Formation and stability of a nitric oxide donor: S-nitroso-N-acetylpenicillamine

The Journal of Physical Chemistry. B
Itai Chipinda, Reuben H Simoyi

Abstract

The formation, reaction dynamics, and detailed kinetics and mechanism of the reaction between nitrous acid and N-acetylpenicillamine (NAP) to produce S-nitroso-N-acetylpenicillamine (SNAP) was studied in acidic medium. The nitrous acid was prepared in situ by the rapid reaction between sodium nitrite and hydrochloric acid. The reaction is first order in nitrite and NAP. It is also first order in acid in pH conditions at or slightly higher than the pK(a) of nitrous acid. In lower pH conditions, the catalytic effect of acid quickly saturates. Higher acid concentrations also induce a faster decomposition rate of the SNAP, thus precluding the quantitative formation of SNAP from HNO2 and NAP. Both HPLC and quadrupole time-of-flight mass spectrometry techniques proved that SNAP was the sole product produced. No nitrosation occurred on the secondary amine center in NAP, and only the thiol group reacted to form the nitrosothiol. Cu(I) ions were found to be effective SNAP-decomposition catalysts. Cu(II) ions had no effect on the stability of SNAP. Ambient oxygen in reaction solutions was found to have no effect on initial rates of formation of SNAP, products obtained, and stability of SNAP. The formation of SNAP occurs through two disti...Continue Reading

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Citations

Aug 19, 2007·Nitric Oxide : Biology and Chemistry·Jean-François RoyAnn M English
Aug 6, 2016·International Journal of Polymeric Materials·Marcus J GoudieHitesh Handa
Nov 4, 2016·Journal of Biomedical Materials Research. Part a·Marcus J GoudieHitesh Handa
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Mar 11, 2021·Biomaterials Science·Manjyot Kaur ChugElizabeth J Brisbois
Jul 30, 2010·The Journal of Physical Chemistry. B·Moshood K MorakinyoReuben H Simoyi
Mar 10, 2011·The Journal of Physical Chemistry. B·Ernesto E MoranAnn M English
Nov 25, 2021·ACS Applied Materials & Interfaces·Mark GarrenHitesh Handa

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