Synthesis and evaluation of intercalating somatostatin receptor binding peptide conjugates for endoradiotherapy

Journal of Pharmacy and Pharmaceutical Sciences

Volumn 10, Issue 2, 2007, Pages

  Graham, Keith ^a,b   Wang, Qin ^a,c   Boy, Regine Garcia ^a   Eisenhut, Michael ^d   Haberkorn, Uwe ^a   Mier, Walter ^a  

^a UNIVERSITY HOSPITAL HEIDELBERG   (Germany)

^b BAYER PHARMA AG   (Germany)

^c Vion Pharmaceuticals Incorporated   (United States)

^d GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

Endoradiotherapy; Intercalators; Nuclear localization; Peptides; Somatostatin

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID 4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL 6 AMINOHEXYLIC ACID OCTREOTIDE[3 TYROSINE]; 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID AMINO 4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL OCTREOTIDE[3 TYROSINE]; [2 [2 (4 BENZYLOXYPHENYL)BENZIMIDAZOL 5 YL]BENZIMIDAZOLE 5 CARBONYL] DEXTRO PHENYLALANINE CYCLO(CYSTEINYLTYROSINE DEXTRO TRYPTOPHANYLLYSYLTHREONYLCYSTEINE)THREONINE HYDROXIDE; [2 [2 (4 HYDROXYPHENYL)BENZIMIDAZOL 5 YL]BENZIMIDAZOLE 5 CARBONYL] DEXTRO PHENYLALANINE CYCLO(CYSTEINYLTYROSINE DEXTRO TRYPTOPHANYLLYSYLTHREONYLCYSTEINE)THREONINE HYDROXIDE; [2 [2 (4 METHOXYPHENYL)BENZIMIDAZOL 5 YL]BENZIMIDAZOLE 5 CARBONYL] DEXTRO PHENYLALANINE CYCLO(CYSTEINYLTYROSINE DEXTRO TRYPTOPHANYLLYSYLTHREONYLCYSTEINE)THREONINE HYDROXIDE; [2 [2 [4 (1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID AMINOMETHYLPHENYL)]BENZIMIDAZOL 5 YL]BENZIMIDAZOLE 5 CARBONYL] DEXTRO PHENYLALANINE CYCLO(CYSTEINYLTYROSINE DEXTRO TRYPTOPHANYLLYSYLTHREONYLCYSTEINE)THREONINE HYDROXIDE; [2 [2 [4 (AMINOMETHYL)PHENYL]BENZIMIDAZOL 5 YL]BENZIMIDAZOLE 5 CARBONYL] DEXTRO PHENYLALANINE CYCLO(CYSTEINYLTYROSINE DEXTRO TRYPTOPHANYLLYSYLTHREONYLCYSTEINE)THREONINE HYDROXIDE; AMINO 4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL OCTREOTIDE[3 TYROSINE]; ANTINEOPLASTIC AGENT; METHOXY 4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL OCTREOTIDE[3 TYROSINE]; OCTREOTIDE; OCTREOTIDE[3 TYROSINE]; PEPTIDE DERIVATIVE; SOMATOSTATIN RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE MICROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; INTERCALATION COMPLEX; NONHUMAN; RADIOISOTOPE THERAPY; RAT; SOLID PHASE SYNTHESIS;

ANIMALS; BENZIMIDAZOLES; BINDING, COMPETITIVE; BISBENZIMIDE; CELL MEMBRANE; CEREBRAL CORTEX; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCENT DYES; HETEROCYCLIC COMPOUNDS, 1-RING; INTERCALATING AGENTS; MICROSCOPY, FLUORESCENCE; PEPTIDES, CYCLIC; RADIOPHARMACEUTICALS; RADIOTHERAPY; RATS; RECEPTORS, SOMATOSTATIN;

