Micro-PET imaging of β-glucuronidase activity by the hydrophobic conversion of a glucuronide probe

Radiology

Volumn 252, Issue 3, 2009, Pages 754-762

  Tzou, Shey Cherng ^a   Roffler, Steve ^b   Chuang, Kuo Hsiang ^a   Yeh, Hsin Pei ^c   Kao, Chien Han ^a   Su, Yu Cheng ^c   Cheng, Chiu Min ^a   Tseng, Wei Lung ^d   Shiea, Jentaie ^d   Harm, I Hong ^a   Cheng, Kai Wen ^a   Chen, Bing Mae ^b   Hwang, Jeng Jong ^c   Cheng, Tian Lu ^a,d   Wang, Hsin Ell ^c  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b INSTITUTE OF BIOMEDICAL SCIENCES   (Taiwan)

^c NATIONAL YANG MING UNIVERSITY   (Taiwan)

^d NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA GLUCURONIDASE; GLUCURONIDE; IODINE 124; IODINE 131; PHENOLPHTHALEIN; PHENOLPHTHALEIN GLUCURONIDE I 124; PHENOLPHTHALEIN GLUCURONIDE I 131; PHENOLPHTHALEIN I 131; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; AUTORADIOGRAPHY; DIAGNOSTIC IMAGING; ENZYME ACTIVITY; FEMALE; HALF LIFE TIME; HYDROLYSIS; HYDROPHOBICITY; IMAGING SYSTEM; IODINATION; MICRO-POSITRON EMISSION TOMOGRAPHY; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOACTIVITY; TISSUE DISTRIBUTION; TUMOR DIAGNOSIS;

ANIMALS; CELL LINE, TUMOR; COLONIC NEOPLASMS; FEMALE; GLUCURONIDASE; HYDROPHOBICITY; IODINE RADIOISOTOPES; MICE; MICE, INBRED BALB C; NEOPLASMS, EXPERIMENTAL; PHENOLPHTHALEINS; POSITRON-EMISSION TOMOGRAPHY; STATISTICS, NONPARAMETRIC;

EID: 70349272317     PISSN: 00338419     EISSN: 15271315     Source Type: Journal    
DOI: 10.1148/radiol.2523082055     Document Type: Article

References (45)

