Bioconjugate Chem. 1999, 10, 701−702
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CORRECTIONS Volume 10, Number 2, March/April 1999.
Silvio Aime,* Mauro Botta, Simonetta Geninatti Crich, Giovanni Giovenzana, Giovanni Palmisano, and Massimo Sisti NOVEL PARAMAGNETIC MACROMOLECULAR COMPLEXES DERIVED FROM THE LINKAGE OF A MACROCYCLIC GD(III) COMPLEX TO POLYAMINO ACIDS THROUGH A SQUARIC ACID MOIETY On page 195, the reaction arrows in Schemes 3 and 4 should be replaced with T. In addition, on page 195, right column, in the sixth sentence of the second full paragraph, the following change should be made. “Thus, the strong upfield shift of C-3 suggests a large decrease of its carbonylic character, which is consistent with a shift in the equilibrium represented in Scheme 4.” should be changed to “Thus, the strong upfield shift of C-3 suggests a large decrease of its carbonylic character, which is indicative that A-2 contributes more to the resonance hybrid than A-1.” BC990056M 10.1021/bc990056m Published on Web 06/25/1999
Volume 10, Number 3, May/June 1999.
Clemens Decristoforo and Stephen J. Mather* PREPARATION, 99mTC-LABELING, AND IN VITRO CHARACTERIZATION OF HYNIC AND N3S MODIFIED RC-160 AND [TYR3]OCTREOTIDE On pages 437 and 438, the numbers were omitted from the corresponding references. The Literature Cited should appear as follows. LITERATURE CITED (1) Eising, E. G., Bier, D., Knust, E. J., and Reiners, C. (1996) Somatostatin-receptor scintigraphy. Methods, indications, results. Radiologe 36, 81-88. (2) Lamberts, S. W., Chayvialle, J. A., and Krenning, E. P. (1993) The visualization of gastroenteropancreatic endocrine tumors. Digestion 54 (Suppl. 1), 92-97. (3) Vekemans, M. C., Urbain, J. L., and Charkes, D. (1995) Advances in radio-imaging of neuroendocrine tumors. Curr. Opin. Oncol. 7, 63-67. (4) Krenning, E. P., Kwekkeboom, D. J., Bakker, W. H., Breeman, W. A., Kooij, P. P., Oei, H. Y., van Hangen, M., Postema, P. T., de Jong M., and Reubi J. C. (1993) Somatostatin receptor scintigraphy with [111In-DTPA-D-Phe] and [123I-Tyr]octreotide: The Rotterdam experience with more than 1000 patients. Eur. J. Nucl. Med. 20, 716-731. (5) Srkalovic, G., Cai, R. Z., and Schally, A. V. (1990) Evaluation of receptors for somatostatin in various tumors using different analogues. J. Clin. Endocrinol. Metab. 70, 661-669. (6) Liebow, C., Reilly, C., Serrano, M., and Schally, A. V. (1989) Somatostain analogues inhibit growth of pancreatic cancer
by stimulating tyrosine phosphatase. Proc. Natl. Acad. Sci. U.S.A. 86, 2003-2007. (7) Pinski, J., Milovanovic, T. Y., Yano, T., Hamaoui, A., Radulovic, S., Cai, R. Z., and Schally, A. V. (1992) Biological activity and receptor binding characteristics to various human tumors of acetylated somatostatin receptors. Proc. Soc. Exp. Biol. Med. 200, 49-56. (8) Banks, W. A., Schally, A. V., Barrera, C. M., Fasold, M. B., Durham, D. A., Csernus, V. J., and Kastin, A. J. (1990) Permeability of the murine blood brain barrier to some octapeptide analogues of somatostatin. Proc. Natl. Acad. Sci. U.S.A. 87, 6762-6766. (9) Breeman, W. A. P., Hofland, L. J., Bakker, W. H., van der Pluijm, M., van Koetsveld, P. M., de Jong, M., Setyono-Han, B., Kwekkeboom, D. J., Visser, T. J., Lamberts, S. W. J., and Krenning, E. P. (1993) Radioiodinated somatostatin analogue RC-160: preparation, biological activity, in vivo application in rats and comparison with [123I-Tyr3]octreotide. Eur. J. Nucl. Med. 20, 1089-1094. (10) Breeman, W. A. P., Hofland, L. J., Pluijm, M.van-der, van