE; IODINE 123;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; GLUCOSE METABOLISM; HUMAN; HUMAN CELL; ISOTOPE LABELING; MOUSE; PHARMACOKINETICS; RAT;

EID: 0030061587     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/0969-8051(95)02004-7     Document Type: Article

References (45)

1. Barnett J. E. G., Holman G. D. and Munday K. A. (1973) Structural requirements for binding to the sugar-transport system of the human erythrocyte. Biochem. J. 131, 211-221.
2. Barnett J. E. G., Holman G. D., Chalkley R. A. and Munday K. A. (1975) Evidence for two asymmetric conformational states in the human erythrocyte sugar-transport system. Biochem. J. 145, 417-429.
3. Baumstark F. (1874) Eigenthümliche bildung einer aethyliden-verbindung. Ber. Dtsch. Chem. Ges. 7, 1172-1175.
4. Bessell E. M., Foster A. B. and Weswood J. H. (1972) The use of deoxyfluoro-D-glucopyranoses and related compounds in a study of yeast hexokinase specificity. Biochem. J. 128, 199-204.
5. Bignan G. (1993) Synthèse d'analogues iodés du D-glucose. Thèse, Université Joseph Foutier, Grenoble.
6. Bignan G., Mathieu J. P., Mauclaire L., Morin C. and Vidal M. (1993a) Synthesis of radiolabelled ω-iodoalkylglucosides. J. Labelled Compd. Radiopharm. 32, 584-585.
7. Bignan G., Morin C. and Vidal M. (1993b) Synthesis of 3-O-(2-iodoethyl)-D-glucose, a stable iodo derivative of D-glucose for medical imaging. Carbohydr. Res. 248, 371-374.
8. Blondel B., Roijeu I. and Cheneval J. P. (1971) Heart cell in culture: A simple method for increasing the proportion of myoblastes. Experientia 27, 356-358.
9. Brauns D. H. (1925) Optical rotation and atomic dimension. J. Am. Chem. Soc. 47, 1285-1298.
10. Demole E. (1876) Ueber einen angeblichen umlagerungsfall in der fettreihe. Ber. Dtsch. Chem. Ges. 9, 743-747.
11. Fischer E. and Fischer H. (1910) Derivatives of lactose and maltose; two new glycosides. Ber. Dtsch. Chem. Ges. 43, 2521-2536.
12. 11C-2-deoxy-D-glucose and halogenated deoxyglucose derivatives. J. Labelled Compd. Radiopharm. 16, 7-9.
13. Goodman M. M., Callahan A. P. and Knapp F. F. (1987) Design, synthesis and evaluation of 2-deoxy-2-iodovinyl-branched carbohydrates as potential brain imaging agents. J. Labelled Compd. Radiopharm. 23, 1269-1270.
14. Goodman M. M., Kabalka G. W., Waterhouse R. N. and Daniel G. B. (1991) Synthesis of iodine-123 labeled 3-O-(E)-3-iodopropen-2-yl-D-glucose: A potential new agent for the assessment of glucose transport into the brain and heart using SPECT. J. Labelled Compd. Radiopharm. 30, 278-279.
15. 125I]iodovinyl-D-allose: A new strategy for the preparation of in vivo stable radioiodinated carbohydrates. J. Nucl. Med. 26, 121.
16. Goodman M. M., Knapp F. F. and Callahan A. P. (1986) Synthesis and evaluation of radioiodinated 2-deoxy-2-iodovinyl altrose derivatives as potential brain imaging agents. J. Nucl. Med. 27, 1054-1055.
17. 125I]iodoethenyl)-D-allose: A new strategy for preparation of in vivo stable radioiodinated carbohydrates. NUC Compact 21, 64-69.
18. Hamant S., Mathieu J. P., Morin C., Trimcev I. and Vidal M. (1994) The β-iodoethoxyl group: A stable unit for radioiodination. Bioorg. Med. Chem. Letters 4, 1687-1690.
19. Harary I. and Farley B. (1963) In vitro studies on single beating rat heart cells. I. Growth and organisation. Exp. Cell. Res. 29, 451-465.
20. 2+. FEBS Let. 141, 37-40.
21. Helferich B. and Lutzmann H. (1939) Glucoside der isäthionsaüre und ihres äthylesters. Über emulsin. Justus Liebigs Ann. Chem. 541, 1-16.
22. Henry C., Koumanov F., Ghezzi C., Mathieu J. P., Hamant S., de Leiris J. and Comet M. (1995) Experimental models, protocols and reference values for evaluation of iodinated analogues of glucose. Nucl. Med. Biol. 22, 875-885.
