1244040-64-9

Usage

Uses

Used in Bioorthogonal Chemistry:
2,5-dioxopyrrolidin-1-yl 5-((4-(1,2,4,5-tetrazin-3-yl)benzyl)amino)-5-oxopentanoate is used as a bioorthogonal reagent for inverse electron demand Diels-Alder cycloaddition reactions. The tetrazinyl group within the molecule reacts with strained alkenes, such as transcyclooctene, norbornene, and cyclopropene, to form a stable covalent linkage. This property makes it a valuable tool for applications in biological imaging and bioconjugation, where the need for selective and non-disruptive labeling is crucial.
Used in Small Molecule and Biomolecule Modification:
In the field of chemical biology, 2,5-dioxopyrrolidin-1-yl 5-((4-(1,2,4,5-tetrazin-3-yl)benzyl)amino)-5-oxopentanoate is used as a modifying agent for small molecules and biomolecules. The succinimidyl ester functional group reacts with amine groups present in target molecules, allowing for the attachment of the tetrazinyl-benzyl moiety. This modification can be employed to study the function and interactions of biomolecules or to enhance the properties of small molecules in various applications.
Used in Surface Modification:
2,5-dioxopyrrolidin-1-yl 5-((4-(1,2,4,5-tetrazin-3-yl)benzyl)amino)-5-oxopentanoate is also used for surface modification, where the succinimidyl ester group can react with amine-containing surfaces, such as proteins or amine-functionalized materials. This modification can be utilized to introduce new functionalities or properties to the surface, such as improved biocompatibility, enhanced cell adhesion, or specific binding capabilities for targeted applications.

Upstream product

• 108-55-4 glutaric anhydride, 
• 74124-79-1 di(succinimido) carbonate 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 1225146-53-1 5-(4-(1,2,4,5-tetrazin-3-yl)benzylamino)-5-oxopentanoic acid 
• 15996-76-6 4-cyanobenzylamine hydrochloride 
• 1092689-33-2 (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanamine hydrochloride 
• 946852-96-6 5-(4-(cyano)benzylamino)-5-oxopentanoic acid 

Downstream Products

• 1474019-97-0 (E)-5-((5-((4-(1,2,4,5-tetrazin-3-yl)benzyl)amino)-5-oxopentanamido)methyl)-2-((2-((2,2-dimethyl-4-oxo-3,8,11,14-tetraoxa-5-azahexadecan-16-yl)oxy)-4-hydroxyphenyl)diazenyl)benzoic acid 

Relevant academic research and scientific papers

68Ga chelating bioorthogonal tetrazine polymers for the multistep labeling of cancer biomarkers

We have developed a 68Ga metal chelating bioorthogonal tetrazine dextran probe that is highly reactive with trans-cyclooctene modified monoclonal antibodies for multistep imaging applications. Confocal microscopy and positron emission tomography (PET) were used to characterize the dextran probe in vitro and in vivo. the Partner Organisations 2014.

Targeting Infiltrating Myeloid Cells in Gastric Cancer Using a Pretargeted Imaging Strategy Based on Bio-Orthogonal Diels–Alder Click Chemistry and Comparison with 89Zr-Labeled Anti-CD11b Positron Emission Tomography Imaging

Gastric cancer (GC) is a common cancer worldwide, with high incidence and mortality rates. Therefore, early and precise diagnosis is critical to improving GC prognosis. Tumor-associated myeloid cells infiltrate the tumor microenvironment (TME) and can produce immunosuppressive effects in the early stage of the tumor. The surface integrin receptor CD11b is widely expressed in the specific subsets of myeloid cells, and it has the characteristics of high abundance, high specificity, and high potential for targeted immunotherapy. In this study, two strategies for labeling anti-CD11b, including 89Zr-DFO-anti-CD11b and pretargeted imaging (68Ga-NOTA-polypeptide-PEG11-Tz/anti-CD11b-TCO), were used to evaluate the value of early diagnosis of GC and confirm the advantages of the pretargeted strategy for the diagnosis of GC. Pretargeted molecular probe 68Ga-NOTA-polypeptide-PEG11-Tz was synthesized. The binding affinity of the Tz-radioligand to CD11b was evaluated in vitro, and its blood pharmacokinetic test was performed in vivo. Moreover, the anti-CD11b antibody was conjugated with a p-isothiocyanatobenzyl-desferrioxamine (SCN-DFO) chelator and radiolabeled with zirconium-89. Biodistribution and positron-emission computed tomography imaging experiments were performed in MGC-803 tumor-bearing model mice to evaluate the value of the early diagnosis of GC. Histological evaluation of MGC-803 tumors was conducted to confirm the infiltration of the GC TME with CD11b+ myeloid cells. 68Ga-NOTA-polypeptide-PEG11-Tz was successfully radiosynthesized, with the radiochemical purity above 95%, as confirmed by reversed-phase high-performance liquid chromatography. The radioligand showed favorable stability in normal saline and phosphate-buffered saline, good affinity to RAW264.7 cells, and rapid blood clearance in mice. The results of biodistribution and imaging experiments using the pretargeted method showed that the tumor/muscle ratios were 5.17 ± 2.98, 5.94 ± 1.46, and 4.46 ± 2.73 at the pretargeting intervals of 24, 48, and 72 h, respectively. The experimental results using the method of the directly labeling antibody (89Zr-DFO-anti-CD11b) showed that, despite radioactive accumulation in the tumor, there was a higher level of radioactive accumulation in normal tissues. The tumor/muscle ratios were 1.09 ± 0.67, 1.66 ± 0.95, 2.94 ± 1.24, 3.64 ± 1.21, and 3.55 ± 1.64 at 1, 24, 48, 72, and 120 h. The current research proved the value of 68Ga-NOTA-polypeptide-PEG11-Tz/anti-CD11b-TCO in the diagnosis of GC using the pretargeted strategy. Compared to 89Zr-DFO-anti-CD11b, the image contrast achieved by the pretargeted strategy was relatively improved, and the background accumulation of the probe was relatively low. These advantages can improve the diagnostic efficiency for GC and provide supporting evidence for radioimmunotherapy targeting CD11b receptors.

Interfacial tetrazine click chemistry mediated assembly of multifunctional colloidosomes

We demonstrate that tetrazine ligation chemistry can be employed to cross-link and assemble gold nanoparticles at the water-oil interface to create plasmonic colloidosomes. These biocompatible colloidosomes exhibit size tunabilityviacontrollable ligation kinetics and display high encapsulation efficiency, size-selective permeability, and surface-enhanced Raman scattering (SERS)-based sensing modality.

COMPOSITIONS AND METHODS FOR DELIVERING A SUBSTANCE TO A BIOLOGICAL TARGET

The present application provides compositions and methods using bioorthogonal inverse electron demand Diels-Alder cycloaddition reaction for rapid and specific covalent delivery of a payload to a ligand bound to a biological target.