As a common feature, only N(2) and N(2)O were found as gaseous, nitrogen-containing oxidation products, while NH(3) was the unique reduced species detected. Efficient catalytic processes leading to the disproportionation of HA by these iron(III) porphyrinates were evidenced for the first time. The reactions of hydroxylamine (HA) with several water-soluble iron(III) porphyrinate compounds, namely iron(III) meso-tetrakis-(N-ethylpyridinium-2yl)- porphyrinate ((5+)), iron(III) meso-tetrakis-(4-sulphonatophenyl)- porphyrinate ((3-)), and microperoxidase 11 () were studied for different / ratios, under anaerobic conditions at neutral pH.
PMID:16704201ĭisproportionation of hydroxylamine by water-soluble iron(III) porphyrinate compounds.īari, Sara E Amorebieta, ValentÃn T Gutiérrez, MarÃa M Olabe, José A Doctorovich, Fabio Taken together, this work enables preparation of useful quantities of water-soluble, bioconjugatable porphyrins in a compact architecture for applications in the life sciences. The resulting conjugate performed comparably to a commercially available fluorescein isothiocyanate-labeled antibody with Jurkat cells in flow cytometry and fluorescence microscopy assays. Covalent attachment was carried out in aqueous solution with the unprotected porphyrin diphosphonate and a monoclonal antibody against the T-cell receptor CD3ε. The six such porphyrins reported here are highly water-soluble (≥20 mM at room temperature in water at pH 7) as determined by visual inspection, UV–vis absorption spectroscopy, or 1H NMR spectroscopy. A 4-(carboxymethyloxy)phenyl group provides the bioconjugatable tether.
The two hydroxy groups in the swallowtail motif of each of the resulting zinc porphyrins can be transformed to the corresponding diphosphate or diphosphonate product. The incorporation of the swallowtail motif relies on rational synthetic methods whereby a 1,9-bis(N-propylimino)dipyrromethane (bearing a bioconjugatable tether at the 5-position) is condensed with a dipyrromethane (bearing a protected 1,5-dihydroxypent-3-yl unit at the 5-position). Such “swallowtail†motifs bearing a polar group (hydroxy, dihydroxyphosphoryl, dihydroxyphosphoryloxy) at the terminus of each branch have now been incorporated at a meso site in trans-AB- porphyrins. Branched alkyl groups attached at the branching site to the porphyrin meso position are known to impart high organic solubility.
Lindsey, Jonathan S.Ī broad range of applications requires access to water-soluble, bioconjugatable porphyrins. Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubilityīorbas, K.
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