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S -Carboxymethyl-L-cysteine (CMC) is an antioxidant and mucolytic commonly prescribed to patients with chronic obstructive pulmonary disease. In humans, CMC is rapidly metabolized to S -carboxymethyl-L-cysteine sulfoxide (CMCO). In this study, we assessed structural and functional similarities between CMC and CMCO. X-Ray diffraction analysis provided detailed structural information about CMCO, which exists as a 1:1 mixture of epimers, due to the emergence of a new chiral center at the sulfur atom. Both CMC and CMCO epimers protected model DNA from copper-mediated hydroxyl free radical damage. Using an insulated transposable construct for reporting activity of the cellular stress-responsive transcription factors Nrf2, p53, NF-κB, and AP-1, we demonstrate that CMCO, especially its (4 R )-epimer, is comparable to CMC in their ability to mitigate the effects of oxidative stress and pro-inflammatory stimuli in human alveolar (A549) and bronchial epithelial (BEAS-2B) cells. The results of these in vitro studies suggest that CMCO retains, at least partially, the antioxidant potential of CMC and may inform pharmacodynamics considerations of CMC use in clinics.

Structure, Antioxidant and Anti-inflammatory Activities of the (4R)- and (4S)-epimers of S-Carboxymethyl-L-cysteine Sulfoxide