Improved synthesis and iodination of a cleavable photoactivated probe

Journal Article · Sat Aug 15 00:00:00 EDT 1987 · Anal. Biochem.; (United States)

DOI:https://doi.org/10.1016/0003-2697(87)90204-1· OSTI ID:5607510

Murphy, H R; Harris, Jr, H W

J. B. Denny and G. Blobel have described the synthesis of a water-soluble novel heterobifunctional /sup 125/I-labeled photocrosslinking reagent, N-(4-(p-azido-m-(/sup 125/I)iodophenylazo)benzoyl)-3-aminopropionyl-N'- oxysulfosuccinimide, which contains a cleavable internal azo bond. We report several modifications of their synthesis which greatly increase the yield of a synthetic intermediate, N-(4-(p-aminophenylazo)benzoyl)-3-aminopropionic acid (compound VII). Evidence is presented that direct iodination of compound VII with chloramine-T produces low yields of /sup 125/I-labeled compound VII in a reaction which is difficult to control. Alternatively, the yield of /sup 125/I-labeled reagent can be greatly improved if the iodination is performed following the derivatization of N-(4-(p-axidophenylazo)benzoyl)-3-aminopropionyl-N'-oxysulfosuc cinimide (compound IX) to a ligand such as dextran. We have demonstrated the transfer of /sup 125/I label from the reagent when derivatized to amino-dextran to proteins in solution after photolysis and cleavage of this /sup 125/I-labeled reagent.

• Research Organization: National Heart, Lung and Blood Institute, Bethesda, MD
• OSTI ID: 5607510
• Journal Information: Anal. Biochem.; (United States), Vol. 165:1
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
REAGENTS
CHEMICAL PREPARATION
CLEAVAGE
IODINE 125
LIGANDS
PHOTOLYSIS
TRACER TECHNIQUES
BETA DECAY RADIOISOTOPES
CHEMICAL REACTIONS
CRYSTAL STRUCTURE
DAYS LIVING RADIOISOTOPES
DECOMPOSITION
ELECTRON CAPTURE RADIOISOTOPES
INTERMEDIATE MASS NUCLEI
IODINE ISOTOPES
ISOTOPE APPLICATIONS
ISOTOPES
MICROSTRUCTURE
NUCLEI
ODD-EVEN NUCLEI
PHOTOCHEMICAL REACTIONS
RADIOISOTOPES
SYNTHESIS
550201* - Biochemistry- Tracer Techniques