Development of peptide and protein based radiopharmaceuticals

Current Pharmaceutical Design

Volumn 20, Issue 14, 2014, Pages 2250-2267

  Wynendaele, Evelien ^a   Bracke, Nathalie ^a   Stalmans, Sofie ^a   De Spiegeleer, Bart ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Drug development process; Peptide; Protein; Quality control; Radiolabelling procedures

Indexed keywords

ARCITUMOMAB TC 99M; BESILESOMAB; CAPROMAB PENDETIDE IN 111; CARBON 14; CHELATING AGENT; IBRITUMOMAB TIUXETAN; NOFETUMOMAB MERPENTAN TC 99M; PENTETREOTIDE; PEPTIDE; PROTEIN; RADIOISOTOPE; RADIOPHARMACEUTICAL AGENT; RADIOSENSITIZING AGENT; SULESOMAB TC 99M; TOSITUMOMAB I 131; TRACER; PHOTOPROTEIN; RADIOACTIVE IODINE; RECEPTOR;

ARTICLE; BINDING ASSAY; CELL INTERACTION; CHELATION; COMPLEX FORMATION; DOSIMETRY; FLUORINATION; HUMAN; IN VITRO STUDY; IN VIVO STUDY; INFECTION; INFLAMMATION; IODINATION; ISOTOPE LABELING; KIDNEY PARENCHYMA; LIVER; NONHUMAN; ONCOLOGY; PRIORITY JOURNAL; QUALITY CONTROL; RADIOACTIVITY; RADIOCHEMISTRY; RADIOIODINATION; RADIOLYSIS; RADIOSENSITIVITY; RECEPTOR BINDING; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; ANIMAL; CHEMISTRY; DIAGNOSTIC USE; METABOLISM; PHYSIOLOGY; TISSUE DISTRIBUTION; TRENDS;

ANIMALS; HUMANS; IODINE RADIOISOTOPES; LUMINESCENT PROTEINS; PEPTIDES; RADIOPHARMACEUTICALS; RECEPTORS, PEPTIDE; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 84903735721     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/13816128113196660663     Document Type: Article

References (198)

1. Bhutia SK, Maiti TK. Targeting tumors with peptides from natural sources. Trends Biotechnol 2008; 26: 210-7.
2. Jong M, Kwekkeboom D, Valkema R, Krenning EP. Radiolabelled peptides for tumour therapy: current status and future directions. Plenary lecture at the EANM 2002. Eur J Nucl Med Mol Imaging 2003; 30: 463-9.
3. Okarvi SM. Peptide-based radiopharmaceuticals and cytotoxic conjugates: Potential tools against cancer. Cancer Treat Rev 2008; 34: 13-26.
4. Adessi C, Soto C. Converting a peptide into a drug: strategies to improve stability and bioavailability. Curr Med Chem 2002; 9: 963-78.
5. Okarvi SM. Peptide-Based Radiopharmaceuticals: Future Tools for Diagnostic Imaging of Cancers and Other Diseases. Med Res Rev 2004; 24: 357-97.
6. Leader B, Baca QJ, Golan DE. Protein therapeutics: a summary and pharmacological classification. Nat Rev Drug Discov 2008; 7: 21-39.
7. Wells JA, McClendon CL. Reaching for high-hanging fruit in drug discovery at protein-protein interfaces. Nature 2007; 450: 1001-9.
8. Olafsen T, Wu AM. Antibody Vectors for Imaging. Semin Nucl Med 2010; 40: 167-81.
9. Broisat A, Hernot S, Toczek J, et al. Nanobodies Targeting Mouse/Human VCAM1 for the Nuclear Imaging of Atherosclerotic Lesions. Circ Res 2012; 110: 927-37.
10. Vosjan MJWD, Vercammen J, Kolkman JA, Stigter-van Walsum M, Revets H, van Dongen GAMS. Nanobodies Targeting the Hepatocyte Growth Factor: Potential New Drugs for Molecular Cancer Therapy. Mol Cancer Ther 2012; 11: 1017-25.
11. Vaneycken I, D'Huyvetter M, Hernot S, et al. Immuno-imaging using nanobodies. Curr Opin Biotechnol 2011; 22: 877-81.
12. Gainkam LOT, Caveliers V, Devoogdt N, et al. Localization, mechanism and reduction of renal retention of technetium-99m labelled epidermal growth factor receptor-specific nanobody in mice. Contrast Media Mol Imaging 2011; 6: 85-92.
13. Tijink BM, Laeremans T, Budde M, et al. Improved tumor targeting of anti-epidermal growth factor receptor Nanobodies through albumin binding: taking advantage of modular Nanobody technology. Mol Cancer Ther 2008; 7: 2288-97.
14. D'Huyvetter M, Aerts A, Xavier C, et al. Development of 177Lunanobodies for radioimmunotherapy of HER2-positive breast cancer: evaluation of different bifunctional chelators. Contrast Media Mol Imaging 2012; 7: 254-64.
15. Koopmans KP, Glaudemans AW. Rationale for the use of radiolabelled peptides in diagnosis and therapy. Eur J Nucl Med Mol Imaging 2012; 39 Suppl 1: S4-10.
16. Knight LC. Non-oncologic applications of radiolabeled peptides in nuclear medicine. Q J Nucl Med 2003; 47: 279-91.
17. Vernon A, Ballard C, Modo M. Neuroimaging for Lewy body disease: Is the in vivo molecular imaging of-synuclein neuropathology required and feasible? Brain Res Rev 2010; 65: 28-55.
