Decomposition of Piloty's acid derivatives – Toward the understanding of factors controlling HNO release

• Published in: Archives of biochemistry and biophysics Vol. 661; pp. 132 - 144
• Main Authors: Smulik-Izydorczyk, Renata, Rostkowski, Michał, Gerbich, Angelika, Jarmoc, Dominika, Adamus, Jan, Leszczyńska, Agnieszka, Michalski, Radosław, Marcinek, Andrzej, Kramkowski, Karol, Sikora, Adam
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01.01.2019
• Subjects: Angeli's salt; Azanone; N-hydroxysulfonamides; Nitroxyl; Piloty's acid; Platelets; Thrombosis; Nitroxyl; Piloty's acid; N-hydroxysulfonamides; 2-CF3PhSO2; Thrombosis; 2-ClPhSO2; Azanone; dtpa; 2-BrPA; PA; AS; o-MitoPhNO2; 2-CF3PA; cyclo-o-MitoPh; o-MitoPhB(OH)2; Angeli's salt; 2-ClPA; o-MitoPhOH; Platelets; 2-BrPhSO2; PC1
• ISSN: 0003-9861; 1096-0384
• DOI: 10.1016/j.abb.2018.11.012

The recent interest in the clinical applications of Piloty's acid derivatives as HNO donors for the treatment of cardiovascular system dysfunction has led us to the examination of factors controlling HNO release from selected ortho-substituted N-hydroxysulfonamides. Here we present the kinetic and quantum mechanical studies on the mechanism of HNO release from selected ortho-substituted N-hydroxysulfonamides and in vivo examination of the antiaggregatory properties of N-hydroxy-(2-bromobenzene)sulfonamide complex with sodium salt of β-cyclodextrin sulfobutyl ethers-ethyl ethers as compared with Angeli's salt. [Display omitted] •Kinetic characterization of ortho-substituted Piloty's acid derivatives is shown.•DFT calculations helped to understand the effects exerted by substituents.•Antithrombotic activity of 2-BrPA and Angeli's salt in vivo is studied.