Koetsveld, P. M., de Jong, M., Setyono-Han, B., Bakker, W. H., Kweekeboom, D. J., Visser, T. J., Lamberts, S. W. J., and Krenning, E. P. (1994) A new radiolabeled somatostatin analogue [111In-DTPA-D-Phe1]RC-160: preparation, biological activity, receptor scintigraphy in rats and comparison with [111In-DTPA-D-Phe1]octreotide. Eur. J. Nucl. Med. 21, 328335. (11) Zamora, P. O., Gulhke, S., Bender, H., Diekmann, D., Rhodes, B. A., Biersack, H. J., and Knapp, F. F., Jr. (1996) Experimental radiotherapy of receptor-positive human prostate adenocarcinoma with 188Re-RC-160, a directly radiolabeled somatostatin analogue. Int. J. Cancer 65, 214-20. (12) Liu, S., Edwards, D. S., and Barrett, J. A. (1997) 99mTc labeling of highly potent small peptides. Bioconjugate Chem. 8, 621-636.
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(13) Vallabhajosula, S., Moyer, B. R., Lister-James, J., McBride, B. J., Lipszyk, H., Lee, H., Bastidas, D., and Dean, R. T. (1996) Preclinical evaluation of Technetium-99m-Labeled Somatostatin Receptor-Binding Peptides. J. Nucl. Med. 37, 1016-1022. (14) Maina, T., Stolz, B., Albert, R., Bruns, C., Koch, P., and Ma¨cke, H. (1994). Synthesis and biological evaluation of a new somatostatin analogue (SDZ 219-387) labeled with technetium-99m. Eur. J. Nucl. Med. 21, 437-444. (15) Maina, T., Stolz, B., Albert, R., Nock, B., Bruns, C., and Ma¨cke, H. (1995) Synthesis, radiochemistry and biological evaluation of 99mTc[N4-(D)PHE1]-octreotide, a new octreotide derivative with high affinity for somatostatin receptors. in Technetium and Rhenium in Chemistry and Nuclear Medicine 4 (M. Nicolini, G. Banoli, and U. Mazzi, Eds.) pp 395-400, SG Editorali, Padova. (16) Ma¨cke, H. R. and Behe, M. (1996) New octreotide derivatives labeled with technetium-99m. J. Nucl. Med. 37, 29P (abstr. 107). (17) Thakur, M. L., Kolan, H., Wiaderkiewicz, R., Pallela, V. R., Duggaraju, R., and Schally, A. V. (1997) Radiolabeled Somatostatin analogues in Prostate Cancer. Nucl. Med. Biol. 24, 105-113. (18) Kolan, H., Li, J., and Thakur, M. L. (1996) Sandostatin Labeled with 99mTc: In Vitro Stability, In Vivo Validity and Comparison with 111In-DTPA-Octreotide. Peptide Res. 9, 144150. (19) Abrams, M. J., Juweid, M., tenKate, C. I., Schwartz, D. A., Hauser, M. M., Gaul, F. E., Fuccello, A. J., Rubin, R. H., Strauss, H. W., and Fischman, A. J. (1990) Technetium-99mhuman polyclonal IgG radiolabeled via the hydrazino nicotinamide derivative for imaging focal sites of infection in rats. J. Nucl. Med. 31, 2022-2028. (20) Kasina, S., Sanderson, J. A., Fitzner, J. N., Srinivasan, A., Rao, T. N., Hobson, L. J., Reno, J. M., Axworthy, D. B., Beaumier, P. L., and Fritzberg, A. R. (1998) Simplified preformed chelate protein radiolabeling with technetium-99m nercaptoacetamidoadipoylglycylglycine (N3S-Adipate). Bioconjugate Chem. 9, 108-117. (21) Hnatowich, D. J., Qu, T., Chang, F., Ley, A. C., Ladner, R. C., and Rusckowski, M. (1998) Labeling peptides with technetium-99m using a bifunctional chelator of a N-hydroxysuccinimide ester of mercaptoacetyltriglycine. J. Nucl. Med. 39, 56-64. (22) Hnatowich, D. J., Virzi, F., Fogorasi, M., Rusckowski, M., and Winnard, P. (1994) Can a cysteine challenge assay predict the in vivo behavior of 99mTc-labeled antibodies. Nucl. Med. Biol. 21, 1035-1044. (23) Stalteri, M. A., Bansal, S., Hider, R., and Mather, S. J. (1999) Comparison of the stability of technetium labeled peptides to challenge with cysteine. Bioconjugate Chem. 10, 130-136.
