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Analysis of the HNO and NO donating properties of alicyclic amine diazeniumdiolates.

Abstract
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.
AuthorsGaurav Bharadwaj, Patricia G Z Benini, Debashree Basudhar, Cyf N Ramos-Colon, Gail M Johnson, Marti M Larriva, Larry K Keefer, Daniela Andrei, Katrina M Miranda
JournalNitric oxide : biology and chemistry (Nitric Oxide) Vol. 42 Pg. 70-8 (Nov 15 2014) ISSN: 1089-8611 [Electronic] United States
PMID25192820 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, N.I.H., Intramural)
CopyrightCopyright © 2014 Elsevier Inc. All rights reserved.
Chemical References
  • Azo Compounds
  • diazeniumdiolate
  • Nitric Oxide
Topics
  • Azo Compounds (chemistry)
  • Magnetic Resonance Spectroscopy
  • Nitric Oxide (metabolism)
  • Spectrophotometry, Ultraviolet

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