Improved radioiodination of 1,2-dipalmitoyl-3-IPPA via a tributyltin intermediate.

Abstract

1,2-Palmitoyl-3-[15-(4-iodophenyl)pentadecan-3-oyl]-rac-glycerol (MIPAG) is a new agent for the clinical evaluation of pancreatic lipase activity and has demonstrated promise in preliminary clinical studies with patients affected with pancreatic insufficiency. Iodine-131-MIPAG was initially prepared via thallium-iodide displacement. Because of the need for a simple method which is amendable for the routine clinical use of MIPAG we have investigated the preparation and radioiodination of MIPAG utilizing the tributyltin precursor, 1,2-palmitoyl-3-[15-(4-tributylstannylphenyl)pentadecan-3-oy l]-rac-glycerol (TBT-MIPAG, 2). Compound 2 was prepared via the condensation of 1,2-palmitoyl-rac-glycerol with 15-(4-tributylstannylphenyl)pentadecanoic acid (TBT-PPA) prepared from 4-bromophenylacetylene. Electrophilic radioiodination using peracetic acid with sodium iodide-125 in ethanol at 80 degrees C for 60 min afforded I-125-MIPAG in 65.9% (+/- 11.5%) yield and radiochemical purity of 94% (+/- 3.0%) after C-18 Sep-Pak purification (n = 6). This improved method for radioiodination utilizing TBT-MIPAG now provides radioiodinated MIPAG for routine clinical evaluation.

• Authors: D W McPherson, H Luo, J Kropp, F F Knapp Jr
• Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine (Appl Radiat Isot) Vol. 51 Issue 4 Pg. 411-7 (Oct 1999) ISSN: 0969-8043 [Print] England
• PMID: 10464915 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• 15-(4-tributylstannylphenyl)pentadecanoic acid
• Fatty Acids
• Glycerides
• Iodine Radioisotopes
• Iodobenzenes
• Radiopharmaceuticals
• Trialkyltin Compounds
• Triglycerides
• 1,2-dipalmitoyl-3-(15-(4-iodophenyl)pentadecanoyl)-rac-glycerol
• tributyltin
• palmitoyl glycerol

Topics

• Fatty Acids (chemistry)
• Glycerides (chemistry)
• Iodine Radioisotopes (chemistry)
• Iodobenzenes (chemical synthesis)
• Isotope Labeling (methods)
• Radiopharmaceuticals (chemical synthesis)
• Trialkyltin Compounds (chemistry)
• Triglycerides (chemical synthesis)