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SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization.

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Sulfur(VI) Fluoride Exchange (SuFEx) click chemistry enables rapid synthesis of novel anticancer drug candidates. This new method quickly generates and tests arylfluorosulfates, revealing compounds with enhanced potency against cancer cells.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Drug Discovery

Background:

  • Sulfur(VI) Fluoride Exchange (SuFEx) is an emerging click chemistry technique.
  • SuFEx chemistry offers a versatile platform for synthesizing novel compounds.
  • Its application in drug discovery is an underexplored area.

Purpose of the Study:

  • To develop and validate an in situ method for SuFEx chemistry in 96-well plates.
  • To enable rapid synthesis and biological screening of arylfluorosulfate derivatives.
  • To explore the potential of SuFEx in late-stage functionalization of anticancer drugs.

Main Methods:

  • Developed an in situ SuFEx reaction for converting phenols to arylfluorosulfates.
  • Utilized automated synthesis and screening for rapid assessment of biological activity.
  • Performed late-stage functionalization of known anticancer drugs.

Main Results:

  • Identified three arylfluorosulfates with improved anticancer cell proliferation activity.
  • The Fulvestrant fluorosulfate derivative showed enhanced activity in ER+ breast cancer cells.
  • The Combretastatin A4 fluorosulfate derivative exhibited a 70-fold increase in potency against drug-resistant colon cancer cells.

Conclusions:

  • The developed in situ SuFEx method is compatible with automated synthesis and screening.
  • This approach facilitates the discovery of novel drug candidates with enhanced therapeutic properties.
  • SuFEx chemistry holds significant promise for accelerating drug discovery and development.