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Updated: Jun 9, 2026

Analytical Techniques for Assaying Nitric Oxide Bioactivity
Published on: June 18, 2012
"Click" reaction in conjunction with diazeniumdiolate chemistry: developing high-load nitric oxide donors
Oyebola A Oladeinde1, Sam Y Hong, Ryan J Holland
1Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702, USA.
Abstract:
The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO(4)/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.
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