The synthesis and chelation chemistry of DOTA - Peptide conjugates

Bioconjugate Chemistry

Volumn 19, Issue 2, 2008, Pages 391-402

  De León Rodríguez, Luis M ^a   Kovacs, Zoltan ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; COORDINATION REACTIONS; MAGNETIC RESONANCE IMAGING; MEDICAL APPLICATIONS; METAL COMPLEXES; SYNTHESIS (CHEMICAL);

BI-FUNCTIONAL; BIOMEDICAL APPLICATIONS; MRI CONTRAST AGENTS; SOLID PHASE SYNTHESIS; SOLUTION PHASE SYNTHESIS; TARGETED IMAGING; TARGETED THERAPEUTICS; TETRAACETIC ACID;

PEPTIDES;

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; CONTRAST MEDIUM; METAL COMPLEX; RADIOPHARMACEUTICAL AGENT;

CHELATION; DRUG SYNTHESIS; IMAGING; NUCLEAR MAGNETIC RESONANCE IMAGING; REVIEW; SOLID;

EID: 39749134777     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700328s     Document Type: Review

References (129)

1. Smith, G. P., and Petrenko, V. A. (1997) Phage display. Chem. Rev. 97, 391-410.
2. 177Lu-DOTA-biotin pretargeted by CC49 scFv-streptavidin fusion protein in xenograft-bearing nude mice. Nucl. Med. Biol. 31, 213-223.
3. Woods, M., Kovacs, Z., Kiraly, R., Brücher, E., Zhang, S., and Sherry, A. D. (2004) Solution dynamics and stability of lanthanide(III) (S)-2-(p-nitrobenzyl)DOTA complexes. Inorg. Chem. 43, 2845-2851.
4. Duncan, J. R., Franano, F. N., Edward, W. B., and Welch, M. J. E. (1994) Evidence of gadolinium dissociation from protein-DTPA-gadolinium complexes. Invest. Radiol. 29, S58-S61.
5. 2-, used as a contrast agent in magnetic resonance imaging. Chem. - Eur. J. 6, 719-724.
6. Bousquet, J. C., Saini, S., Stark, D. D., Hahn, P. F., Nigam, M., Wittenberg, J., and Ferrucci, J. T., Jr. (1988) Gd-DOTA: characterization of a new paramagnetic complex. Radiology 166, 693-698.
7. Weinmann, H. J., Laniado, M., and Mützel, W. (1984) Pharmacokinetics of gadolinium-DTPA/dimeglumine after intravenous injection into healthy volunteers. Physiol. Chem. Phys. Med. NMR 16, 167-172.
8. Zangos, S., Hammerstingl, R., Mack, M. G., Straub, R., Engelmann, K., Eichler, K., Balzer, T., and Vogl, T. J. (2001) Renal enhancement and excretion of the hepatobiliary contrast agent Gd-EOB-DTPA. Rofo-Fortschr. Röntg. 173, 1034-1040.
9. Cremonesi, M., Ferrari, M., Bodei, L., Tosi, G., and Paganelli, G. (2006) Dosimetry in peptide radionuclide receptor therapy: a review. J. Nucl. Med. 47, 1467-1475.
10. Liu, S., and Edwards, D. S. (2001) Bifunctional chelators for therapeutic lanthanide radiopharmaceuticals. Bioconjugate Chem. 12, 7-34.
11. 64Cu-labeled DOTA-linker-bombesin(7- 14) analogues containing different amino acid linker moieties. Bioconjugate Chem. 18, 1110-1117.
12. 111In-labeled RGD peptide. Nucl. Med. Biol. 34, 29-35.
13. Li, L., Yazaki, P. J., Anderson, A.-L., Crow, D., Colcher, D., Wu, A. M., Williams, L. E., Wong, J. Y. C., Raubitschek, A., and Shively, J. E. (2006) Improved biodistribution and radioimmunoimaging with poly(ethylene glycol)-DOTA-conjugated anti-CEA diabody. Bioconjugate Chem. 17, 68-76.