(24) Hofland, L. J., van Knoetsveld, P. M., Wouters, N., Waaijers, M., Reubi, J. C., and Lamberts, S. W. J. (1992) Dissociation of antiproliferative and antihormoral effects of somatostatin analogue octreotide on 7315b pituitary tumor cells. Endocrinology 131, 571-577. (25) Hofland, L. J., van Knoetsveld, P. M., Waaijers, M., and Lamberts, S. W. (1996) Internalisation of isotope-coupled somatostatin analoges. Digestion 57 (Suppl. 1), 2-6. (26) Taylor, J. E., Theveniau, M. A., Bashirzadeh, R., Reisine, T., and Eden, P. A. (1994) Detection of somatostatin receptor subtype 2 (SSTR2) in established tumors and tumor cell lines: evidence for SST2 heterogeneity. Peptides 15, 12291236. (27) Liu, S., Edwards, D. S., Looby, R. J., Harris, A. R., Poirier, M. J., Barrett, J. A., Heminway, S. J., and Carroll, T. R. (1996) Labeling a hydrazino nicotinamide-modified cyclic IIb/IIIa receptor antagonist with 99mTc using aminocarboxylates as coligands. Bioconjugate Chem. 7, 63-71. (28) Edwards, D. S., Liu, S., Barrett, J. A., Harris, A. R., Looby, R. J., Ziegler, M. C., Heminway, S. J., and Carroll, T. R. (1997) New and versatile ternary ligand system for technetiumradiopharmaceuticals: water soluble phosphines and tricine as coligands in labeling a hydrazinonicotinamide-modifies cyclic glycoprotein IIb/IIIa receptor antagonist with 99mTc. Bioconjugate Chem. 8, 146-154. (29) Liu, S., Edwards, D. S., and Harris, A. R. (1998) A novel tenary ligand system for 99mTc-labeling of hydrazio nicotinamide-modified biologically active molecules using imine-Ncontaining heterocycles as coligands, Bioconjugate Chem. 9, 583-595. (30) Bormans, G., Cleynhens, B., Adriaens, P., Vanbilloen, H., de Roo M., and Verbruggen, A. (1995) Investigation of the labeling characteristics of 99mTc-Mercaptoacetyltriglycine. Nucl. Med. Biol. 22, 339-349. (31) Millar, A. M. and O’Brien, L. M. (1990) An investigation of factors that might influence the radiochemical purity and stability of 99mTc-MAG3. Eur. J. Nucl. Med. 16, 615-619. (32) Noll, B., Johannsen, B., and Spies, H. (1995) Sources of radiochemical impurities in the 99mTc/S-unprotected MAG3 system. Nucl. Med. Biol. 22, 1057-1062. (33) Breeman, W. A. P., Van Hagen, P. M., Kwekkebroom, D. K., Visser, T. J., and Krenning, E. P. (1998) Somatostatin receptor scintigraphy using [111In-DTPA0]RC160 in humans: a comparison with [111In-DTPA0]octreotide. Eur. J. Nucl. Med. 25, 182-186.
BC9900688 10.1021/bc9900688 Published on Web 07/19/1999
