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Related Concept Videos

2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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For successful DNA replication, the unwinding of double-stranded DNA must be accompanied by stabilization and protection of the separated single strands of the DNA. This crucial task is performed by single-strand DNA-binding (SSB) proteins. They bind to the DNA in a sequence-independent manner, which means that the nitrogenous bases of the DNA need not be present in a specific order for binding of SSB proteins to it. The binding of SSB proteins straightens single-stranded DNA (ssDNA) and makes...
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Related Experiment Video

Updated: Sep 16, 2025

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Warhead Strategy for Targeted Protein S-Nitrosation.

Chen Zhang1, Hui Ye1, Duorui Ji1

  • 1Center of Drug Discovery, State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 211198, P. R. China.

Journal of the American Chemical Society
|July 12, 2025
PubMed
Summary

Researchers developed targeted S-nitrosation agents (TSNOs) to modify proteins like Bruton's tyrosine kinase (BTK) in vivo. This novel approach shows promise for cancer treatment by enhancing therapeutic effects beyond simple inhibition.

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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Oncology

Background:

  • Protein post-translational modifications (PTMs) are crucial in disease pathogenesis.
  • Targeted protein S-nitrosation for in vivo disease treatment is challenging due to nitric oxide (NO) diffusion.
  • Existing strategies for PTM regulation, like phosphorylation and acetylation, have advanced, but S-nitrosation remains less explored.

Purpose of the Study:

  • To design and synthesize novel agents for targeted in vivo S-nitrosation.
  • To investigate the efficacy of these agents against Bruton's tyrosine kinase (BTK) and other targets.
  • To explore the therapeutic potential of targeted S-nitrosation in cancer treatment.

Main Methods:

  • Design and synthesis of α-(NONOate-O2-yl) methyl acrylamides as NO-releasing warheads.
  • Development of targeted S-nitrosation agents (TSNOs) by linking warheads to BTK-specific scaffolds.
  • In vitro and in vivo proteomic studies to confirm targeted S-nitrosation of BTK at Cys527.
  • Evaluation of antitumor activity and mechanistic studies comparing TSNO1 with ibrutinib.

Main Results:

  • Successfully synthesized TSNO1-6 compounds that covalently bind to BTK and release NO in situ.
  • TSNO1 demonstrated targeted S-nitrosation of BTK at Cys527 in cellular and tissue proteomic analyses.
  • TSNO1 exhibited promising in vitro and in vivo antitumor activity.
  • S-nitrosation at Cys527 enhanced BTK phosphorylation inhibition at Tyr551, leading to improved therapeutic benefits.
  • The strategy was successfully extended to other targets like FGFR4 and HER2.

Conclusions:

  • The developed warhead strategy enables targeted modulation of protein S-nitrosation in vivo.
  • TSNOs represent a novel therapeutic approach for diseases involving aberrant BTK activity.
  • Targeted S-nitrosation offers potential advantages over existing covalent inhibitors by providing dual inhibition mechanisms.