764701
2,5-Dioxo-1-pyrrolidinyl 5-[4-(1,2,4,5-tetrazin-3-yl)benzylamino]-5-oxopentanoate
≥90%
Synonym(s):
5-Oxo-5-[[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]amino]pentanoic acid 2,5-dioxo-1-pyrrolidinyl ester, Benzylamino tetrazine N-hydroxysuccinimidyl ester, Benzylaminotetrazine-NHS, Bz-Tz-NHS
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About This Item
Empirical Formula (Hill Notation):
C18H18N6O5
CAS Number:
Molecular Weight:
398.37
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22
Assay:
≥90%
Form:
solid
assay
≥90%
form
solid
reaction suitability
reaction type: click chemistry, reagent type: linker
functional group
NHS ester
storage temp.
−20°C
SMILES string
O=C(CCCC(ON1C(CCC1=O)=O)=O)NCC(C=C2)=CC=C2C3=NN=CN=N3
InChI
1S/C18H18N6O5/c25-14(2-1-3-17(28)29-24-15(26)8-9-16(24)27)19-10-12-4-6-13(7-5-12)18-22-20-11-21-23-18/h4-7,11H,1-3,8-10H2,(H,19,25)
InChI key
QDUUJWMNSUXICN-UHFFFAOYSA-N
Application
2,5-Dioxo-1-pyrrolidinyl 5-[4-(1,2,4,5-tetrazin-3-yl)benzylamino]-5-oxopentanoate may be used in the synthesis of Tz-PEG11-1,4,7-triazacyclononane-N,N,N-triacetate, a precursor for Al[18F]-NOTA-labeled tetrazine radio ligand useful in 18F-based pretargeted PET imaging system.
Succinimidyl ester functionalized tetrazine for inverse electron demand Diels-Alder cycloaddition reactions. Succinimidyl ester will react with amines for small molecule, biomolecule or surface modification. Tetrazine will react with strained alkenes such as transcyclooctene, norbornene and cyclopropene to yield a stable covalent linkage. Tetrazines have proven useful in bioorthogonal reactions for many biological imaging and bioconjugation applications.
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18F-Based Pretargeted PET Imaging Based on Bioorthogonal Diels?Alder Click Chemistry
Meyer JP, et al.
Bioconjugate Chemistry, 27(2), 298-301 (2015)
Specific Binding of Liposomal Nanoparticles through Inverse Electron?Demand Diels?Alder Click Chemistry.
Brand C, et al.
ChemistryOpen null
Rosemery Membreno et al.
Journal of visualized experiments : JoVE, (143) (2019-02-19)
While radioimmunotherapy (RIT) is a promising approach for the treatment of cancer, the long pharmacokinetic half-life of radiolabeled antibodies can result in high radiation doses to healthy tissues. Perhaps not surprisingly, several different strategies have been developed to circumvent this
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 764701-5MG | 04061833231067 |
| 764701-1MG | 04061826701652 |
| 764701-25MG | 04061833231050 |