EDTA bis-(methyl tyrosinate): a chelating peptoid peroxynitrite scavenger.
Conjugation of ethylenediaminetetra-acetic acid (EDTA) to methyl tyrosinate generates a chelating peptoid EDTA bis-(methyl tyrosinate), (EBMT). Peroxynitrite-mediated nitration was studied for the free peptoid and its ferric and cupric complexes. The nitration products were monitored by electronic absorption spectroscopy at lambda(max) of 420 nm (mono-nitrated) and 440 nm (di-nitrated). Peak deconvolution was effected by pH manipulation as the mono-nitrated analogue of tyrosine exhibited a bathochromic shift from 365 nm (below its pK(a) of 6.8) to 420 nm. Rates of nitration were: free peptoid <Cu(II) complex <<Fe(III) complex. These results demonstrate the potential of EBMT to act as a radical scavenging chelating peptoid antioxidant.
School of Pharmacy and Biomolecular Sciences, University of Brighton, Cockcroft Building, Moulsecoomb, UK.
Anna E O
AE
Fisher
Declan P
DP
Naughton
D002614:Chelating Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D004492:Edetic Acid / Q000737:chemistry; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007249:Inflammation / Q000188:drug therapy; D007501:Iron / Q000737:chemistry; D007700:Kinetics; D008781:Methyltyrosines / Q000737:chemistry; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry; D030421:Peroxynitrous Acid / Q000737:chemistry*; D013057:Spectrum Analysis
D002614:Chelating Agents; D016166:Free Radical Scavengers; D008781:Methyltyrosines; D034444:Peptoids; D030421:Peroxynitrous Acid; D003300:Copper; D004492:Edetic Acid; D007501:Iron