14. Kumaresan, P. R., Natarajan, A., Song, A., Wang, X., Liu, R., DeNardo, G., DeNardo, S., and Lam, K. S. (2007) Development of tissue plasminogen activator specific "on demand cleavable" (ODC) linkers for radioimmunotherapy by screening one-bead-one-compound combinatorial peptide libraries. Bioconjugate Chem. 18, 175-182.
15. Deshpande, S. V., DeNardo, S. J., Kukis, D. L., Moi, M. K., McCall, M. J., DeNardo, G. L., and Meares, C. F. (1990) Yttrium-90-labeled monoclonal antibody for therapy: labeling by a new macrocyclic bifunctional chelating agent. J. Nucl. Med. 31, 473-479.
16. Renn, O., and Meares, C. F. (1992) Large-scale synthesis of the bifunctional chelating agent 2-(p-nitrobenzyl)-1,4,7,10-tetraazacyclododecane-N, N′,N″,N‴-tetraacetic acid, and the determination of its enantiomeric purity by chiral chromatography. Bioconjugate Chem. 3, 563-569.
17. McMurry, T. J., Brechbiel, M., Kumar, K., and Gansow, O. A. (1992) Convenient synthesis of bifunctional tetraaza macrocycles. Bioconjugate Chem. 3, 108-117.
18. Cooper, M. S., Sabbah, E., and Mather, S. J. (2006) Conjugation of chelating agents to proteins and radiolabeling with trivalent metallic isotopes. Nat. Protoc. 1, 314-317.
19. Chappell, L. L., Ma, D., Milenic, D. E., Garmestani, K., Venditto, V., Beitzel, M. P., and Brechbiel, M. W. (2003) Synthesis and evaluation of novel bifunctional chelating agents based on 1,4,7,10-tetraazacyclododecane-N, N′,N",N"′-tetraacetic acid for radiolabeling proteins. Nucl. Med. Biol. 30, 581-595.
20. Chappell, L. L., Rogers, B. E., Khazaeli, M. B., Mayo, M. S., Buchsbaum, D. J., and Brechbiel, M. W. (1999) Improved synthesis of the bifunctional chelating agent 1,4,7,10-tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)- N′,N",N-tris(acetic acid) cyclododecane (PA-DOTA). Bioorg. Med. Chem. 7, 2313-2320.
21. Cheng, R. C., Fordyce, W. A., Goeckeler, W. F., Kruper, W. J., Baughman, S., Garlich, J. R., Kiefer, G. E., McMillan, K., Simon, J., Wilson, D. A., and Frank, R. K. (1989) Tetraazacyclododecane macrocyclic bifunctional chelants, complexes thereof and their antibody conjugates. WO Patent No. 8912631.
22. Sieving, P. F., Watson, A. D., and Rocklage, S. M. (1990) Preparation and characterization of paramagnetic polychelates and their protein conjugates. Bioconjugate Chem. 1, 65-71.
23. Lewis, M. R., Raubitschek, A., and Shively, J. E. (1994) A facile, water-soluble method for modification of proteins with DOTA. Use of elevated temperature and optimized pH to achieve high specific activity and high chelate stability in radiolabeled immunoconjugates. Bioconjugate Chem. 5, 565-576.
24. Lewis, M. R., Kao, J. Y., Anderson, A.-L., Shively, J. E., and Raubitschek, A. (2001) An improved method for conjugating monoclonal antibodies with N-hydroxysulfosuccinimidyl DOTA. Bioconjugate Chem. 12, 320-324.
25. Kovacs, Z., Mudigonda, D. S., and Sherry, A. D. (2005) Preparation of cyclic tertiary amine chelating agents for labeling biomolecules using preformed active esters. US Patent No. 6838557.
26. 90Y-labeled DOTA analogues conjugated to B72.3. Nucl. Med. Biol. 34, 493-502.
