929706-89-8

Basic information

• Product Name: N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]-4-[18F]-fluorobenzamide
• Synonyms: N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]-4-[18F]-fluorobenzamide
• CAS NO: 929706-89-8
• Molecular Weight: 261.242
• Mol File: 929706-89-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]-4-[18F]-fluorobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]-4-[18F]-fluorobenzamide(929706-89-8)
• EPA Substance Registry System: N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]-4-[18F]-fluorobenzamide(929706-89-8)

Safety Data

• Hazardous Substances Data: 929706-89-8(Hazardous Substances Data)

Upstream product

• 223699-69-2 2,3,4,5,6-pentamethylbenzyl 4-trimethylammoniobenzoate trifluoromethanesulfonate 
• 146474-00-2 N-(2-aminoethyl)maleimide trifluoroacetate 
• 124915-06-6 ethyl 4-(N,N,N-trimethylammonium)-1-benzoate triflate 
• 141762-27-8 N-succinimidyl 4-[18F]fluorobenzoate 
• 538-75-0 dicyclohexyl-carbodiimide 
• 125923-10-6 1-(2-aminoethyl)-1H-pyrrole-2,5-dione 
• 10011-97-9 4-[¹⁸F]fluorobenzoic acid 

Relevant articles and documents

18F-Labeled wild-type annexin V: Comparison of random and site-selective radiolabeling methods

Early stage apoptosis is characterized by the externalization of phosphatidylserine (PS) from the inner leaflet of the plasma membrane to the outer periphery. Consequently, PS represents an excellent target for non-invasive imaging of apoptosis by positron emission tomography. Annexin V is a 36 kDa protein which binds with high affinity to PS. Radiolabeling of wild-type annexin V with fluorine-18 (18F) can be accomplished via random acylation of 23 amine groups (22 lysine residues and one N-terminal amine) with [18F]SFB or site-specific alkylation reaction on cysteine residue at position 315 with maleimide-containing prosthetic groups like [18F]FBEM. The effect upon random and site-directed 18F labeling of annexin V was studied with EL4 mouse lymphoma cells. Both, randomly and site-selectively radiolabeled annexin V demonstrated comparable binding to apoptotic EL4 cells. This finding suggests that the 18F radiolabeling method has no significant effect on the ability of 18F-labeled wild-type annexin V to bind PS in apoptotic cells.

Preliminary biological evaluation of 18F-FBEM-Cys-annexin V a novel apoptosis imaging agent

A novel annexin V derivative (Cys-Annexin V) with a single cysteine residue at its C-terminal has been developed and successfully labeled site-specifically with 18F-FBEM. 18F-FBEM was synthesized by coupling 18F-fluorobenzoic acid (18F-FBA) with N-(2-aminoethyl)maleimide using optimized reaction conditions. The yield of 18F-FBEM-Cys-Annexin V was 71.5% ± 2.0% (n = 4, based on the starting 18F-FBEM, non-decay corrected). The radiochemical purity of 18F-FBEM-Cys-Annexin V was >95%. The specific radioactivities of 18F-FBEM and 18F-FBEM-Cys-Annexin V were >150 and 3.17 GBq/μmol, respectively. Like the 1st generation 18F-SFB-Annexin V, the novel 18F-FBEM-Cys-Annexin V mainly shows renal and to a lesser extent, hepatobiliary excretion in normal mice. In rat hepatic apoptosis models a 3.88 ± 0.05 (n = 4, 1 h) and 10.35 ± 0.08 (n = 4, 2 h) increase in hepatic uptake of 18F-FBEM-Cys-Annexin V compared to normal rats was observed after injection via the tail vein. The liver uptake ratio (treated/control) at 2 h p.i. as measured via microPET correlated with the ratio of apoptotic nuclei in liver observed using TUNEL histochemistry, indicating that the novel 18F-FBEM-Cys-Annexin V is a potential apoptosis imaging agent.

RADIOLABELED AFFIBODY MOLECULES

The invention provides a radiolabeled affibody molecule comprising a fragment of an IgG-binding domain of protein A from Staphylococcus aureus, a bifunctional linker, and a radiolabel comprising 18F or 76Br, wherein the bifunctional