Liposidomycin, the first reported nucleoside antibiotic inhibitor of peptidoglycan biosynthesis translocase I: The discovery of liposidomycin and related compounds with a perspective on their application to new antibiotics

J Antibiot (Tokyo). 2019 Dec;72(12):877-889. doi: 10.1038/s41429-019-0241-5. Epub 2019 Oct 4.

Abstract

Liposidomycin is a uridyl liponucleoside antibiotic isolated from Streptomyces griseosporeus RK-1061. It was discovered by Isono in 1985, who had previously isolated and developed a related peptidyl nucleoside antibiotic, polyoxin, a specific inhibitor of chitin synthases, as a pesticide. He subsequently isolated liposidomycin, a specific inhibitor of bacterial peptidoglycan biosynthesis from actinomycetes, using a similar approach to the discovery of polyoxin. Liposidomycin has no cytotoxicity against BALB/3T3 cells but has antimicrobial activity against Mycobacterium spp. through inhibition of MraY (MurX) [phospho-N-acetylmuramoyl-pentapeptide transferase (translocase I, EC 2.7.8.13)]. Since the discovery of liposidomycin, several liposidomycin-type antibiotics, including caprazamycin, A-90289, and muraminomycin, have been reported, and their total synthesis and/or biosynthetic cluster genes have been studied. Most advanced, a semisynthetic compound derived from caprazamycin, CPZEN-45, is being developed as an antituberculosis agent. Translocase I is an interesting and tractable molecular target for new antituberculosis and antibiotic drug discovery against multidrug-resistant bacteria. This review is dedicated to Dr Isono on the occasion of his 88th birthday to recognize his role in the study of nucleoside antibiotics.

Publication types

  • Review

MeSH terms

  • Aminoglycosides / chemistry
  • Aminoglycosides / pharmacology*
  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Azepines / chemistry
  • Azepines / pharmacology
  • Bacterial Proteins / antagonists & inhibitors
  • Chitin Synthase / antagonists & inhibitors
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Mice
  • Peptidoglycan / metabolism*
  • Pyrimidine Nucleosides / chemistry
  • Pyrimidine Nucleosides / pharmacology
  • Transferases (Other Substituted Phosphate Groups)
  • Transferases / antagonists & inhibitors
  • Tunicamycin / chemistry
  • Tunicamycin / pharmacology
  • Uracil / analogs & derivatives
  • Uracil / chemistry
  • Uracil / pharmacology
  • Uridine / analogs & derivatives
  • Uridine / chemistry
  • Uridine / pharmacology

Substances

  • A 90289A
  • Aminoglycosides
  • Anti-Bacterial Agents
  • Azepines
  • Bacterial Proteins
  • Enzyme Inhibitors
  • Peptidoglycan
  • Pyrimidine Nucleosides
  • caprazamycin A
  • liposidomycins
  • Tunicamycin
  • polyoxin
  • Uracil
  • Transferases
  • Chitin Synthase
  • Transferases (Other Substituted Phosphate Groups)
  • mraY protein, Bacteria
  • Uridine