N-benzyl-2-(6,8-dichloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl) -N-(6-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)hexyl)acetamide as a new fluorescent probe for peripheral benzodiazepine receptor and microglial cell visualization

Bioconjugate Chemistry

Volumn 18, Issue 5, 2007, Pages 1397-1407

  Laquintana, Valentino ^a   Denora, Nunzio ^a   Lopedota, Angela ^a   Suzuki, Hiromi ^b   Sawada, Makoto ^b   Serra, Mariangela ^c   Biggio, Giovanni ^c   Latrofa, Andrea ^a   Trapani, Giuseppe ^a   Liso, Gaetano ^a  

^a UNIVERSITY OF BARI   (Italy)

^b NAGOYA UNIVERSITY   (Japan)

^c Cittadella Univ di Monserrato   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BLOOD VESSELS; DEXTRAN; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; PROBES;

BENZODIAZEPINES; FLUORESCEIN ISOTHIOCYANATE; IMIDAZOPYRIDINES; LOCALISATION; MICROGLIA; MICROGLIAL CELLS; MITOCHONDRIAS; NEW FLUORESCENT PROBES; OXADIAZOL; RECEPTOR CELLS;

VISUALIZATION;

BENZODIAZEPINE RECEPTOR; FLUNITRAZEPAM; FLUORESCEIN ISOTHIOCYANATE DEXTRAN; FLUORESCENT DYE; IMIDAZOPYRIDINE DERIVATIVE; IMIDAZOPYRIMIDINE DERIVATIVE; N BENZYL 2 [6,8 DICHLORO 2 (4 CHLOROPHENYL)IMIDAZO[1,2 A]PYRIDIN 3 YL] N [6 (7 NITROBENZO[C][1,2,5]OXADIAZOL 4 YLAMINO)HEXYL]ACETAMIDE; N SEC BUTYL 1 (2 CHLOROPHENYL) N METHYL 3 ISOQUINOLINECARBOXAMIDE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING COMPETITION; BLOOD BRAIN BARRIER; CELL ACTIVATION; CELL IMAGING; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG PENETRATION; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; FLUORESCENCE; FLUORESCENCE MICROSCOPY; IC 50; IMAGING; LIVER; MALE; MICROGLIA; NONHUMAN; PROTEIN LOCALIZATION; RAT;

EID: 34648840352     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060393c     Document Type: Article

References (35)

