Puromycin Dihydrochloride | CAS 58-58-2 | AG Scientific, Inc.

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Puromycin Dihydrochloride

P-1033
  • CAS: 58-58-2
  • Formula: C22H29N7O5 2HCl
  • MW: 544.4
  • Appearance: White to off-white powder
  • Purity: ≥99%

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Puromycin dihydrochloride is the hydrochloride salt form of puromycin, an aminoglycoside antibiotic isolated from the bacterium Streptomyces alboniger. Acting as an analog of the 3' terminal end of aminoacyl-tRNA, puromycin incorporates itself into a growing polypeptide chain and causes its premature termination, thereby inhibiting protein synthesis. This agent has antimicrobial, antitrypanosomal, and antineoplastic properties. Puromycin's main application is in cell biology as a selective antibiotic agent in cell culture systems for selecting mammalian cell lines, which have been transformed by vectors that express puromycin-N-acetyl-transferase (PAC). It can also be used in cell culture. Puromycin’s longstanding application as a gene selection antibiotic has a powerful new role in genome editing utilizing the CRISPR/Cas9 system.

 

Recently researchers have developed a prodrug strategy for selective cancer therapy using a masked cytotoxic agent Fmoc-Lys(Ac)-Puromycin, which can be sequentially activated by histone deacetylases (HDACs) and cathepsin L (CTSL) to kill cancer cells expressing high levels of both enzymes. The data gathered indicates that Fmoc-Lys(Ac)-Puromycin can substantially improve anti-cancer efficacy and can be developed into a potential selective cancer therapy.

Additional Information

SynonymsStylomycin dihydrochloride, CL 13900 dihydrochloride, CL16536, NSC 3055, P638 dihydrochloride.
Product #P-1033
CAS #58-58-2
Chemical Name(S) 3'-[[2-Amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyladenosine,3'-(a-Amino-p-methoxy-hydocinnamamido)-3'-dexoy-N,N-dimethyladenosine.2HCl
FormulaC22H29N7O5 2HCl
MW544.4
AppearanceWhite to off-white powder
Purity≥99%
SolubilitySoluble in water (50 mg/ml), ethanol (~1 mg/ml), DMSO (~13 mg/ml), DMF (~14 mg/ml), and PBS, pH 72 (~10 mg/ml)
Melting Point175-177 °C
Storage Temp-20°C
Therapeutic AreaInfectious Diseases
UseAn aminonuclease antibiotic used for selection and maintenance of cell lines expressing a transfected pac gene

Additional Information

Merck Index14: 7943
MDL NumberMFCD00866328
ChemACXX1001900-0
InChIInChI=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
SMILESCN(C)C1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)NC(=O)C(CC4=CC=C(C=C4)OC)N)O

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GHS Pictograms
RTECSAU7350000
UN #'SUN 2811
PACKING GROUPI

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msds 1P-1033, Puromycin dihydrochloride, SDS, diamond format.pdf
Certificate of Analysis 1P-1033, J1277.pdf
Certificate of Analysis 2P-1033, J1006D.pdf
Certificate of Analysis 3P-1033, J1006C.pdf
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CitationsVaksman, Olga, et al. "Exosome-derived miRNAs and ovarian carcinoma progression." Carcinogenesis 35.9 (2014): 2113-2120.
Shivanna, Sowmya, et al. "The aryl hydrocarbon receptor is a critical regulator of tissue factor stability and an antithrombotic target in uremia." Journal of the American Society of Nephrology 27.1 (2016): 189-201.
Weitzenfeld, Polina, et al. "Chemokine axes in breast cancer: factors of the tumor microenvironment reshape the CCR7-driven metastatic spread of luminal-A breast tumors." Journal of leukocyte biology 99.6 (2016): 1009-1025.
Seo-hee, Nam. Novel Functions of Lysyl-TRNA Synthetase in Invasive Dissemination of Colon Cancer Cells in 3D Microenvironment. Edited by Lee Jung Won, Seoul National University Graduate School, 2017.
Bergson, Shir, et al. "Fluorescent Tagging and Cellular Distribution of the Kaposi's Sarcoma-Associated Herpesvirus (KSHV) Open Reading Frame 45 (ORF45) Tegument Protein." Journal of virology (2014): JVI-01091.
Now, Hesung, and Joo-Yeon Yoo. "AG490 and PF431396 sensitive tyrosine kinase control the population heterogeneity of basal STAT1 activity in Ube1l deficient cells." PloS one 11.7 (2016): e0159453.
Gelgor, Anastasia, et al. "Nucleolar stress enhances lytic reactivation of the Kaposi's sarcoma-associated herpesvirus." Oncotarget 9.17 (2018): 13822.
Zurawski, Gerard, et al. "Antigen presenting cell targeted cancer vaccines." U.S. Patent Application No. 14/819,909.
Brody, Yehuda, et al. "The in vivo kinetics of RNA polymerase II elongation during co-transcriptional splicing." PLoS biology 9.1 (2011): e1000573.
Ganesan, Kumaresan, et al. "Inhibition of gastric cancer invasion and metastasis by PLA2G2A, a novel b-catenin/TCF target gene." Cancer research 68.11 (2008): 4277-4286.
ReferenceThe Aryl Hydrocarbon Receptor Binds to E2F1 and Inhibits E2F1-induced Apoptosis
High TCL1 expression and intact T-cell receptor signaling define a hyperproliferative subset of T-cell prolymphocytic leukemia
AG490 and PF431396 Sensitive Tyrosine Kinase Control the Population Heterogeneity of Basal STAT1 Activity in Ube1l Deficient Cells - Hesung Now, Joo-Yeon Yoo

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