Development of hypoxia enhanced 111In-labeled bombesin conjugates: Design, synthesis, and in vitro evaluation in pc-3 human prostate cancer

Bioconjugate Chemistry

Volumn 23, Issue 3, 2012, Pages 527-537

  Wagh, Nilesh K ^a   Zhou, Zhengyuan ^a   Ogbomo, Sunny M ^a   Shi, Wen ^a   Brusnahan, Susan K ^a   Garrison, Jered C ^a,b,c  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^c UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; PEPTIDES; PURIFICATION; TUMORS; UROLOGY;

DESIGN SYNTHESIS; HUMAN PROSTATE CANCER; HYPOXIC CONDITION; IN-VITRO; IN-VITRO EVALUATION; NITROIMIDAZOLES; NORMOXIC CONDITIONS; PROSTATE CANCERS; RECEPTOR EXPRESSION; TRAPPING AGENT;

DISEASES;

2 NITROIMIDAZOLE DERIVATIVE; BOMBESIN DERIVATIVE; GASTRIN RELEASING PEPTIDE RECEPTOR; INDIUM 111;

ARTICLE; BINDING COMPETITION; CANCER CELL CULTURE; CONJUGATE; CONTROLLED STUDY; DRUG DESIGN; DRUG PURIFICATION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; DRUG TARGETING; GENE EXPRESSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYPOXIA; IN VITRO STUDY; ISOTOPE LABELING; MALE; PHARMACOPHORE; PROSTATE CANCER; RECEPTOR AFFINITY;

EID: 84863356373     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200600w     Document Type: Article

References (42)

