Effectiveness of quenchers to reduce radiolysis of 111- or 177-labelled methionine-containing regulatory peptides. maintaining radiochemical purity as measured by HPLC

Current Topics in Medicinal Chemistry

Volumn 12, Issue 23, 2012, Pages 2677-2685

  de Blois, Erik ^a   Chan, Ho Sze ^a   Konijnenberg, Mark ^a   de Zanger, Rory ^a   Breeman, Wouter A P ^a  

^a ERASMUS MEDICAL CENTER   (Netherlands)

Author keywords

Gastrin releasing peptide; HPLC; Methionine; Minigastrin; Quenchers; Radiochemical purity; Radiolysis; Regulatory peptides

Indexed keywords

ALCOHOL; ASCORBIC ACID; BOMBESIN; FREE RADICAL; GENTISIC ACID; HISTIDINE; LUTETIUM 177; MELATONIN; METHIONINE; PENTETIC ACID; PHENYLALANINE; PROLINE; THREONINE; TRYPTOPHAN; TYROSINE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DOSIMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; PHARMACOPHORE; QUALITY CONTROL; RADIATION DETECTION; RADIATION DOSE; RADIOASSAY; RADIOLYSIS; RECEPTOR AFFINITY; ROOM TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

CHELATING AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EXCIPIENTS; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; INDIUM RADIOISOTOPES; ISOTOPE LABELING; LUTETIUM; METHIONINE; PENTETIC ACID; PEPTIDES; PROTEIN STABILITY; RADIOACTIVITY; RADIOMETRY; RADIOPHARMACEUTICALS;

EID: 84874837524     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026611212230005     Document Type: Article

References (48)

