Developing Photoactive Coumarin-Caged N-Hydroxysulfonamides for Generation of Nitroxyl (HNO)
Abstract
:1. Introduction
2. Results
2.1. Characterization of the Photoproducts in CD3CN/Phosphate Buffer Mixtures
2.2. Evidence for HNO Generation Using a Phosphine Trap
2.3. Effect of O2
2.4. Determination of the pKa Values for 8a and 8b
2.5. Determination of the pKa Values for 8b
2.6. Effect of pH on the Photoproducts
2.7. Effect of the Excitation Wavelength on the Photoproducts
2.8. Effect of Triplet Quenchers on the Photoproducts
2.9. Photoproduct Quantum Yield
3. Discussion
4. Conclusions
5. Materials and Methods
5.1. General Information
5.2. Photolysis Experiments
5.3. Determination of pKa by UV–Vis Spectroscopy
5.4. Determination of pKa by NMR Spectroscopy
5.5. Determination of the Photoproduct Quantum Yields (Φ)
5.6. Synthesis of HNO Donors BHC-ONHSO2R (R = CF3 (8a), CH3 (8b) and (2-SO2Me)Ph- (8c)) and the Related Photoproducts
5.6.1. 6-Bromo-4-chloromethyl-7-hydroxycoumarin (2)
5.6.2. 6-Bromo-7-hydroxymethylcoumarin (3)
5.6.3. 6-Bromo-7-O-(methoxymethyl)-4-hydroxymethylcoumarin (4)
5.6.4. 2-[[6-Bromo-7-O-(methoxymethyl)coumarin-4-yl]methoxy)]isoindoline-1,3-dione (5)
5.6.5. O-[[6-Bromo-7-O-(methoxymethyl)coumarin-4-yl]methyl]hydroxylamine (6)
5.6.6. 1,1,1-Trifluoro-N-[(6-bromo-7-O-(methoxymethyl)coumarin-4-yl)methoxy]methanesulfonamide (7a)
5.6.7. N-[(6-Bromo-7-O-(methoxymethyl)coumarin-4-yl)methoxy]methanesulfonamide (7b)
5.6.8. N-[(6-Bromo-7-O-(methoxymethyl)coumarin-4-yl)methoxy]-2-methanesulfonyl-benzenesulfonamide (7c)
5.6.9. 1,1,1-Trifluoro-N-[(6-bromo-7-hydroxycoumarin-4-yl)methoxy]methanesulfonamide (8a)
5.6.10. N-[(6-Bromo-7-hydroxycoumarin-4-yl)methoxy]methanesulfonamide (8b)
5.6.11. N-[(6-Bromo-7-hydroxycoumarin-4-yl)methoxy]-2-methanesulfonylbenzenesulfonamide (8c)
5.6.12. Alternative Approach to Intermediate 5 via 11
5.6.13. 6-Bromo-7-O-(methoxymethyl)-4-chloromethylcoumarin (11)
5.6.14. 2-[(6-Bromo-7-O-(methoxymethyl)coumarin-4-yl)methoxy]isoindoline-1,3-dione (5)
5.6.15. 6-Bromo-7-hydroxycoumarin-4-aldoxime (13)
Supplementary Materials
Author Contributions
Funding
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Percentage of Photoproducts | |||||
---|---|---|---|---|---|
Solvent Ratio, % v/v (30 mM Phosphate Buffer, pH 7.0/CD3CN) | CH3SO2NH2 | CH3SO2NHOH | CH3SO2− | CH3SO3− | Unknown |
00/100 | 82 | 8 | 3 | 3 | 4 |
60/40 | 93 | 1 | 0 | 0 | 2 |
90/10 | 79 | 5 | 2 | 9 | 5 |
pH | Percentages of Photoproducts | |
---|---|---|
CF3SO2− | CF3SO2NH2 | |
2.1 a | 4 | 96 |
5.0 b | 19 | 81 |
7.0 a | 20 | 80 |
10.0 c | 19 | 81 |
pH | Percentage of Photoproducts | ||||
---|---|---|---|---|---|
CH3SO2NH2 | CH3SO2NHOH | CH3SO2− | CH3SO3− | Unknown | |
2.1 a | 78 | 8 | 2 | 6 | 6 |
5.0 b | 78 | 8 | 2 | 5 | 7 |
7.0 c | 81 | 11 | 4 | 4 | 0 |
10.0 d | 40 | 4 | 48 | 8 | 0 |
10.7 e | 39 | 5 | 54 | 2 | 0 |
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Rahman, M.S.; Bharadwaj, V.; Lautaha, A.K.H.S.; Sampson, P.; Brasch, N.E.; Seed, A.J. Developing Photoactive Coumarin-Caged N-Hydroxysulfonamides for Generation of Nitroxyl (HNO). Molecules 2024, 29, 3918. https://doi.org/10.3390/molecules29163918
Rahman MS, Bharadwaj V, Lautaha AKHS, Sampson P, Brasch NE, Seed AJ. Developing Photoactive Coumarin-Caged N-Hydroxysulfonamides for Generation of Nitroxyl (HNO). Molecules. 2024; 29(16):3918. https://doi.org/10.3390/molecules29163918
Chicago/Turabian StyleRahman, Mohammad S., Vinay Bharadwaj, Anau K. H. S. Lautaha, Paul Sampson, Nicola E. Brasch, and Alexander J. Seed. 2024. "Developing Photoactive Coumarin-Caged N-Hydroxysulfonamides for Generation of Nitroxyl (HNO)" Molecules 29, no. 16: 3918. https://doi.org/10.3390/molecules29163918