Puromycin
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Non-proprietary name | Puromycin | |||||||||||||||
other names |
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Molecular formula | C 22 H 29 N 7 O 5 | |||||||||||||||
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properties | ||||||||||||||||
Molar mass | 471.51 g mol −1 | |||||||||||||||
Physical state |
firmly |
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Melting point |
175.5-177 ° C |
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solubility |
moderate in water (50.3 g l −1 at 25 ° C) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Puromycin , also Purimycin, is a nucleoside antibiotic isolated from Streptomycetes ( Streptomyces alboniger ) , which inhibits protein biosynthesis and is therefore effective against some tumors , amoebas , trypanosomes and worms . Since it is also toxic to humans , it is mainly used in experiments in microbiology and cell biology . Structurally, it is derived from adenosine or from N 6 , N 6 -dimethyladenosine .
effect
Puromycin works in two ways:
- Translation Termination: Puromycin inhibits translation by initiating premature termination. This happens because the puromycin binds to the entry site (A site) of the ribosome during the peptidyl transfer instead of a tyrosyl tRNA . Part of the molecule resembles the 3 'end (CCA) of the aminoacyl-tRNAs. For this reason, the elongated polypeptide chain is transferred to the pseudo-amino acid arm of the puromycin and translation terminates prematurely.
- Inhibition of protein import: Puromycin inhibits protein import into mitochondria by hindering an intramitochondrial, ATP- dependent reaction.
use
Puromycin is used for research purposes only. Due to its toxic effect on eukaryotic cells, it is not suitable for therapeutic purposes. Puromycin thus represents a borderline case between antibiotic and toxin .
Possible applications in research are the selection of genetically modified cell lines and the inhibition of so-called puromycin-sensitive aminopeptidases . Other aminopeptidases are also inhibited by puromycin to varying degrees.
Web links
- Puromycin at Fermentek (English)
Individual evidence
- ↑ a b c Entry on Puromycin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- ↑ a b Data sheet Puromycin dihydrochloride from Streptomyces alboniger from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
- ↑ MA Darken: Puromycin inhibition of protein synthesis. In: Pharmacol. Rev. 16, 1964, pp. 223-243. PMID 14211122 .
- ↑ RW Roberts, JW Szostak: RNA-peptide fusions for the in vitro selection of peptides and proteins. In: Proceedings of the National Academy of Sciences . Volume 94, No. 23, Nov 11, 1997, pp. 12297-12302. PMID 9356443 .