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

Gaurav 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

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14 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)70-78
Number of pages9
JournalNitric Oxide - Biology and Chemistry
Volume42
DOIs
StatePublished - Nov 15 2014

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Keywords

  • Angeli's salt
  • Diazeniumdiolate
  • IPA/NO
  • Nitric oxide
  • Nitroxyl
  • Tamoxifen

ASJC Scopus subject areas

  • Biochemistry
  • Physiology
  • Clinical Biochemistry
  • Cancer Research

Cite this

Bharadwaj, G., Benini, P. G. Z., Basudhar, D., Ramos-Colon, C. N., Johnson, G. M., Larriva, M. M., Keefer, L. K., Andrei, D., & Miranda, K. M. (2014). Analysis of the HNO and NO donating properties of alicyclic amine diazeniumdiolates. Nitric Oxide - Biology and Chemistry, 42, 70-78. https://doi.org/10.1016/j.niox.2014.08.013