Preparation of N-succinimidyl 3-[*I] iodobenzoate:: an agent for the indirect radioiodination of proteins

被引:51
作者
Vaidyanathan, Ganesan [1 ]
Zalutsky, Michael R. [1 ]
机构
[1] Duke Univ, Med Ctr, Dept Radiol, Durham, NC 27710 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1038/nprot.2006.99
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A procedure for the synthesis of N-succinimidyl 3-iodobenzoate labeled with any iodine isotope ([* I] SIB), which is an agent used in the radioiodination of proteins and peptides, from its tin precursor N-succinimidyl 3-(tri-n-butylstannyl) benzoate (STB) is described. Also included are protocols for the synthesis of an unlabeled standard of SIB and the tin precursor. Radioiododestannylation of STB using tert-butylhydroperoxide as the oxidant gives [* I] SIB in 80% radiochemical yields. The total time for the synthesis of [* I] SIB from STB is similar to 95 min. Use of [* I] SIB yields radioiodinated proteins that are considerably more stable in vivo than those radioiodinated by the direct electrophilic method.
引用
收藏
页码:707 / 713
页数:7
相关论文
共 17 条
[1]   LABELING OF PROTEINS TO HIGH SPECIFIC RADIOACTIVITIES BY CONJUGATION TO A I-125-CONTAINING ACYLATING AGENT - APPLICATION TO RADIOIMMUNOASSAY [J].
BOLTON, AE ;
HUNTER, WM .
BIOCHEMICAL JOURNAL, 1973, 133 (03) :529-538
[2]   C-5-disubstituted barbiturates as potential molecular probes for noninvasive matrix metalloproteinase imaging [J].
Breyholz, HJ ;
Schäfers, M ;
Wagner, S ;
Höltke, C ;
Faust, A ;
Rabeneck, H ;
Levkau, B ;
Schober, O ;
Kopka, K .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) :3400-3409
[3]  
CARRASQUILLO JA, 1988, ANTIBODIES RADIODIAG, P169
[4]   Functional comparison of annexin V analogues labeled indirectly and directly with iodine-124 [J].
Dekker, B ;
Keen, H ;
Shaw, D ;
Disley, L ;
Hastings, D ;
Hadfield, J ;
Reader, A ;
Allan, D ;
Julyan, P ;
Watson, A ;
Zweit, J .
NUCLEAR MEDICINE AND BIOLOGY, 2005, 32 (04) :403-413
[5]  
GARG PK, 1989, APPL RADIAT ISOTOPES, V40, P485
[6]   PREPARATION OF IODINE-131 LABELLED HUMAN GROWTH HORMONE OF HIGH SPECIFIC ACTIVITY [J].
HUNTER, WM ;
GREENWOOD, FC .
NATURE, 1962, 194 (4827) :495-&
[7]  
KOEHRLE J, 1986, J BIOL CHEM, V261, P1613
[8]   A new convenient route to radioiodinated N-succinimidyl 3- and 4-iodobenzoate, two reagents for radioiodination of proteins [J].
Koziorowski, J ;
Henssen, C ;
Weinreich, R .
APPLIED RADIATION AND ISOTOPES, 1998, 49 (08) :955-959
[9]   IMPACT OF THE HIGH TYROSINE FRACTION IN COMPLEMENTARITY-DETERMINING REGIONS - MEASURED AND PREDICTED EFFECTS OF RADIOIODINATION ON IGG IMMUNOREACTIVITY [J].
NIKULA, TK ;
BOCCHIA, M ;
CURCIO, MJ ;
SGOUROS, G ;
MA, Y ;
FINN, RD ;
SCHEINBERG, DA .
MOLECULAR IMMUNOLOGY, 1995, 32 (12) :865-872
[10]   CLONING AND SEQUENCING OF V-GENES FROM ANTI-OSTEOSARCOMA MONOCLONAL-ANTIBODIES TP-1 AND TP-3 - LOCATION OF LYSINE RESIDUES AND IMPLICATIONS FOR RADIOLABELING [J].
OLAFSEN, T ;
BRULAND, OS ;
ZALUTSKY, MR ;
SANDLIE, I .
NUCLEAR MEDICINE AND BIOLOGY, 1995, 22 (06) :765-771