1. Laverman, P., et al., Targeting of a CCK(2) receptor splice variant with (111)In-labelled cholecystokinin-8 (CCK8) and (111)In- labelled minigastrin. Eur. J. Nucl. Med. Mol. Imaging, 2008. 35(2): p. 386-92.
2. Froberg, A.C., et al., Comparison of three radiolabelled peptide analogues for CCK-2 receptor scintigraphy in medullary thyroid carcinoma. Eur J Nucl Med Mol Imaging, 2009. 36(8): p. 1265-72.
3. Brom, M., et al., Preclinical evaluation of 68Ga-DOTA-minigastrin for the detection of cholecystokinin-2/gastrin receptor-positive tumors. Mol. Imaging, 2011. 10(2): p. 144-52.
4. Wild, D., et al., Alpha- versus beta-particle radiopeptide therapy in a human prostate cancer model (213Bi-DOTA-PESIN and 213Bi-AMBA versus 177Lu-DOTA-PESIN). Cancer Res., 2011. 71(3): p. 1009-18
5. Liu, I.H., et al., Multimodality imaging and preclinical evaluation of 177Lu-AMBA for human prostate tumours in a murine model. Anticancer Res, 2010. 30(10): p. 4039-48.
6. Waser, B., et al., Selective in vitro targeting of GRP and NMB receptors in human tumours with the new bombesin tracer 177Lu-AMBA. Eur. J. Nucl. Med. Mol. Imaging, 2007. 34(1): p. 95-100.
7. Breeman, W.A., et al., Radiolabelled regulatory peptides for imaging and therapy. Anticancer Agents Med Chem., 2007. 7(3): p. 345-57.
8. Eckelman, W.C., J.A. Frank, and M. Brechbiel, Theory and practice of imaging saturable binding sites. Invest Radiol., 2002. 37(3): p. 101-6.
9. Nunn, A.D.; K.E. Linder, and M.F. Tweedle., Can receptors be imaged with MRI agents? Q. J. Nucl. Med., 1997. 41(2): p. 155-62.
10. Langstrom B., P.H., Positron emitting tracers in studies of neurotransmission and receptor binding. A.D. Nunn, Editor. 1992, Dekker: New York. p. 221-266.
11. von Guggenberg, E., et al., Preclinical Evaluation of Radiolabeled DOTA-Derivatized Cyclic Minigastrin Analogs for Targeting Cholecystokinin Receptor Expressing Malignancies. Mol. Imaging Biol., 2011.
12. Nock, B.A., et al., CCK-2/gastrin receptor-targeted tumor imaging with (99m)Tc-labeled minigastrin analogs. J. Nucl. Med., 2005. 46(10): p. 1727-36.
13. Breeman, W.A., et al., Optimised labeling, preclinical and initial clinical aspects of CCK-2 receptor-targeting with 3 radiolabeled peptides. Nucl. Med. Biol., 2008. 35(8): p. 839-49.
14. Sosabowski, J.K.; and S.J. Mather., Conjugation of DOTA-like chelating agents to peptides and radiolabeling with trivalent metallic isotopes. Nat. Protoc., 2006. 1(2): p. 972-6.
15. Jay-Gerin, J.P.; and C. Ferradini., A new estimate of the (OH)-O-center dot radical yield at early times in the radiolysis of liquid water. Chemical Physics Letters, 2000. 317(3-5): p. 388-391.
16. Swiatla-Wojcik, D.; and G.V. Buxton, On the possible role of the reaction H-center dot+H2O -> H-2+(center dot)OHin the radiolysis of water at high temperatures. Radiation Physics and Chemistry, 2005. 74(3-4): p. 210-219.
17. Garrison, W.M., Reaction-Mechanisms in the Radiolysis of Peptides, Polypeptides, and Proteins. Chemical Reviews, 1987. 87(2): p. 381-398.
18. Jonah, C.D., A Short History of the Radiation-Chemistry of Water. Radiation Research, 1995. 144(2): p. 141-147.
19. Slegers, C.; and B. Tilquin, Theoretical approach to the destruction or sterilization of drugs in aqueous solution. Radiation Physics and Chemistry, 2005. 72(2-3): p. 363-365.
20. Lantry, L.E. et al., 177Lu-AMBA: Synthesis and characterization of a selective 177Lu-labeled GRP-R agonist for systemic radiotherapy of prostate cancer. J. Nucl. Med., 2006. 47(7): p. 1144-52.
21. Chen, J., et al., Synthesis, stabilization and formulation of [177Lu]Lu-AMBA, a systemic radiotherapeutic agent for Gastrin Releasing Peptide receptor positive tumors. Appl Radiat Isot, 2008.66(4): p. 497-505.
22. Reubi, J.C.; J.C Schaer.; and B Waser., Cholecystokinin(CCK)-A and CCK-B/gastrin receptors in human tumors. Cancer Res., 1997. 57(7): p. 1377-86.
23. Liu, S.; and D.S. Edwards. Stabilization of (90)y-labeled DOTA-biomolecule conjugates using gentisic acid and ascorbic acid. Bioconjug Chem., 2001. 12(4): p. 554-8.
24. Ihde, A.J., The History of Free Radicals and Moses Gomberg's Contributions. Pure and Applied Chemistry, 1967. 30: p. 1-16.