18. Cherry SR. The 2006 Henry N. Wagner Lecture: Of mice and men (and positrons)-advances in PET imaging technology. J Nucl Med 2006; 47: 1735-45.
19. Chen K, Conti PS. Target-specific delivery of peptide-based probes for PET imaging. Adv Drug Deliv Rev 2010; 62: 1005-22.
20. Massoud TF, Gambhir SS. Molecular imaging in living subjects: seeing fundamental biological processes in a new light. Genes Dev 2003; 17: 545-80.
21. Trott CM, Ouyang J, El Fakhri G. Comparison of simultaneous and sequential SPECT imaging for discrimination tasks in assessment of cardiac defects. Phys Med Biol 2010; 55: 6897-910.
22. El Fakhri G, Moore SC, Maksud P, Aurengo A, Kijewski MF. Absolute Activity Quantitation in Simultaneous 123I/99mTc Brain SPECT. J Nucl Med 2001; 42: 300-8.
23. Fani M, Maecke HR, Okarvi SM. Radiolabeled Peptides: Valuable Tools for the Detection and Treatment of Cancer. Theranostics 2012, 2: 481-501.
24. Eberle AN, Mild G. Receptor-mediated tumor targeting with radiopeptides. Part 1. General principles and methods. J Recept Signal Transduct Res 2009; 29: 1-37.
25. Verbruggen A, Coenen HH, Deverre J, et al. Guideline to regulations for radiopharmaceuticals in early phase clinical trials in the EU. Eur J Nucl Med Mol Imaging 2008; 35: 2144-51.
26. Ramachandran GN, Sasisekharan V. Conformaton of polypeptides and proteins. Adv Protein Chem 1968, 23: 283-438.
27. Liapakis G, Fitzpatrick D, Hoeger C, Rivier J, Vandlen R, Reisine T. Identification of Ligand Binding Determinants in the Somatostatin Receptor Subtypes 1 and 2. J Biol Chem 1996; 271: 20331-9.
28. Gomes I, Grushko JS, Golebiewska U, et al. Novel endogenous peptide agonists of cannabinoid receptors. FASEB J 2009; 23: 3020-9.
29. Kopchick JJ, Parkinson C, Stevens EC, Trainer PJ. Growth hormone receptor antagonists: discovery, development and use in patients with acromegaly. Endocr Rev 2002; 23: 623-46.
30. Loot AE, van Buiten A, Roks AJ, Henning RH. The suitability of iodinated Angiotensin-(1-7) peptides as pharmacological tools. J Pharmacol Toxicol Methods 2005; 51: 51-5.
31. Tait JF, Smith C, Levashova Z, Patel B, Blankenberg FG, Vanderheyden JL. Improved detection of cell death in vivo with annexin V radiolabeled by site-specific methods. J Nucl Med 2006; 47: 1546-53.
32. Harris RJ, Kabakoff B, Macchi FD, et al. Identification of multiple sources of charge heterogeneity in a recombinant antibody. J Chromatogr B Biomed Sci Appl 2001; 752: 233-45.
33. Fani M, Maecke HR. Radiopharmaceutical development of radiolabelled peptides. Eur J Nucl Med Mol Imaging 2012; 39 Suppl 1: S11-30.
34. Jakubowski N, Messerschmidt J, Anorbe MG, Waentig L, Hayen H, Roos PH. Labelling of proteins by use of iodination and detection by ICP-MS. J Anal At Spectrom 2008; 23: 1487-96.
35. Voet D, Voet JG, Pratt CW. Fundamentals of Biochemistry. 2nd ed. Hoboken: Wiley 2006.
36. Schumacher TN, Mayr LM, Minor DL Jr, Milhollen MA, Burgess MW, Kim PS. Identification of D-peptide ligands through mirrorimage phage display. Science 1996; 271: 1854-7.
37. Modlin IM, Pavel M, Kidd M, Gustafsson BI. Review article: somatostatin analogues in the treatment of gastroenteropancreatic neuroendocrine (carcinoid) tumours. Aliment Pharmacol Ther 2010; 31: 169-88.
38. Lawrence EO, inventor; Research Corporation N.Y., assignee. Method and apparatus for the acceleration of ions. United States patent US 1948384 1934 Feb.
39. Rathore N, Gellman SH, de Pablo JJ. Thermodynamic stability of beta-peptide helices and the role of cyclic residues. Biophys J 2006; 9: 3425-35.
40. Seebach D, Matthews JL. Beta-peptides: a surprise at every turn. Chem Comm 1997; 21: 2015-22.
41. Schiller PW, Nguyen TMD, Berezowska I, Dupuis S. Synthesis and in vitro opioid activity profiles of DALDA analogues. Eur J Med Chem 2000, 35: 895-901.
42. Grünewald J, Hunt GS, Dong L, et al. Mechanistic studies of the immunochemical termination of self-tolerance with unnatural amino acids. Proc Natl Acad Sci USA 2009; 106: 4337-42.
43. Shirakawa M, Yamamto T, Nakai K, et al. Synthesis and evaluation of a novel liposome containing BPA-peptide conjugate for BNCT. Appl Radiat Isot 2009; 67(7-8 Suppl): S88-90.
