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Usage

Uses

Used in Bioconjugation Applications:
Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS is used as a bioconjugation agent for the attachment of proteins, peptides, and other biomolecules. Its maleimide group reacts specifically with thiol groups, enabling the formation of stable covalent bonds between the compound and target molecules.
Used in Crosslinking Applications:
In crosslinking applications, Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS is used to form covalent bonds between molecules, such as proteins or peptides, to create stable complexes. The reactivity of the maleimide group with thiol-containing molecules allows for the efficient formation of these crosslinks.
Used in Targeted Drug Delivery Systems:
Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS is used as a component in the development of targeted drug delivery systems. Its ability to form covalent bonds with biomolecules allows for the attachment of therapeutic agents to specific targeting ligands, enabling the selective delivery of drugs to desired cellular or tissue targets.
Used in Biotechnology Applications:
In the biotechnology industry, Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid-NHS is employed for various applications, including the creation of biosensors, the development of immunoassays, and the fabrication of biocompatible materials. Its versatility and reactivity make it a valuable tool for a wide range of biotechnological applications.

Upstream product

• 108-31-6 maleic anhydride 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 1197-18-8 trans-4-aminomethyl-cyclohexyl-carboxylic acid 
• 69907-68-2 trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid 
• 5672-89-9 N-trifluoroacetoxy succinimide 
• 69907-67-1 (1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carboxylic acid 
• 953817-12-4 C₁₂H₁₇NO₅ 
• 1337538-63-2 trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate 

Downstream Products

• 1292779-17-9 cyclo(L-Arginyl-glycyl-L-asparagyl-D-phenylalanyl-L-[εN-(trans-[4-(1-maleimido)methyl]cyclohexylcarbonyl)]lysine) trifluoroacetate 
• 1337538-59-6 C₂₂H₂₉N₃O₇ 
• 1337538-58-5 6-((1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxamido)hexanoic acid 

Relevant academic research and scientific papers

Rapid Diels-Alder Cross-linking of Cell Encapsulating Hydrogels

Recent efforts in the design of hydrogel biomaterials have focused on better mimicking the native cellular microenvironment to direct cell fate. To simultaneously control multiple material parameters, several orthogonal chemistries may be needed. However, present strategies to prepare cell-encapsulating hydrogels make use of relatively few chemical reactions. To expand this chemical toolkit, we report the preparation of hydrogels based on a Diels-Alder reaction between fulvenes and maleimides with markedly improved gelation kinetics and hydrolytic stability. Fulvene-maleimide gels cross-link up to 10-times faster than other commonly used DA reaction pairs and remain stable for months under physiological conditions. Furthermore, fulvene-maleimide gels presenting relevant biochemical cues, such as cell-adhesive ligands and proteolytic degradability, support the culture of human mesenchymal stromal cells. Finally, this rapid DA reaction was combined with an orthogonal click reaction to demonstrate how the use of selective chemistries can provide new avenues to incorporate multiple functionalities in hydrogel materials.

Refining method of SMCC

The invention relates to the purification/refining of a compound, and specifically discloses a refining method of SMCC. The refining method disclosed by the invention comprises the following steps: taking acetonitrile as the solvent of a SMCC crude produc

PHARMACEUTICAL COMPOSITIONS COMPRISING MACROLIDE DIASTEREOMERS, METHODS OF THEIR SYNTHESIS AND THERAPEUTIC USES

The disclosure relates to compositions comprising diastereomer of a macrolide exhibiting improved therapeutic profile in the context of inhibiting cell proliferation compared to the corresponding compositions comprising mixture of diastereomers. The discl

Azide-alkyne cycloaddition for universal post-synthetic modifications of nucleic acids and effective synthesis of bioactive nucleic acid conjugates

The regioselective post-synthetic modifications of nucleic acids are essential to studies of these molecules for science and applications. Here we report a facile universal approach by harnessing versatile phosphoramidation reactions to regioselectively incorporate alkynyl/azido groups into post-synthetic nucleic acids primed with phosphate at the 5′ termini. With and without the presence of copper, the modified nucleic acids were subjected to azide-alkyne cycloaddition to afford various nucleic acid conjugates including a peptide-oligonucleotide conjugate (POC) with high yield. The POC was inoculated with human A549 cells and demonstrated excellent cell-penetrating ability despite cell deformation caused by a small amount of residual copper chelated to the POC. The combination of phosphoramidation and azide-alkyne cycloaddition reactions thus provides a universal regioselective strategy to post-synthetically modify nucleic acids. This study also explicated the toxicity of residual copper in synthesized bioconjugates destined for biological systems. This journal is the Partner Organisations 2014.

Synthesis and evaluation of cyclic RGD-boron cluster conjugates to develop tumor-selective boron carriers for boron neutron capture therapy

Boron-containing agents play a key role in successful boron neutron capture therapy (BNCT). Icosahedral boron cluster-Arg-Gly-Asp (RGD) peptide conjugates were designed, synthesized, and evaluated for the biodistribution to develop tumor-selective boron c

In situ formation of N-trifluoroacetoxy succinimide (TFA-NHS): One-pot formation of succinimidyl esters, N-trifluoroacetyl amino acid succinimidyl esters, and N-maleoyl amino acid succinimidyl esters

A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.

Convenient preparation of N-maleoyl amino acid succinimido esters using N-trifluoroacetoxysuccinimide

One-pot cyclization and esterification of readily available maleamic acid derivatives using N-trifluoroacetoxysuccinimide provide a convenient and cost-effective route to a variety of useful N-maleoyl amino acid N-hydroxysuccinimido esters. Copyright Taylor & Francis Group, LLC.

Facile synthesis of reagents containing a terminal maleimido ligand linked to an active ester

Condensation of ω-amino acids with maleic anhydride to yield maleamino acids and subsequent esterification with N-hydroxysuccinimide, 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, or pentafluorophenol to give the corresponding esters in a one pot procedure are described. The reagents can be isolated and purified without chromatography in 7-55% yields.