Puromycin

Structural formula
General
Non-proprietary name	Puromycin
other names	Purimycin; ( S ) -3 '- ((2-Amino-3- (4-methoxyphenyl) -1-oxopropyl) amino) -3'-deoxy- N , N -dimethyladenosine;
Molecular formula	C 22 H 29 N 7 O 5
External identifiers / databases
PubChem	439530
ChemSpider	388623
DrugBank	DB08437
Wikidata	Q424696
Drug information
Drug class	antibiotic
properties
Molar mass	471.51 g mol −1
Physical state	firmly
Melting point	175.5-177 ° C
solubility	moderate in water (50.3 g l −1 at 25 ° C)
safety instructions
GHS labeling of hazardous substances Dihydrochloride; Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	20 mg kg −1 ( LD 50 , mouse , oral )
	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 .

[ChemIDplus-1] Entry on Puromycin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-2] Data sheet Puromycin dihydrochloride from Streptomyces alboniger from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

[3] MA Darken: Puromycin inhibition of protein synthesis. In: Pharmacol. Rev. 16, 1964, pp. 223-243. PMID 14211122 .

[4] 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 .