{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,12]],"date-time":"2026-03-12T05:59:39Z","timestamp":1773295179469,"version":"3.50.1"},"reference-count":58,"publisher":"American Chemical Society (ACS)","issue":"2","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Bioconjugate Chem."],"published-print":{"date-parts":[[2003,3,1]]},"DOI":"10.1021\/bc025636p","type":"journal-article","created":{"date-parts":[[2003,3,19]],"date-time":"2003-03-19T05:59:12Z","timestamp":1048053552000},"page":"331-341","source":"Crossref","is-referenced-by-count":29,"title":["<i>N<\/i>-Succinimidyl 3-[<sup>131<\/sup>I]Iodo-4-phosphonomethylbenzoate ([<sup>131<\/sup>I]SIPMB), a Negatively Charged Substituent-Bearing Acylation Agent for the Radioiodination of Peptides and mAbs"],"prefix":"10.1021","volume":"14","author":[{"given":"Sriram","family":"Shankar","sequence":"first","affiliation":[{"name":"Department of Radiology, Duke University Medical Center, Box 3808, Durham, North Carolina 27710"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ganesan","family":"Vaidyanathan","sequence":"additional","affiliation":[{"name":"Department of Radiology, Duke University Medical Center, Box 3808, Durham, North Carolina 27710"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Donna","family":"Affleck","sequence":"additional","affiliation":[{"name":"Department of Radiology, Duke University Medical Center, Box 3808, Durham, North Carolina 27710"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Phillip C.","family":"Welsh","sequence":"additional","affiliation":[{"name":"Department of Radiology, Duke University Medical Center, Box 3808, Durham, North Carolina 27710"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael R.","family":"Zalutsky","sequence":"additional","affiliation":[{"name":"Department of Radiology, Duke University Medical Center, Box 3808, Durham, North Carolina 27710"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2003,2,7]]},"reference":[{"key":"bc025636pb00001\/bc025636pb00001_1","volume-title":"Synthesis and radioiodination of tyramine cellobiose for labeling monoclonal antibodies. Nucl. Med. Biol. 15, 557\u2212561","author":"Ali S.","year":"1988"},{"key":"bc025636pb00002\/bc025636pb00002_1","volume-title":"Radiolabeled metabolites of proteins play a critical role in radioactivity elimination from the liver. Nucl. Med. Biol. 22, 555\u2212564","author":"Arano Y.","year":"1995"},{"key":"bc025636pb00003\/bc025636pb00003_1","volume-title":"Tetrahedron 52","author":"Baczko K.","year":"1996"},{"key":"bc025636pb00004\/bc025636pb00004_1","doi-asserted-by":"crossref","DOI":"10.1021\/cr00044a004","volume":"81","author":"Bhattacharya A. K.","year":"1981","journal-title":"Chem. Rev."},{"key":"bc025636pb00005\/bc025636pb00005_1","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1042\/bj0480096","volume":"48","author":"Bray H. G.","year":"1951","journal-title":"Biochem. J."},{"key":"bc025636pb00006\/bc025636pb00006_1","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1042\/bj1180047","volume":"118","author":"Bridges J. W.","year":"1970","journal-title":"Biochem. J."},{"key":"bc025636pb00007\/bc025636pb00007_1","doi-asserted-by":"crossref","DOI":"10.1021\/jm00109a008","volume":"34","author":"Burke T. R.","year":"1991","journal-title":"J. Med. Chem."},{"key":"bc025636pb00008\/bc025636pb00008_1","volume":"75","author":"Crofts P. C.","year":"1953","journal-title":"J. Am. Chem. Soc."},{"key":"bc025636pb00009\/bc025636pb00009_1","volume-title":"Somatostatin receptor-targeted radionuclide therapy of tumors:\u2009 Preclinical and clinical findings. Sem. Nuc. Med. 32, 133\u2212140","author":"de Jong M.","year":"2002"},{"key":"bc025636pb00010\/bc025636pb00010_1","volume":"34","author":"Duncan J. R.","year":"1993","journal-title":"J. Nuc. Med."