2. Academic Validation
  3. Synthesis and anti-cancer potential of the positional isomers of NOSH-aspirin (NBS-1120) a dual nitric oxide and hydrogen sulfide releasing hybrid

Synthesis and anti-cancer potential of the positional isomers of NOSH-aspirin (NBS-1120) a dual nitric oxide and hydrogen sulfide releasing hybrid

  • Bioorg Med Chem Lett. 2015 Oct 15;25(20):4677-82. doi: 10.1016/j.bmcl.2015.08.023.
Federica Vannini 1,  Andrew C MacKessack-Leitch 2,  Erin K Eschbach 1,  Mitali Chattopadhyay 1,  Ravinder Kodela 1,  Khosrow Kashfi 3
Affiliations

Affiliations

  • 1 Department of Physiology, Pharmacology and Neuroscience, Sophie Davis School of Biomedical Education, City University of New York Medical School, 138th Street and Convent Avenue, New York, NY 10031, USA.
  • 2 Department of Physiology, Pharmacology and Neuroscience, Sophie Davis School of Biomedical Education, City University of New York Medical School, 138th Street and Convent Avenue, New York, NY 10031, USA; EaStCHEM School of Chemistry, University of St. Andrews, St. Andrews, Fife KY16 9ST, UK.
  • 3 Department of Physiology, Pharmacology and Neuroscience, Sophie Davis School of Biomedical Education, City University of New York Medical School, 138th Street and Convent Avenue, New York, NY 10031, USA; Avicenna Pharmaceuticals Inc., 555 West 57th Street, New York, NY 10019, USA. Electronic address: kashfi@med.cuny.edu.
PMID: 26323873 DOI: 10.1016/j.bmcl.2015.08.023
Abstract

We recently reported the synthesis of NOSH-aspirin, a novel hybrid compound capable of releasing both nitric oxide (NO) and hydrogen sulfide (H2S). In NOSH-aspirin, the two moieties that release NO and H2S are covalently linked at the 1, 2 positions of acetyl salicylic acid, i.e., ortho-NOSH-aspirin. Here we report on the synthesis of meta- and para-NOSH-aspirins. We also made a head-to-head evaluation of the effects of these three positional isomers of NOSH-aspirin on colon Cancer cell kinetics and induction of Reactive Oxygen Species, which in recent years has emerged as a key event in causing Cancer cell regression. Electron donating/withdrawing groups incorporated about the benzoate moiety significantly affected the potency of these compounds with respect to colon Cancer cell growth inhibition.

Keywords

Cell kinetics; Colon cancer; Hydrogen sulfide; NOSH-aspirin; Nitric oxide; Reactive oxygen species.

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