PB183, a sigma receptor ligand, as a potential PET probe for the imaging of prostate adenocarcinoma

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 6, 2008, Pages 1990-1993

  Colabufo, Nicola Antonio ^a   Abate, Carmen ^a   Contino, Marialessandra ^a   Inglese, Carmela ^a   Niso, Mauro ^a   Berardi, Francesco ^a   Perrone, Roberto ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Cyclohexylpiperazine derivative; PB183; PB28; PET; Prostate adenocarcinoma; TRAMP cells

Indexed keywords

CYCLOHEXYLPIPERAZINE DERIVATIVE; PB 167; PB 183; PB 28; PIPERAZINE DERIVATIVE; RECEPTOR SUBTYPE; SIGMA RECEPTOR LIGAND; TRACER; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; IMAGING; MOLECULAR PROBE; MOUSE; NONHUMAN; PHARMACODYNAMICS; POSITRON EMISSION TOMOGRAPHY; PROSTATE ADENOCARCINOMA; RECEPTOR AFFINITY;

ADENOCARCINOMA; ANIMALS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLOW CYTOMETRY; MALE; MICE; MICE, TRANSGENIC; MOLECULAR STRUCTURE; NAPHTHALENES; P-GLYCOPROTEIN; PIPERAZINES; POSITRON-EMISSION TOMOGRAPHY; PROSTATIC NEOPLASMS; RECEPTORS, SIGMA;

EID: 40749153072     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.109     Document Type: Article

References (32)

