Directed Biosynthesis of Iso-aclacinomycins with Improved Anticancer Activity

Org Lett. 2020 Jan 3;22(1):150-154. doi: 10.1021/acs.orglett.9b04069. Epub 2019 Dec 12.

Abstract

A four-enzyme catalyzed hydroxy regioisomerization of anthracycline was integrated into the biosynthetic pathway of aclacinomycin A (ALM-A), to generate a series of iso-ALMs via directed combinatorial biosynthesis combined with precursor-directed mutasynthesis. Most of the newly acquired iso-ALMs exhibit obviously (1-5-fold) improved antitumor activity. Therefore, we not only developed iso-ALMs with potential as clinical drugs but also demonstrated the utility of this tailoring tool for modification of anthracycline antibiotics in drug discovery and development.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aclarubicin / analogs & derivatives*
  • Aclarubicin / biosynthesis
  • Aclarubicin / chemistry
  • Aclarubicin / pharmacology
  • Antibiotics, Antineoplastic / biosynthesis
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Conformation
  • Polyketide Synthases / metabolism*
  • Streptomyces / chemistry
  • Streptomyces / metabolism

Substances

  • Antibiotics, Antineoplastic
  • aclacinomycins
  • Aclarubicin
  • Polyketide Synthases

Supplementary concepts

  • Streptomyces galilaeus