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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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Identifying Per- and Polyfluorinated Chemical Species with a Combined Targeted and Non-Targeted-Screening High-Resolution Mass Spectrometry Workflow
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Cysteine-Based Perfluorinated Derivatives: A Theoretical and Experimental Study.

Sisa Chalán-Gualán1, Iván Ramos-Tomillero2, Thibault Terencio1

  • 1School of Chemical Science and Engineering, Yachay Tech University, Yachay City of Knowledge, Urcuqui, Ecuador.

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|May 3, 2023
PubMed
Summary

New perfluoroaromatic compounds based on cysteine were synthesized for bioconjugation. Decafluorobiphenyl (DFBP) derivatives show potential as anticancer and anti-inflammatory agents by targeting topoisomerase II and COX-2.

Keywords:
amino acidsbioconjugationmolecular dockingperfluorinationspectral simulation

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Bioconjugation Chemistry

Background:

  • Cysteine-based perfluoroaromatic compounds offer a versatile platform for molecular construction.
  • Hexafluorobenzene (HFB) and decafluorobiphenyl (DFBP) serve as core structures for novel derivatives.
  • Perfluorinated compounds can function as stable, non-cleavable linkers in bioconjugates.

Purpose of the Study:

  • To synthesize and characterize novel cysteine-based perfluoroaromatic compounds.
  • To establish perfluorinated derivatives as effective linkers for antibody bioconjugation.
  • To evaluate the potential therapeutic applications of these derivatives as anticancer and anti-inflammatory agents.

Main Methods:

  • Synthesis of HFB and DFBP derivatives.
  • Monoalkylation of thiol molecules using HFB and DFBP.
  • Preparation of antibody-perfluorinated conjugates via two distinct thiol-based strategies.
  • Spectroscopic characterization (FTIR, 19F NMR) and theoretical calculations.
  • Molecular docking against topoisomerase II and COX-2.

Main Results:

  • DFBP demonstrated higher efficacy in monoalkylation of thiols compared to HFB.
  • Successful bioconjugation of antibodies with perfluorinated linkers without compromising antibody integrity.
  • Excellent correlation between experimental and calculated spectroscopic data (19F NMR, FTIR).
  • Molecular docking predicted strong binding affinity of DFBP derivatives to topoisomerase II α and COX-2.

Conclusions:

  • Cysteine-based perfluoroaromatic compounds, particularly DFBP derivatives, are effective building blocks for bioconjugation.
  • These compounds can serve as stable linkers in antibody-drug conjugates.
  • DFBP derivatives show significant promise as potential anticancer and anti-inflammatory agents.