- Development of Photoactivatable Nitroxyl (HNO) Donors Incorporating the (3-Hydroxy-2-naphthalenyl)methyl Phototrigger
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A new family of photoactivatable HNO donors of general structure RSO2NHO-PT [where PT represents the (3-hydroxy-2-naphthalenyl)methyl (3,2-HMN) phototrigger] has been developed, which rapidly releases HNO. Photogeneration of HNO was demonstrated using the vitamin B12 derivative aquacobalamin as a trapping agent. The amount of sulfonate RSO2– produced was essentially the same as the amount of HNO released upon photolysis, providing a convenient method to indirectly quantify HNO release. Two competing pathways were also observed; a pathway involving O–N bond cleavage leading to release of a sulfonamide, and a pathway resulting in release of the parent Nhydroxysulfonamide RSO2NHOH (for HNO donors with Me- and Ph-containing leaving groups only). Up to approximately 70 % of the HNO-generating pathway was observed with the CF3-containing leaving group, with HNO generation favored for small percentages of aqueous buffer in the acetonitrile/pH 7.00 phosphate buffer solvent mixture. Characterization of the photoproducts obtained from steady-state irradiation by NMR spectroscopy showed that the desired HNO-generating pathway was less favored for HNO donors with Me- and Ph-containing leaving groups compared to the CF3-containing leaving group, suggesting that the excellent CF3-containing leaving group promotes HNO generation.
- Zhou, Yang,Cink, Ruth B.,Fejedelem, Zachary A.,Cather Simpson,Seed, Alexander J.,Sampson, Paul,Brasch, Nicola E.
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p. 1745 - 1755
(2018/04/17)
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- Photo-cleavable analog of BAPTA for the fast and efficient release of Ca2+
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A new photocleavable analog of BAPTA chelating ligand has a high affinity towards Ca2+ ions (K = 2.5 × 106 M-1). The use of photolabile 3-(hydroxymethyl)-2-naphthol core in the design of photo-BAPTA allows for the efficient (Φ = 0. 63) and very fast (τ 2+ ions upon 300 or 350 nm irradiation.
- Sutton, Mariia V.,McKinley, Matthew,Kulasekharan, Revathy,Popik, Vladimir V.
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supporting information
p. 5598 - 5601
(2017/07/07)
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