Journal
NITRIC OXIDE-BIOLOGY AND CHEMISTRY
Volume 42, Issue -, Pages 70-78Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.niox.2014.08.013
Keywords
Nitroxyl; Nitric oxide; Diazeniumdiolate; IPA/NO; Angeli's salt; Tamoxifen
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Funding
- Intramural NIH HHS Funding Source: Medline
- NIGMS NIH HHS [R01 GM076247, R01-GM076247] Funding Source: Medline
- NATIONAL CANCER INSTITUTE [ZIABC005673] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM076247] Funding Source: NIH RePORTER
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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 alpha-negative breast cancer cells. (C) 2014 Elsevier Inc. All rights reserved.
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