Development of superior bone scintigraphic agent from a series of 99mTc-labeled zoledronic acid derivatives

Applied Radiation and Isotopes

Volumn 70, Issue 5, 2012, Pages 848-855

  Lin, Jianguo ^a   Qiu, Ling ^a   Cheng, Wen ^a   Luo, Shineng ^a   Xue, Li ^a   Zhang, Shu ^a  

^a BEIJING HOSPITAL   (China)

Author keywords

99mTc IPeDP; Biodistribution; Bone imaging; Diphosphonic acid; Pharmacokinetics

Indexed keywords

99MTC-IPEDP; BIODISTRIBUTIONS; BIOLOGICAL PERFORMANCE; BONE IMAGING; DIPHOSPHONIC ACID; FUNCTION OF TIME; IN-VITRO; IN-VIVO; POST INJECTION; PRECLINICAL STUDIES; RADIO-HPLC; RADIOCHEMICAL PURITY; SCINTIGRAPHIC IMAGES; SKELETAL SYSTEM; SOFT TISSUE; TECHNETIUM-99M; ZOLEDRONIC ACID;

BUTANE; PHARMACOKINETICS; TECHNETIUM; TISSUE; VISUALIZATION;

BONE;

TECHNETIUM 99M; ZOLEDRONIC ACID;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BONE SCINTISCANNING; CONTROLLED STUDY; EXPERIMENTAL RABBIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMAGE ANALYSIS; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; MOUSE; NONHUMAN; PRIORITY JOURNAL; QUALITY CONTROL; RADIATION DETECTOR; SKELETON; SOFT TISSUE; STRUCTURE ANALYSIS;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIPHOSPHONATES; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; ORGANOTECHNETIUM COMPOUNDS; RABBITS; RADIOMETRY; RADIONUCLIDE IMAGING; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84862786927     PISSN: 09698043     EISSN: 18729800     Source Type: Journal    
DOI: 10.1016/j.apradiso.2011.12.019     Document Type: Article

References (31)