44. Bischoff R, Cordier Y, Rasmussen UB, et al. Synthesis and characterization of photoactivatable peptide agonists of the human thrombin receptor. FEBS Lett 1994; 349: 301-6.
45. Cremonesi M, Ferrari M, Bodei L, Tosi G, Paganelli G. Dosimetry in Peptide Radionuclide Receptor Therapy: A Review. J Nucl Med 2006; 47: 1467-75.
46. Kassis AI, Adelstein SJ. Radiobiologic Principles in Radionuclide Therapy. J Nucl Med 2005; 46: 4S-12S.
47. European Directorate for the Quality of Medicines and HealthCare, European Pharmacopoeia 7.5. Strassbourg: Council of Europe 2011.
48. Shwartz SC, inventor; Ohana I, inventor; U.C.G. Technologies, assignee. SPECT gamma camera. United States patent US 6943355 B2 2005 Sep.
49. Dadachova E. Cancer Therapy with Alpha-Emitters Labeled Peptides. Semin Nucl Med 2010; 40: 204-8.
50. LBNL Isotopes Project-LUNDS Universitet. WWW Table of Radioactive Isotopes [homepage on the Internet]. Firestone RB, Ekström LP [cited 2012 Aug 8]. Available from: http://ie.lbl.gov/toi/index.asp
51. Mausner LF, Srivastava SC. Selection of radionuclides for radioimmunotherapy. Med Phys 1993; 20: 503-9.
52. Bushberg JT, Seibert JA, Leidholdt EM, Boone JM. The essential physics of medical imaging. 2nd ed. Philadelphia: Lippincott Williams & Wilkins 2001.
53. National Research Council (US) and Institute of Medicine (US) Committee on State of the Science of Nuclear Medicine. Advancing Nuclear Medicine Through Innovation. Washington (DC): National Academies Press (US) 2007.
54. Lebowitz E, Richards P. Radionuclide Generator Systems. Semin Nucl Med 1974; 4: 257-68.
55. Miller BT. Acylation of Peptide Hydroxyl Group with the Bolton-Hunter Reagent. Biochem Biophys Res Commun 1996; 218: 377-82.
56. Lane DJ, Richardson DR. William Hunter and radioiodination: revolutions in the labelling of proteins with radionuclides of iodine. Biochem J 2011; doi:10.1042/BJ20111293.
57. Khan IU, Beck-Sickinger AG. Targeted Tumor Diagnosis and Therapy with Peptide Hormones as Radiopharmaceuticals. Anticancer Agents Med Chem 2008; 8: 186-99.
58. Wilbur DS, Hadley SW, Hylarides MD, et al. Development of a Stable Radioiodinating Reagent to Label Monoclonal Antibodies for Radiotherapy of Cancer. J Nucl Med 1989; 30: 216-26.
59. Brechbiel MW. Bifunctional Chelates for Metal Nuclides. Q J Nucl Med Mol Imaging 2008; 52: 166-73.
60. Liu S. Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides. Adv Drug Deliv Rev 2008; 60: 1347-70.
61. Bartholomä MD. Recent developments in the design of bifunctional chelators for metal-based radiopharmaceuticals used in Positron Emission Tomography. Inorganica Chim Acta 2012; 389: 36-51.
62. Bartholomä MD, Louie AS, Valliant JF, Zubieta J. Technetium and Gallium Derived Radiopharmaceuticals: Comparing and Contrasting the Chemistry of Two Important Radiometals for the Molecular Imaging Era. Chem Rev 2010; 110: 2903-20.
63. Clarke ET, Martell AE. Stabilities of the Fe(III), Ga(III) and In(III) chelates of N, N′, N″-triazacyclononanetriacetic acid. Inorg Chim Acta 1991; 181: 273-80.
64. Byegard J, Skarnemark G, Skalberg M. The stability of some metal EDTA, DTPA and DOTA complexes: Application as tracers in groundwater studies. J Radioanal Nucl Chem 1999; 241: 281-90.
65. Harris WR, Chen Y, Wein K. Equilibrium Constants for the Binding of Indium(III) to Human Serum Transferrin. Inorg Chem 1994; 33: 4991-8.
66. Craft JM, De Silva RA, Lears KA, et al. In vitro and in vivo evaluation of a 64Cu-labeled NOTA-Bn-SCN-Aoc-bombesin analogue in gastrin-releasing peptide receptor expressing prostate cancer. Nucl Med Biol 2012; 39: 609-16.
67. Cooper MS, Ma MT, Sunassee K, et al. Comparison of 64Cu-Complexing Bifunctional Chelators for Radioimmunoconjugation: Labeling Efficiency, Specific Activity, and in vitro/in vivo Stability. Bioconjugate Chem 2012; 23: 1029-39.
68. Dijkgraaf I, Liu S, Kruijtzer J, et al. Effects of linker variation on the in vitro and in vivo characteristics of an 111In-labeled RGD peptide. Nucl Med Biol 2007; 34: 29-35.
69. Autio A, Henttinen T, Sipilä HJ, Jalkanen S, Roivainen A. Mini-PEG spacering of VAP-1-targeting 68Ga-DOTAVAP-P1 peptide improves PET imaging of inflammation. EJNMMI Res 2011; 1: 1-7.
