Puromycin

• Purimycin
• (S)- 3'-( (2- amino-3 - (4- methoxyphenyl) - 1 - oxopropyl ) amino) - 3 ' -deoxy- N, N- dimethyladenosine

• 53-79-2
• 58-58-2 ( dihydrochloride)

Antibiotic

From 175.5 to 177 ° C

Moderately in water ( 50.3 g · l-1 at 25 ° C)

Dihydrochloride

Attention

20 mg · kg -1 ( LD50, mouse, oral)

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Puromycin, also Purimycin is from streptomycetes ( Streptomyces alboniger ) isolated nucleoside antibiotic which inhibits protein biosynthesis and thus is 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 N6, N6 - dimethyladenosine.

Effect

Puromycin acts in two ways:

• Termination of translation: puromycin inhibits translation by initiating premature termination. This is achieved by the fact that the puromycin binds during Peptidyltransfers instead of a tyrosyl- tRNA to the entry point (A- site) of the ribosome. A part of this molecule is similar to the 3 'end (CCA) of the aminoacyl- tRNAs. For this reason the polypeptide is located in the elongation is transferred to the puromycin of Pseudoaminosäurearm and leads to a premature termination of translation.
• Inhibition of protein import: puromycin inhibits protein import into mitochondria by interfering with an intramitochondrial ATP- dependent reaction.

Use

Puromycin is used exclusively for research purposes. 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 dar.

Possible applications in the research are the selection of genetically modified cell lines and inhibition of so-called puromycin - sensitive aminopeptidases. Other aminopeptidases are inhibited by puromycin with varying degrees of effect.