1. Haisma HJ, van Muijen M, Pinedo HM, Boven E. Comparison of two anthracycline-based prodrugs for activation by a monoclonal antibody-beta- glucuronidase conjugate in the specific treatment of cancer. Cell Biophys 1994;24-25:185-192.
2. Houba PH, Boven E, van der Meulen-Muileman IH, et al. A novel doxorubicinglucuronide prodrug DOX-GA3 for tumour-selective chemotherapy: distribution and efficacy in experimental human ovarian cancer. Br J Cancer 2001;84(4):550-557. (Pubitemid 32215885)
3. Schmidt F, Monneret C. Prodrug mono therapy: synthesis and biological evaluation of an etoposide glucuronide-prodrug. Bioorg Med Chem 2003;11(10):2277-2283. (Pubitemid 36457855)
4. Angenault S, Thirot S, Schmidt F, Monneret C, Pfeiffer B, Renard P. Cancer chemotherapy: a SN-38 (7-ethyl-10-hydroxycamptothecin) glucuronide prodrug for treatment by a PMT (Prodrug MonoTherapy) strategy. Bioorg Med Chem Lett 2003;13(5):947-950. (Pubitemid 36255573)
5. Leu YL, Roffler SR, Chern JW. Design and synthesis of water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT). J Med Chem 1999;42(18):3623-3628.
6. de Bont DB, Leenders RG, Haisma HJ, van der Meulen-Muileman I, Scheeren HW. Synthesis and biological activity of beta-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT. Bioorg Med Chem 1997;5(2):405-414.
7. Bouvier E, Thirot S, Schmidt F, Monneret C. First enzymatically activated Taxotere prodrugs designed for ADEPT and PMT. Bioorg Med Chem 2004;12(5):969-977. (Pubitemid 38251290)
8. Cheng TL, Chen BM, Chern JW, Wu MF, Roffler SR. Efficient clearance of poly(ethylene glycol)-modified immunoenzyme with anti-PEG monoclonal antibody for prodrug cancer therapy. Bioconjug Chem 2000;11(2):258-266.
9. Wang SM, Chern JW, Yeh MY, Ng JC, Tung E, Roffler SR. Specific activation of glucuronide prodrugs by antibody-targeted enzyme conjugates for cancer therapy. Cancer Res 1992;52(16):4484-4491.
10. de Graaf M, Boven E, Scheeren HW, Haisma HJ, Pinedo HM. Beta-glucuronidase-mediated drug release. Curr Pharm Des 2002;8(15):1391-1403.
11. Chen BM, Cheng TL, Tzou SC, Roffler SR. Potentiation of antitumor immunity by antibody-directed enzyme prodrug therapy. Int J Cancer 2001;94(6):850-858. (Pubitemid 33032834)
12. Chen KC, Cheng TL, Leu YL, et al. Membrane-localized activation of glucuronide prodrugs by beta-glucuronidase enzymes. Cancer Gene Ther 2007;14(2):187-200.
13. Chuang KH, Cheng CM, Roffler SR, et al. Combination cancer therapy by hapten-targeted prodrug-activating enzymes and cytokines. Bioconjug Chem 2006;17(3):707-714.
14. Hedley D, Ogilvie L, Springer C. Carboxypeptidase-G2-based gene-directed enzyme-prodrug therapy: a new weapon in the GDEPT armoury. Nat Rev Cancer 2007;7(11):870-879. (Pubitemid 350010854)
15. Cheng CM, Lu YL, Chuang KH, et al. Tumor-targeting prodrug-activating bacteria for cancer therapy. Cancer Gene Ther 2008;15(6):393-401.
16. Prijovich ZM, Chen BM, Leu YL, Chern JW, Roffler SR. Anti-tumour activity and toxicity of the new prodrug 9-aminocamptothecin glucuronide (9ACG) in mice. Br J Cancer 2002;86(10):1634-1638.
17. Bosslet K, Straub R, Blumrich M, et al. Elucidation of the mechanism enabling tumor selective prodrug monotherapy. Cancer Res 1998;58(6):1195-1201. (Pubitemid 28183208)
18. Connors TA, Whisson ME. Cure of mice bearing advanced plasma cell tumours with aniline mustard: the relationship between glucuronidase activity and tumour sensitivity. Nature 1966;210(5038):866-867.
19. Schumacher U, Adam E, Zangemeister-Wittke U, Gossrau R. Histochemistry of therapeutically relevant enzymes in human tumours transplanted into severe combined immunodeficient (SCID) mice: nitric oxide synthase-associated diaphorase, beta-D-glucuronidase and non-specific alkaline phosphatase. Acta Histochem 1996;98(4):381-387. (Pubitemid 26400996)
20. Kopen GC, Prockop DJ, Phinney DG. Enhanced in situ detection of beta-glucuronidase activity in murine tissue. J Histochem Cytochem 1999;47(7):965-968.
21. Lorincz M, Roederer M, Diwu Z, Herzenberg LA, Nolan GP. Enzyme-generated intracellular fluorescence for single-cell reporter gene analysis utilizing Escherichia coli beta-glucuronidase. Cytometry 1996;24(4):321-329. (Pubitemid 26285612)
22. Nimmo-Smith RH. p-Nitrophenyl-beta-glucuronide as substrate for beta-glucuronidase. Biochim Biophys Acta 1961;50:166-169.
