Hybrid peptide dendrimers for imaging of chemokine receptor 4 (CXCR4) expression

Molecular Pharmaceutics

Volumn 8, Issue 6, 2011, Pages 2444-2453

  Kuil, Joeri ^a,b   Buckle, Tessa ^a,b   Oldenburg, Joppe ^a   Yuan, Hushan ^c   Borowsky, Alexander D ^d   Josephson, Lee ^c   Van Leeuwen, Fijs W B ^a,b  

^a ANTONI VAN LEEUWENHOEK HOSPITAL   (Netherlands)

^b LEIDEN UNIVERSITY MEDICAL CENTER   (Netherlands)

^c MASSACHUSETTS GENERAL HOSPITAL   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

CXCR4; dendrimers; fluorescence; multimodal hybrid imaging; peptides; SPECT CT

Indexed keywords

CHELATE; CHEMOKINE RECEPTOR CXCR4; CYCLOPEPTIDE; DENDRIMER; PENTETIC ACID; TETRAMER; TZ 14011; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; COMPUTER ASSISTED TOMOGRAPHY; CONFOCAL MICROSCOPY; CONTROLLED STUDY; GENE OVEREXPRESSION; HUMAN; HUMAN TISSUE; HYBRID; MEMBRANE TRANSPORT; MOLECULAR IMAGING; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN MULTIMERIZATION; PROTEIN TARGETING; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

CELL LINE, TUMOR; CELL SURVIVAL; DENDRIMERS; DIAGNOSTIC IMAGING; DIMERIZATION; FLUORESCENT DYES; GENE EXPRESSION PROFILING; GENE EXPRESSION REGULATION; HUMANS; MICROSCOPY, CONFOCAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; RECEPTORS, CXCR4;

EID: 82955172980     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp200401p     Document Type: Article

References (52)

