Puromycin, dihydrochloride

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Puromycin, dihydrochloride P-1033
  • CAS: 58-58-2
  • Formula: C22H29N7O5 2HCl
  • MW: 544.4
  • Purity: >98% by HPLC

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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). 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 potential selective cancer therapy.

 

Additional Information

Synonyms Stylomycin 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
Formula C22H29N7O5 2HCl
MW 544.4
Purity >98% by HPLC
Solubility Soluble 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 Point 175-177 °C
Boiling Point 752.16 °C
Storage Temp -20°C
Therapeutic Area Infectious Diseases
Use An aminonuclease antibiotic used for selection and maintenance of cell lines expressing a transfected pac gene

Additional Information

Merck Index 14: 7943
MDL Number MFCD00866328
ChemACX X1001900-0
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
SMILES CN(C)C1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)NC(=O)C(CC4=CC=C(C=C4)OC)N)O

Additional Information

RTECS AU7350000
UN #'S UN 2811
PACKING GROUP I

Additional Information

msds 1 P-1033, SDS.pdf
Certificate of Analysis 1 P-1033, H1215B.pdf
Certificate of Analysis 2 P-1033, H1215A.pdf
Certificate of Analysis 3 P-1033, H1215.pdf

Additional Information

Citations CELL BIOLOGY:\n CBP and p300 are cytoplasmic E4 polyubiquitin ligases for p53\n Dingding Shi, Marius S. Pop, Roman Kulikov, Ian M. Love, Andrew L. Kung, and Steven R. Grossman\n PNAS, Sep 2009; 106: 16275 - 16280.
NEOPLASIA:\n High TCL1 expression and intact T-cell receptor signaling define a hyperproliferative subset of T-cell prolymphocytic leukemia\n Marco Herling, Kaushali A. Patel, Michael A. Teitell, Marina Konopleva, Farhad Ravandi, Ryuji Kobayashi, and Dan Jones\n Blood, Jan 2008; 111: 328 - 337.
Ligand-Independent Regulation of Transforming Growth Factor 1 Expression and Cell Cycle Progression by the Aryl Hydrocarbon Receptor - Xiaoqing Chang, Yunxia Fan, Saikumar Karyala, Sandy Schwemberger, Craig R. Tomlinson, Maureen A. Sartor, and Alvaro Puga
The mTORC1 signaling repressors REDD1/2 are rapidly induced and activation of p70S6K1 by leucine is defective in skeletal muscle of an immobilized rat hindlimb\n Andrew R. Kelleher, Scot R. Kimball, Michael D. Dennis, Rudolf J. Schilder, and Leonard S. Jefferson\n Am J Physiol Endocrinol Metab, Jan 2013; 304: E229 - E236.
Inhibition of Gastric Cancer Invasion and Metastasis by PLA2G2A, a Novel Beta-Catenin/TCF Target Gene Kumaresan Ganesan, Tatiana Ivanova, Yonghui Wu, Vikneswari Rajasegaran, Jeanie Wu, Ming Hui Lee, Kun Yu, Sun Young Rha, Hyun Cheol Chung, Bauke Ylstra, Gerrit Meijer, Kon Oi Lian, Heike Grabsch, and Patrick Tan
The Aryl Hydrocarbon Receptor Binds to E2F1 and Inhibits E2F1-induced Apoptosis\n Jennifer L. Marlowe, Yunxia Fan, Xiaoqing Chang, Li Peng, Erik S. Knudsen, Ying Xia, and Alvaro Puga\n Mol. Biol. Cell, Aug 2008; 19: 3263 - 3271.
STRUCTURE AND ASSEMBLY:\n Fluorescent Tagging and Cellular Distribution of the Kaposi's Sarcoma-Associated Herpesvirus ORF45 Tegument Protein\n Shir Bergson, Inna Kalt, Inbal Itzhak, Kevin F. Brulois, Jae U. Jung, and Ronit Sarid\n J. Virol., Nov 2014; 88: 12839 - 12852.
PATHOGENESIS AND IMMUNITY:\n Hepatitis C Virus Entry Is Impaired by Claudin-1 Downregulation in Diacylglycerol Acyltransferase-1-Deficient Cells\n Pil Soo Sung, Asako Murayama, Wonseok Kang, Myung-Sun Kim, Seung Kew Yoon, Masayoshi Fukasawa, Masuo Kondoh, Jin-Soo Kim, Hyongbum Kim, Takanobu Kato, and Eui-Cheol Shin\n J. Virol., Aug 2014; 88: 9233 - 9244.
Exosome-derived miRNAs and ovarian carcinoma progression - Olga Vaksman Claes Tropé Ben Davidson Reuven Reich
Reference The Aryl Hydrocarbon Receptor Binds to E2F1\nand 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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