70. Harris JM, Chess RB. Effect of PEGylation on pharmaceuticals. Nat Rev Drug Discov 2003; 2: 214-21.
71. Vergote V, Bodé S, Peremans K, et al. Analysis of iodinated peptides by LC-DAD/ESI ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 2007; 850: 213-20.
72. Bailey GS. The Chloramine T Method for Radiolabeling Protein. In: Walker JM. Ed. The Protein Protocols Handbook, 2nd Edition. Totowa: Humana Press 2002.
73. Vergote V, Baert B, Vandermeulen E, et al. LC-UV/MS characterization and DOE optimization of the iodinated peptide obestatin. J Pharm Biomed Anal 2008; 46: 127-36.
74. Salacinski PR, McLean C, Sykes JE, Clement-Jones VV, Lowry P. Iodination of Proteins, Glycoproteins, and Peptides Using a Solid-Phase Oxidizing Agent, 1,3,4,6-Tetrachloro-3α,6α-diphenyl Glycoluril (Iodogen). Anal Biochem 1981; 117: 136-146.
75. Bailey GS. The Iodogen Method for Radiolabeling Protein. In: Walker JM. Ed. The Protein Protocols Handbook, 2nd Edition. Totowa: Humana Press 2002.
76. Hunter WM, Greenwood FC. Preparation of Iodine-131 Labelled Human Growth Hormone of High Specific Activity. Nature 1962; 194: 495-6.
77. Yamada A, Traboulsi A, Dittert L, Hussain AA. Chloramine-T in Radiolabeling Techniques. III. Radioiodination of Biomolecules Containing Thioether Groups. Anal Biochem 2000; 277: 232-5.
78. Marchalonis JJ. An Enzymic Method for the Trace Iodination of Immunoglobulins and other Proteins. Biochem J 1969; 113: 299-305.
79. Huber RE, Edwards LA, Carne TJ. Studies on the Mechanism of the Iodination of Tyrosine by Lactoperoxidase. J Biol Chem 1989; 264: 1381-6.
80. Markwell MA. A New Solid-State Reagent to Iodinate Proteins. Anal Biochem 1982; 125: 427-32.
81. Bailey GS. The Bolton and Hunter Method for Radiolabeling Protein. In: Walker JM. Ed. The Protein Protocols Handbook, 2nd Edition. Totowa: Humana Press 2002.
82. Meares CF, McCall MJ, Reardan DT, Goodwin DA, Diamanti CI, McTigue M. Conjugation of antibodies with bifunctional chelating agents: isothiocyanate and bromoacetamide reagents, methods of analysis, and subsequent addition of metal ions. Anal Biochem 1984; 142: 68-78.
83. Tolmachev V, Xu H, Wållberg H, et al. Evaluation of a maleimido derivative of CHX-A" DTPA for site-specific labeling of Affibody molecules. Bioconjug Chem 2008; 19: 1579-87.
84. Shen BQ, Xu K, Liu L, et al. Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates. Nat Biotechnol 2012; 30: 184-9.
85. Palanki MS, Bhat A, Lappe RW, et al. Development of novel linkers to conjugate pharmacophores to a carrier antibody. Bioorg Med Chem Lett 2012; 22: 4249-53.
86. Liu S, Liu H, Jiang H, Xu Y, Zhang H, Cheng Z. One-step radiosynthesis of 18F-AlF-NOTA-RGD2 for tumor angiogenesis PET imaging. Eur J Nucl Med Mol Imaging 2011; 38: 1732-41.
87. McBride WJ, D'Souza CA, Sharkey RM, Goldenberg DM. The radiolabeling of proteins by the [18F]AlF method. Appl Radiat Isot 2012; 70: 200-4.
88. Jacobson O, Zhu L, Ma Y, et al. A rapid and simple one-step F-18 labeling of peptides. Bioconjug Chem 2011; 22: 422-428.
89. Campbell-Verduyn LS, Mirfeizi L, Schoonen AK, Dierckx RA, Elsinga PH, Feringa BL. Strain-promoted copper-free "click" chemistry for 18F radiolabeling of bombesin. Angew Chem Int Ed Engl 2011; 50: 11117-20.
90. Chersi A, Trinca ML, Camera M. 14C-labeling of synthetic peptides. J Immunol Methods 1988; 110: 271-3.
91. Schumacher TN, Tsomides TJ. In vitro Radiolabeling of Peptides and Proteins. Curr Protoc Protein Sci 2001; Chapter 3: unit 3.3.
92. Vergote V, Burvenich C, Van de Wiele C, De Spiegeleer B. Quality specifications for peptide drugs: a regulatory-pharmaceutical approach. J Pept Sci 2009; 15: 697-710.
93. Eisenhut M, Haberkorn U. Molecular Position of Radiolabels and Its Impact on Functional Integrity of Proteins. J Nucl Med 2006; 47: 1400-2.
94. Van Dorpe S, Verbeken M, Wynendaele E, De Spiegeleer B. Purity Profiling of Peptide Drugs. J Bioanal Biomed 2011; S6: doi 10.4172/1948-593X.S6-003.
95. Verbeken M, Wynendaele E, Lefebvre RA, Goossens E, De Spiegeleer B. The influence of peptide impurity profiles on functional tissue-organ bath response: The 11-mer peptide INSL6[151-161]case. Anal Biochem 2012; 421: 547-55.
