Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H29N7O5 |
| Molecular Weight | 471.5096 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C[C@H](N)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N3C=NC4=C3N=CN=C4N(C)C)C=C1
InChI
InChIKey=RXWNCPJZOCPEPQ-NVWDDTSBSA-N
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
DescriptionSources: https://www.drugbank.ca/drugs/DB08437https://www.drugbank.ca/drugs/DB08437 | https://www.ncbi.nlm.nih.gov/pubmed/4949424 | https://www.ncbi.nlm.nih.gov/pubmed/18313307Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68011691 | https://www.ncbi.nlm.nih.gov/pubmed/4590173
Sources: https://www.drugbank.ca/drugs/DB08437https://www.drugbank.ca/drugs/DB08437 | https://www.ncbi.nlm.nih.gov/pubmed/4949424 | https://www.ncbi.nlm.nih.gov/pubmed/18313307
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68011691 | https://www.ncbi.nlm.nih.gov/pubmed/4590173
Puromycin dihydrochloride belongs to the aminonucleoside family of antibiotics and is isolated from Streptomyces alboniger. Since the partial structure of this antibiotic showed it to be a purine derivative, puromycin was assigned as its generic name. Puromycin is a broad spectrum antibiotic and antibacterial agent. It is active against Gram-positive microorganisms, less active against acid-fast bacilli, and weakly active against Gram-negative microorganisms. It acts very quickly and can kill 99% of the cells within 2 days. It also exhibits antitumor activity in studies on brain tumor cells. Puromycin is a protein synthesis inhibitor that causes premature chain termination by acting as an analog of the 3’-terminal end of aminoacyl-tRNA. It has been used to study transcriptional regulatory mechanisms that control the sequential and coordinate expression of genes during cell differentiation.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains. | 1973 Sep |
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| Ribosome structure: localization of N6,N6-dimethyladenosine by electron microscopy of a ribosome-antibody complex. | 1977 Apr |
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| Indication for central vagal endorphinergic control of heart rate in dogs. | 1981 May 22 |
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| Superinduction of cytochrome P1-450 gene transcription by inhibition of protein synthesis in wild type and variant mouse hepatoma cells. | 1985 May 10 |
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| Drug-associated glomerulopathies. | 1986 |
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| Analogs of 3'-amino-3'-deoxyadenosine inhibit HIV-1 replication. | 1989 Dec |
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| Effects of YM264, a novel PAF antagonist, on puromycin aminonucleoside-induced nephropathy in the rat. | 1991 Apr 30 |
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| Superinduction of 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible expression of aldehyde dehydrogenase by the inhibition of protein synthesis. | 1991 Oct 31 |
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| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
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| Alterations in the distribution of plasma fibronectin and the ultrastructure of podocytes in the peripheral glomerular loops in nephrotic rats. | 1998 Nov |
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| Induction of heme oxygenase-1 by phenylarsine oxide. Studies in cultured primary liver cells. | 2001 Oct |
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| Induction and superinduction of 2,3,7,8-tetrachlorodibenzo-rho-dioxin-inducible poly(ADP-ribose) polymerase: role of the aryl hydrocarbon receptor/aryl hydrocarbon receptor nuclear translocator transcription activation domains and a labile transcription repressor. | 2002 Aug 15 |
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| Synergistic activation of human LDL receptor expression by SCAP ligand and cytokine oncostatin M. | 2003 Jan 1 |
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| M-CSF, TNFalpha and RANK ligand promote osteoclast survival by signaling through mTOR/S6 kinase. | 2003 Oct |
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| Superinduction of CYP1A1 in MCF10A cultures by cycloheximide, anisomycin, and puromycin: a process independent of effects on protein translation and unrelated to suppression of aryl hydrocarbon receptor proteolysis by the proteasome. | 2004 Oct |
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| Oligonucleotide-based microarray analysis of retinoic acid target genes in the protochordate, Ciona intestinalis. | 2005 Aug |
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| Functional consequences of integrin-linked kinase activation in podocyte damage. | 2005 Feb |
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| RNA-editing-mediated exon evolution. | 2007 |
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| Biological characteristics of Chinese hamster ovary cells transfected with bovine Prnp. | 2007 Jun |
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| Increased cyclosporine bioavailability induced by experimental nephrotic syndrome in rats. | 2007 May |
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| A new generation of pPRIG-based retroviral vectors. | 2007 Nov 30 |
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| A function for a specific zinc metalloprotease of African trypanosomes. | 2007 Oct 19 |
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| Thyroid cancer imaging in vivo by targeting the anti-apoptotic molecule galectin-3. | 2008 |
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| HPV16 E7-dependent transformation activates NHE1 through a PKA-RhoA-induced inhibition of p38alpha. | 2008 |
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| Melatonin antagonizes the intrinsic pathway of apoptosis via mitochondrial targeting of Bcl-2. | 2008 Apr |
