Synthesis and in vitro/in vivo evaluation of novel99mTc(CO) 3-folates

Bioconjugate Chemistry

Volumn 17, Issue 3, 2006, Pages 797-806

  Müller, Cristina ^a   Schubiger, P August ^a,b   Schibli, Roger ^a,b  

^a PAUL SCHERRER INSTITUTE   (Switzerland)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLATION; CHELATION; COORDINATION REACTIONS; HISTOLOGY; ORGANOMETALLICS; PHARMACOKINETICS; RADIATION; RADIOACTIVITY;

FOLATE RECEPTOR; FOLATES; FOLIC ACIDS; IN-VITRO; IN-VIVO; PHARMACOKINETIC PROFILES; POST INJECTION; SYNTHESISED; VITRO AND IN VIVO; VIVO EVALUATION;

TUMORS;

4 CARBOXYGLUTAMIC ACID; BIS(PYRIDYLMETHYL)AMINE; CARBON MONOXIDE; CHELATING AGENT; FOLATE RECEPTOR; FOLIC ACID CARBON MONOXIDE TECHNETIUM 99M; FOLIC ACID DERIVATIVE; MONOCARBOXYLATE TRANSPORTER; ORGANOMETALLIC COMPOUND; PICOLYLAMINE MONOACETIC ACID; TECHNETIUM 99M; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; CONTRAST RADIOGRAPHY; CONTROLLED STUDY; EVALUATION RESEARCH; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INTESTINE; LIVER; MOUSE; NONHUMAN; PRODUCT RECOVERY; RADIOACTIVITY; RADIOISOTOPE DIAGNOSIS; RECEPTOR AFFINITY; SYNTHESIS; TIME; TUMOR XENOGRAFT; XERORADIOGRAPHY;

MUS MUSCULUS;

EID: 33646933762     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc050323q     Document Type: Article

References (37)