},{"key":"bc025636pb00011\/bc025636pb00011_1","doi-asserted-by":"crossref","DOI":"10.1021\/cr60307a003","volume":"77","author":"Engel R.","year":"1977","journal-title":"Chem. Rev."},{"key":"bc025636pb00012\/bc025636pb00012_1","volume-title":"Novel limonene phosphonate and farnesyl diphosphonate analogues:\u2009 Design, synthesis, and evaluation as potential protein-farnesyl transferase inhibitors. Bioorg. Med. Chem. 7, 241\u2212250","author":"Eummer J. T.","year":"1999"},{"key":"bc025636pb00013\/bc025636pb00013_1","unstructured":"Foulon, C. F., Reist, C. J., Bigner, D. D., and Zalutsky, M R. (2000) Radioiodination via D-amino acid peptide enhances cellular retention and tumor xenograft targeting of an internalizing anti-epidermal growth factor receptor variant III monoclonal antibody.Cancer Res. 60,4453\u22124460."},{"key":"bc025636pb00014\/bc025636pb00014_1","volume-title":"Positively charged templates for labeling internalizing antibodies:\u2009 Comparison of N-succinimidyl 5-iodo-3-pyridinecarboxylate and the D-amino acid peptide KRYRR. Nucl. Med. Biol. 28, 769\u2212777","author":"Foulon C. F.","year":"2001"},{"key":"bc025636pb00015\/bc025636pb00015_1","doi-asserted-by":"crossref","first-page":"E10","DOI":"10.1208\/ps030210","volume":"3","author":"Franz R. G.","year":"2001","journal-title":"AAPS Pharm. Sci."},{"key":"bc025636pb00016\/bc025636pb00016_1","volume-title":"Intracellular catabolism of radiolabeled anti-\u03bc antibodies by malignant B-cells. Cancer Res. 52, 2907\u22122915","author":"Geissler F.","year":"1992"},{"key":"bc025636pb00017\/bc025636pb00017_1","volume-title":"Single-dose versus fractionated radioimmunotherapy of human colon carcinoma xenografts using 131I-labeled multivalent CC49 single-chain FVS. Clin. Cancer Res. 7, 175\u2212184","author":"Goel A.","year":"2001"},{"key":"bc025636pb00018\/bc025636pb00018_1","volume-title":"Labeling of monoclonal antibodies with diethylenetriaminepentaacetic acid-appended radioiodinated peptides containing d-amino acids. Bioconjugate Chem. 10, 231\u2212240","author":"Govindan S. V.","year":"1999"},{"key":"bc025636pb00019\/bc025636pb00019_1","volume-title":"Protecting Groups in Organic Synthesis","author":"Green T. W.","year":"1991","edition":"2"},{"key":"bc025636pb00020\/bc025636pb00020_1","volume-title":"Lipoic acid impairs glycine conjugation of benzoic acid and renal excretion of benzoylglycine. Drug Metab. Dispos. 24, 682\u2212688","author":"Gregus Z.","year":"1996"},{"key":"bc025636pb00021\/bc025636pb00021_1","doi-asserted-by":"crossref","first-page":"64","DOI":"10.3109\/00498257609151612","volume":"6","author":"Hirom P. C.","year":"1976","journal-title":"Xenobiotica"},{"key":"bc025636pb00022\/bc025636pb00022_1","doi-asserted-by":"crossref","unstructured":"Holtzman, E. (1989)Lysosomes, pp 95\u2212100, Plenum Press, New York.","DOI":"10.1007\/978-1-4899-2540-4"},{"key":"bc025636pb00023\/bc025636pb00023_1","volume-title":"Amino Acid Conjugation. Conjugation Reactions in Drug Metabolism","author":"Hutt A. J.","year":"1990"},{"key":"bc025636pb00024\/bc025636pb00024_1","volume-title":"Radioimmunotherapy of cancer:\u2009 Using monoclonal antibodies to target radiotherapy. Curr. Pharm. Des. 6, 1399\u22121418","author":"Illidge T. M.","year":"2000"},{"key":"bc025636pb00025\/bc025636pb00025_1","volume-title":"The in vivo behavior of Copper-64-labeled azamacrocyclic complexes. Nuc. Med. Biol. 25, 523\u2212530","author":"Jones-Wilson T. M.","year":"1998"},{"key":"bc025636pb00026\/bc025636pb00026_1","doi-asserted-by":"crossref","first-page":"2958","DOI":"10.1021\/jo00389a069","volume":"52","author":"Keck G. E.","year":"1987","journal-title":"J. Org. Chem."