96. ICH: harmonisation for better health [homepage on the Internet]. Topics under Harmonisation [cited 2012 Aug 8]. Available from: http://www.ich.org/
97. European Medicines Agency: Science, Medicines, Health [homepage on the Internet]. Concept paper on the revision of the guideline on radiopharmaceuticals based on monoclonal antibodies [cited 2012 Aug 8]. Available from: http://www.ema.europa.eu/
98. European Medicines Agency: Science, Medicines, Health [homepage on the Internet]. Guideline on radiopharmaceuticals [cited 2012 Aug 8]. Available from: http://www.ema.europa.eu/
99. Farstad BS, Penuelas I. Radiopharmaceutical Manufacturing. In: Gad SC. Ed. Pharmaceutical Manufacturing Handbook: Production and Processes, Volume 10. Hoboken: Wiley 2007.
100. Meyer G, Coenen HH, Waters SL, et al. Quality Assurance and Quality Control of Short-Lived Radiopharmaceuticals for PET. In: Stöcklin G and Pike VW. Eds. Radiopharmaceuticals for Positron Emission Tomography: Methodological Aspects. Dordrecht: Kluwer Academic Publishers 2010.
101. The United States Pharmacopeia, USP 33/NF 28. The Standard of Quality. USP Monographs: Indium In 111 Pentetreotide Injection. Rockville: The United States Pharmacopeial Convention 2010.
102. Hnatowich DJ. A method for the preparation and quality control of 68Ga radiopharmaceuticals. J Nucl Med 1975; 16: 764-8.
103. Vallabhajosula S, Killeen RP, Osborne JR. Altered Biodistribution of Radiopharmaceuticals: Role of Radiochemical/Pharmaceutical Purity, Physiological, and Pharmacologic Factors. Semin Nucl Med 2010; 40: 220-41.
104. The United States Pharmacopeia, USP 33/NF 28. The Standard of Quality. Rockville: The United States Pharmacopeial Convention 2010.
105. Amin KC, Patel S, Doke A, Saha GB. An Alternative Method for Determining the Radiochemical Purity of 99mTc-Tetrofosmin. J Nucl Med Technol 2011; 39: 51-4.
106. The United States Pharmacopeia, USP 33/NF 28. The Standard of Quality. USP Monographs: Indium In 111 Ibritumomab Tiuxetan Injection. Rockville: The United States Pharmacopeial Convention 2010.
107. European Directorate for the Quality of Medicines and HealthCare, European Pharmacopoeia 7.5. 01/2008:1918 Fluorodopa (18F) (prepared by electrophilic substitution) injection. Strassbourg: Council of Europe 2011.
108. European Directorate for the Quality of Medicines and HealthCare, European Pharmacopoeia 7.5. 01/2009:0296 Technetium (99mTc) macrosalb injection. Strassbourg: Council of Europe 2011.
109. The United States Pharmacopeia, USP 33/NF 28. The Standard of Quality. USP Monographs: Technetium Tc 99m Albumin Aggregated Injection. Rockville: The United States Pharmacopeial Convention 2010.
110. Petersson J, Sánchez-Crespo A, Larsson SA, Mure M. Physiological imaging of the lung: single-photon-emission computed tomography (SPECT). J Appl Physiol 2007; 102: 468-76.
111. The United States Pharmacopeia, USP 33/NF 28. The Standard of Quality. USP Monographs: Fluorodopa F 18 Injection. Rockville: The United States Pharmacopeial Convention 2010.
112. Lapi SE, Welch MJ. A historical perspective on the specific activity of radiopharmaceuticals: what have we learned in the 35 years of the ISRC? Nucl Med Biol 2012; 39: 601-8.
113. AltaBioscience [homepage on the Internet]. Introduction to Synthetic Peptides [cited 2012 Oct 19]. Available from: http://www.altabioscience.com/
114. European Directorate for the Quality of Medicines and HealthCare, European Pharmacopoeia 7.5. 01/2010:20256 Amino acid analysis. Strassbourg: Council of Europe 2011.
115. The United States Pharmacopeia, USP 33/NF 28. The Standard of Quality. General Chapters: 1052 Biotechnology-derived articles: amino acid analysis. Rockville: The United States Pharmacopeial Convention 2010.
116. Food and Drug Administration. Guidance for Industry for the Submission of Chemistry, Manufacturing, and Controls Information for Synthetic Peptide Substances 2004.
117. Swietlow A, Lax R. Quality control in peptide manufacturing: specifications for GMP peptides. Pept Chem 2004; 7-8: 22-4.
118. Brom M, Joosten L, Oyen WJG, Gotthardt M, Boerman OC. Improved labelling of DTPA-and DOTA-conjugated peptides and antibodies with 111In in HEPES and MES buffer.
119. Kwekkeboom D, Krenning EP, de Jong M. Peptide Receptor Imaging and Therapy. J Nucl Med 2000; 41: 1704-13.
120. Breeman WAP, Kwekkeboom DJ, Kooij PPM, et al. Effect of Dose and Specific Activiy on Tissue Distribution of Indium-111-Pentetreotide in Rats. J Nucl Med 1995; 36: 623-7.
121. Salako QA, O'Donnell RT, DeNardo SJ. Effects of Radiolysis on Yttrium-90-Labeled Lym-1 Antibody Preparations. J Nucl Med 1998; 39: 667-70.