1. Leamon, C. P., and Low, P. S. (1993) Membrane folate-binding proteins are responsible for folate-protein conjugate endocytosis into cultured cells. Biochem. J. 291, 855-860.
2. Leamon, C. P., and Low, P. S. (2001) Folate-mediated targeting: from diagnostics to drug and gene delivery. Drug Discovery Today 6, 44-51.
3. Leamon, C. P., Pastan, I., and Low, P. S. (1993) Cytotoxicity of folate-pseudomonas exotoxin conjugates toward tumor cells-contribution of translocation domain. J. Biol. Chem. 268, 24847-24854.
4. Leamon, C. P., and Low, P. S. (1994) Selective targeting of malignant cells with cytotoxin-folate conjugates. J. Drug Targeting 2, 101-112.
5. Konda, S. D., Aref, M., Wang, S., Brechbiel, M., and Wiener, E. C. (2001) Specific targeting of folate-dendrimer MRI contrast agents to the high affinity fo late receptor expressed in ovarian tumor xenografts. Magn. Reson. Mater. Phys., Biol. Med. 12, 104-113.
6. Lee, J. W., Lu, J. Y., Low, P. S., and Fuchs, P. L. (2002) Synthesis and evaluation of Taxol-folic acid conjugates as targeted antineoplastics. Bioorg. Med. Chem. 10, 2397-2414.
7. Hofland, H. E. J., Masson, C., Iginla, S., Osetinsky, I., Reddy, J. A., Leamon, C. P., Scherman, D., Bessodes, M., and Wils, P. (2002) Folate-targeted gene transfer in vivo. Mol. Ther. 5, 739-744.
8. Leamon, C. P., Cooper, S. R., and Hardee, G. E. (2003) Folate-liposome-mediated antisense oligodeoxynucleotide targeting to cancer cells: evaluation in vitro and in vivo. Bioconjugate Chem. 14, 738-747.
9. Matulic-Adamic, J., Sanseverino, M., and Beigelman, L. (2002) An efficient synthesis of the ribozyme-folate conjugate. Tetrahedron Lett. 43, 4439-4441.
10. Mathias, C. J., Wang, S., Waters, D. J., Turek, J. J., Low, P. S., and Green, M. A. (1998) Indium-111-DTPA-folate as a potential folate-receptor- targeted radiopharmaceutical. J. Nucl. Med. 39, 1579-1585.
11. 111In]In-DTPA-folate, a folate-receptor-targeted radiopharmaceutical. Nucl. Med. Biol. 25, 585-587.
12. 99mTc-HYNIC- folate: a novel receptor-based targeted radiopharmaceutical for tumor imaging. J. Nucl. Med. 40, 1563-1569.
13. 99mTc-based radiopharmaceutical. Bioconjugate Chem. 13, 1200-1210.
14. 99mTc-EC20 for imaging folate receptor-positive tumors. J. Nucl. Med. 45, 857-866.
15. Ke, C. Y., Mathias, C. J., and Green, M. A. (2003) The folate receptor as a molecular target for tumor-selective radionuclide delivery. Nucl. Med. Biol. 30, 811-817.
16. 99mTc-technetium(I)- and Rerhenium(I)-folate derivatives for potential use in nuclear medicine. J. Organomet. Chem. 689, 4712-4721.
17. 99mTc-pteroate radiotracers for folate receptor-positive tumor targeting. Eur. J. Nucl. Med. Mol. Imaging, in press.
18. Pons, J. F., Fauchere, J. L., Lamaty, F., Molla, A., and Lazaro, R. (1998) A constrained diketopiperazine as a new scaffold for the synthesis of peptidomimetics. Eur. J. Org. Chem., 853-859.
19. 3] (APPA = [(5-aminopentyl)-pyridin-2-yl- methyl-amino]-acetic acid). Nucl. Med. Biol. 30, 465-470.
20. 2)}]. Inorg. Chem. 41, 6417-6425.
21. 99mTc complexes for correlating fluorescence and radioimaging studies. J. Am. Chem. Soc. 126, 8598-8599.
22. +]G. Bioconjugate Chem. 15, 128-136.
23. Nomura, M., Shuto, S., and Matsuda, A. (2000) Nucleosides and nucleotides, part 196 - Development of an efficient intermediate, α-[2-(trimethylsilyl)ethoxy]-2-Nr-[2-(trimethylsilyl)ethoxycarbonyl] -folic acid, for the synthesis of folate (γ)-conjugates, and its application to the synthesis of folate-nucleoside conjugates. J. Org. Chem. 65, 5016-5021.
24. Antony, A. C., Kane, M. A., Portillo, R. M., Elwood, P. C., and Kolhouse, J. F. (1985) Studies of the role of a particulate folate-binding protein in the uptake of 5-methyltetrahydrofolate by cultured human KB cells. J. Biol. Chem. 260, 4911-4917.
25. Dixon, K. H., Mulligan, T., Chung, K. N., Elwood, P. C., and Cowan, K. H. (1992) Effects of folate receptor expression following stable transfection into wild type and methotrexate transport-deficient ZR-75-1 human breast cancer cells. J. Biol. Chem. 267, 24140-24147.
26. Ladino, C. A., Chari, R. V. J., Bourret, L. A., Kedersha, N. L., and Goldmacher, V. S. (1997) Folate-maytansinoids: target-selective drugs of low molecular weight. Int. J. Cancer 73, 859-864.
27. Goresky, C. A., Watanabe, H., and Johns, D. G. (1963) Renal excretion of folic acid. J. Clin. Invest. 42, 1841.
28. Morshed, K. M., and McMartin, K. E. (1996) In vitro characterization of renal reabsorption and secretion of folate using primary cultures of human kidney cells. J. Nutr. Biochem. 7, 276-281.
29. Birn, H., Selhub, J., and Christensen, E. I. (1993) Internalization and intracellular transport of folate-binding protein in rat kidney proximal tubule. Am. J. Physiol. 264, C302-C310.
30. Birn, H., Spiegelstein, O., Christensen, E. I., and Finnell, R. H. (2005) Renal tubular reabsorption of folate mediated by folate binding protein 1. J. Am. Soc. Nephrol. 16, 608-615.
31. McMartin, K. E., Morshed, K. M., Hazenmartin, D. J., and Sens, D. A. (1992) Folate transport and binding by cultured human proximal tubule cells. Am. J. Physiol. 263, F841-F848.
32. Selhub, J., Emmanouel, D., Stavropoulos, T., and Arnold, R. (1987) Renal folate absorption and the kidney folate binding protein. I. Urinary clearance studies. Am. J. Physiol. 252, F750-F756.
33. Selhub, J., and Rosenberg, I. H. (1978) Demonstration of high-affinity folate binding activity associated with brush border membranes of rat kidney. Proc. Natl. Acad. Sci. U.S.A. 75, 3090-3093.
34. Ross, J. F., Chaudhuri, P. K., and Ratnam, M. (1994) Differential regulation of folate receptor isoforms in normal and malignant tissues in-vivo and in established cell-lines-physiological and clinical implications. Cancer 73, 2432-2443.
35. Parker, N., Turk, M. J., Westrick, E., Lewis, J. D., Low, P. S., and Leamon, C. P. (2005) Folate receptor expression in carcinomas and normal tissues determined by a quantitative radioligand binding assay. Anal. Biochem. 338, 284-293.
36. 3-DTPA-folate as a folate-receptor-targeted radiopharmaceutical. Nucl. Med. Biol. 29, 569-573.
37. 99mTc-EC20 for Imaging Folate Receptor-Positive Tumors. J. Nucl. Med. 45, 857-866.