Literature DB >> 23489625

Piloty's acid derivative with improved nitroxyl-releasing characteristics.

Kazuyuki Aizawa1, Hidehiko Nakagawa, Kazuya Matsuo, Kodai Kawai, Naoya Ieda, Takayoshi Suzuki, Naoki Miyata.   

Abstract

Recent studies have shown that nitroxyl (HNO) ((1)HNO/(3)NO(-)), which is the one-electron-reduced form of nitric oxide (NO), has unique biological activities, especially in the cardiovascular system, and HNO-releasing agents may have therapeutic potential. Since few HNO donors are available for use under physiological conditions, we synthesized and evaluated a series of Piloty's acid (PA) derivatives and evaluated their HNO-releasing activity under physiological conditions. N-Hydroxy-2-nitrobenzenesulfonamide (17) was the most efficient HNO donor among our synthesized PA derivatives, including the lead compound, 2-bromo-N-hydroxybenzenesulfonamide (2). The high HNO-releasing activity is suggested to be due to electronic and steric effects. Compound 17 may be a useful tool for biological experiments.
Copyright © 2013 Elsevier Ltd. All rights reserved.

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Year:  2013        PMID: 23489625     DOI: 10.1016/j.bmcl.2013.02.062

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  9 in total

Review 1.  Recent advances in the chemical biology of nitroxyl (HNO) detection and generation.

Authors:  Zhengrui Miao; S Bruce King
Journal:  Nitric Oxide       Date:  2016-04-20       Impact factor: 4.427

2.  A selective phosphine-based fluorescent probe for nitroxyl in living cells.

Authors:  Zhengrui Miao; Julie A Reisz; Susan M Mitroka; Jia Pan; Ming Xian; S Bruce King
Journal:  Bioorg Med Chem Lett       Date:  2014-11-21       Impact factor: 2.823

3.  A Mononuclear, Nonheme FeII-Piloty's Acid (PhSO2NHOH) Adduct: An Intermediate in the Production of {FeNO}7/8 Complexes from Piloty's Acid.

Authors:  Alex M Confer; Avery C Vilbert; Aniruddha Dey; Kyle M Lancaster; David P Goldberg
Journal:  J Am Chem Soc       Date:  2019-04-17       Impact factor: 15.419

4.  Ring expansions of acyloxy nitroso compounds.

Authors:  Mallinath B Hadimani; Rajeswari Mukherjee; Ranjan Banerjee; Mai E Shoman; Omar M Aly; S Bruce King
Journal:  Tetrahedron Lett       Date:  2015-10-21       Impact factor: 2.415

5.  Synthesis of Nitric Oxide Donors Derived from Piloty's Acid and Study of Their Effects on Dopamine Secretion from PC12 Cells.

Authors:  Daniele Sanna; Gaia Rocchitta; Maria Serra; Marcello Abbondio; Pier Andrea Serra; Rossana Migheli; Lidia De Luca; Eugenio Garribba; Andrea Porcheddu
Journal:  Pharmaceuticals (Basel)       Date:  2017-09-05

6.  Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic C-Nucleophiles.

Authors:  Angelika Artelska; Monika Rola; Michał Rostkowski; Marlena Pięta; Jakub Pięta; Radosław Michalski; Adam Bartłomiej Sikora
Journal:  Int J Mol Sci       Date:  2021-11-30       Impact factor: 5.923

7.  Para-Substituted O-Benzyl Sulfohydroxamic Acid Derivatives as Redox-Triggered Nitroxyl (HNO) Sources.

Authors:  Yueming Long; Zijun Xia; Allison M Rice; S Bruce King
Journal:  Molecules       Date:  2022-08-19       Impact factor: 4.927

8.  Induction of caveolin-3/eNOS complex by nitroxyl (HNO) ameliorates diabetic cardiomyopathy.

Authors:  Hai-Jian Sun; Si-Ping Xiong; Zhi-Yuan Wu; Lei Cao; Meng-Yuan Zhu; Philip K Moore; Jin-Song Bian
Journal:  Redox Biol       Date:  2020-03-05       Impact factor: 11.799

9.  Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH.

Authors:  Renata Smulik-Izydorczyk; Karolina Dębowska; Michał Rostkowski; Jan Adamus; Radosław Michalski; Adam Sikora
Journal:  Cell Biochem Biophys       Date:  2021-05-05       Impact factor: 2.194

  9 in total

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