1. Quirion R., Bowen W.D., Itzhak Y., Junien J.L., Musacchio J.M., Rothman R.B., Su T.P., Tam S., and Taylor D.P. Trends Pharmacol. Sci. 13 (1992) 85
2. Hanner M., Moebius F.F., Flandorfer A., Knaus H., Striessnig J., Kempner E., and Glossmann H. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 8072
3. Moebius F.F., Fitzly B.U., Wietzorrek G., Haidekker A., Eder A., and Glossmann H. Biochem. J. 374 (2003) 229
4. Colabufo N.A., Abate C., Berardi F., Contino M., Niso M., and Perrone R. J. Med. Chem. 49 (2006) 4153
5. Su T.P. In: Izthak Y. (Ed). The Sigma Receptor (1994), Academic Press, London 21-44
6. Vilner B.J., John C.S., and Bowen W.D. Cancer Res. 55 (1995) 408
7. Colabufo N.A., Berardi F., Contino M., Ferorelli S., Niso M., Perrone R., Pagliarulo A., Saponaro P., and Pagliarulo V. Cancer Lett. 237 (2006) 83
8. Kassiou M., Dannals F.R., Liu X., Wong D.F., Ravert H.T., and Scheffel U.A. Bioorg. Med. Chem. 13 (2005) 3626
9. Tu Z., Dence C.S., Ponde D.E., Jones L., Wheeler K.T., Welch M.J., and Mach R.H. Nucl. Med. Biol. 32 (2005) 423
10. van Waarde A., Buursma A.R., Hospers G.A., Kawamura K., Kobayashi T., Ishii K., Oda K., Ishiwata K., Vaalburg W., and Elsinga P.H. J. Nucl. Med. 45 (2004) 1939
11. Elsinga P.H., Tsukada H., Harada N., Kakiuchi T., Kawamura K., Vaalburg W., Kimura Y., Kobayashi T., and Ishiwata K. Synapse 52 (2004) 29
12. Ishiwata K., Kobayashi T., Kawamura K., Matsuno K., and Senda M. Nucl. Med. Biol. 28 (2001) 787
13. Colabufo N.A., Berardi F., Contino M., Niso M., Abate C., Perrone R., and Tortorella V. Naunyn-uSchmiedeberg's Arch. Pharmacol. 370 (2004) 106
14. Berardi F., Ferorelli S., Abate C., Colabufo N.A., Contino M., Perrone R., and Tortorella V. J. Med. Chem. 47 (2004) 2308
15. Colabufo N.A., Berardi F., Contino M., Fazio F., Matarrese M., Moresco R.M., Niso M., Perrone R., and Tortorella V. J. Pharm. Pharmacol. 57 (2005) 1453
16. Azzariti A., Colabufo N.A., Berardi F., Porcelli L., Niso M., Simone M.G., Perrone R., and Paradiso A. Mol. Cancer Ther. 5 (2006) 1807 Preparation of Caco-2 cell monolayer: Caco-2 cells grown in medium as previously reported were harvested with trypsin-EDTA and seeded onto MultiScreen Caco-2 Assay System at a density of 10,000 cells per well. The culture medium was replaced every 48 h for the first 6 days and every 24 h thereafter. After 21 days in the culture, the Caco-2 monolayer was utilized for the permeability experiments. The Transepithelial Electrical Resistance (TEER) of the monolayers was measured daily before and after the experiment using a Millicell-ERS system (Millipore). Generally, TEER values obtained were greater than 1000 Ω for a 21-day culture
17. Drug transport experiments: Apical to basolateral permeability of drugs was measured under various conditions of incubation time (30, 60, 120 min) and drug concentrations (10-100 μM). Drugs were dissolved in Hanks' balanced salt solution (HBSS, pH 7.4) and sterile filtered. After 21 days cell growth, the medium was removed from filter wells and from the receiver plate. The filter wells were filled with 75 μl of fresh HBSS buffer and the receiver plate with 250 μl per well of the same buffer. This procedure was repeated twice and the plates were incubated at 37 °C for 30 min. After the incubation time, the HBSS buffer was removed and drug solutions were added to the filter well (75 μl). HBSS without the drug was added to the receiver plate (250 μl). The plates were incubated at 37 °C for the desired time. After incubation time, samples were removed from the apical (filter well) and basolateral (receiver plate) side of the monolayer and the drug concentrations were determined by HPLC analytical method.
18. HPLC analysis: Samples from in vitro permeation studies were analysed by using a reverse-phase HPLC equipped with a Perkin-Elmer series 200 LC pump and a Perkin-Elmer 785A UV/VIS detector. UV signals were monitored and obtained peaks integrated using a personal computer running Perkin-Elmer Turbochrom Software. The column used was a Phenomenex Prodigy ODS-3 RP-18 (250 × 4.6 mm, 5 μm particle size). The samples were eluted with ammonium formate (5 mM; pH adjusted to 5 with formic acid) and acetonitrile (95:5 v/v) at a flow rate of 1 ml/min. The wavelength for UV absorbance was set at 230 nm. The sample injection volume was 20 μl.
19. Peng F., Lu X., Janisse J., Muzik O., and Shields F. J. Nucl. Med. 47 (2006) 1649
20. Narayanan B.A., Narayanan N.K., Pittman B., and Reddy B.S. Clin. Cancer Res. 15 (2004) 7727
21. 3H]pentazocine concentrations ranging from 0.1 to 50 nM. Samples contained 400 μg of membrane protein and radioligand. The non-specific binding was determined in the presence of 10 μM (+)-pentazocine. Samples were incubated in a final volume of 500 μl of 50 mM Tris-HCl, pH 8.0, for 120 min at 25 °C and the following manipulations were as described above for sigma-2 receptors.
22. Berardi F., Ferorelli S., Colabufo N.A., Leopoldo M., Perrone R., and Tortorella V. Bioorg. Med. Chem. 9 (2001) 1325
23. Crawford K.W., and Bowen W.D. Cancer Res. 62 (2002) 313
24. Spruce B.A., Campbell L.A., McTavish N., Cooper M.A., Appleyard M.V., O'Neill M., Howie J., Samson J., Watt S., Murray K., McLean D., Leslie N.R., Safrany S.T., Ferguson M.J., Peters J.A., Prescott A.R., Box G., Hayes A., Nutley B., Raynaud F., Downes C.P., Lambert J.J., Thompson A.M., and Eccles S. Cancer Res. 64 (2004) 4875
25. Standard protocols are reported in. Colabufo N.A., Berardi F., Cantore M., Perrone M.G., Contino M., Inglese C., Niso M., Perrone R., Azzariti A., Simone G.M., Porcelli L., and Paradiso A. Bioorg. Med. Chem. 16 (2008) 362
26. Kawamura K., Tsukada H., Shiba K., Tsuji C., Harada N., Kimura Y., and Ishiwata K. Nucl. Med. Biol. 34 (2007) 571
27. Kawamura K., Kimura Y., Tsukada H., Kobayashi T., Nishiyama S., Kakiuchi T., Ohba H., Harada N., Matsuno K., Ishii K., and Ishiwata K. Neurobiol. Aging 24 (2003) 745
28. Ishiwata K., Tsukada H., Kawamura K., Kimura Y., Nishiyama S., Kobayashi T., Matsuno K., and Senda M. Synapse 40 (2001) 235
29. van Waarde A., Jager P.L., Ishiwata K., Dierckx R.A., and Elsinga P.H. J. Nucl. Med. 47 (2006) 150
30. Tu Z., Xu J., Jones L.A., Li S., Dumstorff C., Vangveravong S., Chen D.L., Wheeler K.T., Welch M.J., and Mach R.H. J. Med. Chem. 50 (2007) 3194
31. Kashiwagi H., McDunn J.E., Simon Jr. P.O., Goedegebuure1 P.S., Xu J., Jones L., Chang K., Johnston F., Trinkaus K., Hotchkiss R., Mach R.H., and Hawkins W.G. Mol. Cancer 6 (2007) 48
32. Hashimoto K., and Ishiwata K. Curr. Pharm. Des. 12 (2006) 3857