Radiosynthesis and evaluation of 5-[ 125I]Iodoindol-3-yl-β- D-galactopyranoside as a β-galactosidase imaging radioligand

Molecular Imaging

Volumn 7, Issue 4, 2008, Pages 187-197

  Van Dort, Marcian E ^a   Lee, Kuei C ^a   Hamilton, Christin A ^a   Rehemtulla, Alnawaz ^a   Ross, Brian D ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CULTURED CELLS; GALACTOPYRANOSIDE; GALACTOSIDASE; GLIOMA CELL LINES; IN-VIVO; INTRATUMORAL INJECTIONS; METABOLITE ANALYSIS; NUDE MOUSE; ON DYNAMICS; RADIOCHEMICAL PURITIES; RADIOCHEMICAL YIELDS; RADIOLIGAND; RADIOSYNTHESIS; RENAL CLEARANCES; SINGLE-PHOTON EMISSION COMPUTED TOMOGRAPHIES; SPECT IMAGING; SYSTEMIC ADMINISTRATIONS;

CELL CULTURE; COMPUTERIZED TOMOGRAPHY; DIAGNOSTIC RADIOGRAPHY; ONCOLOGY; RADIATION; RADIOACTIVITY; SUBSTRATES; SYNTHESIS (CHEMICAL);

TUMORS;

5 (125I)IODOINDOL 3 YL BETA D GALACTOPYRANOSIDE; 5-(125I)IODOINDOL-3-YL-BETA-D-GALACTOPYRANOSIDE; BETA GALACTOSIDASE; DIAGNOSTIC AGENT; GALACTOSE; GALACTOSIDE; RADIOACTIVE IODINE;

ANIMAL; ARTICLE; BLOOD; CANCER TRANSPLANTATION; GENE EXPRESSION; HUMAN; METABOLIC CLEARANCE RATE; METABOLISM; METHODOLOGY; MOUSE; NUDE MOUSE; RADIOASSAY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; SYNTHESIS; TUMOR CELL LINE; WHOLE BODY IMAGING;

ANIMALS; BETA-GALACTOSIDASE; CELL LINE, TUMOR; GALACTOSE; GALACTOSIDES; GENE EXPRESSION; HUMANS; IODINE RADIOISOTOPES; METABOLIC CLEARANCE RATE; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; RADIOLIGAND ASSAY; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON; WHOLE BODY IMAGING;

EID: 61949130212     PISSN: 15353508     EISSN: None     Source Type: Journal    
DOI: 10.2310/7290.2008.00020     Document Type: Article

References (25)

1. Schenborn E, Groskreutz D. Reporter gene vectors and assays. Mol Biotechnol 1999;13:29-44.
2. Kamiya M, Kobayashi H, Hama Y, et al. An enzymatically activated fluorescence probe for targeted tumor imaging. J Am Chem Soc 2007;129:3918-29.
3. Chilvers KF, Perry JD, James AL, Reed RH. Synthesis and evaluation of novel fluorogenic substrates for the detection of bacterial beta-galactosidase. J Appl Microbiol 2001;91:1118-30.
4. Pocsi I, Taylor SA, Richardson AC, et al. Comparison of several new chromogenic galactosides as substrates for various beta-D-galactosidases. Biochim Biophys Acta 1993;1163:54-60.
5. Blasberg R. PET imaging of gene expression. Eur J Cancer 2002;38:2137-46.
6. Haberkorn U, Mier W, Eisenhut M. Scintigraphic imaging of gene expression and gene transfer. Curr Med Chem 2005;12:779-94.
7. Herschman HR. PET reporter genes for noninvasive imaging of gene therapy, cell tracking and transgenic analysis. Crit Rev Oncol Hematol 2004;51:191-204.
8. Ho NH, Weissleder R, Tung CH. A self-immolative reporter for beta-galactosidase sensing. Chembio-chemistry 2007;8:560-6.
9. Josserand V, Texier-Nogues I, Huber P, et al. Non-invasive in vivo optical imaging of the lacZ and lue gene expression in mice. Gene Ther 2007;14:1587-93.
10. Tung CH, Zeng Q, Shah K, et al. In vivo imaging of beta-galactosidase activity using far red fluorescent switch. Cancer Res 2004;64:1579-83.
11. Wehrman TS, von Degenfeld G, Krutzik PO, et al. Luminescent imaging of beta-galactosidase activity in living subjects using sequential reporter-enzyme luminescence. Nat Methods 2006;3:295-301.
12. Louie AY, Huber MM, Ahrens ET, et al. In vivo visualization of gene expression using magnetic resonance imaging. Nat Biotechnol 2000;18:321-5.
13. Choi JH, Choe YS, Lee KH, et al. Synthesis of radioiodine-labeled 2-phenylethyl 1-thio-beta-D-galactopyranoside for imaging of LacZ gene expression. Carbohydr Res 2003;338:29-34.
14. Lee KH, Byun SS, Choi JH, et al. Targeting of lacZ reporter gene expression with radioiodine-labelled phenylethyl-beta-d-thiogalactopyranoside. Eur J Nucl Med Mol Imaging 2004;31:433-8.
15. Kiernan JA. Indigogenic substrates for detection and localization of enzymes. Biotech Histochem 2007;82:73-103.
16. Horwitz JP, Chua J, Curby RJ, et al. Substrates for cytochemical demonstration of enzyme activity. I. Some substituted 3-indolyl-beta-D- glycopyranosides. J Med Chem 1964;7:574-5.
17. 125I-labeled cholinergic nerve marker (-)-5-iodobenzovesamicol. Nucl Med Biol 1993;20:929-37.
18. Rothwell JA, Day AJ, Morgan MR. Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids. J Agrie Food Chem 2005;53:4355-60.
19. Dess DK, Kleine HP, Weinberg DV, et al. Phase-transfer catalyzed synthesis of acetylated aryl b-D-glucopyranosides and aryl b-D- galactopyranosides. Synthesis 1981; (Issue 11): 883-5.
20. Kleine HPW, Weinberg DV, Kaufman RJ, Sidhu RS. Phase-transfer-catalyzed synthesis of 2,3,4,6-tetra-O-acetyl-b-D-galactopyranosides. Carbohydr Res 1985;142:333-7.
21. Hatch N, Sarid J. Glial fibrillary acidic protein transcriptional regulation is independent of a TFIID-binding down-stream initiator sequence. J Neurochem 1994;63:2003-9.
22. Cohen JC, Larson JE, Killeen E, et al. CFTR and Wnt/beta-catenin signaling in lung development. BMC Dev Biol 2008;8:70.
23. Ding Z, Maubach G, Masamune A, Zhuo L. Glial fibrillary acidic protein promoter targets pancreatic stellate cells. Dig Liver Dis 2008; (In Press) [Epub ahead of print].
24. Jeong JH, Jin JS, Kim HN, et al. Expression of Runx2 transcription factor in non-skeletal tissues, sperm and brain. J Cellular Physiol 2008; 217: 511-7.
25. Weber K, Sund H, Wallenfels K. [On the nature of the binding between subunits in the molecule of beta-galactosidase from E. coli.] Biochem Z 1964;339:498-500.