Formulation development and manufacturing of a gastrin/CCK-2 receptor targeting peptide as an intermediate drug product for a clinical imaging study

European Journal of Pharmaceutical Sciences

Volumn 31, Issue 2, 2007, Pages 102-111

  Sosabowski, Jane K ^a   Lee, Myrto ^b   Dekker, Bronwen A ^a   Simmons, Ben P ^b   Singh, Surjeet ^b   Beresford, Hayden ^b   Hagan, Susan A ^b   McKenzie, Andrew J ^c   Mather, Stephen J ^a   Watson, Susan A ^c  

^a ST BARTHOLOMEW S HOSPITAL   (United Kingdom)

^b Aphton BioPharma   (United Kingdom)

^c UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

CCK 2 receptor; Oxidation; Peptide; Radiopharmaceutical; Stability

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID HISTIDYLHISTIDYLGLUTAMYLALANYLTYROSYLGLYCYLTRYPTOPHYLMETHIONYLASPARTYL PHENYLALANINAMIDE; ANTIOXIDANT; BUFFER; CHOLECYSTOKININ B RECEPTOR; GASTRIN DERIVATIVE; GLYCEROL DERIVATIVE; INDIUM 111; LIGAND; METHIONINE; PHOSPHATE BUFFERED SALINE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DILUTION; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG FORMULATION; DRUG MANUFACTURE; DRUG STABILITY; DRUG TARGETING; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RECEPTOR AFFINITY;

ANIMALS; CELL LINE, TUMOR; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG PACKAGING; DRUG STABILITY; DRUG STORAGE; GASTRINS; HYDROGEN-ION CONCENTRATION; INDIUM RADIOISOTOPES; ISOTOPE LABELING; MALE; METHIONINE; MICE; MICE, NUDE; NEOPLASMS, EXPERIMENTAL; OLIGOPEPTIDES; OXIDATION-REDUCTION; RADIOPHARMACEUTICALS; RECEPTOR, CHOLECYSTOKININ B; REPRODUCIBILITY OF RESULTS; SOLUBILITY; SOLUTIONS; TECHNOLOGY, PHARMACEUTICAL; TEMPERATURE; TIME FACTORS;

EID: 34247504636     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2007.02.007     Document Type: Article

References (21)