27. Lu, S. X., Takach, E. J., Solomon, M., Zhu, Q., Law, S.-J., and Hsieh, F. Y. (2005) Mass spectral analyses of labile DOTA-NHS and heterogeneity determination of DOTA or DM1 conjugated anti-PSMA antibody for prostate cancer therapy. J. Pharm. Sci. 94, 788-797.
28. Mier, W., Hoffend, J., Krämer, S., Schuhmacher, J., Hull, W. E., Eisenhut, M., and Haberkorn, U. (2005) Conjugation of DOTA using isolated phenolic active esters: the labeling and biodistribution of albumin as blood pool marker. Bioconjugate Chem. 16, 237-240.
29. Mukai, T., Namba, S., Arano, Y., Ono, M., Fujioka, Y., Uehara, T., Ogawa, K., Konishi, J., and Saji, H. (2002) Synthesis and evaluation of a monoreactive DOTA derivative for indium-111-based residualizing label to estimate protein pharmacokinetics. J. Pharm. Pharmacol. 54, 1073-1081.
30. Lewis, M. R., and Shively, J. E. (1998) Maleimidocysteineamido-DOTA derivatives: new reagents for radiometal chelate conjugation to antibody sulfhydryl groups undergo pH-dependent cleavage reactions. Bioconjugate Chem. 9, 72-86.
31. Li, L., Tsai, S.-W., Anderson, A.-L., Keire, D. A., Raubitschek, A. A., and Shively, J. E. (2002) Vinyl sulfone bifunctional derivatives of DOTA allow sulfhydryl- or amino-directed coupling to antibodies. Conjugates retain immunoreactivity and have similar biodistributions. Bioconjugate Chem. 13, 110-115.
32. 111In-labeled ST-peptide analog for specific-targeting of human colon cancers. Nucl. Med. Biol. 28, 903-909.
33. 3]-octreotide (SMT487): two conjugates for systemic delivery of radiotherapeutical nuclides to somatostatin receptor positive tumors in man. Bioorg. Med. Chem. Lett. 8, 1207-1210.
34. 3-octreotate using unprotected DOTA. Tetrahedron Lett. 44, 2393-2396.
35. 64Cu-labeled RGD peptide. Bioconjugate Chem. 15, 41-49.
36. 64Cu-labeled tetrameric RGD peptide. J. Nucl. Med. 46, 1707-1718.
37. Yoo, B., and Pagel, M. (2006) A facile synthesis of α-amino-DOTA as a versatile molecular imaging probe. Tetrahedron Lett. 47, 7327-7330.
38. Heppeler, A., Froidevaux, S., Mäcke, H. R., Jermann, E., Béhé, M., Powell, P., and Hennig, M. (1999) Radiometal-labelled macrocyclic chelator-derivatized somatostatin analogue with superb tumour-targeting properties and potential for receptor-mediated internal radiotherapy. Chem. - Eur. J. 5, 1974-1981.
39. Rosseto, R., and Hajdu, J. (2005) A rapid and efficient method for migration-free acylation of lysophospholipids: synthesis of phosphatidylcholines with sn-2-chain-terminal reporter groups. Tetrahedron Lett. 46, 2941-2944.
40. Wängler, B., Beck, C., Wagner-Utermann, U., Schirrmacher, E., Bauer, C., Rösch, F., Schirrmacher, R., and Eisenhut, M. (2006) Application of tris-allyl-DOTA in the preparation of DOTA-peptide conjugates. Tetrahedron Lett. 47, 5985-5988.
41. Jaakkola, L., Ylikoski, A., and Hovinen, J. (2006) Simple synthesis of a building block for solid-phase labeling of oligonucleotides with 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA). Bioconjugate Chem. 17, 1105-1107.
42. Anelli, P. L., Lattuada, L., Gabellini, M., and Recanati, P. (2001) DOTA tris(phenylmethyl) ester: a new useful synthon for the synthesis of DOTA monoamides containing acid-labile bonds. Bioconjugate Chem. 12, 1081-1084.