1. Anastasiadis, A. G., Stisser, B. C., Ghafar, M. A., Burchardt, M., and Buttyan, R. (2002) Tumor hypoxia and the progression of prostate cancer Current Urology Reports 3, 222-228
2. Brown, J. M. and William, W. R. (2004) Exploiting tumour hypoxia in cancer treatment Nat. Rev. Cancer 4, 437-447 (Pubitemid 38745529)
3. Höckel, M. and Vaupel, P. (2001) Tumor hypoxia: Definitions and current clinical, biologic, and molecular aspects J. Natl. Cancer Inst. 93, 266-276 (Pubitemid 32219813)
4. Movsas, B., Chapman, J. D., Greenberg, R. E., Hanlon, A. L., Horwitz, E. M., Pinover, W. H., Stobbe, C., and Hanks, G. E. (2000) Increasing levels of hypoxia in prostate carcinoma correlate significantly with increasing clinical stage and patient age-An Eppendorf pO(2) study Cancer 89, 2018-2024
5. Movsas, B., Chapman, J. D., Hanlon, A. L., Horwitz, E. M., Pinover, W. H., Greenberg, R. E., Stobbe, C., and Hanks, G. E. (2001) Hypoxia in human prostate carcinoma-An Eppendorf Po-2 study American Journal of Clinical Oncology-Cancer Clinical Trials 24, 458-461 (Pubitemid 32959102)
6. Weinmann, M., Welz, S., and Bamberg, M. (2003) Hypoxic radiosensitizers and hypoxic cytotoxins in radiation oncology Curr. Med. Chem.: Anti-Cancer Agents 3, 364-374 (Pubitemid 37045715)
7. Nunn, A., Linder, K., and Strauss, H. W. (1995) Nitroimidazoles and Imaging Hypoxia Eur. J. Nucl. Med. 22, 265-280
8. Krohn, K. A., Link, J. M., and Mason, R. P. (2008) Molecular imaging of hypoxia J. Nucl. Med. 49 (Suppl 2) 129S-148S (Pubitemid 351948041)
9. Chapman, J. D., Engelhardt, E. L., Stobbe, C. C., Schneider, R. F., and Gerald, G. E. (1998) Measuring hypoxia and predicting tumor radioresistance with nuclear medicine assays Radiother. Oncol. 46, 229-237 (Pubitemid 28157272)
10. Engelhardt, E. L., Schneider, R. F., Seeholzer, S. H., Stobbe, C. C., and Chapman, J. D. (2002) The synthesis and radiolabeling of 2-nitroimidazole derivatives of cyclam and their preclinical evaluation as positive markers of tumor hypoxia J. Nucl. Med. 43, 837-850 (Pubitemid 34663308)
11. Evans, S. M., Kachur, A. V., Shiue, C.-Y., Hustinx, R., Jenkins, W. T., Shive, G. G., Karp, J. S., Alavi, A., Lord, E. M., Dolbier, W. R., Jr., and Koch, C. J. (2000) Noninvasive detection of tumor hypoxia using the 2-nitroimidazole [F-18]EF1 J. Nucl. Med. 41, 327-336 (Pubitemid 30091355)
12. Yamamoto, F., Oka, H., Antoku, S., Ichiya, Y., Masuda, K., and Maeda, M. (1999) Synthesis and characterization of lipophilic 1-[F-18]fluoroalkyl-2- nitroimidazoles for imaging hypoxia Biol. Pharm. Bull. 22, 590-597 (Pubitemid 29314014)
13. Yang, D. J., Ilgan, S., Higuchi, T., Zareneyrizi, F., Oh, C.-S., Liu, C.-W., Kim, E. E., and Podoloff, D. A. (1999) Noninvasive assessment of tumor hypoxia with Tc-99m labeled metronidazole Pharm. Res. 16, 743-750 (Pubitemid 29227106)
14. Jensen, R. T., Battey, J. F., Spindel, E. R., and Benya, R. V. (2008) International union of pharmacology. LXVIII. Mammalian bombesin receptors: Nomenclature, distribution, pharmacology, signaling, and functions in normal and disease states Pharmacol. Rev. 60, 1-42 (Pubitemid 351439216)
15. Markwalder, R. and Reubi, J. C. (1999) Gastrin-releasing peptide receptors in the human prostate: Relation to neoplastic transformation Cancer Res. 59, 1152-1159 (Pubitemid 29135980)
16. Gugger, M. and Reubi, J. C. (1999) Gastrin-releasing peptide receptors in non-neoplastic and neoplastic human breast Am. J. Pathol. 155, 2067-2076
17. Fleischmann, A., Laderach, U., Friess, H., Buechler, M. W., and Reubi, J. C. (2000) Bombesin receptors in distinct tissue compartments of human pancreatic diseases Lab. Invest. 80, 1807-1817 (Pubitemid 32012750)
18. Cornelio, D. B., Roesler, R., and Schwartsmann, G. (2007) Gastrin-releasing peptide receptor as a molecular target in experimental anticancer therapy Ann. Oncol. 18, 1457-1466 (Pubitemid 47365477)
19. 14] bombesin(6-14) Clin. Cancer Res. 8, 1139-1146 (Pubitemid 35177367)
20. Ananias, H. J., de Jong, I. J., Dierckx, R. A., van de Wiele, C., Helfrich, W., and Elsinga, P. H. (2008) Nuclear imaging of prostate cancer with gastrin-releasing-peptide-receptor targeted radiopharmaceuticals Curr. Pharm. Des. 14, 3033-3047
21. 64Cu bombesin analogs: Side-by-side comparison of the CB-TE2A and DOTA chelation systems J. Nucl. Med. 48, 1327-1337 (Pubitemid 47242799)
22. Garrison, J. C., Rold, T. L., Sieckman, G. L., Naz, F., Sublett, S. V., Figueroa, S. D., Volkert, W. A., and Hoffman, T. J. (2008) Evaluation of the pharmacokinetic effects of various linking group using the 111In-DOTA-X-BBN(7- 14)NH2 structural paradigm in a prostate cancer model Bioconjugate Chem. 19, 1803-1812
