39028-25-6

Usage

Uses

Used in Biochemistry and Molecular Biology:
N-succinimidyl 4-iodobenzoate is used as a bioconjugation reagent for the labeling of proteins and peptides. It facilitates the formation of stable amide bonds with amino groups, making it suitable for applications in fluorescence microscopy, western blotting, and other analytical techniques.
Used in Fluorescence Microscopy:
N-succinimidyl 4-iodobenzoate is used as a fluorescent labeling agent for proteins and peptides. Its ability to form stable amide bonds allows for the attachment of fluorescent tags, enabling the visualization and tracking of protein dynamics within biological systems.
Used in Western Blotting:
N-succinimidyl 4-iodobenzoate is used as a detection reagent in western blotting. It can be used to label proteins with specific probes, allowing for the identification and quantification of target proteins in complex samples.
Used in Radiolabeling Studies:
The iodobenzoate group in N-succinimidyl 4-iodobenzoate can be utilized for radiolabeling studies. It provides a means to incorporate radioactive isotopes into proteins and peptides, facilitating the tracking of molecular interactions and the study of biological processes in vivo.
Used in Drug Development:
N-succinimidyl 4-iodobenzoate can be employed in the development of targeted drug delivery systems. Its ability to form stable conjugates with proteins and peptides allows for the attachment of therapeutic agents to specific biomolecules, potentially enhancing the efficacy and selectivity of drug treatments.

InChI:InChI=1/C11H8INO4/c12-8-3-1-7(2-4-8)11(16)17-13-9(14)5-6-10(13)15/h1-4H,5-6H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 619-58-9 4-iodobenzoic acid 
• 336611-57-5 N-succinimidyl-4-[3,3-(1,4-butanediyl)-triazene]benzoate 
• 150-13-0 4-amino-benzoic acid 
• 309287-40-9 1-(4-carboxyphenyl)-3,3-(1,4-butanediyl)-triazene 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 
• 618-51-9 3-Iodobenzoic acid 

Downstream Products

• 1101867-68-8 C₅₀H₆₈IN₇O₁₀ 
• 866529-77-3 (C₅H₅)W(CO)3C₆H₄C(O)ONC₄H₄O₂ 
• 107759-58-0 4-(tributylstannyl)benzoic acid N-hydroxyl succinimidyl ester 
• 1093733-07-3 2-[3-[5-(4-iodo-benzoylamino)-1-(4-methoxy-benzyloxycarbonyl)-pentyl]-ureido]-pentanedioic acid bis-(4-methoxybenzyl)ester 
• 1339952-59-8 (S)-2-(3-(carboxymethyl)ureido)-6-(4-iodobenzamido)hexanoic acid 
• 1348480-71-6 (S)-2-(3-(3-carboxypropyl)ureido)-6-(4-iodobenzamido)hexanoic acid 
• 1349838-42-1 (S)-1-(3-(1-carboxy-5-(4-iodobenzamido)pentyl)ureido)cyclopropanecarboxylic acid 
• 1349858-93-0 (S)-2-(3-((S)-1-carboxybut-3-ynyl)ureido)-6-(4-iodobenzamido)hexanoic acid 
• 1339952-62-3 (S)-2-(3-((S)-1-carboxybutyl)ureido)-6-(4-iodobenzamido)hexanoic acid 
• 1347928-23-7 (S)-2-(3-((S)-1-carboxy-2-cyanoethyl)ureido)-6-(4-iodobenzamido)hexanoic acid 
• 1348347-64-7 (S)-2-(3-((S)-3-amino-1-carboxy-3-oxopropyl)ureido)-6-(4-iodobenzamido)hexanoic acid 
• 1339952-74-7 (S)-2-(3-((S)-1-carboxy-3-(methylthio)propyl)ureido)-6-(4-iodobenzamido)hexanoic acid 
• 1349036-48-1 (S)-2-(3-((S)-4-(acetylthio)-1-carboxybutyl)ureido)-6-(4-iodobenzamido)hexanoic acid 

Relevant academic research and scientific papers

Copper-mediated radioiodination reaction through aryl boronic acid or ester precursor and its application to direct radiolabeling of a cyclic peptide

A copper-mediated radioiodination using aryl boronic precursors is attracting attention as a solution to oxidative iododestannylation and nickel-mediated radioiodination drawbacks. The copper-mediated radiolabeling method allows radioiodination at room te

Novel β- And γ-Amino Acid-Derived Inhibitors of Prostate-Specific Membrane Antigen

Prostate-specific membrane antigen (PSMA) is an excellent biomarker for the early diagnosis of prostate cancer progression and metastasis. The most promising PSMA-targeted agents in the clinical phase are based on the Lys-urea-Glu motif, in which Lys and Glu are α-(l)-amino acids. In this study, we aimed to determine the effect of β- and γ-amino acids in the S1 pocket on the binding affinity for PSMA. We synthesized and evaluated the β- and γ-amino acid analogues with (S)- or (R)-configuration with keeping α-(l)-Glu as the S1′-binding pharmacophore. The structure-activity relationship studies identified that compound 13c, a β-amino acid analogue with (R)-configuration, exhibited the most potent PSMA inhibitory activity with an IC50 value of 3.97 nM. The X-ray crystal structure of PSMA in complex with 13c provided a mechanistic basis for the stereochemical preference of PSMA, which can guide the development of future PSMA inhibitors.