43. Hsieh, H. P., Wu, Y. T., Chen, S. T., and Wang, K. T. (1999) Direct solid-phase synthesis of octreotide conjugates: precursors for use as tumor-targeted radiopharmaceuticals. Bioorg. Med. Chem. 7, 1797-1803.
44. Eisenwiener, K. P., Powell, P., and Mäcke, H. R. (2000) A convenient synthesis of novel bifunctional prochelators for coupling to bioactive peptides for radiometal labelling. Bioorg. Med. Chem. Lett. 10, 2133-2135.
45. Mäcke, H. R., Eisenwiener, K., and Powell, P. (2002) Prochelators for the preparation of radiometal labeled molecules having improved biological properties. PCT Int. Appl. WO Patent No. 2002024235.
46. Amedio, J. C., Caravan, P. D., Jacques, V., Zhou, K. L., Levy, S., Kalageropoulos, S., and Greenfield, M. (2005). Preparation of optically pure and enriched isomers of DOTA-type chelating ligands, and contrast agents. PCT Int. App. WO Patent No. 2005001415.
47. Bhorade, R., Weissleder, R., Nakakoshi, T., Moore, A., and Tung, C. H. (2000) Macrocyclic chelators with paramagnetic cations are internalized into mammalian cells via a HIV-tat derived membrane translocation peptide. Bioconjugate Chem. II, 301-305.
48. Prantner, A. M., Sharma, V., Garbow, J. R., and Piwnica-Worms, D. (2003) Synthesis and characterization of a Gd-DOTA-D-permeation peptide for magnetic resonance relaxation enhancement of intracellular targets. Mol. Imaging 2 333-341.
49. Mier, W., Graham, K. A. N., Wang, Q., Krämer, S., Hoffend, J., Eisenhut, M., and Haberkorn, U. (2004) Synthesis of peptide conjugated chelator oligomers for endoradiotherapy and MRT imaging. Tetrahedron Lett. 45, 5453-5455.
50. 3-octreotate. Tetrahedron Lett. 43, 5021-5024.
51. De León-Rodríguez, L. M., Kovacs, Z., and Sherry, A. D. (2005) Chemistry for DOTA peptide labeling at phenylalanine residues: on the road to preparing peptide ligand tagged libraries. Lett. Org. Chem. 2, 160-164.
52. De León-Rodríguez, L. M., Kovacs, Z., Dieckmann, G. R., and Sherry, A. D. (2004) Solid-phase synthesis of DOTA-peptides. Chem. - Eur. J. 10, 1149-1155.
53. Gallazzi, F., Wang, Y., Jia, F., Shenoy, N., Landon, L. A., Hannink, M., Lever, S. Z., and Lewis, M. R. (2003) Synthesis of radiometal-labeled and fluorescent cell-permeating peptide-PNA conjugates for targeting the bcl-2 proto-oncogene. Bioconjugate Chem. 14, 1083-1095.
54. Sosabowski, J. K., and Mather, S. J. (2006) Conjugation of DOTA-like chelating agents to peptides and radiolabeling with trivalent metallic isotopes. Nat. Protoc. 1, 972-976.
55. Peterson, J. J., Pak, R. H., and Meares, C. F. (1999) Total solid-phase synthesis of 1,4,7,10-tetraazacyclododecane-N,N′,N″,N‴- tetraacetic acid-functionalized peptides for radioimmunotherapy. Bioconjugate Chem. 10, 316-320.
56. Yoo, B., and Pagel, M. D. (2007) Peptidyl molecular imaging contrast agents using a new solid-phase peptide synthesis approach. Bioconjugate Chem. 18, 903-911.
57. Benetollo, F., Bombieri, G., Calabi, L., Aime, S., and Botta, M. (2003) Structural variations across the lanthanide series of macrocyclic DOTA complexes: insights into the design of contrast agents for magnetic resonance imaging. Inorg. Chem. 42, 148-157.
