Versatile conjugation of octreotide to dendrimers by cycloaddition ("click") chemistry to yield high-affinity multivalent cyclic peptide dendrimers

Bioconjugate Chemistry

Volumn 20, Issue 7, 2009, Pages 1323-1331

  Yim, Cheng Bin ^a,b   Boerman, Otto C ^b   De Visser, Monique ^c   De Jong, Marion ^c   Dechesne, Annemarie C ^a   Rijkers, Dirk T S ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b RADBOUD UNIVERSITY MEDICAL CENTER   (Netherlands)

^c ERASMUS MEDICAL CENTER   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPOUNDS; DENDRIMERS; DIAGNOSIS; PEPTIDES; TUMORS;

BINDING AFFINITIES; CELL/B.E; CLICK CHEMISTRY; CYCLIC PEPTIDES; CYCLOADDITIONS; HIGH AFFINITY; OCTREOTIDE; PEPTIDE DENDRIMERS; SOMATOSTATIN RECEPTORS; TUMOUR CELLS;

BINDING ENERGY;

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,17 TETRAACETIC ACID OCTREOTIDE[3 TYROSINE] CONJUGATE; ALKYNE DERIVATIVE; AZIDE; COPPER; CYCLOPEPTIDE; DENDRIMER; MONOMER; OCTREOTIDE; OCTREOTIDE[3 TYROSINE]; SOMATOSTATIN RECEPTOR 2; TETRAMER; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING COMPETITION; BRAIN TISSUE; CATALYSIS; CATALYST; CONJUGATE; CONTROLLED STUDY; CYCLOADDITION; DIPOLE; DRUG CONJUGATION; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GENE EXPRESSION; NONHUMAN; RAT; RECEPTOR AFFINITY;

RATTUS;

EID: 67650698519     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc900052n     Document Type: Article

References (55)

