Nitric Oxide (NO) is a free radical gas that is involved in a variety of biological processes including regulation vascular tone, neuronal signaling, and host defense.1,2 Nitroxyl (HNO) is the one electron reduced form of nitric oxide. Piloty’s acid is one of the best known and most widely used HNO donors. Under basic conditions Piloty’s acid decomposes to HNO and benzenesulfinate anion. The rate of HNO release at pH 7 is very slow (t1/2 = 5500 minutes) making its use most effective above pH 8.0. The half-life of Piloty’s acid decreases with an increase in pH to 561, 90, and 33 minutes at pH 8.0, 9.0, and 10.0, respectively.3 Piloty’s acid also inhibits yeast aldehyde dehydrogenase with an IC50 or 48 µM.4
1
Beckman, J.S., and Koppenol, W.H. Nitric oxide, superoxide, and peroxynitrite: The good, the bad, and the ugly. Am J Physiol271C1424-C1437(1996).
2
Bredt, D.S., and Snyder, S.H. Nitric oxide: A physiologic messenger molecule. Annu Rev Biochem63175-195(1994).
3
hughes, M.N., and Cammack, R. Synthesis, chemistry, and application of nitroxyl ion releasers sodium trioxodinitrate or Angeli’s Salt and Piloty’s Acid. Methods Enzymol301279-287(1999).
4
Nagasawa, H.T., Kawle, S.P., Elberling, J.A., et al. Prodrugs of nitroxyl as potential aldehyde dehydrogenase inhibitors vis-à-vis vascular smooth muscle relaxants. J Med Chem381865-1871(1995).
Synonyms
Benzenesulphonydroxamic acid
Formal Name
N-hydroxy-benzenesulfonamide
CAS Number
599-71-3
Molecular Formula
C6H7NO3S
Formula Weight
173.2
Formulation
A crystalline solid
Purity
>98%
λmax
219 nm
Stability
2 years
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
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ON([H])S(C1=CC=CC=C1)(=O)=O
Background Reading
Bredt, D.S., and Snyder, S.H. Nitric oxide: A physiologic messenger molecule. Annu Rev Biochem63175-195(1994).
hughes, M.N., and Cammack, R. Synthesis, chemistry, and application of nitroxyl ion releasers sodium trioxodinitrate or Angeli’s Salt and Piloty’s Acid. Methods Enzymol301279-287(1999).
Beckman, J.S., and Koppenol, W.H. Nitric oxide, superoxide, and peroxynitrite: The good, the bad, and the ugly. Am J Physiol271C1424-C1437(1996).
Nagasawa, H.T., Kawle, S.P., Elberling, J.A., et al. Prodrugs of nitroxyl as potential aldehyde dehydrogenase inhibitors vis-à-vis vascular smooth muscle relaxants. J Med Chem381865-1871(1995).