58. Chang, C. A., Francesconi, L. C., Malley, M. F., Kumar, K., Gougoutas, J. Z., Tweedle, M. F., Lee, D. W., and Wilson, L. J. (1993) Synthesis, characterization, and crystal structures of M(DO3A) (M = Fe, Gd) and Na[M(DOTA)] (M = Fe, Y, Gd). Inorg. Chem. 32, 3501-3508.
59. Meyer, M., Dahaoui-Gindrey, V., Lecomte, C., and Guilard, R. (1998) Conformations and coordination schemes of carboxylate and carbamoyl derivatives of the tetraazamacrocycles cyclen and cyclam, and the relation to their protonation states. Coord. Chem. Rev. 178-180, 1313-1405.
60. Howard, J. A. K., Kenwright, A. M., Moloney, J. M., Parker, D., Woods, M., Port, M., Navet, M., and Rousseau, O. (1998) Structure and dynamics of all of the stereoisomers of europium complexes of tetra(carboxyethyl) derivatives of dota: ring inversion is decoupled from cooperative arm rotation in the RRRR and RRRS isomers. Chem. Commun. 13, 1381-1382.
61. Woods, M., Kovacs, Z., Zhang, S., and Sherry, A. D. (2003) Towards the rational design of magnetic resonance imaging contrast agents: isolation of the two coordination isomers of lanthanide DOTA-type complexes. Angew. Chem., Int. Ed. 42, 5889-5892.
62. 111In-labeled DOTA-biomolecule conjugates. Inorg. Chem. 42, 8831-8837.
63. Szilágyi, E., Tóth, E., Kovács, Z., Platzek, J., Radüchel, B., and Brücher, E. (2000) Equilibria and formation kinetics of some cyclen derivative complexes of lanthanides. Inorg. Chim. Acta 298, 226-234.
64. Chong, H.-S., Garmestani, K., Ma, D., Milenic, D. E., Overstreet, T., and Brechbiel, M. W. (2002) Synthesis and biological evaluation of novel macrocyclic ligands with pendent donor groups as potential yttrium chelators for radioimmunotherapy with improved complex formation kinetics. J. Med. Chem. 45, 3458-3464.
65. Breeman, W. A. P., de Blois, E., Bakker, W. H., and Krenning, E. P. (2006) Radionuclide Peptide Cancer Therapy, (Chinol, M., and Paganelli, G., Eds.) pp 119-125, Taylor & Francis, New York.
66. Wild, D., Schmitt, J. S., Ginj, M., Mäcke, H. R., Bernard, B. F., Krenning, E., De Jong, M., Wenger, S., and Reubi, J.-C. (2003) DOTA-NOC, a high-affinity ligand of somatostatin receptor subtypes 2, 3 and 5 for labelling with various radiometals. Eur. J. Nucl. Med. Mol. Imaging 30, 1338-1347.
67. Laznicek, M., Laznickova, A., Mäcke, H. R., Eisenwiener, K., Reubi, J.-C., and Wenger, S. (2002) Octreotide and octreotate derivatives radiolabeled with yttrium: pharmacokinetics in rats. Cancer Biother. Radiopharm. 17, 527-533.
68. 177Lu]-DOTA-ZHER2:342-3 affibody molecule, a candidate agent for locoregional treatment of urinary bladder carcinoma. Int. J. Mol. Med. 19, 285-291.
69. 166Ho-1,4,7,10-tetraazacyclododecane-N,N′, N″,N‴-tetraacetic acid: a bifunctional chelating agent for radiopharmaceuticals. Asian J. Chem. 19, 391-395.
70. 90Y-labeled E. coli heat-stable enterotoxin for specific targeting of uroguanylin receptors on human colon cancers. Nucl. Med. Biol. 33, 481-488.
71. 177Lu labeling of a DOTA-conjugated vitronectin receptor antagonist useful for tumor therapy. Bioconjugate Chem. 12, 559-568.
