Nitroxyl (HNO) donors have been shown to elicit a variety of pharmacological responses, ranging from tumoricidal effects to treatment of heart failure. Isopropylamine-based diazeniumdiolates have been shown to produce HNO on decomposition under physiological conditions. Herein, we report the synthesis and HNO release profiles of primary alicyclic amine-based diazeniumdiolates. These compounds extend the range of known diazeniumdiolate-based HNO donors. Acetoxymethyl ester-protected diazeniumdiolates were also synthesized to improve purification and cellular uptake. The acetoxymethyl derivative of cyclopentylamine diazeniumdiolate not only showed higher cytotoxicity toward cancer cells as compared to the parent anion but was also effective in combination with tamoxifen for targeting estrogen receptor α-negative breast cancer cells.
Nitroxyl (n class="Chemical">HNO) donors have been shown to elicit a variety of pharmacological responses, ranging from tumoricidal effects to treatment of heart failure. Isopropylamine-based diazeniumdiolates have been shown to produce HNO on decomposition under physiological conditions. Herein, we report the synthesis andHNO release profiles of primary alicyclic amine-based diazeniumdiolates. These compounds extend the range of known diazeniumdiolate-based HNOdonors. Acetoxymethyl ester-protected diazeniumdiolates were also synthesized to improve purification and cellular uptake. The acetoxymethyl derivative of cyclopentylamine diazeniumdiolate not only showed higher cytotoxicity toward cancer cells as compared to the parent anion but was also effective in combination with tamoxifen for targeting estrogen receptor α-negative breast cancer cells.
Authors: Antti J Väänänen; Pertteli Salmenperä; Mika Hukkanen; Pekka Rauhala; Esko Kankuri Journal: Free Radic Biol Med Date: 2006-05-04 Impact factor: 7.376
Authors: Ryan J Holland; Rika Paulisch; Zhao Cao; Larry K Keefer; Joseph E Saavedra; Sonia Donzelli Journal: Nitric Oxide Date: 2013-10-11 Impact factor: 4.427
Authors: Joseph E Saavedra; D Scott Bohle; Kamilah N Smith; Clifford George; Jeffrey R Deschamps; Damon Parrish; Joseph Ivanic; Yan-Ni Wang; Michael L Citro; Larry K Keefer Journal: J Am Chem Soc Date: 2004-10-13 Impact factor: 15.419
Authors: H Kojima; N Nakatsubo; K Kikuchi; S Kawahara; Y Kirino; H Nagoshi; Y Hirata; T Nagano Journal: Anal Chem Date: 1998-07-01 Impact factor: 6.986
Authors: Debashree Basudhar; Lisa A Ridnour; Robert Cheng; Aparna H Kesarwala; Julie Heinecke; David A Wink Journal: Coord Chem Rev Date: 2016-01-01 Impact factor: 22.315