1. Teicher, B. A.; Fricker, S. P. CXCL12 (SDF-1)/CXCR4 pathway in cancer Clin. Cancer Res. 2010, 16, 2927-2931
2. Kulbe, H.; Levinson, N. R.; Balkwill, F.; Wilson, J. L. The chemokine network in cancer-much more than directing cell movement Int. J. Dev. Biol. 2004, 48, 489-496 (Pubitemid 39360399)
3. Furusato, B.; Mohamed, A.; Uhlen, M.; Rhim, J. S. CXCR4 and cancer Pathol. Int. 2010, 60, 497-505
4. 64Cu]AMD3100 positron emission tomography Cancer Res. 2010, 70, 3935-3944
5. Hassan, S.; Buchanan, M.; Jahan, K.; Aguilar-Mahecha, A.; Gaboury, L.; Muller, W. J.; Alsawafi, Y.; Mourskaia, A. A.; Siegel, P. M.; Salvucci, O.; Basik, M. CXCR4 peptide antagonist inhibits primary breast tumor growth, metastasis and enhances the efficacy of anti-VEGF treatment or docetaxel in a transgenic mouse model Int. J. Cancer 2011, 129, 225-232
6. Azab, A. K.; Runnels, J. M.; Pitsillides, C.; Moreau, A. S.; Azab, F.; Leleu, X.; Jia, X.; Wright, R.; Ospina, B.; Carlson, A. L.; Alt, C.; Burwick, N.; Roccaro, A. M.; Ngo, H. T.; Farag, M.; Melhem, M. R.; Sacco, A.; Munshi, N. C.; Hideshima, T.; Rollins, B. J.; Anderson, K. C.; Kung, A. L.; Lin, C. P.; Ghobrial, I. M. CXCR4 inhibitor AMD3100 disrupts the interaction of multiple myeloma cells with the bone marrow microenvironment and enhances their sensitivity to therapy Blood 2009, 113, 4341-4351
7. Nervi, B.; Ramirez, P.; Rettig, M. P.; Uy, G. L.; Holt, M. S.; Ritchey, J. K.; Prior, J. L.; Piwnica-Worms, D.; Bridger, G.; Ley, T. J.; DiPersio, J. F. Chemosensitization of acute myeloid leukemia (AML) following mobilization by the CXCR4 antagonist AMD3100 Blood 2009, 113, 6206-6214
8. Fujii, N.; Oishi, S.; Hiramatsu, K.; Araki, T.; Ueda, S.; Tamamura, H.; Otaka, A.; Kusano, S.; Terakubo, S.; Nakashima, H.; Broach, J. A.; Trent, J. O.; Wang, Z. X.; Peiper, S. C. Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries Angew. Chem., Int. Ed. 2003, 42, 3251-3253 (Pubitemid 36917168)
9. Tamamura, H.; Hiramatsu, K.; Kusano, S.; Terakubo, S.; Yamamoto, N.; Trent, J. O.; Wang, Z.; Peiper, S. C.; Nakashima, H.; Otaka, A.; Fujii, N. Synthesis of potent CXCR4 inhibitors possessing low cytotoxicity and improved biostability based on T140 derivatives Org. Biomol. Chem. 2003, 1, 3656-3662
10. Kuil, J.; Buckle, T.; Yuan, H.; Van den Berg, N. S.; Oishi, S.; Fujii, N.; Josephson, L.; Van Leeuwen, F. W. B. Synthesis and evaluation of a bimodal CXCR4 antagonistic peptide Bioconjugate Chem. 2011, 22, 859-864
11. Kuil, J.; Steunenberg, P.; Chin, P. T. K.; Oldenburg, J.; Jalink, K.; Velders, A. H.; Van Leeuwen, F. W. B. Peptide-functionalized luminescent iridium complexes for lifetime imaging of CXCR4 expression ChemBioChem 2011, 12, 1897-1903
12. Nomura, W.; Tanabe, Y.; Tsutsumi, H.; Tanaka, T.; Ohba, K.; Yamamoto, N.; Tamamura, H. Fluorophore labeling enables imaging and evaluation of specific CXCR4-ligand interaction at the cell membrane for fluorescence-based screening Bioconjugate Chem. 2008, 19, 1917-1920
13. Oishi, S.; Masuda, R.; Evans, B.; Ueda, S.; Goto, Y.; Ohno, H.; Hirasawa, A.; Tsujimoto, G.; Wang, Z.; Peiper, S. C.; Naito, T.; Kodama, E.; Matsuoka, M.; Fujii, N. Synthesis and application of fluorescein- and biotin-labeled molecular probes for the chemokine receptor CXCR4 ChemBioChem 2008, 9, 1154-1158
14. Nishizawa, K.; Nishiyama, H.; Oishi, S.; Tanahara, N.; Kotani, H.; Mikami, Y.; Toda, Y.; Evans, B. J.; Peiper, S. C.; Saito, R.; Watanabe, J.; Fujii, N.; Ogawa, O. Fluorescent imaging of high-grade bladder cancer using a specific antagonist for chemokine receptor CXCR4 Int. J. Cancer 2010, 127, 1180-1187
15. Van den Berg, N. S.; Buckle, T.; Kuil, J.; Wesseling, J.; Van Leeuwen, F. W. B. Direct fluorescent detection of CXCR4 using a targeted peptide antagonist Transl. Oncol. 2011, 4, 224-230