72. 177Lu at high specific activities. Eur. J. Nucl. Med. Mol. Imaging 30, 917-920.
73. Stimmel, J. B., and Kull, F. C., Jr. (1998) Samarium-153 and lutetium-177 chelation properties of selected macrocyclic and acyclic ligands. Nucl. Med. Biol. 25, 117-125.
74. Stimmel, J. B., Stockstill, M. E., and Kull, F. C., Jr. (1995) Yttrium-90 chelation properties of tetraazatetraacetic acid macrocycles, diethylenetriaminepentaacetic acid analogues, and a novel terpyridine acyclic chelator. Bioconjugate Chem. 6, 219-225.
75. 90Y- labeled DOTA-biomolecule conjugates using gentisic acid and ascorbic acid. Bioconjugate Chem. 12, 554-558.
76. Nitz, M., Sherawat, M., Franz, K. J., Peisach, E., Allen, K. N., and Imperiali, B. (2004) Structural origin of the high affinity of a chemically evolved lanthanide-binding peptide. Angew. Chem., Int. Ed. 43, 3682-3685.
77. Su, X.-C., Huber, T., Dixon, N. E., and Otting, G. (2006) Site-specific labeling of proteins with a rigid lanthanide-binding tag. ChemBioChem 7, 1599-1604.
78. Nunn, A. D., Linder, K. E., and Tweedle, M. F. (1997) Can receptors be imaged with MRI agents? Q. J. Nucl. Med. 41, 155-162.
79. Caravan, P., Ellison, J. J., McMurry, T. J., and Lauffer, R. B. (1999) Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications. Chem. Rev. 99, 2293-2352.
80. De León-Rodríguez, L. M., Ortiz, A., Weiner, A. L., Zhang, S., Kovacs, Z., Kodadek, T., and Sherry, A. D. (2002) Magnetic resonance imaging detects a specific peptide-protein binding event. J. Am. Chem. Soc. 124, 3514-3515.
81. Han, Y., and Kodadek, T. (2000) Peptides selected to bind the Gal80 repressor are potent transcriptional activation domains in yeast. J. Biol. Chem. 275, 14979-14984.
82. Meade, T. J., and Allen, M. J. (2004) Functional MRI agents for cancer imaging. PCT Int. App. WO Patent No. 2004037210.
83. Bull, S. R., Guler, M. O., Bras, R. E., Venkatasubramanian, P. N., Stupp, S. I., and Meade, T. J. (2005) Magnetic resonance imaging of self-assembled biomaterial scaffolds. Bioconjugate Chem. 16, 1343-1348.
84. Allen, M. J., MacRenaris, K. W., Venkatasubramanian, P. N., and Meade, T. J. (2004) Cellular delivery of MRI contrast agents. Chem. Biol. 11, 301-307.
85. Chinol, M., and Paganelli, M., Eds. (2006) Radionuclide Peptide Cancer Therapy, Taylor & Francis, New York.
86. Dasgupta, P. (2004) Somatostatin analogues: multiple roles in cellular proliferation, neoplasia, and angiogenesis. Pharmacol. Ther. 102, 61-85.
87. Janecka, A., Zubrzycka, M., and Janecki, T. (2001) Somatostatin analogs. J. Pept. Res. 58, 91-107.
88. Ginj, M., Zhang, H., Waser, B., Cescato, R., Wild, D., Wang, X., Erchegyi, J., Rivier, J., Mäcke, H. R., and Reubi, J. C. (2006) Radiolabeled somatostatin receptor antagonists are preferable to agonists for in vivo peptide receptor targeting of tumors. Proc. Natl. Acad. Sci. U.S.A. 103, 16436-16441.
89. Ginj, M., Hinni, K., Tschumi, S., Schulz, S., and Maecke, H. R. (2005) Trifunctional somatostatin-based derivatives designed for targeted radiotherapy using auger electron emitters. J. Nucl. Med. 46, 2097-2103.