Synthesis and evaluation of novel radioiodinated PSMA targeting ligands for potential radiotherapy of prostate cancer

Radioligand therapy (RLT) using prostate-specific membrane antigen (PSMA) targeting ligands is an attractive option for the treatment of Prostate cancer (PCa) and its metastases. We report herein a series of radioiodinated glutamate-urea-lysine-phenylalan

PROSTATE-SPECIFIC MEMBRANE ANTIGEN (PSMA) INHIBITORS AS diAGNOSTIC AND RAdiONUCLIDE THERAPEUTIC AGENTS

The present disclosure relates to compounds according to Formula I. These compounds display very good binding affinities to the PSMA binding sites. They comprise a radioactive isotope or a chelating moiety that can be labeled with a radioactive metal such as [68Ga]or [177Lu]. The present disclosure also relates to pharmaceutical compositions comprising a pharmaceutical acceptable carrier and a compound of Formula I or a complex thereof, or a pharmaceutically acceptable salt thereof.

Rapid Cu-Catalyzed [211At]Astatination and [125I]Iodination of Boronic Esters at Room Temperature

Access to 211At- and 125I-radiolabeled compounds in excellent RCCs and RCYs was achieved in just 10 min at room temperature using a Cu catalyst. The reaction conditions are applicable to a broad class of aryl and heteroaryl boronic reagents with varying steric and electronic properties as well as late-stage astatination and iodination of anticancer PARP inhibitors. This protocol eliminates the traditional need for toxic organotin reagents, elevated temperatures, and extended reaction times, providing a more practical and environmentally friendly approach to developing α-emitting radiotherapeutics.

Radioactive iodine labeling method

The invention discloses a radioactive iodine labeling method. Ar-B(OH)2 is allowed to react with NaI in a reaction solvent in the presence of a copper coordination compound so as to obtain Ar-I, so radioactive iodine labeling is realized. The method

RADIOHALIDE-LABELED TARGETED DIAGNOSTICS AND THERAPEUTICS

Disclosed are chemical entities of formula (I) wherein R1, R2 and n are defined herein, and methods of use thereof. These chemical entities are radiative emitters and are useful, e.g., as therapeutic agents for the treatment of, or as diagnostic (e.g., imaging) agents for cancers, e.g., cancers in which PARP1 is overexpressed.

A Highly Efficient Copper-Mediated Radioiodination Approach Using Aryl Boronic Acids

A convenient and quantitative radioiodination method by copper-mediated cross-coupling of aryl boronic acids was developed. The mild labeling conditions, ready availability of the boronic acid substrate, simple operation, broad functional group tolerance and excellent radiochemical yield (RCY) make this a practical strategy for radioiodine labeling without further purification.

Synthesis and evaluation of radioiodinated acyloxymethyl ketones as activity-based probes for cathepsin B

Dipeptidyl (acyloxy)methyl ketones (AOMKs) were functionalized with different iodine-containing prosthetic groups to generate a library of candidate cathepsin B probes. Compound 23a, (S)-20-[(S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-1-(4-iod

Ligand-free palladium-mediated site-specific protein labeling inside gram-negative bacterial pathogens

Palladium, a key transition metal in advancing modern organic synthesis, mediates diverse chemical conversions including many carbon-carbon bond formation reactions between organic compounds. However, expanding palladium chemistry for conjugation of biomolecules such as proteins, particularly within their native cellular context, is still in its infancy. Here we report the site-specific protein labeling inside pathogenic Gram-negative bacterial cells via a ligand-free palladium-mediated cross-coupling reaction. Two rationally designed pyrrolysine analogues bearing an aliphatic alkyne or an iodophenyl handle were first encoded in different enteric bacteria, which offered two facial handles for palladium-mediated Sonogashira coupling reaction on proteins within these pathogens. A GFP-based bioorthogonal reaction screening system was then developed, allowing evaluation of both the efficiency and the biocompatibilty of various palladium reagents in promoting protein-small molecule conjugation. The identified simple compound-Pd(NO3) 2 exhibited high efficiency and biocompatibility for site-specific labeling of proteins in vitro and inside living E. coli cells. This Pd-mediated protein coupling method was further utilized to label and visualize a Type-III Secretion (T3S) toxin-OspF in Shigella cells. Our strategy may be generally applicable for imaging and tracking various virulence proteins within Gram-negative bacterial pathogens.