EID: 34547893478     PISSN: None     EISSN: 14821826     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Kawanishi, S., Hiraku, Y. Amplification of anticancer drug-induced DNA damage and apoptosis by DNA-binding compounds. Curr. Med. Chem. Anticancer Agents, 4:415-419, 2004.
2. Constant, J.F; Fkyerat, A; Demeunynck, M; Laval, J; O'Connor, T.R., L'homme, J. Design of molecules which specifically cleave abasic sites in DNA. Anticancer Drug Des., 5:59-62, 1990.
3. Uusijarvi, H; Bernhardt, P; Rosch, F; Maecke, H.R., Forssell-Aronsson, E. Electron- and positron-emitting radiolanthanides for therapy: aspects of dosimetry and production. J. Nucl. Med., 47:807-814, 2006.
4. Buchegger, F; Perillo-Adamer, F; Dupertuis, Y'M., Bischof Delaloye, A. Auger radiation targeted into DNA: a therapy perspective. Eur. J. Nucl. Med. Mol. Imaging, 33:1352-1363, 2006.
5. Ginj, M; Hinni, K; Tschumi, S; Schulz, S., Maecke, H.R. Trifunctional somatostatin-based derivatives designed for targeted radiotherapy using auger electron emitters. J. Nucl. Med., 46:2097-2103, 2005.
6. Mier, W; Eritja, R; Mohammed, A; Haberkorn, U., Eisenhut, M. Preparation and evaluation of tumor-targeting peptide-oligonucleotide conjugates. Bioconjug. Chem., 11:855-860, 2000.
7. 125I-Tyr3Octreotide by somatostatin receptor-positive cells in vitro and in vivo: implications for somatostatin receptor-targeted radio-guided surgery. Proc. Assoc. Am. Physicians, 111:63-69, 1999.
8. Haberkorn, U; Henze, M; Altmann, A; Jiang, S; Morr, I; Mahmut, M; Peschke, P; Kubler, W; Debus, J., Eisenhut, M. Transfer of the human NaI symporter gene enhances iodide uptake in hepatoma cells. J. Nucl. Med., 42:317-325, 2001.
9. Nouel, D; Gaudriault, G; Houle, M; Reisine, T; Vincent, J.P; Mazella, J., Beaudet, A. Differential internalization of somatostatin in COS-7 cells transfected with SST1 and SST2 receptor subtypes: a confocal microscopic study using novel fluorescent somatostatin derivatives. Endocrinology, 138:296-306, 1997.
10. Schober, A; Bottner, M; Strelau, J; Kinscherf, R; Bonaterra, G.A; Barth, M; Schilling, L; Fairlie, W.D; Breit, S.N., Unsicker, K. Expression of growth differentiation factor-15/macrophage inhibitory cytokine-1 (GDF-15/MIC-1) in the perinatal, adult, and injured rat brain. J. Comp. Neurol., 439:32-45, 2001.
11. Behrens, C; Harrit, N., Nielsen, P.E. Synthesis of a Hoechst 32258 analogue amino acid building block for direct incorporation of a fluorescent, high-affinity DNA binding motif into peptides. Bioconjug. Chem., 12:1021-1027, 2001.
12. Lombardy, R.L; Tanious, F.A; Ramachandran, K; Tidwell, R.R., Wilson, W.D. Synthesis and DNA interactions of benzimidazole dications which have activity against opportunistic infections. J. Med. Chem., 39:1452-1462, 1996.
13. Eynde, J.J.V., Delfosse, F., Lor, P., Haverbeke, Y. V. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, a mild catalyst for the formation of carbon-nitrogen bonds. Tetrahedron, 51:5813-5818, 1995.
14. Ben-Alloum, A, Bakkas, S., Soufiaoui, M. Benzimidazoles: oxydation hétérocyclisante par le nitrobènzene ou le diméthylsulfoxyde sur silice et sous irradiation micro-ondes ou ultra-violet. Tetrahedron Lett., 39:4481-4484, 1998.
15. Singh, P.M, Sasmal, S., Lu, W., Chatterjee, M.N. Synthetic utility of catalytic fe(iii)/fe(ii) redox cycling towards fused heterocycles: a facile access to substituted benzimidazole, bis-benimidazole and imidazopyridine derivatives. Synthesis, 1380-1390, 2000.
16. Göker, H, Ölgen, S., Ertan, R., Akgün, H., Özbey, S., Kendi, E., Topcu, G. Synthesis of Some New Benzimidazole-5(6)-carboxylic acids. J. Heterocyclic Chem., 32:1767-1773, 1995.
17. Ji, Y.H; Bur, D; Hasler, W; Runtz Schmitt, V; Dorn, A; Bailly, C., Waring, M.J., Hochstrasser, R., Leupin, W. Tris-benzimidazole derivatives: design, synthesis and DNA sequence recognition. Bioorg. Med. Chem., 9:2905-2919, 2001.
18. White, A.W., Almassy, R., Calvert, A.H., Curtin, N.J., Griffin, R.J., Hostomsky, Z; Maegley, K; Newell, D.R., Srinivasan, S., Golding, B.T. Resistance-modifying agents. 9. Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase. J. Med. Chem., 43:4084-4097, 2000.
19. Hoffman, T.J., Quinn, TP., Volkert, W.A. Radiometallated receptor-avid peptide conjugates for specific in vivo targeting of cancer cells. Nucl. Med. Biol., 28:527-539, 2001.
20. Hanson, R.N. Synthesis of Auger electron-emitting radiopharmaceuticals. Curr. Pharm. Des., 6:1457-1468, 2000.