23. Sperker B, Schick M, Kroemer HK. High-performance liquid chromatographic quantification of 4-methylumbelliferyl-beta-D-glucuronide as a probe for human beta-glucuronidase activity in tissue homogenates. J Chromatogr B Biomed Appl 1996;685(1):181-184.
24. Su YC, Chuang KH, Wang YM, et al. Gene expression imaging by enzymatic catalysis of a fluorescent probe via membrane-anchored beta-glucuronidase. Gene Ther 2007;14(7):565-574.
25. Sharkey RM, Karacay H, Vallabhajosula S, et al. Metastatic human colonic carcinoma: molecular imaging with pretargeted SPECT and PET in a mouse model. Radiology 2008;246(2):497-507.
26. Diez T, Cabezas JA. Properties of two molecular forms of beta-glucuronidase from the mollusc Littorina littorea L. Eur J Biochem 1979;93(2):301-311.
27. Lin KJ, Ye XX, Yen TC, et al. Biodistribution study of [(123)I] ADAM in mice: correlation with whole body autoradiography. Nucl Med Biol 2002;29(6):643-650.
28. Hagenbuch B, Meier PJ. The superfamily of organic anion transporting polypeptides. Biochim Biophys Acta 2003;1609(1):1-18.
29. Smith NF, Figg WD, Sparreboom A. Role of the liver-specific transporters OATP1B1 and OATP1B3 in governing drug elimination. Expert Opin Drug Metab Toxicol 2005;1(3):429-445.
30. Ishiguro N, Maeda K, Saito A, et al. Establishment of a set of double transfectants coexpressing organic anion transporting polypeptide 1B3 and hepatic efflux transporters for the characterization of the hepatobiliary transport of telmisartan acylglucuronide. Drug Metab Dispos 2008;36(4):796-805.
31. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL. Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol 1996;270(2 pt 2):F326-F331. (Pubitemid 126756324)
32. Shitara Y, Li AP, Kato Y, et al. Function of uptake transporters for taurocholate and estradiol 17beta-D-glucuronide in cryopreserved human hepatocytes. Drug Metab Pharmacokinet 2003;18(1):33-41.
33. Gerk PM, Vore M. Regulation of expression of the multidrug resistance-associated protein 2 (MRP2) and its role in drug disposition. J Pharmacol Exp Ther 2002;302(2):407-415. (Pubitemid 34787202)
34. Horikawa M, Kato Y, Tyson CA, Sugiyama Y. The potential for an interaction between MRP2 (ABCC2) and various therapeutic agents: probenecid as a candidate inhibitor of the biliary excretion of irinotecan metabolites. Drug Metab Pharmacokinet 2002;17(1):23-33.
35. Jager W, Gehring E, Hagenauer B, Aust S, Senderowicz A, Thalhammer T. Biliary excretion of flavopiridol and its glucuronides in the isolated perfused rat liver: role of multidrug resistance protein 2 (Mrp2). Life Sci 2003;73(22):2841-2854. (Pubitemid 37153358)
36. Takasuna K, Hagiwara T, Watanabe K, et al. Optimal antidiarrhea treatment for antitumor agent irinotecan hydrochloride (CPT-11)-induced delayed diarrhea. Cancer Chemother Pharmacol 2006;58(4):494-503. (Pubitemid 43999798)
37. Ghanem CI, Ruiz ML, Villanueva SS, et al. Shift from biliary to urinary elimination of acetaminophen-glucuronide in acetaminophen-pretreated rats. J Pharmacol Exp Ther 2005;315(3):987-995.
38. Namkoong EM, Kim IW, Kim DD, Chung SJ, Shim CK. Effect of probenecid on the biliary excretion of belotecan. Arch Pharm Res 2007;30(11):1482-1488.
39. Ogasawara T, Takikawa H. Biliary excretion of phenolphthalein glucuronide in the rat. Hepatol Res 2001;20(2):221-231. (Pubitemid 33734026)
40. Schipper ML, Cheng Z, Lee SW, et al. micro-PET-based biodistribution of quantum dots in living mice. J Nucl Med 2007;48(9):1511-1518. (Pubitemid 47397401)
41. Al-Nahhas A, Win Z, Szyszko T, et al. Gallium-68 PET: a new frontier in receptor cancer imaging. Anticancer Res 2007;27(6B):4087-4094. (Pubitemid 350212142)
42. Cheng TL, Chou WC, Chen BM, Chern JW, Roffler SR. Characterization of an antineoplastic glucuronide prodrug. Biochem Pharmacol 1999;58(2):325-328.
43. Haisma HJ, Boven E, van Muijen M, de Jong J, van der Vijgh WJ, Pinedo HM. A monoclonal antibody-beta-glucuronidase conjugate as activator of the prodrug epirubicin-glucuronide for specific treatment of cancer. Br J Cancer 1992;66(3):474-478.
44. Stahl PD, Fishman WH. Beta-glucuronidase. In: Bergmeyer J, Grassl M, eds. Methods in enzymatic analysis. Weinheim, Germany: Verlag Chemie, 1984; 246-256.
45. Duimstra JA, Femia FJ, Meade TJ. A gadolinium chelate for detection of beta-glucuronidase: a self-immolative approach. J Am Chem Soc 2005;127(37):12847-12855.