Synthesis of [18F]-labelled Maltose Derivatives as PET Tracers for Imaging Bacterial Infection

Molecular Imaging and Biology

Volumn 17, Issue 2, 2015, Pages 168-176

  Namavari, Mohammad ^a   Gowrishankar, Gayatri ^a   Hoehne, Aileen ^a   Jouannot, Erwan ^a   Gambhir, Sanjiv S ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Bacterial infection; Imaging; Maltose; Positron emission tomography

Indexed keywords

1,2,3 TRI O ACETYL 4 O (2',3', DI O ACETYL 4',6', BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSYL) 6 DEOXY 5 O TRITYL DEXTRO GLUCOPRANOSIDE; 1,2,3 TRI O ACETYL 4 O (2',3', DI O ACETYL 4',6', BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSYL) 6 DEOXY 6 O NOSYL DEXTRO GLUCOPRANOSIDE; 1,2,3 TRI O ACETYL 4 O (2',3', DI O ACETYL 4',6', BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSYL) DEXTRO GLUCOPRANOSIDE; 2,3,6 TRI O ACETYL 4 O (2','3,4',6' TETRA O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) 1 DEOXY 1 O TRIFLYL DEXTRO GLUCOPRANOSIDE; 4 O (ALPHA DEXTRO GLUCOPYRANOSYL) 1 DOEXY 1 DEXTRO GLUCOPYRANOSIDE F 18; 4 O (ALPHA DEXTRO GLUCOPYRANOSYL) 6 DOEXY 6 DEXTRO GLUCOPYRANOSIDE F 18; FLUOROMALTOSE F 18; MALTOSE; PHOSPHATE BUFFERED SALINE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; FLUORINE;

ARTICLE; BACTERIAL INFECTION; DRUG SYNTHESIS; ENERGY RESOURCE; ESCHERICHIA COLI; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROLYSIS; IN VITRO STUDY; MAMMAL CELL; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOACTIVITY; RADIOCHEMISTRY; UPTAKE ASSAY; ANIMAL; BLOOD; CELL LINE; CHEMISTRY; METABOLISM; SCINTISCANNING; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ANIMALS; BACTERIAL INFECTIONS; CELL LINE; CHROMATOGRAPHY, THIN LAYER; ESCHERICHIA COLI; FLUORINE RADIOISOTOPES; HUMANS; MALTOSE; MICE; POSITRON-EMISSION TOMOGRAPHY;

EID: 84925507229     PISSN: 15361632     EISSN: 18602002     Source Type: Journal    
DOI: 10.1007/s11307-014-0793-5     Document Type: Article

References (25)

1. Palestro CJ (2009) Radionuclides imaging of infection: in search of the grail. J Nucl Med 50:671–673
2. Corstens FHM, van der Meer JWM (1999) Nuclear medicine’s role in infection and inflammation. Lancet 354:765–7670
3. 18F-fluordeoxyglucose positron emission tomography. Clin Microbiol Rev 21:209–224
4. Langer O, Mitterhauser M, Brunner M, Zeitlinger M, Wadsak W, Mayer BX, Kletter K, Muller M (2003) Synthesis of [18F]ciprofloxacin for PET studies in humans. Nucl Med Biol 30:285–291
5. Langer O, Brunner M, Zeitlinger M et al (2005) In vitro and in vivo evaluation of [18F]ciprofloxacin for the imaging infection with PET. Eur J Nucl Med Mol Imaging 32:143–150
6. Sasser TA, Van AVermaete AE, White A et al (2013) Bacterial Infection Probes and Imaging Strategies in Clinical Nuclear Medicine and Preclinical Molecular Imaging. Current Topic. Med Chem 13:479–487
7. Petruzz IN, Shanthly N, Thakur M (2009) Recent trend in soft tissue infection imaging. Semin Nucl Med 39:115–123
8. 124I]FIAU- PET/CT. PLoS ONE 2:e1007
9. Ning X, Lee S, Wang Z et al (2011) Maltodextrine-based imaging probes detect bacteria in vivo with high sensitivity and specificity. Nat Mater 10:602–607
10. Dahl MK, Manson MD (1985) interspecific reconstitution of maltose transport and chemotaxis in Escherichia coli with maltose binding protein from various enteric bacteria. J Bactriol 164:1037–1063
11. Gopal S, Berg D, Hagen N et al (2010) Maltose and maltodextrine utilization by listeria monocytogenes depend on an inducible ABC transporter which is repressed by glucose. PLoS ONE 5:e10349
12. Braitsch M, Kahlig H, Kontaxis G et al (2012) Synthesis of fluorinated maltose derivatives for monitoring protein interaction by 19 F NMR. Beilstein J Org Chem 8:448–455
13. Excoffier G, Gagnaire D, Utille J-P (1975) Coupure selective par 1 hydrozine des groupments acetyles anomeres de residus glycosyles acetyls. Carbohydr Res 39:368–373
14. Toshima K (2000) Glycosyl fluorides in glycosidations. Carbohydr Res 327:15–26
15. Lal GS, Pez GP, Pasaresi RJ et al (1999) Bis (2-methyl) aminosulfur trifluoride: a new broad spectrum deoxofluorinating agent with enhanced thermal stability. J Org Chem 64:7048–7054
16. Takeo K, Shinmitsu K (1984) A convenient synthesis of 6′-C-substituted b-maltose heptaacetates and of panose. Carbohydr Res 133:135–145
17. Ye S, Rezende MM, Deng W-P, Herbert B, Daly JW, Johnson RA, Kirk KL (2004) Synthesis of 2′, 5′-dideoxy-2-fluoroadenosine and 2′, 5′-dideoxy-2′,5′-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase. J Med Chem 47:1207–1213
18. Best WM, Stick RV, Tilbrook DMG (1997) The synthesis of some epoxyalkyl-deoxyhalo-β-cellobiosides. Aust J Chem 50:13–18
19. Dutton GGS, Slessor KN (1966) Synthesis of 6′-Substituted Maltose. Cana J Chem 44:1069
20. De Castro KA, Rhee H (2008) Selective nosylation of 1-phenylpropane-1,3-diol and perchloric acid mediated Friedel-Crafts alkylation: key steps for the new and straightforward synthesis of Toletero dine. Synthesis No. 12 P: 1841–1844
21. Tyokuni T, Kumar JSD, Gunawan P et al (2004) Practical and reliable synthesis of 1, 3, 4, 6-tetra-O-acetyl-2-O-trifluoromethanesulffonyl-β-D-mannopyranosyl, a precursor of 2-deoxy-2-[18F]fluoro-D-glucose. Mol Imaging Biol 6:417
22. Young SJM, Weser E (1971) The metabolism of circulating maltose in man. J Clin Inves 50:986–9891
23. Ferenci T (1980) Methyl-α-maltoside and 5-thiomatose: analogs transported by escherichia coli maltose transported system. J Bacteriol 144:7–11
24. Carruthers A, DeZutter J, Ganguly A, Devaskar SU (2009) Will the original glucose transporter isoform please stand up! Am J Physiol Endocrinol Metab 297:E836–48
25. 18F]fluoromaltose as a novel PET tracer for imaging bacterial infection. PLos One (accepted)