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N-(Methyltetrazine-PEG4)-amido-PEG8-3,4-dithiophenolmaleimide
| Catalog Number | R08-0017 |
| Category | Tetrazines |
| Molecular Formula | C52H70N6O15S2 |
| Molecular Weight | 1083.3 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
N-(Methyltetrazine-PEG4)-amido-PEG8-3,4-dithiophenolmaleimide is a heterobifunctional reagent that integrates a methyltetrazine moiety with a maleimide group, linked via polyethylene glycol (PEG) spacers. This compound participates in bioorthogonal chemistry, specifically enabling inverse electron-demand Diels–Alder reactions with trans-cyclooctene-modified biomolecules, alongside thiol-reactive maleimide conjugation pathways. Its dual reactivity is utilized in bioconjugation strategies, facilitating the selective labeling and surface modification of proteins and other macromolecules.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| IUPAC Name | 3-[2-[2-[2-[2-[2-[2-[2-[2-[2,5-dioxo-3,4-bis(phenylsulfanyl)pyrrol-1-yl]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-N-[2-[2-[2-[2-[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethyl]propanamide |
| SMILES | CC1=NN=C(N=N1)C2=CC=C(C=C2)OCCOCCOCCOCCNC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCN3C(=O)C(=C(C3=O)SC4=CC=CC=C4)SC5=CC=CC=C5 |
| InChI | InChI=1S/C52H70N6O15S2/c1-42-54-56-50(57-55-42)43-12-14-44(15-13-43)73-41-40-72-39-38-66-26-23-63-20-17-53-47(59)16-19-62-22-25-65-28-30-68-32-34-70-36-37-71-35-33-69-31-29-67-27-24-64-21-18-58-51(60)48(74-45-8-4-2-5-9-45)49(52(58)61)75-46-10-6-3-7-11-46/h2-15H,16-41H2,1H3,(H,53,59) |
| InChIKey | BCNQGKWIELTKTI-UHFFFAOYSA-N |
Product Specification
| Storage | -20 °C |
Application
N-(Methyltetrazine-PEG4)-amido-PEG8-3,4-dithiophenolmaleimide is a multifunctional, PEGylated click-chemistry reagent designed for bioorthogonal conjugation workflows that combine a tetrazine handle with a maleimide electrophile and a redox-active dithiophenol motif. As a tetrazine-based click component, it is commonly used to enable rapid, selective coupling to strained trans-cyclooctenes (TCO) or related strained alkenes in complex biological or biomaterials settings. The extended PEG spacers and thiol-reactive maleimide functionality support robust surface labeling, probe construction, and modular assembly of imaging or assay reagents while minimizing nonspecific interactions.
1. Cell Surface Labeling
N-(Methyltetrazine-PEG4)-amido-PEG8-3,4-dithiophenolmaleimide is used in workflows that require stable, modular labeling of cell-associated targets such as membrane proteins, surface glycoconjugates, or engineered display systems. The maleimide functionality enables conjugation to thiol-containing ligands, including reduced cysteine motifs on targeting moieties or thiol-terminated polymers, while the tetrazine element supports subsequent bioorthogonal attachment to TCO-bearing partners. PEG spacers help maintain accessibility of reactive groups on crowded surfaces, supporting reproducible probe density and improved labeling uniformity for downstream microscopy, flow-based readouts, or binding assays in research laboratories.
2. Modular Imaging Probe Assembly
N-(Methyltetrazine-PEG4)-amido-PEG8-3,4-dithiophenolmaleimide is well suited for building imaging probes where orthogonal conjugation steps are needed to combine a targeting scaffold with a reporter-bearing module. Researchers commonly use the maleimide handle to attach the reagent to thiolated dyes, nanoparticles, or polymeric carriers, and then use the tetrazine functionality to click onto TCO-functional imaging components or reporter constructs. The PEG architecture supports colloidal stability and reduces aggregation tendencies in probe formulations, which is particularly valuable when assembling multi-component fluorescent, luminescent, or photoactive imaging reagents for molecular imaging and molecular diagnostics development.
3. Biomaterials Surface Functionalization
N-(Methyltetrazine-PEG4)-amido-PEG8-3,4-dithiophenolmaleimide is applied to functionalize biomaterial surfaces and interfaces that require sequential coupling chemistry for creating bioactive coatings or patterned materials. The maleimide group enables attachment to thiol-bearing surface chemistries, including thiolated linkers, thiol-terminated hydrogels, or reduced functional layers used in materials science. After immobilization, the tetrazine handle provides a convenient entry point for later conjugation to TCO-modified biomolecules, peptides, or imaging labels, enabling iterative assembly of functional surfaces without reworking the entire material. This approach supports the creation of multivalent, spatially organized conjugates used in research-grade biomaterials characterization and assay platform development.
4. Diagnostic Reagent Conjugation Platforms
N-(Methyltetrazine-PEG4)-amido-PEG8-3,4-dithiophenolmaleimide is used to construct diagnostic and analytical reagent conjugates where controlled coupling of multiple components is critical. Laboratories often employ the maleimide functionality to incorporate the reagent into thiol-functional capture reagents, affinity ligands, or polymer carriers, and then use tetrazine-mediated click chemistry to attach a second, TCO-functional detection module such as a labeled oligonucleotide, reporter conjugate, or signal-amplifying scaffold. The PEGylated design supports consistent reagent behavior in complex assay buffers and helps reduce nonspecific interactions that can arise from densely functionalized conjugates, supporting reliable reagent assembly for assay development and analytical method optimization.
Computed Properties
| XLogP3 | 2.1 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 21 |
| Rotatable Bond Count | 45 |
| Exact Mass | 1082.43405789 g/mol |
| Monoisotopic Mass | 1082.43405789 g/mol |
| Topological Polar Surface Area | 279Ų |
| Heavy Atom Count | 75 |
| Formal Charge | 0 |
| Complexity | 1480 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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