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Functionality-Independent DNA Encoding of Complex Natural Products.

Peixiang Ma1, Hongtao Xu1, Jie Li1,2,3,4

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Angewandte Chemie (International Ed. in English)
|April 26, 2019
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Summary

DNA-encoded chemical libraries (DELs) combine genetics and synthesis for vast molecular diversity. This study tags natural products with DNA barcodes, creating a novel library that identified a new PARP1 inhibitor.

Keywords:
DNA-encoded librariescombinatorial chemistrydrug discoverynatural products

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Area of Science:

  • Medicinal Chemistry
  • Chemical Biology
  • Drug Discovery

Background:

  • DNA-encoded chemical libraries (DELs) leverage combinatorial chemistry for immense scale, reaching billions to trillions of compounds.
  • Integrating genetic information directly with chemical structures can enhance diversity within DELs.
  • Natural products possess remarkable structural diversity shaped by biological evolution.

Purpose of the Study:

  • To develop a method for annotating complex natural products with DNA barcodes for DEL integration.
  • To explore the use of traditional Chinese medicines (TCMs) as a source for a natural product-enriched DEL (nDEL).
  • To identify novel bioactive compounds, such as enzyme inhibitors, using the nDEL approach.

Main Methods:

  • A late-stage modification toolbox approach was employed to attach amplifiable DNA barcodes to TCM compounds.
  • The end-product labeling method generated isomers with DNA tags at different positions, increasing spatial diversity.
  • The resulting nDEL was screened for bioactive molecules.

Main Results:

  • Successful annotation of TCMs with DNA barcodes, enabling their incorporation into a DEL.
  • The method produced diverse isomers, offering varied spatial orientations for protein binding.
  • A novel PARP1 inhibitor was identified from the nDEL, demonstrating the approach's efficacy.

Conclusions:

  • Traditional Chinese medicines can be effectively incorporated into DNA-encoded libraries through DNA barcoding.
  • This strategy significantly expands chemical diversity and facilitates the discovery of novel therapeutics.
  • The identified PARP1 inhibitor highlights the potential of nDELs in drug discovery.