},{"key":"bc025636pb00027\/bc025636pb00027_1","volume-title":"The pharmacokinetic characteristics 341 of glycolated humanized anti-Tac Fabs are determined by their isoelectric points. Cancer Res. 59, 422\u2212430","author":"Kobayashi H.","year":"1999"},{"key":"bc025636pb00028\/bc025636pb00028_1","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/0022-1759(84)90435-6","volume":"72","author":"Lindmo T.","year":"1984","journal-title":"J. Immunol. Methods"},{"key":"bc025636pb00029\/bc025636pb00029_1","volume-title":"Filtration, transport, and metabolism of proteins. The Kidney:\u2009 Physiology and Pathophysiology","author":"Maack T.","year":"1992"},{"key":"bc025636pb00030\/bc025636pb00030_1","doi-asserted-by":"crossref","DOI":"10.1016\/S0021-9258(18)68193-1","volume":"263","author":"Maxwell J. L.","year":"1988","journal-title":"J. Biol. Chem."},{"key":"bc025636pb00031\/bc025636pb00031_1","volume":"258","author":"Moe Jr., O. A.","year":"1983","journal-title":"J. Biol. Chem."},{"key":"bc025636pb00032\/bc025636pb00032_1","first-page":"70","volume":"27","author":"Murray J. L.","year":"2000","journal-title":"Sem. Oncol."},{"key":"bc025636pb00033\/bc025636pb00033_1","volume-title":"Proc. Natl. Acad. Sci. U. S. A. 91","author":"Nishikawa R.","year":"1994"},{"key":"bc025636pb00034\/bc025636pb00034_1","doi-asserted-by":"crossref","DOI":"10.1042\/bj2120791","volume":"212","author":"Pittman R","year":"1983","journal-title":"Biochem. J."},{"key":"bc025636pb00035\/bc025636pb00035_1","first-page":"2123","volume":"56","author":"Press O. W.","year":"1996","journal-title":"Cancer Res."},{"key":"bc025636pb00036\/bc025636pb00036_1","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1021\/jm950414g","volume":"39","author":"Qian Y.","year":"1996","journal-title":"J. Med. Chem."},{"key":"bc025636pb00037\/bc025636pb00037_1","unstructured":"Reist, C. J., Archer, G. E., Kurpad, S. N., Wikstrand, C. J., Vaidyanathan, G., Willingham, M. C., Moscatello, D. K., Wong, A. J., Bigner, D. D., and Zalutsky, M. R. (1995) Tumor-specific anti-epidermal growth factor receptor variant III monoclonal antibodies:\u2009 Use of the tyramine-cellobiose radioiodination method enhances cellular retention and uptake in tumor xenografts.Cancer Res. 55, 4375\u221282."},{"key":"bc025636pb00038\/bc025636pb00038_1","volume-title":"Radioiodination of internalizing monoclonal antibodies using N-succinimidyl 5-iodo-3-pyridinecarboxylate. Cancer Res. 56, 4970\u22124977","author":"Reist C. J.","year":"1996"},{"key":"bc025636pb00039\/bc025636pb00039_1","unstructured":"Reist, C. J., Archer, G. E., Wikstrand, C. J., Bigner, D. D., and Zalutsky, M. R. (1997) Improved targeting of an anti-epidermal growth factor receptor variant III monoclonal antibody in tumor xenografts after labeling usingN-succinimidyl 5-iodo-3-pyridinecarboxylate.Cancer Res.57, 1510\u22121515."},{"key":"bc025636pb00040\/bc025636pb00040_1","volume-title":"Identification of metabolites of 111In-diethylenetriaminepentaacetic acid-monoclonal antibodies and antibody fragments in vivo. Cancer Res. 55, 5714s\u22125720s","author":"Rogers B. E.","year":"1995"},{"issue":"11","key":"bc025636pb00041\/bc025636pb00041_1","volume":"19","author":"Sneath R. L., Jr.","year":"1976","journal-title":"J. Med. Chem."},{"key":"bc025636pb00042\/bc025636pb00042_1","volume":"45","author":"Sun X.","year":"2002","journal-title":"J. Med. Chem."},{"key":"bc025636pb00043\/bc025636pb00043_1","doi-asserted-by":"crossref","DOI":"10.1096\/fasebj.7.5.8462781","volume":"7","author":"Thorpe S. R.","year":"1993","journal-title":"FASEB J."