23. 123M. J. Labelled Compd. Radiopharm. 20, 391-415.
24. 123I-analogues of D-glucose as potential tracers for glucose utilization in heart and brain Eur. J. Nucl. Med. 8, 237-241.
25. 123I-analogues of D-glucose as potential radiopharmaceuticals. J. Labelled Compd. Radiopharm. 19, 1626-1628.
26. LeFevre P. G. and Marshall J. K. (1959) The attachment of phloretin and analogues to human erythrocytes in connection with inhibition of sugar transport. J. Biol. Chem. 234, 3022-3026.
27. Levine M., Levine S. and Jones M. N. (1971) The effect of temperature on the competitive inhibition of sorbose transfer in human erythrocytes by glucose. Biochim. Biophys. Acta 225, 291-300.
28. Lin S. and Spudich J. A. (1974) Biochemical studies on the mode of action of cytochalasin B. Cytochalasin B binding to red cell membrane in relation to glucose transport. J. Biol. Chem. 249, 5778-5783.
29. Lowry O., Rosebrough N., Lewisfarr A. and Randall R. (1951) Protein measurement with the folin phenol reagent. J. Biol. Chem. 193, 265-275.
30. 123I]-iodobenzyl)glucose. J. Labelled Compd. Radiopharm. 29, 535-545.
31. 123I-iodobenzoylglucosamines: Glucose analogues for heart imaging. J. Labelled Compd. Radiopharm. 33, 327-344.
32. Lutz T., Vo C. V. and Lyter D. M. (1994) Synthesis of an I-123 labelled iodo glucose analogue as a potential imaging agent. Eur. J. Nucl. Med. 21, 785.
33. Magata Y., Inagaki M., Ohmomo Y., Yamada Y., Saji H. and Yokoyama A. (1991) Synthesis and biological evaluation of esterified radioiodinated glucose derivative. J. Labelled Compd. Radiopharm. 30, 300-301.
34. Magata Y., Saji H., Arano Y., Horiuchi K., Torizuka K. and Yokoyama A. (1987) Procurement of radioiodinated glucose derivative and its biological character. Nucl. Med. Biol. 14, 7-13.
35. Magata Y., Saji H., Ohmomo Y., Tanaka C., Konishi J. and Yokoyama A. (1992) Development of a novel radioiodinated glucose derivative with interaction to hexokinase. J. Labelled Compd. Radiopharm. 31, 317-328.
36. McCarter J. D., Adam M. J. and Withers S. G. (1994) 2-Fluoro-2-iodo-mannose and -glucose as potential SPECT imaging agents. J. Labelled Compd. Radiopharm. 35, 250.
37. Morgan H. E., Henderson M. J., Regen D. M. and Park C. R. (1961) Regulation of glucose uptake in muscle. I. The effects of insulin and anoxia on glucose transport and phosphorylation in the isolated, perfused heart of normal rats. J. Biol. Chem. 236, 253-261.
38. Phelps M. E., Huang S. C., Hoffman E. J., Selin C., Sokoloff L. and Kuhl D. E. (1979) Tomographic measurement of local cerebral glucose metabolic rate in humans with (F-18)2-fluoro-2-deoxy-D-glucose: Validation of method. Ann. Neurol. 6, 371-388.
39. Saji H., Magata Y., Arano Y., Horiuchi K., Torizuka K. and Yokoyama A. (1987) 2-O-(p-iodobenzyl)-D-glucose: A new pharmaceutical for SPECT studies of cerebral glucose transport. J. Nucl. Med. 28, 571.
40. Schelbert H. R. and Buxton D. (1988) Insights into coronary desease gained from metabolic imaging. Circulation 78, 496-505.
41. Sols A. and Crane R. K. (1954) Substrate specificity of brain hexokinase. J. Biol. Chem. 210, 581-595.
42. Tsuya A. and Shigematsu A. (1979) Diagnostische Mittel. Patent Application 2817336, Federal Republic of Germany.
43. Wolfrom M. L. and Szarek W. A. (1972) Halogen derivatives. In The Carbohydrates. Chemistry and Biochemistry (Edited by W. Pigman and D. Horton), 2nd edition, pp. 240. Academic Press, New York and London.
44. 82Br-2-Br-DM). J. Nucl. Med. 23, 105.
45. 82Br]bromo-D-mannose and related compounds and their biodistributions in mice. Eur. J. Nucl. Med. 11, 252-256.