N-(2-Aminoethyl)maleimide Trifluoroacetate Salt - CAS 146474-00-2

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A thiol-reactive cross-linking reagent.

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Molecular Formula

C8H9F3N2O4

Molecular Weight

254.16

N-(2-Aminoethyl)maleimide Trifluoroacetate Salt

- Specification
  - Appearance
    
    White powder
    
    Storage
    
    Powder, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    1-(2-aminoethyl)pyrrole-2,5-dione;2,2,2-trifluoroacetic acid
    
    Synonyms
    
    1-(2-aminoethyl)pyrrole-2,5-dione;2,2,2-trifluoroacetic acid; 1-(2-aminoethyl)pyrrole-2,5-dione;2,2,2-trifluoroacetic acid
- Properties
  - Boiling Point
    
    278.1 °C at 760 mmHg
    
    InChI Key
    
    YNHKVOGCDPODMT-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C6H8N2O2.C2HF3O2/c7-3-4-8-5(9)1-2-6(8)10;3-2(4,5)1(6)7/h1-2H,3-4,7H2;(H,6,7)
    
    Canonical SMILES
    
    C1=CC(=O)N(C1=O)CCN.C(=O)(C(F)(F)F)O
- Reference Reading
  - 1. One-pot two-step radiosynthesis of a new (18)F-labeled thiol reactive prosthetic group and its conjugate for insulinoma imaging
    
    Xuyi Yue, Xuefeng Yan, Chenxi Wu, Gang Niu, Ying Ma, Orit Jacobson, Baozhong Shen, Dale O Kiesewetter, Xiaoyuan Chen Mol Pharm. 2014 Nov 3;11(11):3875-84. doi: 10.1021/mp5001857.Epub 2014 May 12.
    
    N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)-6-fluoronicotinamide ([(18)F]FNEM), a novel prosthetic agent that is thiol-specific, was synthesized using a one-pot two-step strategy: (1) (18)F incorporation by a nucleophilic displacement of trimethylammonium substrate under mild conditions; (2) amidation of the resulting 6-[(18)F]fluoronicotinic acid 2,3,5,6-tetrafluorophenyl ester with N-(2-aminoethyl)maleimide trifluoroacetate salt. The radiosynthesis of the maleimide tracer was completed in 75 min from [(18)F]fluoride with 26 ± 5% decay uncorrected radiochemical yield, and specific activity of 19-88 GBq/μmol (decay uncorrected). The in vitro cell uptake, in vivo biodistribution, and positron emission tomography (PET) imaging properties of its conjugation product with [Cys(40)]-exendin-4 were described. [(18)F]FNEM-Cys(40)-exendin-4 showed specific targeting of glucagon-like peptide 1 receptor (GLP-1R) positive insulinomas and comparable imaging results to our recently reported [(18)F]FPenM-Cys(40)-exendin-4.

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