},{"key":"bc025636pb00044\/bc025636pb00044_1","volume-title":"Protein radiohalogenation:\u2009 Observations on the design of N-succinimidyl ester acylation agents. Bioconjugate Chem. 1, 269\u2212273","author":"Vaidyanathan G.","year":"1990"},{"key":"bc025636pb00045\/bc025636pb00045_1","volume-title":"Improved synthesis of N-succinimidyl 4-[18F]fluorobenzoate and its application to the labeling of a monoclonal antibody fragment. Bioconjugate Chem. 5, 352\u2212356","author":"Vaidyanathan G.","year":"1994"},{"key":"bc025636pb00046\/bc025636pb00046_1","volume-title":"Method for radioiodination of proteins using N-succinimidyl 3-hydroxy-4-iodobenzoate. Bioconjugate Chem. 8, 724\u2212729","author":"Vaidyanathan G.","year":"1997"},{"key":"bc025636pb00047\/bc025636pb00047_1","volume-title":"Iodopyridine-for-iodobenzene substitution for use with low molecular weight radiopharmaceuticals:\u2009 application to m-iodobenzylguandine. Bioconjugate Chem. 9, 758\u2212764","author":"Vaidyanathan G.","year":"1998"},{"key":"bc025636pb00048\/bc025636pb00048_1","doi-asserted-by":"crossref","unstructured":"Vaidyanathan, G., Affleck, D. J., Li, J., Welsh, P., and Zalutsky, M. R. (2001) A polar substituent-containing acylation agent for the radioiodination of internalizing monoclonal antibodies:\u2009N-succinimidyl 4-guanidinomethyl-3-[131I]iodobenzoate ([131I]SGMIB).Bioconjugate Chem.12, 428\u2212438.","DOI":"10.1021\/bc0001490"},{"key":"bc025636pb00049\/bc025636pb00049_1","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/S0969-8051(01)00277-3","volume":"29","author":"Vaidyanathan G.","year":"2002","journal-title":"Nucl. Med. Biol."},{"key":"bc025636pb00050\/bc025636pb00050_1","unstructured":"Van Wazer, J. R. (1958)Phosphorus and Its Compounds, pp 384\u2212386, Volume 1, Interscience, New York."},{"key":"bc025636pb00051\/bc025636pb00051_1","volume":"61","author":"Wan S. H.","year":"1972","journal-title":"J. Pharm. Sci."},{"key":"bc025636pb00052\/bc025636pb00052_1","doi-asserted-by":"crossref","DOI":"10.1021\/jm00057a003","volume":"36","author":"Wigerinck P.","year":"1993","journal-title":"J. Med. Chem."},{"key":"bc025636pb00053\/bc025636pb00053_1","volume-title":"Monoclonal antibodies against EGFRvIII are tumor specific and react with breast and lung carcinomas and malignant gliomas. Cancer Res. 55, 3140\u22123148","author":"Wikstrand C. J.","year":"1995"},{"key":"bc025636pb00054\/bc025636pb00054_1","volume-title":"Cell surface localization and density of the tumor-associated variant of the epidermal growth factor receptor EGFRvIII. Cancer Res. 57, 4130\u22124140","author":"Wikstrand C. J.","year":"1997"},{"key":"bc025636pb00055\/bc025636pb00055_1","volume":"4","author":"Wikstrand C. J.","year":"1998","journal-title":"J. Neurol. Virol."},{"key":"bc025636pb00056\/bc025636pb00056_1","volume-title":"Preparation of l-N\u03b1-Fmoc-4-[di-(tert-butyl)-phosphonomethyl]phenylalanine from l-tyrosine. Tetrahedron Asymmetry 19, 3727\u22123734","author":"Yao Z.-J.","year":"1999"},{"key":"bc025636pb00057\/bc025636pb00057_1","first-page":"78","volume":"41","author":"Zalutsky M. R.","year":"1997","journal-title":"Quart. J. Nucl. Med."},{"key":"bc025636pn00001\/bc025636pn00001_1","volume-title":"diethylenetriamine pentaacetic acid","author":"Abbreviations CMC"}],"container-title":["Bioconjugate Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/bc025636p","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,10,12]],"date-time":"2021-10-12T01:55:33Z","timestamp":1634003733000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/bc025636p"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2003,2,7]]},"references-count":58,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2003,3,1]]}},"alternative-id":["10.1021\/bc025636p"],"URL":"https:\/\/doi.org\/10.1021\/bc025636p","relation":{},"ISSN":["1043-1802","1520-4812"],"issn-type":[{"value":"1043-1802","type":"print"},{"value":"1520-4812","type":"electronic"}],"subject":[],"published":{"date-parts":[[2003,2,7]]}}}