Development of novel radiogallium-labeled bone imaging agents using oligo-aspartic acid peptides as carriers

PLoS ONE

Volumn 8, Issue 12, 2013, Pages

  Ogawa, Kazuma ^a   Ishizaki, Atsushi ^a   Takai, Kenichiro ^a   Kitamura, Yoji ^a   Kiwada, Tatsuto ^a   Shiba, Kazuhiro ^a   Odani, Akira ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALENDRONIC ACID; ASPARTIC ACID; BISPHOSPHONIC ACID DERIVATIVE; GALLIUM 68; HYDROXYAPATITE; OLIGO ASPARTIC ACID; TETRAXETAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING ASSAY; BONE DISEASE; BONE METASTASIS; CHELATION; CHEMICAL BINDING; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; DRUG DESIGN; DRUG DISTRIBUTION; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; POSITRON EMISSION TOMOGRAPHY; PROTEIN BINDING; RADIOACTIVITY; SYNTHESIS;

BONE AND BONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DURAPATITE; GALLIUM RADIOISOTOPES; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; MOLECULAR STRUCTURE; PEPTIDES; POSITRON-EMISSION TOMOGRAPHY; SOLID-PHASE SYNTHESIS TECHNIQUES;

EID: 84896700064     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0084335     Document Type: Article

References (49)

