N-acetylcysteine (NAC) exhibits diverse pharmacological effects due to the free radical
scavenging ability of the reduced thiol. Extensive deacetylation in liver, high protein binding and
poor permeability results in low bioavailability of NAC. These setbacks are also the contributing
factors in failure to confirm the benefits of NAC in prevention of diseases involving oxidative stress.
Present study was aimed at improving the bioavailability of NAC by conjugating it with morpholinoethanol
into a morpholinoethyl ester conjugate (A-2). A-2 was synthesized by DCC coupling and
the structure was confirmed by IR, 1H-NMR, 13C-NMR, elemental analysis and mass spectroscopy.
This conjugate was screened in ovalbumin-induced airway hyperresponsiveness for various lung
function parameters where it exhibited significant ameliorating effect; interestingly at half the equimolar
dose of NAC. Thus, A-2 has the potential to be used as a substitute for NAC in conditions involving
airway hyperresponsiveness and airway eosinophilia.
Keywords: N-acetylcysteine, morpholinoethyl ester conjugate, poor bioavailability, airway hyperresponsiveness, ovalbumin.
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