Characterization of diazeniumdiolate nitric oxide donors by electrospray ionization mass spectrometry

ANYL 316

Edgardo Rivera-Tirado, er12@uakron.edu1, Marcos Lopez, marcoslopez@mcw.edu2, Daniel J. Smith, djs5@uakron.edu1, and Chrys Wesdemiotis, wesdemiotis@uakron.edu1. (1) Department of Chemistry, The University of Akron, Knight Chemical Laboratory, 190 E. Buchtel Commons, Akron, OH 44325-3601, (2) Free Radical Research Center and Department of Biophysics, Medical College of Wisconsin, 8701 Watertown Plank Rd, Milwaukee, WI 53226
Diazeniumdiolates, commonly known as NONOates, have been widely used in biomedical research due to their ability to release nitric oxide (NO) spontaneously under physiological conditions. In spite of the widespread use of such compounds in biological studies, their mass spectrometry characterization has been challenging, due to their instability and spontaneous NO release. In order to understand the reactivity of these types of compounds, the gas phase chemistry of diazeniumdiolate ions was investigated using electrospray ionization mass spectrometry (ESI-MS) and diazeniumdiolate samples that are commercially available (i.e. Diethylamine NONOate, DETA NONOate, Spermine NONOate, Angeli's Salt, MAHMA NONOate, PROLI NONOate, Dipropylenetriamine NONOate, PAPA NONOate, and Sulpho NONOate). Our results demonstrate that ESI-MS, along with tandem mass spectrometry (MS/MS), provides both information about the intrinsic chemistry of diazeniumdiolate ions as well as a means for their structural characterization.