1. Yoneda T, Sasaki A, Mundy GR (1994) Osteolytic bone metastasis in breast cancer. Breast Cancer Res Treat 32: 73-84. (Pubitemid 24322250)
2. Subramanian G, Mfee JG, Blair RJ, Kallfelz FA, Thomas FD (1975) Technetium-99m-methylene diphosphonate-a superior agent for skeletal imaging: comparison with other technetium complexes. J Nucl Med 16: 744-755.
3. 99mTchydroxymethane diphosphonate: a new bone imaging agent with a low tin content. Radiology 136: 209-211.
4. Love C, Din AS, Tomas MB, Kalapparambath TP, Palestro CJ (2003) Radionuclide bone imaging: an illustrative review. Radiographics 23: 341-358. (Pubitemid 37431266)
5. Mari C, Catafau A, Carrio I (1999) Bone scintigraphy and metabolic disorders. Q J Nucl Med 43: 259-267. (Pubitemid 29500582)
6. Lavender JP, Khan RA, Hughes SP (1979) Blood flow and tracer uptake in normal and abnormal canine bone: comparisons with Sr-85 microspheres, Kr-81m, and Tc-99m MDP. J Nucl Med 20: 413-418. (Pubitemid 9175851)
7. m-MDP. Br J Radiol 62: 314-317.
8. Budd RS, Hodgson GS, Hare WS (1989) The relation of radionuclide uptake by bone to the rate of calcium mineralization. II: Patient studies using 99Tcm-MDP. Br J Radiol 62: 318-320. (Pubitemid 19088497)
9. Galasko CS (1980) Mechanism of uptake of bone imaging isotopes by skeletal metastases. Clin Nucl Med 5: 565-568.
10. Libson K, Deutsch E, Barnett BL (1980) Structural characterization of a technetium-99-diphosphonate complex. Implications for the chemistry of technetium-99m skeletal imaging agents. J Am Chem Soc 102: 2476-2478.
11. 4)-MDP radiopharmaceutical analogues. Int J Appl Radiat Isot 34: 1577-1584.
12. 99mTc-chelate-conjugated bisphosphonate with high affinity for bone as a bone scintigraphic agent. J Nucl Med 47: 2042-2047.
13. 99mTc-EC with aminomethylenediphosphonate in the search for a bone tracer with fast clearance from soft tissue. Bioconjug Chem 13: 16-22.
14. 99mTc(I) tricarbonyl complex potentially useful as bone-seeking agent: synthesis and biological evaluation. J Biol Inorg Chem 12: 667-679.
15. de Rosales RTM, Finucane C, Mather SJ, Blower PJ (2009) Bifunctional bisphosphonate complexes for the diagnosis and therapy of bone metastases. Chem Commun: 4847-4849.
16. Ogawa K, Mukai T, Arano Y, Hanaoka H, Hashimoto K, et al. (2004) Design of a radiopharmaceutical for the palliation of painful bone metastases: rhenium-186-labeled bisphosphonate derivative. J Labelled Cmp Radiopharm 47: 753-761. (Pubitemid 39425351)
17. Ogawa K, Mukai T, Arano Y, Otaka A, Ueda M, et al. (2006) Rhenium-186-monoaminemonoamidedithiol-conjugated bisphosphonate derivatives for bone pain palliation. Nucl Med Biol 33: 513-520. (Pubitemid 43729852)
18. Ogawa K, Mukai T, Arano Y, Ono M, Hanaoka H, et al. (2005) Development of a rhenium-186-labeled MAG3-conjugated bisphosphonate for the palliation of metastatic bone pain based on the concept of bifunctional radiopharmaceuticals. Bioconjug Chem 16: 751-757. (Pubitemid 41026160)
19. 186Re-complex-conjugated bisphosphonate for the palliation of metastatic bone pain in an animal model. J Nucl Med 48: 122-127.
20. 186Re-MAG3-HBP), an agent for treatment of painful bone metastases. Eur J Nucl Med Mol Imaging 36: 115-121.
21. 186Re chelate-conjugated bisphosphonate for the development of new radiopharmaceuticals for bones. Nucl Med Biol 34: 79-87.
22. 3-dipicolylamine-alendronate: a new bisphosphonate conjugate for the radiotherapy of bone metastases. Bioconjug Chem 21: 811-815.
23. Ogawa K, Mukai T (2009) Targeted imaging and therapy for bone metastases: control of pharmacokinetics of bone-targeted radiopharmaceuticals. J Drug Deliv Sci Tec 19: 171-176.
24. Vitha T, Kubicek V, Hermann P, Elst LV, Muller RN, et al. (2008) Lanthanide(III) complexes of bis(phosphonate) monoamide analogues of DOTA: bone-seeking agents for imaging and therapy. J Med Chem 51: 677-683. (Pubitemid 351252296)
25. 90Y]DOTA-conjugated bisphosphonate for treatment of painful bone metastases. Nucl Med Biol 36: 129-135.
26. Kubicek V, Rudovsky J, Kotek J, Hermann P, Vander Elst L, et al. (2005) A bisphosphonate monoamide analogue of DOTA: a potential agent for bone targeting. J Am Chem Soc 127: 16477-16485. (Pubitemid 41740397)
27. Blau M, Nagler W, Bender MA (1962) Fluorine-18: a new isotope for bone scanning. J Nucl Med 3: 332-334.
28. Even-Sapir E, Metser U, Mishani E, Lievshitz G, Lerman H, et al. (2006) The detection of bone metastases in patients with high-risk prostate cancer: 99c-MDP Planar bone scintigraphy, single- and multi-field-of-view SPECT, 18F-fluoride PET, and 18F-fluoride PET/CT. J Nucl Med 47: 287-297. (Pubitemid 46780894)
29. Zhernosekov KP, Filosofov DV, Baum RP, Aschoff P, Bihl H, et al. (2007) Processing of generator-produced 68 Ga for medical application. J Nucl Med 48: 1741-1748.
30. Notni J, Plutnar J, Wester HJ (2012) Bone-seeking TRAP conjugates: surprising observations and their implications on the development of gallium-68-labeled bisphosphonates. EJNMMI Res 2: 13.
31. 68Ga-BPAMD: PET-imaging of bone metastases with a generator based positron emitter. Nucl Med Biol 39: 993-999.
32. 68Ga-chelate-conjugated bisphosphonate as a bone-seeking agent for PET imaging. Nucl Med Biol 38: 1011-1018.
33. Ogawa K, Takai K, Kanbara H, Kiwada T, Kitamura Y, et al. (2011) Preparation and evaluation of a radiogallium complex-conjugated bisphosphonate as a bone scintigraphy agent. Nucl Med Biol 38: 631-636.
34. 68Ga-bisphosphonates: first human study. Eur J Nucl Med Mol Imaging 37: 834.
35. Butler WT (1989) The nature and significance of osteopontin. Connect Tissue Res 23: 123-136.
36. Oldberg A, Franzen A, Heinegard D (1988) The primary structure of a cell-binding bone sialoprotein. J Biol Chem 263: 19430-19432. (Pubitemid 19016419)
37. Oldberg A, Franzen A, Heinegard D (1986) Cloning and sequence analysis of rat bone sialoprotein (osteopontin) cDNA reveals an Arg-Gly-Asp cell-binding sequence. Proc Natl Acad Sci U S A 83: 8819-8823. (Pubitemid 17223492)
38. Kasugai S, Fujisawa R, Waki Y, Miyamoto K, Ohya K (2000) Selective drug delivery system to bone: small peptide (Asp)6 conjugation. J Bone Miner Res 15: 936-943. (Pubitemid 30233418)
39. Yokogawa K, Miya K, Sekido T, Higashi Y, Nomura M, et al. (2001) Selective delivery of estradiol to bone by aspartic acid oligopeptide and its effects on ovariectomized mice. Endocrinology 142: 1228-1233. (Pubitemid 32202833)
40. Wang D, Miller S, Sima M, Kopeckova P, Kopecek J (2003) Synthesis and evaluation of water-soluble polymeric bone-targeted drug delivery systems. Bioconjug Chem 14: 853-859. (Pubitemid 37157997)
41. Kaiser E, Colescott RL, Bossinger CD, Cook PI (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal Biochem 34: 595-598.
42. Ogawa K, Washiyama K (2012) Bone target radiotracers for palliative therapy of bone metastases. Curr Med Chem 19: 3290-3300.
43. Ogawa K, Saji H (2011) Advances in drug design of radiometal-based imaging agents for bone disorders. Int J Mol Imaging 2011: 537687.
44. Sekido T, Sakura N, Higashi Y, Miya K, Nitta Y, et al. (2001) Novel drug delivery system to bone using acidic oligopeptide: pharmacokinetic characteristics and pharmacological potential. J Drug Target 9: 111-121. (Pubitemid 32725449)
45. Meyer JL, Nancollas GH (1973) The influence of multidentate organic phosphonates on the crystal growth of hydroxyapatite. Calcif Tissue Res 13: 295-303.
46. Wang D, Miller SC, Shlyakhtenko LS, Portillo AM, Liu XM, et al. (2007) Osteotropic Peptide that differentiates functional domains of the skeleton. Bioconjug Chem 18: 1375-1378. (Pubitemid 47464042)
47. 18F-FDG PET/CT. Eur J Nucl Med Mol Imaging 36: 1807-1812.
48. Demirkan B, Baskan Z, Alacacioglu A, Gorken IB, Bekis R, et al. (2005) False negative bone scintigraphy in a patient with primary breast cancer: a possible transient phenomenon of bisphosphonate (alendronate) treatment. Tumori 91: 77-80. (Pubitemid 40469393)
49. Notni J, Pohle K, Wester HJ (2012) Comparative gallium-68 labeling of TRAP-, NOTA-, and DOTA-peptides: practical consequences for the future of gallium-68-PET. EJNMMI Res 2: 28.