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Incorporation of carbon-14 in the biosynthesis of the macrolide antibiotic, LL-F28249-alpha

Z H Ahmed1, R R Fiala, M W Bullock

  • 1Agricultural Research Division, American Cyanamid Company, Princeton, New Jersey 08543-0400.

The Journal of Antibiotics
|April 1, 1993
PubMed

Insights

Researchers synthesized carbon-14 labeled nemadectin and moxidectin using labeled acetate, propionate, and isobutyrate. This enables tracking of these compounds in biological systems for drug development.

Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Nemadectin is a potent anthelmintic compound.
  • Moxidectin, a nemadectin derivative, is under development as an ectoparasiticide.
  • Radiolabeling is crucial for pharmacokinetic and metabolic studies of drug candidates.

Purpose of the Study:

  • To synthesize carbon-14 labeled nemadectin and moxidectin.
  • To determine the positions of radiolabeling in nemadectin using Nuclear Magnetic Resonance (NMR) spectroscopy.
  • To facilitate the development and study of moxidectin as an ectoparasiticide.

Main Methods:

  • Fermentation of nemadectin using a mixture of 14C-labeled acetate, propionate, and isobutyrate.
  • Synthesis of 14C-labeled moxidectin from the isolated 14C-labeled nemadectin.
  • 13C NMR analysis of 13C-labeled nemadectin, synthesized using 13C-labeled precursors, to determine labeled positions.

Main Results:

  • Isolation of 76 mCi of 14C-labeled nemadectin with a specific activity of 35.2 microCi/mg.
  • Successful synthesis of 14C-labeled moxidectin.
  • Determination of radiolabeled positions in nemadectin via 13C NMR analysis.

Conclusions:

  • The study successfully produced radiolabeled nemadectin and moxidectin.
  • The synthetic methods are suitable for producing labeled compounds for drug development.
  • The labeled compounds will aid in understanding the pharmacokinetics and efficacy of moxidectin.

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