1. Behe M., and Behr T.M. Cholecystokinin-B (CCK-B)/gastrin receptor targeting peptides for staging and therapy of medullary thyroid cancer and other CCK-B receptor expressing malignancies. Biopolymers 66 (2002) 399-418
2. Behe M., Becker W., Gotthardt M., Angerstein C., and Behr T.M. Improved kinetic stability of DTPA-dGlu as compared with conventional monofunctional DTPA in chelating indium and yttrium: preclinical and initial clinical evaluation of radiometal labelled minigastrin derivatives. Eur. J. Nucl. Med. Mol. Imaging 30 (2003) 1140-1146
3. Behr T.M., and Behe M.P. Cholecystokinin-B/gastrin receptor-targeting peptides for staging and therapy of medullary thyroid cancer and other cholecystokinin-B receptor-expressing malignancies. Semin. Nucl. Med. 32 (2002) 97-109
4. Breeman W.A., De Jong M., Visser T.J., Erion J.L., and Krenning E.P. Optimising conditions for radiolabelling of DOTA-peptides with 90Y, 111In and 177Lu at high specific activities. Eur. J. Nucl. Med. Mol. Imaging 30 (2003) 917-920
5. Dufield D.R., Wilson G.S., Glass R.S., and Schoneich C. Selective site-specific fenton oxidation of methionine in model peptides: evidence for a metal-bound oxidant. J. Pharm. Sci. 93 (2004) 1122-1130
6. Gotthardt M., Boermann O.C., Behr T.M., Behe M.P., and Oyen W.J. Development and clinical application of peptide-based radiopharmaceuticals. Curr. Pharm. Des. 10 (2004) 2951-2963
7. Guggenberg E.V., Mikolajczak R., Janota B., Riccabona G., and Decristoforo C. Radiopharmaceutical development of a freeze-dried kit formulation for the preparation of [99mTc-EDDA-HYNIC-D-Phe1, Tyr3]-octreotide, a somatostatin analog for tumor diagnosis. J. Pharm. Sci. 93 (2004) 2497-2506
8. Heppeler A., Froidevaux S., Eberle A.N., and Maecke H.R. Receptor targeting for tumor localisation and therapy with radiopeptides. Curr. Med. Chem. 7 (2000) 971-994
9. Kwekkeboom D.J., Bakker W.H., Kooij P.P., Erion J., Srinivasan A., de Jong M., Reubi J.C., and Krenning E.P. Cholecystokinin receptor imaging using an octapeptide DTPA-CCK analogue in patients with medullary thyroid carcinoma. Eur. J. Nucl. Med. Mol. Imaging 27 (2000) 1312-1317
10. Li S., Schoneich C., Wilson G.S., and Borchardt R.T. Chemical pathways of peptide degradation. V. Ascorbic acid promotes rather than inhibits the oxidation of methionine to methionine sulfoxide in small model peptides. Pharm. Res. 10 (1993) 1572-1579
11. Liu S., Edwards D.S., Harris A.R., Ziegler M.C., Poirier M.J., Ewels B.A., Diluzio W.R., and Hui P. Towards developing a non-SnCl2 formulation for RP444, a new radiopharmaceutical for thrombus imaging. J. Pharm. Sci. 90 (2001) 114-123
12. Mather, S.J., McKenzie, A.J., Sosabowski, J.K., Morris, T.M., Ellison, D., Watson, S.A., in press. Selection of radiolabelled gastrin analogues for peptide receptor targeted radionuclide therapy. J. Nucl. Med.
13. Nock B.A., Maina T., Behe M., Nikolopoulou A., Gotthardt M., Schmitt J.S., Behr T.M., and Macke H.R. CCK-2/gastrin receptor-targeted tumor imaging with (99m)Tc-labeled minigastrin analogs. J. Nucl. Med. 46 (2005) 1727-1736
14. Reubi J.C., and Waser B. Unexpected high incidence of cholecystokinin-B/gastrin receptors in human medullary thyroid carcinomas. Int. J. Cancer 67 (1996) 644-647
15. Reubi J.C., Schaer J.C., and Waser B. Cholecystokinin (CCK)-A and CCK-B gastrin receptors in human tumors. Cancer Res. 57 (1997) 1377-1386
16. Schmitz F., Otte J.M., Stechele H.U., Reimann B., Banasiewicz T., Folsch U.R., Schmidt W.E., and Herzig K.H. CCK-B/gastrin receptors in human colorectal cancer. Eur. J. Clin. Invest. 31 (2001) 812-820
17. Schoneich C., Zhao F., Wilson G.S., and Borchardt R.T. Iron-thiolate induced oxidation of methionine to methionine sulfoxide in small model peptides. Intramolecular catalysis by histidine. Biochim. Biophys. Acta 1158 (1993) 307-322
18. Sosabowski J.K., and Mather S.J. Conjugation of DOTA-like chelating agents to peptides and radiolabeling with trivalent metallic isotopes. Nat. Protoc. 1 (2006) 972-976
19. Stadtman E.R. Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Annu. Rev. Biochem. 62 (1993) 797-821
20. von Guggenberg E., Behe M., Behr T.M., Saurer M., Seppi T., and Decristoforo C. 99mTc-labeling and in vitro and in vivo evaluation of HYNIC- and (Nalpha-His)acetic acid-modified [D-Glu1]-minigastrin. Bioconjug. Chem. 15 (2004) 864-871
21. Wang W. Instability, stabilization, and formulation of liquid protein pharmaceuticals. Int. J. Pharm. 185 (1999) 129-188