Puromycin

Puromycin is a derivative of the glomerular epithelial cell toxin puromycin aminonucleoside (Cay-15509) and an inhibitor of protein synthesis that has been found in S. alboniger. 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. It inhibits protein synthesis by 99% in vitro. 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). 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.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: DMF: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: 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.