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

Bioorganic & Medicinal Chemistry Letters
Federica VanniniKhosrow Kashfi

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.

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Citations

May 16, 2017·Journal of Medicinal Chemistry·Zhangjian HuangYihua Zhang
May 12, 2018·Future Medicinal Chemistry·Mohd Imran AnsariMohd Kamil Hussain
Jul 22, 2018·Current Medicinal Chemistry·Aysegul HanikogluTomris Ozben
Feb 20, 2019·Journal of Experimental & Clinical Cancer Research : CR·Dan YangQing Yang
Nov 8, 2017·Chemical Reviews·Milos R FilipovicRuma Banerjee

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