2,5-Dioxopyrrolidin-1-Yl 4-Methyl-4-((2-Methyl-5-Oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-Yl)disulfanyl)pentanoate - CAS 1286715-33-0

2,5-Dioxopyrrolidin-1-Yl 4-Methyl-4-((2-Methyl-5-Oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-Yl)disulfanyl)pentanoate - CAS 1286715-33-0 Catalog number: BADC-00580

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2, 5-Dioxopyrrolidin-1-yl 4-methyl-4-((2-methyl-5-oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-yl)disulfanyl)pentanoate is a linker for antibody-drug-conjugation (ADC).

Category
ADCs Linker
Product Name
2,5-Dioxopyrrolidin-1-Yl 4-Methyl-4-((2-Methyl-5-Oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-Yl)disulfanyl)pentanoate
CAS
1286715-33-0
Catalog Number
BADC-00580
Molecular Formula
C21H37NO6S2Si
Molecular Weight
491.74
2,5-Dioxopyrrolidin-1-Yl 4-Methyl-4-((2-Methyl-5-Oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-Yl)disulfanyl)pentanoate

Ordering Information

Catalog Number Size Price Quantity
BADC-00580 -- $-- Inquiry
Description
2, 5-Dioxopyrrolidin-1-yl 4-methyl-4-((2-methyl-5-oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-yl)disulfanyl)pentanoate is a linker for antibody-drug-conjugation (ADC).
Synonyms
2-trimethylsilylethyl 4-[[5-(2,5-dioxopyrrolidin-1-yl)oxy-2-methyl-5-oxopentan-2-yl]disulfanyl]-4-methylpentanoate
Canonical SMILES
CC(C)(CCC(=O)OCC[Si](C)(C)C)SSC(C)(C)CCC(=O)ON1C(=O)CCC1=O
InChI
InChI=1S/C21H37NO6S2Si/c1-20(2,12-10-18(25)27-14-15-31(5,6)7)29-30-21(3,4)13-11-19(26)28-22-16(23)8-9-17(22)24/h8-15H2,1-7H3
InChIKey
JZRMFTBOKQUORG-UHFFFAOYSA-N
Shipping
Room temperature, or blue ice upon request.

One of the primary applications of 2,5-Dioxopyrrolidin-1-Yl 4-Methyl-4-((2-Methyl-5-Oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-Yl)disulfanyl)pentanoate is in the field of bioconjugation. This compound is frequently used as a linker in the conjugation of biological molecules such as peptides, proteins, and nucleotides. The presence of the N-hydroxysuccinimide (NHS) ester group allows for high efficiency in forming stable amide bonds with primary amines found in biomolecules. This ability to form covalent attachments under mild conditions makes it invaluable in creating targeted drug delivery systems, biosensors, and diagnostic tools.

Another significant application is in the synthesis of prodrugs. In medicinal chemistry, this compound can be utilized to modify active pharmaceutical ingredients (APIs) in a way that enhances their pharmacokinetic properties, including bioavailability and solubility. The disulfide linkage in the structure serves as a strategic point of modification, often breaking down in the reducing environment of the intracellular space to release the active drug. This property makes it a vital component in the development of sophisticated prodrug systems that improve the therapeutic index of pharmaceuticals.

In materials science, 2,5-Dioxopyrrolidin-1-Yl 4-Methyl-4-((2-Methyl-5-Oxo-5-(2-(trimethylsilyl)ethoxy)pentan-2-Yl)disulfanyl)pentanoate finds application as a crosslinking agent. Its ability to form stable covalent bonds under mild conditions makes it perfect for linking polymers to form hydrogels and other polymeric networks. These materials are extensively used in drug delivery, tissue engineering, and wound healing applications. The controlled release of therapeutics and the creation of biocompatible scaffolds for tissue regeneration are just some of the critical contributions of this compound to advanced materials science.

Lastly, this compound plays a crucial role in the development of antibody-drug conjugates (ADCs). ADCs are a class of highly potent biopharmaceutical drugs designed as a targeted cancer therapy. By acting as a linker, this compound ensures that the cytotoxic drug remains attached to the antibody until it reaches the tumor cell. Upon internalization by the cancer cell, the disulfide bond is reduced, releasing the cytotoxic agent. This targeted delivery minimizes the adverse effects on healthy cells and enhances the therapeutic efficacy against cancerous cells, thereby representing a sophisticated approach to cancer treatment.

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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