An inhibitor of protein synthesis
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Alternative(s)
13884Puromycin (hydrochloride)
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Puromycin

Item No. 35841

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3′-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3′-deoxy-N,N-dimethyl-adenosine
CAS Number
53-79-2
Synonyms
  • CL 13,900
Molecular Formula
C22H29N7O5
Formula Weight
471.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O[C@H]([C@@H]1NC([C@@H](N)CC2=CC=C(OC)C=C2)=O)[C@@H](O[C@@H]1CO)N3C(N=CN=C4N(C)C)=C4N=C3
InChi Code
InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1
InChi Key
RXWNCPJZOCPEPQ-NVWDDTSBSA-N
Origin
Bacterium/Streptomyces alboniger
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Puromycin is a derivative of the glomerular epithelial cell toxin puromycin aminonucleoside (Item No. 15509) and an inhibitor of protein synthesis that has been found in S. alboniger.1,2,3,4,5,6 Puromycin is structurally similar to the amino acid-bearing end of tRNA, which allows it to enter the ribosome during protein synthesis, bind to the nascent polypeptide chain, and halt chain elongation.2,3,4 It inhibits protein synthesis by 99% in vitro.5 Puromycin is also an inhibitor of puromycin-sensitive aminopeptidase (PSA) and aminopeptidase N (APN; IC50s = 9.7 and 41 µM, respectively). It reduces the viability of HL-60 human promyelocytic leukemia and MOLT-4 human acute lymphoblastic leukemia cells (EC50s = 0.055 and 0.17 µM, respectively). Puromycin is active against the chloroquine-sensitive and -resistant P. falciparum strains T9-96 and K1 (IC50s = 0.024 and 0.023 µM, respectively).6 Puromycin has been used as a selective marker in cell culture systems and has been chemically modified for use in labeling or imaging newly synthesized proteins.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Abou-Zeid, A.-Z.A., Shaheen, A.B., and El-Dewany, A.I. Fermentative production of puromycin by Streptomyces alboniger. J. Chem. Technol. Biotechnol. 23(11), 837-845 (1973).

    2. Rodriguez-Fonseca, C., Phan, H., Long, K.S., et al. Puromycin-rRNA interaction sites at the peptidyl transferase center. RNA 6(5), 744-754 (2000).

    3. Azzam, M.E., and Algranati, I.D. Mechanism of puromycin action: Fate of ribosomes after release of nascent protein chains from polysomes. Proc. Natl. Acad. Sci. USA 70(12), 3866-3869 (1973).

    4. Lührmann, R., Bald, R., Stöffler-Meilicke, M., et al. Localization of the puromycin binding site on the large ribosomal subunit of Escherichia coli by immunoelectron microscopy. Proc. Natl. Acad. Sci. USA 78(12), 7276-7280 (1981).

    5. Singh, R., Williams, J., and Vince, R. Puromycin based inhibitors of aminopeptidases for the potential treatment of hematologic malignancies. Eur. J. Med. Chem. 139, 325-336 (2017).

    6. Ekong, R.M., Kirby, G.C., Patel, G., et al. Comparison of the in vitro activities of quassinoids with activity against Plasmodium falciparum, anisomycin and some other inhibitors of eukaryotic protein synthesis. Biochem. Pharmacol. 40(2), 297-301 (1990).

    7. Aviner, R. The science of puromycin: From studies of ribosome function to applications in biotechnology. Comput. Struct. Biotechnol. J. 18, 1074-1083 (2020).