122. Reilly RM. Monoclonal Antibody and Peptide-Targeted Radiotherapy of Cancer. Hoboken: Wiley 2010.
123. European Medicines Agency: Science, Medicines, Health [homepage on the Internet]. European public assessment reports [cited 2012 Aug 6]. Available from: http://www.ema.europa.eu/
124. Liu S, Edwards DS. Stabilization of 90Y-Labeled DOTABiomolecule Conjugates Using Gentisic Acid and Ascorbic Acid. Bioconjugate Chem 2001; 12: 554-8.
125. Chakrabarti MC, Le N, Paik CH, De Graff WG, Carrasquillo JA. Prevention of Radiolysis of Monoclonal Antibody during Labeling. J Nucl Med 1996; 37: 1384-8.
126. Pujatti PB, Massicano AV, Mengatti J, de Araújo EB. Preparation of [In-111]-labeled-DTPA-bombesin conjugates at high specific activity and stability: Evaluation of labelling parameters and potential stabilizers. Appl Radiat Isot 2012; 70: 856-63.
127. Wahl RL, Wissing J, del Rosario R, Zasadny KR. Inhibition of Autoradiolysis of Radiolabeled Monoclonal Antibodies by Cryopreservation. J Nucl Med 1990; 31: 84-9.
128. Ma D, Lu F, Overstreet T, Milenic DE, Brechbiel MW. Novel chelating agents for potential clinical applications of copper. Nucl Med Biol 2002; 29: 91-105.
129. Bass LA, Wang M, Welch MJ, Anderson CJ. In vivo Transchelation of Copper-64 from TETA-Octreotide to Superoxide Dismutase in Rat Liver. Bioconjugate Chem 2000; 11: 527-32.
130. De Spiegeleer B, Van Dorpe S, Vergote V, et al. In vitro metabolic stability of iodinated obestatin peptides. Peptides 2012; 33: 272-8.
131. Vergote V, Van Dorpe S, Peremans K, Burvenich C, De Spiegeleer B. In vitro metabolic stability of obestatin: Kinetics and identification of cleavage products. Peptides 2008; 29: 1740-8.
132. Karstad R, Isaksen G, Wynendaele E, et al. Targeting the S1 and S3 subsite of trypsin with unnatural cationic amino acids generates antimicrobial peptides with potential for oral administration. J Med Chem 2012; 55: 6294-305.
133. Mitulovic G, Mechtler K. HPLC techniques for proteomics analysis-a short overview of latest developments. Brief Funct Genomic Proteomic 2006; 5: 249-60.
134. Yoshida T. Peptide separation by Hydrophilic-Interaction Chromatography: a review. J Biochem Biophys Methods 2004; 60: 265-80.
135. Chakraborty AB, Berger SJ. Optimization of Reversed-Phase Peptide Liquid Chromatography Ultraviolet Mass Spectrometry Analyses Using an Automated Blending Methodology. J Biomol Tech 2005; 16: 325-33.
136. Stulik K, Pacakova V, Suchankova J, Claessens HA. Stationary phases for peptide analysis by high performance liquid chromatography: a review. Anal Chim Acta; 352: 1-19.
137. Mant CT, Cepeniene D, Hodges RS. Reversed-phase HPLC of peptides: Assessing column and solvent selectivity on standard, polar-embedded and polar endcapped columns. J Sep Sci 2010; 33: 3005-21.
138. Van Dorpe S, Vergote V, Pezeshki A, Burvenich C, Peremans K, De Spiegeleer B. Hydrophilic interaction LC of peptides: Columns comparison and clustering. J Sep Sci 2010; 33: 728-39.
139. Alpert AJ. Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. J Chromatogr 1990; 499: 177-96.
140. Reubi JC. Peptide Receptors as Molecular Targets for Cancer Diagnosis and Therapy. Endocr Rev 2003; 24: 389-427.
141. Schottelius M, Wester H. Molecular imaging targeting peptide receptors. Methods 2009; 48: 161-77.
142. Vergote V, Van Dorpe S, Verbeken M, et al. Development of peptide receptor binding assays: Methods to avoid false negatives. Regul Pept 2009; 158: 97-102.
143. Bylund DB, Toews ML. Radioligand binding methods: practical guide and tips. Am J Physiol 1993; 265: L421-9.
144. Davenport AP, Russell FD. Radioligand binding assays: theory and practice. In: Mather SJ. Ed. Current Directions in Radiopharmaceutical Research and Development. Heidelberg: Springer 1996.
145. Hulme EC, Trevethick MA. Ligand binding assays at equilibrium: validation and interpretation. Br J Pharmacol 2010; 161: 1219-37.
146. Molenaar P, O'Reilly G, Sharkey A, et al. Characterization and localization of endothelin receptor subtypes in the human atrioventricular conducting system and myocardium. Circ Res 1993; 72: 526-38.
147. Fu Y, Létourneau M, Chatenet D, Dupuis J, Fournier A. Characterization of iodinated adrenomedullin derivatives suitable for lung nuclear medicine. Nucl Med Biol 2011; 38: 867-74.
148. Bruns C, Lewis I, Briner U, Meno-Tetang G, Weckbecker G. SOM230: a novel somatostatin peptidomimetic with broad somatotropin release inhibiting factor (SRIF) receptor binding and a unique antisecretory profile. Eur J Endocrinol 2002; 146: 707-16.
149. Bender F, Roach P, Tsortos A, et al. Development of a combined surface plasmon resonance/surface acoustic wace device for the characterization of biomolecules. Meas Sci Technol 2009; 20: 1-6.