90. Ginj, M., and Maecke, H. R. (2005) Synthesis of trifunctional somatostatin based derivatives for improved cellular and subcellular uptake. Tetrahedron Lett. 46, 2821-2824.
91. Tucker, G. C. (2006) Integrins: molecular targets in cancer therapy. Curr. Oncol. Rep. 8, 96-103.
92. V integrin inhibitors and cancer therapy. Curr. Opin. Invest. Drugs 4, 722-731.
93. Meyer, A., Auernheimer, J., Modlinger, A., and Kessler, H. (2006) Targeting RGD recognizing integrins: drug development, biomaterial research, tumor imaging and targeting. Curr. Pharm. Des. 12, 2723-2747.
94. 3 integrin by multimerisation of RGD peptides. Eur. J. Nucl. Med. Mol. Imaging 34, 267-273.
95. Kiessling, L. L., Gestwicki, J. E., and Strong, L. E. (2006) Synthetic multivalent ligands as probes of signal transduction. Angew. Chem., Int. Ed. 45, 2348-2368.
96. Mammen, M., Chio, 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, 2755-2794.
97. 3 integrin binding peptides in a nude mouse model. Cancer Res. 62, 6146-6151.
98. 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, 935-944.
99. 3-integrin expression. J. Nucl. Med. 45, 1776-1783.
100. 3-targeted imaging of lung cancer. Neoplasia 7, 271-279.
101. Nilsson, F. Y., and Tolmachev, V. (2007) Affibody molecules: new protein domains for molecular imaging and targeted tumor therapy. Curr. Opin. Drug Discovery Dev. 10, 167-175.
102. Tolmachev, V., Orlova, A., Nilsson, F. Y., Feldwisch, J., Wennborg, A., and Abrahmsen, L. (2007) Affibody molecules: potential for in vivo imaging of molecular targets for cancer therapy. Exp. Opin. Biol. Ther. 7, 555-568.
103. 177Lu-labeled HER2-specific affibody molecule. Cancer Res. 67, 2773-2782.
104. 99mTc to tumor-targeting affibody molecules. Bioconjugate Chem. 18, 549-558.
105. Orlova, A., Tolmachev, V., Pehrson, R., Lindborg, M., Tran, T., Sandström, M., Nilsson, F. Y., Wennborg, A., Abrahmsén, L., and Feldwisch, J. (2007) Synthetic affibody molecules: a novel class of affinity ligands for molecular imaging of HER2-expressing malignant tumors. Cancer Res. 67, 2178-2186.
106. Wängler, C., Buchmann, I., Eisenhut, M., Haberkorn, U., and Mier, W. (2007) Radiolabeled peptides and proteins in cancer therapy. Protein Pept. Lett. 14, 273-279.
107. Breeman, W. A., Kwekkeboom, D. J., de Blois, E., de Jong, M., Visser, T. J., and Krenning, E. P. (2007) Radiolabelled regulatory peptides for imaging and therapy. Anti-cancer Agents Med. Chem. 7, 345-357.
108. Reubi, J. C., Mäcke, H. R., and Krenning, E. P. (2005) Candidates for peptide receptor radiotherapy today and in the future. J. Nucl. Med. 46, Suppl. 1 67S-75S.
109. Milenic, D. E., Brady, E. D., and Brechbiel, M. W. (2004) Antibody-targeted radiation cancer therapy. Nat. Rev. Drug Discovery 3, 488-499.
110. 3 antagonists as radiopharmaceuticals for tumor radiotherapy. Top. Curr. Chem. 252 (Contrast Agents III), 193-216.
111. de Jong, M., Kwekkeboom, D., Valkema, R., and Krenning, E. P. (2003) Radiolabelled peptides for tumour therapy: current status and future directions. Plenary lecture at the EANM 2002. Eur. J. Nucl. Med. Mol. Imaging 30, 463-469.