1. Brazeau, P., Vale, W., Burgus, R., Ling, N., Butcher, M., Rivier, J., and Guillemin, R. (1973) Hypothalamic polypeptide that inhibits the secretion of immunoreactive pituitary growth hormone. Science 179, 77-9.
2. Reichlin, S. (1983) Somatostatin. N. Engl. J. Med. 309, 1495-501.
3. Reichlin, S. (1983) Somatostatin (Second of two parts). N. Engl. J. Med. 309, 1556-63.
4. de Herder, W. W., Hofland, L. J., van der Lely, A. J., and Lamberts, S. W. J. (2003) Somatostatin receptors in gastroen-teropancreatic neuroendocrine tumours. Endocr. Relat. Cancer 10, 451-8.
5. Lamberts, S. W. J., Krenning, E. P., and Reubi, J.-C. (1991) The role of somatostatin and its analogs in the diagnosis and treatment of tumors. Endocr. Rev. 12, 450-82.
6. Patel, Y. C. (1999) Somatostatin and its receptor family. Front. Neuroendocrinol. 20, 157-98.
7. de Jong, M., Kwekkeboom, D. J., Valkema, R., and Krenning, E. P. (2003) Radiolabelled peptides for tumour therapy: current status and future directions. Eur. J. Nucl. Med. Mol. Imaging 30, 463-9.
8. van Eijck, C. H. J. (2005) Treatment of advanced endocrine gastroenteropancreatic tumours using radiolabelled somatostatin analogues. Br. J. Surg. 92, 1333-4.
9. Kaltsas, G. A., Papadogias, D., Makras, P., and Grossman, A. B. (2005) Treatment of advanced neuroendocrine tumours with radiolabelled somatostatin analogues. Endocr. Relat. Cancer 12, 683-99.
10. Kwekkeboom, D. J., Mueller-Brand, J., Paganelli, G., Anthony, L. B., Pauwels, S., Kvols, L. K., O'Dorisio, T. M., Valkema, R., Bodei, L., Chinol, M., Mäcke, H. R., and Krenning, E. P. (2005) Overview of results of peptide receptor radionuclide therapy with 3 radiolabeled somatostatin analogs. J. Nucl. Med. 46, 62S-6S.
11. Forrer, F., Valkema, R., Kwekkeboom, D. J., de Jong, M., and Krenning, E. P. (2007) Peptide receptor radionuclide therapy. Best Pract. Res. Clin. Endocrinol. Metabol. 21, 111-29.
12. Varki, A. (1993) Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 3, 97-130.
13. Mammen, M., Choi, S.-K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. 37, 2754-94.
14. Newkome, G. R., Moorefield, C. N., and Vögtle, F. (2001) Dendrimers and dendrons: concept, synthesis, applications, Wiley, New York.
15. Lee, C. C., MacKay, J. A., Fréchet, J. M. J., and Szoka, F. C. (2005) Designing dendrimers for biological applications. Nat. Biotechnol. 23, 1517-26.
16. Wester, H.-J., and Kessler, H. (2005) Molecular targeting with peptides or peptide-polymer conjugates: Just a question of size. J. Nucl. Med. 46, 1940-5.
17. Thumshirn, G., Hersel, U., Goodman, S. L., and Kessler, H. (2003) Multimeric cyclic RGD peptides as potential tools for tumor targeting: solid-phase peptide synthesis and chemoselective oxime ligation. Chem.-Eur. J. 9, 2717-25.
18. Janssen, M., Frielink, C., Dijkgraaf, I., Oyen, W. J. G., Edwards, D. S., Liu, S., Rajopaghye, M., Massuger, L., Corstens, F. H. M., and Boerman, O. C. (2004) Improved tumor targeting of radiolabeled RGD peptides using rapid dose fractionation. Cancer Biother. Radiopharm. 19, 399-404.
19. 64Cu-labeled tetrameric RGD peptide. J. Nucl. Med. 46, 1707-18.
20. 3 integrin by multimerisation of RGD peptides. Eur. J. Nucl. Med. Mol. Imaging 34, 267-73.
21. Dijkgraaf, I., Rijnders, A. Y., Soede, A., Dechesne, A. C., van Esse, G. W., Brouwer, A. J., Corstens, F. H. M., Boerman, O. C., Rijkers, D. T. S., and Liskamp, R. M. J. (2007) Synthesis of DOTA-conjugated multivalent cyclic-RGD peptide dendrimers via 1,3-dipolar cycloaddition and their biological evaluation: implications for tumor targeting and tumor imaging purposes. Org. Biomol. Chem. 5, 935-44.
22. Autar, R., Khan, A. S., Schad, M., Hacker, J., Liskamp, R. M. J., and Pieters, R. J. (2003) Adhesion inhibition of F1C-fimbriated Escherichia coli and Pseudomonas aeruginosa PAK and PAO by multivalent carbohydrate ligands. ChemBioChem 4, 1317-25.
23. Joosten, J. A. F., Loimaranta, V., Appeldoorn, C. C. M., Haataja, S., Ait El Maate, F., Liskamp, R. M. J., Finne, J., and Pieters, R. J. (2004) Inhibition of Streptococcus suis adhesion by dendritic galabiose compounds at low nanomolar concentration. J. Med. Chem. 47, 6499-508.
24. Arosio, D., Vrasidas, I., Valentini, P., Liskamp, R. M. J., Pieters, R. J., and Bernardi, A. (2004) Synthesis and cholera toxin binding properties of multivalent GM1 mimics. Org. Biomol. Chem. 2, 2113-24.
25. André, S., Pieters, R. J., Vrasidas, I., Kaltner, H., Kuwabara, I., Liu, F.-T., Liskamp, R. M. J., and Gabius, H.-J. (2001) Wedgelike glycodendrimers as inhibitors of binding of mammalian galectins to glycoproteins, lactose maxiclusters, and cell surface glycoconjugates. ChemBioChem 2, 822-30.
26. Joosten, J. A. F., Tholen, N. T. H., Ait El Maate, F., Brouwer, A. J., van Esse, G. W., Rijkers, D. T. S., Liskamp, R. M. J., and Pieters, R. J. (2005) High-yielding microwave-assisted synthesis of triazole-linked glycodendrimers by copper-catalyzed [3 + 2] cycloaddition. Eur. J. Org. Chem. 2005, 3182-5.