23. Hueting, R., Christlieb, M., Dilworth, J. R., Garcia Garayoa, E., Gouverneur, V., Jones, M. W., Maes, V., Schibli, R., Sun, X., and Tourwe, D. A. (2010) Bis(thiosemicarbazones) as bifunctional chelators for the room temperature 64-copper labeling of peptides Dalton Trans 39, 3620-32
24. Gariépy, J., Rémy, S., Zhang, X. G., Ballinger, J. R., Bolewska-Pedyczak, E., Rauth, M., and Bisland, S. K. (2002) A simple two-step approach for introducing a protected diaminedithiol chelator during solid-phase assembly of peptides Bioconjugate Chem. 13, 679-684 (Pubitemid 34527533)
25. Koch, C. J. (2008) Importance of antibody concentration in the assessment of cellular hypoxia by flow cytometry: EF5(1) and Pimonidazole Radiat. Res. 169, 677-688 (Pubitemid 351793457)
26. Ljungkvist, A. S., Bussink, J., Kaanders, J. H., and van der Kogel, A. J. (2007) Dynamics of tumor hypoxia measured with bioreductive hypoxic cell markers Radiat. Res. 167, 127-45 (Pubitemid 46214661)
27. Carnell, D. M., Smith, R. E., Daley, F. M., Saunders, M. I., Bentzen, S. M., and Hoskin, P. J. (2006) An immunohistochemical assessment of hypoxia in prostate carcinoma using Pimonidazole: Implications for radioresistance International Journal of Radiation Oncology Biology Physics 65, 91-99
28. Yaromina, A., Zips, D., Thames, H. D., Eicheler, W., Krause, M., Rosner, A., Haase, M., Petersen, C., Raleigh, J. A., Quennet, V., Walenta, S., Mueller-Klieser, W., and Baumann, M. (2006) Pimonidazole labelling and response to fractionated irradiation of five human squamous cell carcinoma (hSCC) lines in nude mice: the need for a multivariate approach in biomarker studies Radiother. Oncol. 81, 122-9 (Pubitemid 44780780)
29. Raleigh, J. A. and Koch, C. J. (1990) Importance of thiols in the reductive binding of 2-nitroimidazoles to macromolecules Biochem. Pharmacol. 40, 2457-2464
30. Fischman, A. J., Babich, J. W., and Strauss, H. W. (1993) A ticket to ride: peptide radiopharmaceuticals J. Nucl. Med. 34, 2253-2263 (Pubitemid 24002976)
31. Rudin, M. and Weissleder, R. (2003) Molecular imaging in drug discovery and development Nat. Rev. Drug Discovery 2, 123-131 (Pubitemid 37361644)
32. Kaltsas, G., Rockall, A., Papadogias, D., Reznek, R., and Grossman, A. B. (2004) Recent advances in radiological and radionuclide imaging and therapy of neuroendocrine tumours Eur. J. Endocrinol. 151, 15-27 (Pubitemid 39117361)
33. Willmann, J. K., van Bruggen, N., Dinkelborg, L. M., and Gambhir, S. S. (2008) Molecular imaging in drug development Nat. Rev. Drug Discovery 7, 591-607 (Pubitemid 351927724)
34. Brown, J. M. (2000) Exploiting the hypoxic cancer cell: mechanisms and therapeutic strategies Mol. Med. Today 6, 157-162 (Pubitemid 30171366)
35. Piert, M., Machulla, H. J., Picchio, M., Reischl, G., Ziegler, S., Kumar, P., Wester, H. J., Beck, R., McEwan, A. J. B., Wiebe, L. I., and Schwaiger, M. (2005) Hypoxia-specific tumor imaging with F-18-fluoroazomycin arabinoside J. Nucl. Med. 46, 106-113 (Pubitemid 43086004)
36. Reischl, G., Dorow, D. S., Cullinane, C., Katsifis, A., Roselt, P., Binns, D., and Hicks, R. J. (2007) Imaging of tumor hypoxia with [I-124] IAZA in comparison with [F-18] FMISO and [F-18]FAZA-first small animal PET results J. Pharm. Pharm. Sci. 10, 203-211
37. Eschmann, S. M., Paulsen, F., Bedeshem, C., Machulla, H. J., Hehr, T., Bamberg, M., and Bares, R. (2007) Hypoxia-imaging with F-18-misonidazole and PET: Changes of kinetics during radiotherapy of head-and-neck cancer Radiother. Oncol. 83, 406-410 (Pubitemid 46915551)
38. 68Ga-labeling and testing in tumor xenografted mice J. Med. Chem. 53, 6378-6385
39. Dennis, M. F., Stratford, M. R., Wardman, P., and Watts, M. E. (1985) Cellular uptake of misonidazole and analogues with acidic or basic functions International Journal of Radiation Biology and Related Studies in Physics, Chemistry and Medicine 47, 629-643 (Pubitemid 15008084)
40. Gerweck, L. E. (1998) Tumor pH: implications for treatment and novel drug design Semin. Radiat. Oncol. 8, 176-182 (Pubitemid 28323476)
41. Martínez, A., Zudaire, E., Julián, M., Moody, T. W., and Cuttitta, F. (2005) Gastrin-releasing peptide (GRP) induces angiogenesis and the specific GRP blocker 77427 inhibits tumor growth in vitro and in vivo Oncogene 24, 4106-4113 (Pubitemid 40897056)
42. 177Lu-labeled GRP-R agonist for systemic radiotherapy of prostate cancer J. Nucl. Med. 47, 1144-1152 (Pubitemid 47558898)