25. Gomberg, M., An instance of trivalent carbon: Triphenyl-Methyl. J. Am. Chem. Soc., 1900. 22(11): p. 757-771.
26. Gomberg M., Radicals in chemistry: past and present. 1928: Columbia university press. 23.
27. Zegota, H. et al., O-Tyrosine hydroxylation by OH center dot radicals. 2,3-DOPA and 2,5-DOPA formation in gamma-irradiated aqueous solution. Radiation Physics and Chemistry, 2005. 72(1): p. 25-33.
28. Fukumura, T., et al., Stability of C-11-labeled PET radiopharmaceuticals. Applied Radiation and Isotopes, 2004. 61(6):p. 1279-1287.
29. Keithahn, C. and A. Lerchl, 5-hydroxytryptophan is a more potent in vitro hydroxyl radical scavenger than melatonin or vitamin C. Journal of Pineal Research, 2005. 38(1): p. 62-66.
30. Liu, S.; C.E. Ellars.; and D.S. Edwards, Ascorbic acid: useful as a buffer agent and radiolytic stabilizer for metalloradiopharmaceuticals. Bioconjug Chem., 2003. 14(5): p. 1052-6.
31. Reiter, R.J., Melatonin: clinical relevance. Best Practice & Research Clinical Endocrinology & Metabolism, 2003. 17(2): p. 273-285.
32. Reiter, R.J., et al., Melatonin as an antioxidant: biochemical mechanisms and pathophysiological implications in humans. Acta Biochimica Polonica, 2003. 50(4): p. 1129-1146.
33. Schuessler, H., Effect of Ethanol on Radiolysis of Ribonuclease. International Journal of Radiation Biology, 1975. 27(2): p. 171-180.
34. Breeman, W.A., et al., Radiolabelling DOTA-peptides with 68Ga. Eur. J. Nucl. Med. Mol. Imaging, 2005. 32(4): p. 478-85.
35. Chavatte, K., et al., Parameters ruling optimization of radiolabelling of polyamino polycarboxylated functionalized peptide derivatives: a case study report. Nucl. Med. Biol., 2001. 28(6): p. 745-9.
36. Breeman, W.A., et al., Optimising conditions for radiolabelling of DOTA-peptides with 90Y, 111In and 177Lu at high specific activities. Eur. J. Nucl. Med. Mol. Imaging, 2003. 30(6): p. 917-20.
37. Breeman, W.A., et al., The addition of DTPA to [177Lu-DOTA0,Tyr3]octreotate prior to administration reduces rat skeleton uptake of radioactivity. Eur. J. Nucl. Med. Mol. Imaging, 2003. 30(2): p. 312-5.
38. Bakker, W.H., et al., [111In-DTPA-D-Phe1]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptor-positive tumors: synthesis, radiolabeling and in vitro validation. Life Sciences, 1991. 49(22): p. 1583-91.
39. Center for Drug Evaluation and Research (CDER), Reviewer Guidance Validation of Chromatographic Methods. 1994. p. 33.
40. Ocak, M., et al., Comparison of biological stability and metabolism of CCK2 receptor targeting peptides, a collaborative project under COST BM0607. Eur. J. Nucl. Med. Mol. Imaging, 2011. 38(8): p. 1426-35.
41. Liu, S., et al., Isomerism and solution dynamics of (90)Y-labeled DTPA--biomolecule conjugates. Bioconjug Chem, 2001. 12(1): p. 84-91.
42. Asti, M., et al., Influence of cations on the complexation yield of DOTATATE with yttrium and lutetium: a perspective study for enhancing the (90)Y and (177)Lu labeling conditions. Nucl. Med. Biol., 2011. 39(4): p. 509-17
43. Koumarianou, E., et al., Comparison of receptor affinity of natSc-DOTA-TATE versus natGa-DOTA-TATE. Nucl. Med. Rev. Cent. East Eur., 2011. 14(2): p. 85-9.
44. Schroeder, R.P., et al., A standardised study to compare prostate cancer targeting efficacy of five radiolabelled bombesin analogues. Eur. J. Nucl. Med. Mol. Imaging, 2010. 37(7): p. 1386-96.
45. Zhang, H., et al., DOTA-PESIN, a DOTA-conjugated bombesin derivative designed for the imaging and targeted radionuclide treatment of bombesin receptor-positive tumours. Eur. J. Nucl. Med. Mol. Imaging, 2007. 34(8): p. 1198-208.
46. Uehara, S. and H. Nikjoo, Monte Carlo simulation of water radiolysis for low-energy charged particles. Journal of Radiation Research, 2006. 47(1): p. 69-81.
47. Stabin, M.G. and M.W. Konijnenberg, Re-evaluation of absorbed fractions for photons and electrons in spheres of various sizes. J. Nucl. Med., 2000. 41(1): p. 149-60.
48. Brechbiel, M.W., Bifunctional chelates for metal nuclides. Q. J. Nucl. Med. Mol. Imaging, 2008. 52(2): p. 166-73.