27. Huisgen, R. (1984) 1,3-Dipolar cycloadditions - introduction, survey, mechanism. 1,3-Dipolar cycloaddition chemistry (Padwa, A., Ed.) pp 1-176, Vol 1, Wiley, New York.
28. Tornøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057-64.
29. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: copper( I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 41, 2596-9.
30. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: diverse chemical function from a few good reactions. Angew. Chem., Int. Ed. 40, 2004-21.
31. I-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 51-68.
32. Moses, J. E., and Moorhouse, A. D. (2007) The growing applications of click chemistry. Chem. Soc. Rev. 36, 1249-62.
33. Fournier, D., Hoogenboom, R., and Schubert, U. S. (2007) Clicking polymers: a straightforward approach to novel macromolecular architectures. Chem. Soc. Rev. 36, 1369-80.
34. Lutz, J.-F., and Zarafshani, Z. (2008) Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry. Adv. Drug Delivery Rev. 60, 958-70.
35. Meldal, M., and Tornøe, C. W. (2008) Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 108, 2952-3015.
36. Mulders, S. J. E., Brouwer, A. J., van der Meer, P. G. J., and Liskamp, R. M. J. (1997) Synthesis of a novel amino acid based dendrimer. Tetrahedron Lett. 38, 631-4.
37. Mulders, S. J. E., Brouwer, A. J., and Liskamp, R. M. J. (1997) Molecular diversity of novel amino acid based dendrimers. Tetrahedron Lett. 38, 3085-8.
38. Brouwer, A. J., Mulders, S. J. E., and Liskamp, R. M. J. (2001) Convergent synthesis and diversity of amino acid based den-drimers. Eur. J. Org. Chem. 1903-15.
39. Brouwer, A. J., Mulders, S. J. E., and Liskamp, R. M. J. (2005) Synthesis of novel dendrimeric systems containing NLO ligands. Eur. J. Org. Chem. 487-95.
40. Rijkers, D. T. S., van Esse, G. W., Merkx, R., Brouwer, A. J., Jacobs, H. J. F., Pieters, R. J., and Liskamp, R. M. J. (2005) Efficient microwave-assisted synthesis of multivalent dendrimeric peptides using cycloaddition reaction (click) chemistry. Chem. Commun. 4581-3.
41. Kaiser, E., Colescott, R. L., Bossinger, C. D., and Cook, P. I. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34, 595-598.
42. Sarin, V. K., Kent, S. B. H., Tam, J. P., and Merrifield, R. B. (1981) Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction. Anal. Biochem. 117, 147-157.
43. Krchnák, V., Vágner, J., Safár, P., and Lebl, M. (1988) Non-invasive continuous monitoring of solid-phase peptide synthesis by acid-base indicator. Collect. Czech. Chem. Commun. 53, 2542-8.
44. Meienhofer, J., Waki, M., Heimer, E. P., Lambros, T. J., Makofske, R. C., and Chang, C.-D. (1979) Solid phase synthesis without repetitive acidolysis. Preparation of leucyl-alanyl-glycyl-valine using 9- fluorenylmethyloxycarbonylamino acids. Int. J. Pept. Protein Res. 13, 35-42.
45. Arx, E. von, Faupel, M., and Brugger, M. (1976) Das 4,4′- tetramethyldiamino-diphenylmethan reagens (TDM): Eine modifikation der Chlor-o-tolidin Farbereaktion für die Dünnschicht-chromatographie. J. Chromatogr. 120, 224-8.
46. Fields, G. B., and Noble, R. L. (1990) Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 35, 161-214.
47. Tam, J. P., Wu, C.-R., Liu, W., and Zhang, J.-W. (1991) Disulfide bond formation in peptides by dimethyl sulfoxide - scope and applications. J. Am. Chem. Soc. 113, 6657-62.
48. Lipshutz, B. H., Frieman, B. A., and Tomaso, A. E., Jr. (2006) Copper-in-charcoal (Cu/C): heterogeneous, copper-catalyzed asymmetric hydrosilylations. Angew. Chem., Int. Ed. 45, 1259-64.
49. Lipshutz, B. H., and Taft, B. R. (2006) Heterogeneous copper-in-charcoal-catalyzed click chemistry. Angew. Chem., Int. Ed. 45, 8235-8.
50. Knör, S., Modlinger, A., Poethko, T., Schottelius, M., Wester, H.-J., and Kessler, H. (2007) Synthesis of novel 1,4,7,10-tetraazacyclodecane-1, 4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds. Chem.-Eur. J. 13, 6082-90.
51. Reubi, J. C., Kvols, L. K., Waser, B., Nagorney, D. M., Heitz, P. U., Charboneau, J. W., Reading, C. C., and Moertel, C. (1990) Detection of somatostatin receptors in surgical and percutaneous needle biopsy samples of carcinoids and Islet cell carcinomas. Cancer Res. 50, 5969-77.
52. Grandjean, C., Boutonnier, A., Guerreiro, C., Fournier, J.-M., and Mulard, L. A. (2005) On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation. J. Org. Chem. 70, 7123-32.
53. Rodriguez, M., Llinares, M., Doulut, S., Heitz, A., and Martinez, J. (1991) A facile synthesis of chiral N-protected beta-amino alcohols. Tetrahedron Lett. 32, 923-6.
54. Lutz, J.-F. (2008) Copper-free azide-alkyne cycloadditions: new insights and perspectives. Angew. Chem., Int. Ed. 47, 2182-4.
55. van Berkel, S. S., Dirks, T. J., Meeuwissen, S. A., Pingen, D. L. L., Boerman, O. C., Laverman, P., van Delft, F. L., Cornelissen, J. J. L. M., and Rutjes, F. P. J. T. (2008) Application of metal-free triazole formation in the synthesis of cyclic RGD-DTPA conjugates. ChemBioChem 9, 1805-15.