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2,5-dioxopyrrolidin-1-yl 3-Iodo-4-methoxybenzoate

  CAS No.: 727659-89-4   Cat No.: BADC-00686 4.5  

2,5-dioxopyrrolidin-1-yl 3-Iodo-4-methoxybenzoate is an NHS ester ADC linker intermediate with iodinated aromatic group for efficient amine-reactive conjugation and enhanced payload stability in antibody-drug conjugates. Keywords: ADC linker, NHS ester, iodinated linker, amine conjugation, payload stability.

2,5-dioxopyrrolidin-1-yl 3-Iodo-4-methoxybenzoate

Structure of 727659-89-4

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ADC Linker
Molecular Formula
C12H10INO5
Molecular Weight
375.12
Shipping
-20°C (International: -20°C)

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Synonyms
(2,5-dioxopyrrolidin-1-yl) 3-iodo-4-methoxybenzoate
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 3-iodo-4-methoxybenzoate
Canonical SMILES
COC1=C(C=C(C=C1)C(=O)ON2C(=O)CCC2=O)I
InChI
InChI=1S/C12H10INO5/c1-18-9-3-2-7(6-8(9)13)12(17)19-14-10(15)4-5-11(14)16/h2-3,6H,4-5H2,1H3
InChIKey
QAMPCDXKSWCNNT-UHFFFAOYSA-N
Shipping
-20°C (International: -20°C)

Protein Modification and Labeling: 2,5-Dioxopyrrolidin-1-yl 3-Iodo-4-methoxybenzoate is commonly used in protein modification and labeling because of its derivation from N-Hydroxysuccinimide (NHS) esters, which are well-known for their reactivity with primary amines in biomolecules. This compound can facilitate the attachment of various tags or probes to proteins, which is essential in biochemical assays and diagnostic applications. By enabling the conjugation of fluorescent dyes, biotin, or other molecular tags, this ester plays a crucial role in visualizing and tracking proteins in complex biological systems, thereby aiding in protein-protein interaction studies, enzymatic activity assays, and the development of biosensors. Additionally, the functionalization of proteins with these tags can also facilitate their purification and separation using affinity chromatography.

Peptide Synthesis: In the field of peptide synthesis, 2,5-dioxopyrrolidin-1-yl 3-iodo-4-methoxybenzoate serves as an effective reagent for creating active esters essential in forming peptide bonds. NHS esters, including this compound, are frequently utilized to activate carboxyl groups, making them more reactive toward amines. This activation is crucial in solid-phase peptide synthesis (SPPS), where the ester facilitates the coupling of amino acids, contributing to the efficient assembly of peptide chains. The ability to form stable intermediates that can be easily purified and stored enhances the overall efficiency and reliability of the peptide synthesis process, enabling the production of high-purity peptides for pharmaceutical research, therapeutic applications, and structural biology studies.

Drug Development and Delivery: The unique chemical properties of 2,5-dioxopyrrolidin-1-yl 3-iodo-4-methoxybenzoate make it an important compound in drug development and delivery strategies. This ester can be employed to modify drug molecules, improving their pharmacokinetic properties such as solubility, stability, and bioavailability. By attaching various drug carriers or targeting moieties (like antibodies or peptides), this compound facilitates the development of targeted drug delivery systems. These systems enhance the therapeutic index of drugs by concentrating their action at the diseased site while minimizing off-target effects, which is particularly beneficial in cancer therapy and treatments for chronic diseases. Moreover, the use of this ester in prodrug design allows for the controlled release of active pharmaceutical ingredients, optimizing their therapeutic efficacy.

Biosensor Development: In the realm of biosensor technology, 2,5-dioxopyrrolidin-1-yl 3-iodo-4-methoxybenzoate is invaluable for the immobilization of enzymes and other biomolecules on sensor surfaces. When coupled with carbodiimide reagents like EDC, this ester forms stable covalent bonds with enzyme amine groups, anchoring them to sensor substrates. This immobilization ensures that the biological recognition elements retain their activity and are oriented correctly on the sensor surface, crucial for the accurate detection of target analytes. Biosensors developed using this ester are applied in various fields, including medical diagnostics, environmental monitoring, and food safety. The precise and sensitive detection capabilities of these biosensors are vital for early disease diagnosis, real-time monitoring of environmental pollutants, and ensuring the safety and quality of food products.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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