1. Asikoglu M., Durak F.G. The rabbit biodistribution of a therapeutic dose of zoledronic acid labeled with Tc-99m. Appl. Radiat. Isot. 2009, 67:1616-1621.
2. Bartholom M.D., Louie A.S., Valliant J.F., Zubieta J. Technetium and gallium derived radiopharmaceuticals: comparing and contrasting the chemistry of two important radiometals for the molecular imaging era. Chem. Rev. 2010, 110:2903-2920.
3. Berenson J.R. Recommendations for zoledronic acid treatment of patients with bone metastases. Oncologist 2005, 10:52-62.
4. Dilworth J.R., Parrott S.J. The biomedical chemistry of technetium. Chem. Soc. Rev. 1998, 27:43-55.
5. 99mTc-hydroxymethane diphosphonate: a new bone imaging agent with a low tin content. Radiol. 1980, 136:209-211.
6. 99mTc-labeled gemcitabine bisphosphonate drug conjugate as a probe to assess the potential for targeted chemotherapy of metastatic bone cancer. Nucl. Med. Biol. 2006, 33:715-722.
7. 188Re-labeled bisphosphonates aspotential bifunctional agents for therapy in patients with bone metastases. Appl. Radiat. Isot. 2005, 62:541-549.
8. 99mTc]TRODAT-1. Nucl. Med. Biol. 2000, 27:69-75.
9. Green J.R. Bisphosphonates: preclinical review. Oncologist 2004, 9:3-13.
10. Jurisson S.S., Lydon J.D. Potential technetium small molecule radiopharmaceuticals. Chem. Rev. 1999, 99:2205-2218.
11. Koudelkov M., Jedinakova-Krizova V. Thin-layer chromatographic characterization of rhenium complexation with 1-hydroxyethylidenediphosphonic acid. J. Chromatogr. A 2003, 990:317-323.
12. 99mTc-labelled bisphosphonates as superior bone imaging agents. Nucl. Med. Biol. 2011, 38:619-629.
13. Love C., Din A.S., Tomas M.B., Kalapparambath T.P., Palestro C.J. Radionuclide bone imaging: an illustrative review. Radiographics 2003, 23:341-358.
14. Majkowska A., Neves M., Antunes I., Bilewicz A. Complexes of low energy beta emitters 47Sc and 177Lu with zoledronic acid for bone pain therapy. Appl. Radiat. Isot. 2009, 67:11-13.
15. Major P., Lortholary A., Hon J., Abdi E., Mills G., Menssen H.D., Yunus F., Bell R., Body J., Quebe-Fehling E., Seaman J. Zoledronic acid is superior to pamidronate in the treatment of hypercalcemia of malignancy. J. Clin. Oncol. 2001, 19:558-567.
16. Marma M.S., Xia Z.D., Stewart C., Coxon F., Dunford J.E., Baron R., Kashemirov B.A., Ebetino F.H., Triffitt J.T., Russell R.G., McKenna C.E. Synthesis and biological evaluation of α-halogenated bisphosphonate and phosphonocarboxylate analogues of risedronate. J. Med. Chem. 2007, 50:5967-5975.
17. Mari C., Catafau A., Carrio I. Bone scintigraphy and metabolic disorders. Q. J. Nucl. Med. 1999, 43:259-267.
18. Méndez-Rojas M.A., Kharisov B.I., Tsivadze A.Y. Recent advances on technetium complexes: coordination chemistry and medical applications. J. Coord. Chem. 2006, 59:1-63.
19. 99mTc(I)-estradiol-pyridin-2-yl hydrazine derivative for imaging of breast and endometrial cancers. J. Nucl. Med. 2008, 49:978-986.
20. 99mTc-chelate-conjugated bisphosphonate with high affinity for bone as a bone scintigraphic agent. J. Nucl. Med. 2006, 47:2042-2047.
21. 99mTc(I) tricarbonyl complex potentially useful as bone-seeking agent: synthesis and biological evaluation. J. Biol. Inorg. Chem. 2007, 12:667-679.
22. Pauwels E.K., Stokkel M.P. Radiopharmaceuticals for bone lesions. Imaging and therapy in clinical practice. Q. J. Nucl. Med. 2001, 45:18-26.
23. Rogers M.J., Gordon S., Benford H.L., Coxon F.P., Luckman S.P., Monkkonen J., Frith J.C. Cellular and molecular mechanisms of action of bisphosphonates. Cancer 2000, 88:2961-2978.
24. Shigematsu M., Shiomi S., Iwao H., Ochi H. New bone-seeking agent: animal study of Tc-99m-incadronate. Ann. Nucl. Med. 2002, 16:55-59.
25. Subramanian G., McAfee J.G., Blair R.J., Kallfelz F.A., Thomas F.D. Technetium-99m-methylene diphosphonate-a superior agent for skeletal imaging:comparison with other technetium complexes. J. Nucl. Med. 1975, 16:744-755.
26. Valko K. Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution. J. Chromatogr. A 2004, 1037:299-310.
27. Vallner J.J. Binding of drugs by albumin and plasma protein. J. Pharm. Sci. 1977, 66:447-465.
28. 99mTc-EC with aminomethylene diphosphonate in the search for a bone tracer with fast clearance from soft tissue. Bioconjugate Chem. 2002, 13:16-22.
29. Widler L., Jaeggi K.A., Glatt M., Müller K., Bachmann R., Bisping M., Born A.R., Cortesi R., Guiglia G., Jeker H., Klein R., Ramseier U., Schmid J., Schreiber G., Seltenmeyer Y., Green J.R. Highly potent geminal bisphosphonates from pamidronate disodium (aredia) to zoledronic acid (zometa). J. Med. Chem. 2002, 45:3721-3738.
30. Xue F.S., Liao X., Tong S.Y., Liu J.H., Li L., Zou Q., Luo L.K. Pharmacokinetics of vecuronium during acute isovolaemic haemodilution. Br. J. Anaesth. 1997, 79:612-616.
31. Zhang Y.H., Cao R., Yin F.L., Hudock M.P., Guo R.T., Krysiak K., Mukherjee S., Gao Y.G., Robinson H., Song Y.C., No J.H., Bergan K., Leon A., Cass L., Goddard A., Chang T.K., Lin F.Y., Beek E.V., Papapoulos S., Wang A.H.J., Kubo T., Ochi M., Mukkamala D., Oldfield E. Lipophilic bisphosphonates as dual farnesyl/geranylgeranyl diphosphate synthase inhibitors: an X-ray and NMR investigation. J. Am. Chem. Soc. 2009, 131:5153-5162.