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| [Establishment of BHK-21 cell lines stably expressing FMDV 3Dpol gene by retroviral-mediated gene transfer technique]. | 2008 Aug |
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| The changing management of acute bronchitis in Britain, 1940-1970: the impact of antibiotics. | 2008 Jan |
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| Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells. | 2008 Oct |
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| Functional analysis of a dominant negative mutation of interferon regulatory factor 5. | 2009 |
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| Distinct roles for basal and induced COX-2 in podocyte injury. | 2009 Sep |
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| Oxygen consumption can regulate the growth of tumors, a new perspective on the Warburg effect. | 2009 Sep 15 |
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| Caveolae contribute to the apoptosis resistance induced by the alpha(1A)-adrenoceptor in androgen-independent prostate cancer cells. | 2009 Sep 18 |
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| Transplantation of human neural stem cells transduced with Olig2 transcription factor improves locomotor recovery and enhances myelination in the white matter of rat spinal cord following contusive injury. | 2009 Sep 22 |
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| ATP-binding cassette transporters as pitfalls in selection of transgenic cells. | 2010 Apr 15 |
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| Rhabdastrellic acid-A induced autophagy-associated cell death through blocking Akt pathway in human cancer cells. | 2010 Aug 17 |
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| Multi-gene targeted antiangiogenic therapies for experimental corneal neovascularization. | 2010 Feb 27 |
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| The zinc-fingers of KREPA3 are essential for the complete editing of mitochondrial mRNAs in Trypanosoma brucei. | 2010 Jan 27 |
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| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010 Jul |
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| Mechanisms of IL-12 synthesis by human dendritic cells treated with the chemical sensitizer NiSO4. | 2010 Jul 1 |
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| Radiotherapy suppresses angiogenesis in mice through TGF-betaRI/ALK5-dependent inhibition of endothelial cell sprouting. | 2010 Jun 11 |
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| A predictive computational model of the kinetic mechanism of stimulus-induced transducer methylation and feedback regulation through CheY in archaeal phototaxis and chemotaxis. | 2010 Mar 18 |
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| miR-22 forms a regulatory loop in PTEN/AKT pathway and modulates signaling kinetics. | 2010 May 27 |
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| Dentin sialophosphoprotein (DSPP) gene-silencing inhibits key tumorigenic activities in human oral cancer cell line, OSC2. | 2010 Nov 12 |
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| A novel envelope mediated post entry restriction of murine leukaemia virus in human cells is Ref1/TRIM5α independent. | 2010 Oct 7 |
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| Melatonin promotes puromycin-induced apoptosis with activation of caspase-3 and 5'-adenosine monophosphate-activated kinase-alpha in human leukemia HL-60 cells. | 2011 May |
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| Macromolecular synthesis inhibitors perturb glucocorticoid receptor trafficking. | 2011 Sep |
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| Cellular growth kinetics distinguish a cyclophilin inhibitor from an HSP90 inhibitor as a selective inhibitor of hepatitis C virus. | 2012 |
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| DEF6, a novel substrate for the Tec kinase ITK, contains a glutamine-rich aggregation-prone region and forms cytoplasmic granules that co-localize with P-bodies. | 2012 Sep 7 |
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| Identification and evaluation of novel acetolactate synthase inhibitors as antifungal agents. | 2013 May |
|
| TCDD and omeprazole prime platelets through the aryl hydrocarbon receptor (AhR) non-genomic pathway. | 2015 May 19 |
Patents
Sample Use Guides
Mouse J774A.1 macrophages, vascular smooth muscle cells (SMCs) isolated from rabbit aorta, and murine C2C12 myoblasts were treated in vitro with the protein synthesis inhibitor puromycin (24 h with different concentrations of puromycin (0–20 uM) or 35 uM puromycin for 0–48 h). Cell death was initiated in all cell types in a concentration- and time-dependent manner. Macrophage and SMCs death induced by puromycin was characterized by cleavage of procaspase-3 and internucleosomal DNA fragmentation, typical of apoptosis.
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NCI_THESAURUS |
C259
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D011691
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53-79-2
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DTXSID8036788
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1962
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DB08437
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100000080845
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CHEMBL469912
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60255
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C787
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SUB10161MIG
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4A6ZS6Q2CL
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439530
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m9324
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PUROMYCIN
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17939
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
