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N-(4-Hydroxyphenyl)acetamide against diiodine towards polyiodide dianion

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Abstract

The direct reaction of N-(4-hydroxyphenyl)acetamide or paracetamol (C8H9NO2, PACET), a widely used Non Steroidal Anti-Inflammatory Drug (NSAID), with diiodine forms an ionic salt with the formula {[(PACET)2H+]2·(I8)2−} (1) with the simultaneous reduction of iodine to iodide. The compound was characterized by X-ray diffraction analysis. Compound 1 contains the polyiodide (I8)2− counter dianions, in a z-shape conformation. By taking into account secondary I⋯I interaction the shape turns out to be rectangular. Moreover, N-(4-hydroxyphenyl)acetamide inhibits the catalytic activity of horse radish peroxidase (HRP) (a model of thyroid peroxidase (TPO)) on the oxidation of iodides to diiodine by hydrogen peroxide, as evidence of the kinetic and computational studies. The inhibition activity of PACET against the catalytic oxidation of iodides by H2O2 in the presence of FeTPPCl (a model of the active site of TPO) is measured as a result of the yield of I3.

Graphical abstract: N-(4-Hydroxyphenyl)acetamide against diiodine towards polyiodide dianion

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Publication details

The article was received on 05 Apr 2017, accepted on 22 May 2017 and first published on 22 May 2017


Article type: Paper
DOI: 10.1039/C7NJ01117B
Citation: New J. Chem., 2017, Advance Article
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    N-(4-Hydroxyphenyl)acetamide against diiodine towards polyiodide dianion

    C. N. Banti, N. Kourkoumelis, C. P. Raptopoulou, V. Psycharis and S. K. Hadjikakou, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01117B

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