1. Anholt, R. R. H., Pedersen, P. L., De Souza, E. B., and Snyder, S. H. (1986) The peripheral benzodiazepine receptor: localization to the mitochondrial outer membrane. J. Biol. Chem. 261, 576-583.
2. Papadopoulos, V., Baraldi, M., Guilarte, T. R., Knudsen, T. B., Lacapere, J. J., Lindemann, P., Norenberg, M. D., Nutt, D., Weizman, A., Zhang, M. R., and Gavish, M. (2006) Translocator protein (18 kDa): new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular function. Trends Pharmacol. Sci. 27, 402-409.
3. Papadopulos, V., Guarneri, P., Krueger, K. E., Guidotti, A., and Costa, E. (1992) Pregnenolone biosynthesis in C6 glioma cell mitochondria: regulation by a mitochondrial diazepam binding inhibitor receptor. Proc. Natl. Acad. Sci. U.S.A. 89, 5113-5117.
4. Messmer, K., and Reynolds, G. P. (1998) Increased peripheral benzodiazepine binding site in the brain of patients with Huntington's disease. Neurosci. Lett. 241, 53-56.
5. Veenman, L., and Gavish, M. (2000) Peripheral-type benzodiazepine receptors: their implication in brain disease. Drug Dev. Res. 50, 355-370.
6. Benveniste, E. N. (1997) Role of macrophages/microglia in multiple sclerosis and experimental allergic encephalomyelitis. J. Mol. Med. 75, 165-173.
7. Cagnin, A., Brooks, D. J., Kennedy, A. M., Gunn, R. N., Myers, R., and Turkheimer, F. E. (2001) In-vivo measurement of activated microglia in dementia. Lancet 358, 461-467.
8. Kassiou, M., Meikle, S. R., and Banati, R. B. (2005) Ligands for peripheral benzodiazepine binding sites in glial cells. Brain Res. Rev. 48, 207-210.
9. Hardwick, M., Fertikh, D., Culty, M., Li, H., Vidic, B., and Papadopoulos, V. (1999) Peripheral-type benzodiazepine receptor (PBR) in human breast cancer: correlation of breast cancer cell aggressive phenotype with PBR expression, nuclear localization, and PBR-mediated cell proliferation and nuclear transport of cholesterol. Cancer Res. 59, 831-842.
10. Katz, Y., Eitan, A., and Gavish, M. (1990) Increased density of peripheral benzodiazepine binding sites in ovarian carcinomas as compared with benign ovarian tumors and normal ovaries. Clin. Sci. 78, 155-158.
11. Venturini, I., Zaneroli, M. L., Corsi, L., Avallona, R., Farina, F., Alho, H., Baraldi, C., Ferrarese, C., Pecora, N., Frigo, M., Ardizzone, G., Arrigo, A., Pellicci, R., and Baraldi, M. (1998) Up-regulation of peripheral benzodiazepine receptor system in hepatocellular carcinoma. Life Sci. 65, 1269-1280.
12. Hirsch, T., Decaudin, D., Susin, S. A., Marchetti, P., Larochette, N., Resche-Rigon, M., and Kroemer, G. (1998) PK 11195, a ligand of the mitochondrial benzodiazepine receptor, facilitates the induction of apoptosis and reverses Bcl-2 mediated cytoprotection. Exp. Cell Res. 241, 426-34.
13. Sutter, A. P., Maaser, K., Barthel, B., and Scher̈bl, H. (2003) Ligands of the peripheral benzodiazepine receptor induce apoptosis and cell cycle arrest in oesophageal cancer cells: involvement of the p38mapk signalling pathway. Br. J. Cancer 89, 564-572.
14. Xia, W., Spector, S., Hardy, L., Zhao, S., Saluk, A., Alemane, L., and Spector, N. L. (2000) Tumor selective G2/M cell cycle arrest and apoptosis of epithelial and hematological malignancies by BBL22, a benzazepine. Proc. Natl. Acad. Sci. U.S.A. 97, 7494-7499.
15. Galiegue, S., Tinel, N., and Casellas, P. (2003) The peripheral benzodiazepine receptors: a promising therapeutic drug target. Curr. Med. Chem. 10, 1563-1572.
16. Kupczyk-Subotkowaka, L., Siahaan, T. J., Basile, A., Friedman, H. S., Higgins, P. E., Song, D., and Gallo, J. M. (1997) Modulation of melphalan resistance in glioma cells with a peripheral benzodiazepine receptor ligand - melphalan conjugate. J. Med. Chem. 40, 1726-1730.
17. Trapani, G., Laquintana, V., Latrofa, A., Ma, J., Reed, K., Serra, M., Biggio, G., Liso, G., and Gallo, J. M. (2003) Peripheral benzodiazepine receptor ligand - melphalan conjugates for potential selective drug delivery to brain tumors. Bioconjugate Chem. 14, 830-839.
18. Guo, P., Ma, J., Li, S., Guo, Z., Adams, A. L., and Gallo, J. M. (2001) Targeted delivery of a peripheral benzodiazepine receptor ligand - gemcitabine conjugate to brain tumors in a xenograft model. Cancer Chemother. Pharmacol. 48, 169-176.