16. 111In-labeled peptide derivative targeting a chemokine receptor, CXCR4, for imaging tumors Nucl. Med. Biol. 2006, 33, 489-494 (Pubitemid 43729844)
17. Shao, F.; Yuan, H.; Josephson, L.; Weissleder, R.; Hilderbrand, S. A. Facile synthesis of monofunctional pentamethine carbocyanine fluorophores Dyes Pigments 2011, 90, 119-122
18. Garanger, E.; Aikawa, E.; Reynolds, F.; Weissleder, R.; Josephson, L. Simplified syntheses of complex multifunctional nanomaterials Chem. Commun. 2008, 4792-4794
19. Garanger, E.; Blois, J.; Hilderbrand, S. A.; Shao, F.; Josephson, L. Divergent oriented synthesis for the design of reagents for protein conjugation J. Comb. Chem. 2010, 12, 57-64
20. Kuil, J.; Velders, A. H.; Van Leeuwen, F. W. B. Multimodal tumor-targeting peptides functionalized with both a radio-and a fluorescent-label Bioconjugate Chem. 2010, 21, 1709-1719
21. Louie, A. Multimodality imaging probes: design and challenges Chem. Rev. 2010, 110, 3146-3195
22. Thorp-Greenwood, F. L.; Coogan, M. P. Multimodal radio- (PET/SPECT) and fluorescence imaging agents based on metallo-radioisotopes: current applications and prospects for development of new agents Dalton Trans. 2011, 40, 6129-6143
23. Culver, J.; Akers, W.; Achilefu, S. Multimodality molecular imaging with combined optical and SPECT/PET modalities J. Nucl. Med. 2008, 49, 169-172 (Pubitemid 351225675)
24. Lee, S.; Chen, X. Dual-modality probes for in vivo molecular imaging Mol. Imaging 2009, 8, 87-100
25. Buckle, T.; Chin, P. T. K.; van Leeuwen, F. W. B. (Non-targeted) radioactive/fluorescent nanoparticles and their potential in combined pre- and intraoperative imaging during sentinel lymph node resection Nanotechnology 2010, 21, 482001
26. Buckle, T.; van Leeuwen, A. C.; Chin, P. T. K.; Janssen, H.; Muller, S. H.; Jonkers, J.; van Leeuwen, F. W. B. A self-assembled multimodal complex for combined pre- and intraoperative imaging of the sentinel lymph node Nanotechnology 2010, 21, 355101
27. Buckle, T.; Chin, P. T. K.; van den Berg, N. S.; Loo, C. E.; Koops, W.; Gilhuijs, K. G.; van Leeuwen, F. W. B. Tumor bracketing and safety margin estimation using multimodal marker seeds: a proof of concept J. Biomed. Opt. 2010, 15, 056021
28. Van der Poel, H. G.; Buckle, T.; Brouwer, O. R.; Valdés Olmos, R. A.; Van Leeuwen, F. W. B. Intraoperative laparoscopic fluorescence guidance to the sentinel lymph node in prostate cancer patients: clinical proof of concept of an integrated functional imaging approach using a multimodal tracer Eur. Urol. 2011, 60 (4) 826-833
29. Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Synthetic multivalent ligands as probes of signal transduction Angew. Chem., Int. Ed. 2006, 45, 2348-2368 (Pubitemid 44105109)
30. Pieters, R. J. Maximising multivalency effects in protein-carbohydrate interactions Org. Biomol. Chem. 2009, 7, 2013-2025
31. Kuil, J.; Branderhorst, H. M.; Pieters, R. J.; de Mol, N. J.; Liskamp, R. M. J. ITAM-derived phosphopeptide-containing dendrimers as multivalent ligands for Syk tandem SH2 domain Org. Biomol. Chem. 2009, 7, 4088-4094
32. Mammen, M.; Choi, S. K.; Whitesides, G. M. Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors Angew. Chem., Int. Ed. 1998, 37, 2754-2794 (Pubitemid 29008561)
33. Lundquist, J. J.; Toone, E. J. The cluster glycoside effect Chem. Rev. 2002, 102, 555-578 (Pubitemid 35377623)
34. Kitov, P. I.; Bundle, D. R. On the nature of the multivalency effect: a thermodynamic model J. Am. Chem. Soc. 2003, 125, 16271-16284 (Pubitemid 38020650)
35. Reczek, J. J.; Kennedy, A. A.; Halbert, B. T.; Urbach, A. R. Multivalent recognition of peptides by modular self-assembled receptors J. Am. Chem. Soc. 2009, 131, 2408-2415
36. 3 expression in living mice Bioconjugate Chem. 2005, 16, 1433-1441 (Pubitemid 41681509)
