Synthesis and anti-cancer potential of the positional isomers of NOSH-aspirin (NBS-1120) a dual nitric oxide and hydrogen sulfide releasing hybrid
| Autor: | Khosrow Kashfi, Federica Vannini, Ravinder Kodela, Andrew C. MacKessack-Leitch, Erin K. Eschbach, Mitali Chattopadhyay |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Stereochemistry
Hydrogen sulfide Clinical Biochemistry Pharmaceutical Science Antineoplastic Agents Apoptosis Nitric Oxide Biochemistry Article Nitric oxide chemistry.chemical_compound Structure-Activity Relationship Cell Line Tumor Drug Discovery Structure–activity relationship Moiety Humans NOSH-aspirin Disulfides Hydrogen Sulfide Molecular Biology Cell Proliferation chemistry.chemical_classification Reactive oxygen species Nitrates Aspirin Dose-Response Relationship Drug Molecular Structure Cell growth Chemistry Organic Chemistry Cell Cycle Molecular Medicine Drug Screening Assays Antitumor Reactive Oxygen Species HT29 Cells Salicylic acid |
| Zdroj: | Bioorganicmedicinal chemistry letters. 25(20) |
| ISSN: | 1464-3405 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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