150. Ginj M, Zhang H, Waser B, et al. Radiolabeled somatostatin receptor antagonists are preferable to agonists for in vivo peptide receptor targeting of tumors. Proc Natl Acad Sci U. S. A 2006; 103: 16436-41.
151. Bodei L, Paganelli G, Mariani G. Receptor Radionuclide Therapy of Tumors: A Road from Basic Research to Clinical Applications. J Nucl Med 2006; 47: 375-7.
152. Cescato R, Schulz S, Waser B, et al. Internalization of sst2, sst3, and sst5 Receptors: Effects of Somatostatin Agonists and Antagonists. J Nucl Med 2006; 47: 502-11.
153. Williams SP. Tissue distribution studies of protein therapeutics using molecular probes: molecular imaging. AAPS J 2012; 14: 389-99.
154. Perera RM, Zoncu R, Johns TG, et al. Internalization, intracellular trafficking, and biodistribution of monoclonal antibody 806: a novel anti-epidermal growth factor receptor antibody. Neoplasia 2007; 9: 1099-110.
155. Costantini DL, Hu M, Reilly RM. Peptide Motifs for Insertion of Radiolabeled Biomolecules into Cells and Routing to the Nucleus for Cancer Imaging or Radiotherapeutic Applications. Cancer Biother Radiopharm 2008; 23: 3-24.
156. Kersemans V, Cornelissen B. Targeting the Tumour: Cell Penetrating Peptides for Molecular Imaging and Radiotherapy. Pharmaceuticals 2010; 3: 600-20.
157. Torchilin V. Intracellular delivery of protein and peptide therapeutics. Drug Discov Today:Technol 2009; 5: e95-103.
158. Re RN. On the Biological Actions of Intracellular Angiotensin. Hypertension 2000; 35: 1189-90.
159. Fiaschi-Taesch NM, Stewart AF. Minireview: Parathyroid Hormone-Related Protein as an Intracrine Factor-Trafficking Mechanisms and Functional Consequences. Endocrinology 2003; 144: 407-11.
160. Aarts MM, Rix A, Guo J, Bringhurst R, Henderson JE. The Nucleolar Targeting Signal (NTS) of Parathyroid Hormone Related Protein Mediates Endocytosis and Nucleolar Translocation. J Bone Miner Res 1999; 14: 1493-503.
161. Liolios CC, Fragogeorgi EA, Zikos C, et al. Structural modifications of 99mTc-labelled bombesin-like peptides for optimizing pharmacokinetics in prostate tumor targeting. Int J Pharm 2012; 430: 1-17.
162. Boerman OC, Oyen WJ, Corstens FH. Between the Scylla and Charybdis of peptide radionuclide therapy: hitting the tumor and saving the kidney. Eur J Nucl Med 2001; 28: 1447-9.
163. Rolleman EJ, Valkema R, de Jong M, Kooij PP, Krenning EP. Safe and effective inhibition of renal uptake of radiolabelled octreotide by a combination of lysine and arginine. Eur J Nucl Med 2003; 30: 9-15.
164. Akizawa H, Uehara T, Arano Y. Renal uptake and metabolism of radiopharmaceuticals derived from peptides and proteins. Adv Drug Deliv Rev 2008; 60: 1319-28.
165. Vegt E, Wetzels JF, Russel FG, et al. Renal Uptake of Radiolabeled Octreotide in Human Subjects Is Efficiently Inhibited by Succinylated Gelatin. J Nucl Med 2006; 47: 432-6.
166. Siegel JA, Thomas SR, Stubbs JB, et al. MIRD Pamphlet No. 16: Techniques for Quantitative Radiopharmaceutical Biodistribution Data Acquisition and Analysis for Use in Human Radiation Dose Estimates. J Nucl Med 1999; 40: 37S-61S.
167. Van de Wiele C, Dumont F, Dierckx RA, Peers SH, Thornback JR, Slegers G, Thierens H. Biodistribution and Dosimetry of 99mTc-RP527, a Gastrin-Releasing Peptide (GRP) Agonist for the Visualization of GRP Receptor-Expressing Malignancies. J Nucl Med 2001; 42: 1722-7.
168. Baechler S, Hobbs RF, Boubaker A, Buchegger F, He B, Frey EC, Sgouros G. Three-dimensional radiobiological dosimetry of kidneys for treatment planning in peptide receptor radionuclide therapy. Med Phys 2012; 39: 6118-28.
169. Forrer F, Krenning EP, Kooij PP, et al. Bone marrow dosimetry in peptide receptor radionuclide therapy with [177Lu-DOTA0, Tyr3] octreotate. Eur J Nucl Med Mol Imaging 2009; 36: 1138-46.
170. Wehrmann C, Senftleben S, Zachert C, Müller D, Baum RP. Results of Individual Patient Dosimetry in Peptide Receptor Radionuclide Therapy with 177Lu DOTA-TATE and 177Lu DOTA-NOC. Cancer Biother Radiopharm 2007; 22: 406-16.
171. Watson EE, Stabin MG, Siegel JA. MIRD formulation. Med Phys 1993; 20: 511-4.
172. McCollough CH, Schueler BA. Calculation of effective dose. Med Phys 2000; 27: 828-37.
173. Stabin MG. Radiopharmaceuticals for Nuclear Cardiology: Radiation Dosimetry, Uncertainties, and Risk. J Nucl Med 2008; 49: 1555-63.