37. 3-targeted radiotracers: maximizing binding affinity via bivalency Bioconjugate Chem. 2009, 20, 2199-2213
38. Almutairi, A.; Rossin, R.; Shokeen, M.; Hagooly, A.; Ananth, A.; Capoccia, B.; Guillaudeu, S.; Abendschein, D.; Anderson, C. J.; Welch, M. J.; Frechet, J. M. Biodegradable dendritic positron-emitting nanoprobes for the noninvasive imaging of angiogenesis Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 685-690
39. Galibert, M.; Sancey, L.; Renaudet, O.; Coll, J. L.; Dumy, P.; Boturyn, D. Application of click-click chemistry to the synthesis of new multivalent RGD conjugates Org. Biomol. Chem. 2010, 8, 5133-5138
40. Abiraj, K.; Jaccard, H.; Kretzschmar, M.; Helm, L.; Maecke, H. R. Novel DOTA-based prochelator for divalent peptide vectorization: synthesis of dimeric bombesin analogues for multimodality tumor imaging and therapy Chem. Commun. 2008, 3248-3250 (Pubitemid 351989758)
41. Cai, W.; Chen, K.; Li, Z. B.; Gambhir, S. S.; Chen, X. Dual-function probe for PET and near-infrared fluorescence imaging of tumor vasculature J. Nucl. Med. 2007, 48, 1862-1870 (Pubitemid 350099333)
42. Boswell, C. A.; Eck, P. K.; Regino, C. A.; Bernardo, M.; Wong, K. J.; Milenic, D. E.; Choyke, P. L.; Brechbiel, M. W. Synthesis, characterization, and biological evaluation of integrin alphavbeta3-targeted PAMAM dendrimers Mol. Pharmaceutics 2008, 5, 527-539
43. Iyer, A. K.; Khaled, G.; Fang, J.; Maeda, H. Exploiting the enhanced permeability and retention effect for tumor targeting Drug Discovery Today 2006, 11, 812-818 (Pubitemid 44280021)
44. Maglione, J. E.; McGoldrick, E. T.; Young, L. J.; Namba, R.; Gregg, J. P.; Liu, L.; Moghanaki, D.; Ellies, L. G.; Borowsky, A. D.; Cardiff, R. D.; MacLeod, C. L. Polyomavirus middle T-induced mammary intraepithelial neoplasia outgrowths: single origin, divergent evolution, and multiple outcomes Mol. Cancer Ther. 2004, 3, 941-953 (Pubitemid 39199589)
45. Namba, R.; Young, L. J.; Maglione, J. E.; McGoldrick, E. T.; Liu, S.; Wurz, G. T.; DeGregorio, M. W.; Borowsky, A. D.; MacLeod, C. L.; Cardiff, R. D.; Gregg, J. P. Selective estrogen receptor modulators inhibit growth and progression of premalignant lesions in a mouse model of ductal carcinoma in situ Breast Cancer Res. 2005, 7, R881-889
46. Namba, R.; Young, L. J.; Abbey, C. K.; Kim, L.; Damonte, P.; Borowsky, A. D.; Qi, J.; Tepper, C. G.; MacLeod, C. L.; Cardiff, R. D.; Gregg, J. P. Rapamycin inhibits growth of premalignant and malignant mammary lesions in a mouse model of ductal carcinoma in situ Clin. Cancer Res. 2006, 12, 2613-2621
47. Wu, B.; Chien, E. Y. T.; Mol, C. D.; Fenalti, G.; Liu, W.; Katritch, V.; Abagyan, R.; Brooun, A.; Wells, P.; Bi, F. C.; Hamel, D. J.; Kuhn, P.; Handel, T. M.; Cherezov, V.; Stevens, R. C. Structures of the CXCR4 chemokine GPCR with small-molecule and cyclic peptide antagonists Science 2010, 330, 1066-1071
48. Tanaka, T.; Nomura, W.; Narumi, T.; Masuda, A.; Tamamura, H. Bivalent ligands of CXCR4 with rigid linkers for elucidation of the dimerization state in cells J. Am. Chem. Soc. 2010, 132, 15899-15901
49. Yim, C. B.; Boerman, O. C.; de Visser, M.; de Jong, M.; Dechesne, A. C.; Rijkers, D. T. S.; Liskamp, R. M. J. Versatile conjugation of octreotide to dendrimers by cycloaddition (''click'') chemistry to yield high-affinity multivalent cyclic peptide dendrimers Bioconjugate Chem. 2009, 20, 1323-1331
50. 3]octreotide peptides via a combination of Cu(I)-catalyzed ''click'' cycloaddition and thio acid/sulfonyl azide ''sulfo-click'' amidation and their in vivo evaluation J. Med. Chem. 2010, 53, 3944-3953
51. Albertazzi, L.; Serresi, M.; Albanese, A.; Beltram, F. Dendrimer internalization and intracellular trafficking in living cells Mol. Pharmaceutics 2010, 7, 680-688
52. 111indium labeled CXCR4 peptide antagonist.. Am. J. Nucl. Med. Mol. Imaging 2011, in press.