19. Kozikowski, A. P., Kotoula, M., Ma, D., Boujrad, N., Tuckmantel, W., and Papadopoulos, V. (1997) Synthesis and biology of a 7-nitro-2,1,3-benzoxadiazol- 4-yl derivative of 2-phenylindole-3-acetamide: a fluorescent probe for the peripheral-type benzodiazepine receptor. J. Med. Chem. 40, 2435-2439.
20. Manning, H. C., Goebel, T., Thompson, R. C., Price, R. R., Lee, H., and Bornhop, D. J. (2004) Targeted molecular imaging agents for cellular-scale bimodal imaging. Bioconjugate Chem. 15, 1488-1495.
21. Manning, H. C., Smith, S. M., Sexton, M., Haviland, S., Bai, M., Cederquist, K., Stella, N., and Bornhop, D. J. (2006) A peripheral benzodiazepine receptor targeted agent for in vitro imaging and screening. Bioconjugate Chem. 17, 735-740.
22. Chen, Y., Zheng, X., Dobhal, M. P., Gryshuk, A., Morgan, J., Dougherty, T. J., Oseroff, A., and Pandey, R. K. (2005) Methyl pyrophorbide-α analogues: potential fluorescent probes for the peripheral-type benzodiazepine receptor. Effect of central metal in photosensitizing efficacy. J. Med. Chem. 48, 3692-3695.
23. Romeo, E., Auta, J., Kozikowski, A. P., Ma, A., Papadopoulos, V., Puia, G., Costa, E., and Guidotti, A. (1992) 2-Aryl-3-indoleacetamides (FGIN-1): a new class of potent and specific ligands for the mitochondrial DBI receptor. J. Pharmacol. Exp. Ther. 262, 971-978.
24. Le Fur, G., Perrier, M. L., Vaucher, N., Imbault, F., Flamier, A., Uzan, A., Renault, C., Dubroeucq, M. C., and Gueremy, C. (1983) Peripheral benzodiazepine binding sites: effect of PK11195, 1-(2-chlorophenyl)-n-(1- methylpropyl)-3-isoquinolinecarboxamide I. In vitro studies. Life Sci. 32, 1839-1847.
25. Marangos, P. L., Pate, J., Boulenger, J. P., and Clark-Rosenberg, R. (1982) Characterization of peripheral-type benzodiazepine binding sites in brain using [3H]Ro 5-4864. Mol. Pharmacol. 22, 26-32.
26. Okujama, S., Chaki, S., Yoshikawa, R., Ogawa, S., Suzuki, Y., Okubo, T., Nakazato, A., Nagamine, M., and Tomisawa, K. (1999) Neuropharmacological profile of peripheral benzodiazepine receptor agonists, DAA1097 and DAA1106. Life Sci. 16, 1455-1464.
27. Trapani, G., Franco, M., Ricciardi, L., Latrofa, A., Genchi, G., Sanna, E., Tuveri, F., Cagetti, E., Biggio, and Liso, G. (1997) Synthesis and binding affinity of 2-phenyl-imidazo[1,2-a]pyridine derivatives for both central and peripheral benzodiazepine receptors. A new series of high-affinity and selective ligands for the peripheral type. J. Med. Chem. 40, 3109-3118.
28. Trapani, G., Franco, M., Latrofa, A., Ricciardi, L., Carotti, A., Serra, M., Sanna, E., Biggio, G., and Liso, G. (1999) Novel 2-phenyl-imidazo[1,2-a]pyridine derivatives as potent and selective ligands for peripheral benzodiazepine receptors, synthesis, binding affinity, and in vivo studies. J. Med. Chem. 42, 3934-3941.
29. Trapani, G., Laquintana, V., Denora, N., Trapani, A., Lopedota, A., Latrofa, A., Franco, M., Serra, M., Pisu, M. G., Floris, I., Sanna, E., Biggio, G., and Liso, G. (2005) Structure - activity relationships and effects on neuroactive steroids in a series of 2-phenylimidazo-[1,2-a] pyridineacetamide peripheral benzodiazepine receptors ligands. J. Med. Chem. 48, 292-305.
30. Rackham, D. M. (1979) Spectroscopic studies of some imidazo-[1,2-a]pyridine and imidazo[1,2-a]pyrimidine derivatives. Appl. Spectrosc. 33, 561-563.
31. Janssen, M. J., Ensing, K., and De Zeew, R. A. (2000) Fluorescent-labeled ligands for the benzodiazepine receptor. Pharmazie 55, 102-106.
32. Muller, D., Zeltser, I., Bitan, G., and Gilon, C. (1997) Building units for N-backbone cyclic peptides. 3. Synthesis of protected Nα- (ω-aminoalkyl)amino acids and Nα-(ω-carboxyalkyl)amino acids. J. Org. Chem. 62, 411-416.
33. Martin, B., Possémé, F., Le Barbier, C., Careaux, F., Carboni, B., Seiler, N., Moulinoux, J.-P., and Delcros, J.-G. (2001) N-Benzylpolyamines as vectors of boron and fluorine for cancer therapy and imaging: synthesis and biological evaluation. J. Med Chem. 44, 3653-3664.
34. Clark, D. E. (1999) Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood - brain barrier penetration. J. Pharm. Sci. 88, 815-821.
35. Ertl, P., Rohde, B., and Selzer, P. (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J. Med. Chem. 43, 3714-3717.