112. Heppeler, A., Froidevaux, S., Eberle, A. N., and Maecke, H. R. (2000) Receptor targeting for tumor localisation and therapy with radiopeptides. Curr. Med. Chem. 7, 971-994.
113. Weiner, R. E., and Thakur, M. L. (2006) Developments of radiolabeled peptides. Radionuclide Peptide Cancer Therapy, (Chinol, M., and Paganelli, M., Eds.) pp 41-85, Taylor & Francis, New York.
114. Weiner, R. E., and Thakur, M. L. (2005) Radiolabeled peptides in oncology: role in diagnosis and treatment. BioDrugs 19, 145-163.
115. Smith, C. J., Volkert, W. A., and Hoffman, T. J. (2005) Radiolabeled peptide conjugates for targeting of the bombesin receptor superfamily subtypes. Nucl. Med. Biol. 32, 733-740.
116. Aloj, L., and Morelli, G. (2004) Design, synthesis and preclinical evaluation of radiolabeled peptides for diagnosis and therapy. Curr. Pharm. Des. 10, 3009-3031.
117. Smith, C. J., Volkert, W. A., and Hoffman, T. J. (2003) Gastrin releasing peptide (GRP) receptor targeted radiopharmaceuticals: a concise update. Nucl. Med. Biol. 30, 861-868.
118. Fichna, J., and Janecka, A. (2003) Synthesis of target-specific radiolabeled peptides for diagnostic imaging. Bioconjugate Chem. 14, 3-17.
119. Hoffman, T. J., Quinn, T. P., and Volkert, W. A. (2001) Radiometallated receptor-avid peptide conjugates for specific in vivo targeting of cancer cells. Nucl. Med. Biol. 28, 527-539.
120. Tircso, G., Kovacs, Z., and Sherry, A. D. (2006) Equilibrium and formation/dissociation kinetics of some Ln(III)PCTA complexes. Inorg. Chem. 45, 9269-9280.
121. Faulkner, S., Pope, S. J. A., and Burton-Pye, B. P. (2005) Lanthanide complexes for luminescence imaging applications. Appl. Spectrosc. Rev. 40, 1-31.
122. Butlin, N. G., and Meares, C. F. (2006) Antibodies with infinite affinity: origins and applications. Acc. Chem. Res. 39, 780-787.
123. Corneillie, T. M., Whetstone, P. A., and Meares, C. F. (2006) Irreversibly binding anti-metal chelate antibodies: Artificial receptors for pretargeting. J. Inorg. Biochem. 100, 882-890.
124. Corneillie, T. M., Lee, K. C., Whetstone, P. A., Wong, J. P., and Meares, C. F. (2004) Irreversible engineering of the multielement-binding antibody 2D12.5 and its complementary ligands. Bioconjugate Chem. 15, 1392-1402.
125. Hovinen, J. (2006) Synthesis of aminooxy-functionalized lanthanide(III) chelates for carbonyl-group conjugation. Chem. Biodivers. 3, 296-303.
126. 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, 6082-6090.
127. Mattila, K., Siltainsuu, J., Balaspiri, L., Ora, M., and Lönnberg, H. (2005) Derivatization of phosphopeptides with mercapto- and amino-functionalized conjugate groups by phosphate elimination and subsequent Michael addition. Org. Biomol. Chem. 3, 3039-3044.
128. Prasuhn, D. E., Jr., Yeh, R. M., Obenaus, A., Manchester, M., and Finn, M. G. (2007) Viral MRI contrast agents: coordination of Gd by native virions and attachment of Gd complexes by azide-alkyne cycloaddition. Chem. Commun. 1269-1271.
129. Mindt, T. L., Struthers, H., Brans, L., Anguelov, T., Schweinsberg, C., Maes, V., Tourwé, D., and Schibli, R. (2006) "Click to chelate": synthesis and installation of metal chelates into biomolecules in a single step. J. Am. Chem. Soc. 128, 15096-15097.