174. Kim JH, Lee JS, Kang KW, et al. Whole-Body Distribution and Radiation Dosimetry of 68Ga-NOTA-RGD, a Positron Emission Tomography Agent for Angiogenesis Imaging. Cancer Biother Radiopharm 2012; 27: 65-71.
175. Martinez MN. Factors Influencing the Use and Interpretation of Animal Models in the Development of Parenteral Drug Delivery Systems. AAPS J 2011; 13: 632-48.
176. Marchetti S, Schellens JH. The impact of FDA and EMEA guidelines on drug development in relation to Phase 0 trials. Br J Cancer 2007; 97: 577-81.
177. Kummar S, kinders R, Rubinstein L, et al. Compressing drug development timelines in oncology using phase '0' trials. Nat Rev Cancer 2007; 7: 131-9.
178. Ambrosini V, Fani M, Fanti S, Forrer F, Maecke HR. Radiopeptide imaging and therapy in Europe. J Nucl Med 2011; 52 Suppl 2: 42S-55S.
179. Medicare Service Advisory Committee's. OctreoScan scintigraphy for gastro-entero-pancreatic neuroendocrine tumours [cited 2012 Aug 14]. Available from: http://www.health.gov.au/haf/msac
180. European Medicines Agency: Science, Medicines, Health [homepage on the Internet]. European public assessment reports: Zevalin [cited 2012 Aug 14]. Available from: http://www.ema.europa.eu/
181. FDA, U.S. Food and Drug Administration. Protecting and Promoting Your Health [Homepage on the Internet]. Tositumomab and Iodine I 131 Tositumomab Product Approval Information-Licensing Action 6/27/03 [cited 2012 Aug 14]. Available from: http://www.fda.gov/default.htm
182. Medicare Service Advisory Committee's. CEA-Scan for imaging recurrence and/or metastases in patients with histologically demonstrated carcinoma of the colon or rectum [cited 2012 Aug 14]. Available from: http://www.otago.ac.nz/
183. World Health Organization (WHO) [homepage on the Internet]. Cancer, Fact sheet No. 297 [updated 2012 February; cited 2012 August 29]. Available from: http://www.who.int/
184. FDA, U.S. Food and Drug Administration. Protecting and Promoting Your Health [Homepage on the Internet]. FDA Approved Drug Products [cited 2012 Aug 6]. Available from: http://www.fda.gov/default.htm
185. Laverman P, Sosabowski JK, Boerman OC, Oyen WJ. Radiolabelled peptides for oncological diagnosis. Eur J Nucl Med Mol Imaging 2012; 39 Suppl 1: S78-92.
186. Zoller F, Eisenhut M, Haberkorn U, Mier W. Endoradiotherapy in cancer treatment-Basic concepts and future trends. Eur J Pharmacol 2009; 625: 55-62.
187. Reubi JC, Waser B. Concomitant expression of several peptide receptors in neuroendocrine tumours: molecular basis for in vivo multireceptor tumour targeting. Eur J Nucl Med Mol Imaging 2003; 30: 781-93.
188. Zhang X, Xiong Z, Wu Y, et al. Quantitative PET imaging of tumor integrin αvβ3 expression with 18F-FRGD2. J Nucl Med 2006; 47: 113-21.
189. Yu Z, Carlucci G, Ananias HJ, et al. Evaluation of a technetium-99m labeled bombesin homodimer for GRPR imaging in prostate cancer. Amino Acids 2012 [Epub ahead of print].
190. Falciani C, Fabbrini M, Pini A, et al. Synthesis and biological activity of stable branched neurotensin peptides for tumor targeting. Mol Cancer Ther 2007; 6: 2441-8.
191. Sampath L, Kwon S, Ke S, et al. Dual-labeled trastuzumab-based imaging agent for the detection of human epidermal growth factor receptor 2 overexpression in breast cancer. J Nucl Med 2007; 48: 1501-10.
192. ter Horst M, Verwijnen SM, Brouwer E, et al. Locoregional delivery of adenoviral vectors. J Nucl Med 2006; 47: 1483-9.
193. Roivainen A, Jalkanen S, Nanni C. Gallium-labelled peptides for imaging of inflammation. Eur J Nucl Med Mol Imaging 2012; 39 Suppl 1: S68-77.
194. European Medicines Agency: Science, Medicines, Health [homepage on the Internet]. European public assessment reports: LeukoScan [cited 2012 Aug 14]. Available from: http://www.ema.europa.eu/
195. European Medicines Agency: Science, Medicines, Health [homepage on the Internet]. European public assessment reports: Scintimun [cited 2012 Aug 14]. Available from: http://www.ema.europa.eu/
196. Hofland LJ, Capello A, Krenning EP, de Jong M, van Hagen MP. Induction of apoptosis with hybrids of Arg-Gly-Asp molecules and peptides and antimitotic effects of hybrids of cytostatic drugs and peptides. J Nucl Med 2005; 46 Suppl 1: 191S-8S.
197. Zhang Y, Wang TH. Quantum Dot Enabled Molecular Sensing and Diagnostics. Theranostics 2012; 2: 631-54.
198. Akerman ME, Chan WCW, Laakkonen P, Bhatia SN, Ruoslahti E. Nanocrystal targeting in vivo. Proc Natl Acad Sci USA 2002; 99: 12617-21.