Puromycin
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| Category | Antibiotics |
| Catalog number | BBF-02588 |
| CAS | 53-79-2 |
| Molecular Weight | 471.51 |
| Molecular Formula | C22H29N7O5 |
| Purity | >98% by HPLC |
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Description
Puromycin is a nucleoside (purine) antibiotic produced by Str. alboniger. It has broad-spectrum antibacterial effect, and its antibacterial effect on individual strains is weak. It has the effect of inhibiting HeLa cells, glial cells in chicken embryos, tumor cells, and breast cancer in mouse GH. It can inhibit the proliferation of vaccinia virus. It is effective against Trypanosoma horses, dysentery amoeba, and tapeworm infections in animals; it is also effective against Trypanosoma crux and Hymenoptera jiliensis.
Specification
| Synonyms | Stylomycin |
| Storage | -20°C |
| IUPAC Name | (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide |
| Canonical SMILES | CN(C)C1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)NC(=O)C(CC4=CC=C(C=C4)OC)N)O |
| InChI | 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 |
| Source | Streptomyces alboniger |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor); viruses; parasites |
| Melting Point | 175.5-177°C |
| Density | 1.51 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Moderate water solubility. |
Reference Reading
1. Puromycin reactivity does not accurately localize translation at the subcellular level
Rachel Green, Syed Usman Enam, Daniel H Goldman, Nathan M Livingston, Madeline Cassani, Geraldine Seydoux, Boris Zinshteyn Elife . 2020 Aug 26;9:e60303. doi: 10.7554/eLife.60303.
Puromycin is a tyrosyl-tRNA mimic that blocks translation by labeling and releasing elongating polypeptide chains from translating ribosomes. Puromycin has been used in molecular biology research for decades as a translation inhibitor. The development of puromycin antibodies and derivatized puromycin analogs has enabled the quantification of active translation in bulk and single-cell assays. More recently, in vivo puromycylation assays have become popular tools for localizing translating ribosomes in cells. These assays often use elongation inhibitors to purportedly inhibit the release of puromycin-labeled nascent peptides from ribosomes. Using in vitro and in vivo experiments in various eukaryotic systems, we demonstrate that, even in the presence of elongation inhibitors, puromycylated peptides are released and diffuse away from ribosomes. Puromycylation assays reveal subcellular sites, such as nuclei, where puromycylated peptides accumulate post-release and which do not necessarily coincide with sites of active translation. Our findings urge caution when interpreting puromycylation assays in vivo.
2. SUnSET, a nonradioactive method to monitor protein synthesis
Giovanna Clavarino, Enrico K Schmidt, Philippe Pierre, Maurizio Ceppi Nat Methods . 2009 Apr;6(4):275-7. doi: 10.1038/nmeth.1314.
We developed a nonradioactive fluorescence-activated cell sorting-based assay, called surface sensing of translation (SUnSET), which allows the monitoring and quantification of global protein synthesis in individual mammalian cells and in heterogeneous cell populations. We demonstrate here, using mouse dendritic and T cells as a model, that SUnSET offers a technical alternative to classical radioactive labeling methods for the study of mRNA translation and cellular activation.
3. Puromycin based inhibitors of aminopeptidases for the potential treatment of hematologic malignancies
Robert Vince, Jessica Williams, Rohit Singh Eur J Med Chem . 2017 Oct 20;139:325-336. doi: 10.1016/j.ejmech.2017.07.048.
Substantial progress has been described in the study of puromycin and its analogs for antibiotic properties. However, the peptidase inhibitory activity of related analogs has not been explored as extensively. Specifically, inhibiting aminopeptidases for achieving antitumor effect has been sparsely investigated. Herein, we address this challenge by reporting the synthesis of a series of analogs based on the structural template of puromycin. We also present exhaustive biochemical and in vitro analyses in support of our thesis. Analyzing the structure-activity relationship revealed a steric requirement for maximum potency. Effective inhibitors of Puromycin-Sensitive Aminopeptidase (PSA) are disclosed here. These potential therapeutic agents display superior in vitro antitumor potency against two leukemic cell lines, as compared to known inhibitors of aminopeptidases.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
