53-79-2

Basic information

• Product Name: PUROMYCIN
• Synonyms: (s)-3’-((2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3’-deoxy-n,n-dimethy;1-mm;3’-(alpha-amino-p-methoxyhydrocinnamamido)-3’-deoxy-n,n-dimethyl-adenosinl;3’-(l-alpha-amino-p-methoxyhydrocinnamamido)-3’-deoxy-n,n-dimethyladenosine;3123l;6-dimethylamino-9-(3’-(p-methoxy-l-phenylalanylamino)-beta-d-ribofuranosyl)-;achromycin;achromycin(purinederivative)
• CAS NO: 53-79-2
• Molecular Formula: C₂₂H₂₉N₇O₅
• Molecular Weight: 471.51
• Mol File: 53-79-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 175.5-177°
• Boiling Point: 572.65°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.3119 (rough estimate)
• Vapor Pressure: 8.44E-30mmHg at 25°C
• Refractive Index: 1.7010 (estimate)
• PKA: 6.8, 7.2(at 25℃)
• Water Solubility: Soluble in water (50 mg/ml at 20°C).
• CAS DataBase Reference: PUROMYCIN(CAS DataBase Reference)
• NIST Chemistry Reference: PUROMYCIN(53-79-2)
• EPA Substance Registry System: PUROMYCIN(53-79-2)

Safety Data

• RIDADR: 3249
• RTECS: AU7350000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 53-79-2(Hazardous Substances Data)

Usage

Description

Puromycin is an aminonucleoside antibiotic produced by Streptomyces alboniger. It is a very common antibiotic routinely used by scientists in biomedical research to select cells modified by genetic engineering. It specifically inhibits peptidyl transfer on both prokaryotic and eukaryotic ribosomes. The antibiotic inhibits the growth of Gram-positive bacteria and various animal and insect cells. Fungi and Gram-negative bacteria are resistant due to the low permeability of the antibiotic. For more than 30 years, puromycin has been widely used as a basic tool for studying protein synthesis. Now, puromycin hydrochloride is particularly useful for the selection of cell types harboring plasmids carrying puromycin resistance genes. Puromycinresistant cells express pac gene, which encodes an N-acetyl puromycin transferase. The pac gene can be mobilized on a plasmid and used to transfect a host cell in an attempt to provide resistance; therefore, puromycin can be used in gene selections for mammalian host cells. This aminonucleoside antibiotic causes premature chain termination during translation in the ribosomes. Part of the molecule resembles the 30 end of the aminoacylated tRNA. It enters the A site and transfers to the growing chain, causing premature chain release. The exact mechanism of action is unknown, but the 30 position contains an amide linkage instead of the normal ester linkage of tRNA; the amide bond makes the molecule much more resistant to hydrolysis and thus causes the ribosome to become stopped. It is not selective for either prokaryotes or eukaryotes. Also of note, puromycin is critical in mRNA display as it allows the growing peptide chain to be covalently bonded to its own mRNA template. Additionally, puromycin is a reversible inhibitor of dipeptidyl-peptidase II (serine peptidase) and cytosol alanyl aminopeptidase (metallopeptidase). The mechanism of inhibition is not well understood; however, puromycin can be used to distinguish between aminopeptidase M (active) and cytosol alanyl aminopeptidase (inhibited by puromycin) and therefore extremely useful in biochemistry and nephrology research.

Chemical Properties

Crystals.

Uses

Different sources of media describe the Uses of 53-79-2 differently. You can refer to the following data:
1. Puromycin has been widely used as a basic tool in research for studying protein synthesis. It is an antibiotic used by scientists in bioresearch to select cells modified by genetic engineering. It inhibits protein synthesis by binding to RNA. It is also an antineoplastic and antitrypanosomal agent.
2. Puromycin is a nucleoside antibiotic isolated from Streptomyces alboniger in the 1950s as an anti-trypansomal agent with antibiotic activity. Puromycin is non-selective, inhibiting RNA by blocking ribosomal translation. Puromycin is used in cell biology to select mammalian cell lines that have been transformed by vectors that express puromycin-N-acetyl-transferase.
3. Puromycin is an aminonuclease antibiotic produced by the soil actinomycete?Streptomyces alboniger; which induces apoptosis.

Definition

ChEBI: An aminonucleoside antibiotic, derived from the Streptomyces alboniger bacterium, that causes premature chain termination during translation taking place in the ribosome.

Hazard

Toxic to living cells of all kinds.

Toxicity evaluation

Puromycin is a specific metabolic inhibitor of protein synthesis and acts as an aminoacyl-tRNA analog and peptidyl acceptor. The latter causes premature chain termination of the protein and the release of nascent or growing polypeptide chains. In liver, it has been shown to cause fat accumulation without causing death of the hepatocytes. Puromycin causes focal glomerular sclerosis and alters the morphology, localization of anionic sites, and metabolism of renal epithelial cells. This injury is attributable to the production of reactive oxygen species.

InChI:InChI=1/C22H29N7O5.2ClH/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);2*1H/t14-,15+,16+,18+,22?;;/m0../s1

Upstream product

• 58-58-2 puromycin dihydrogen chloride 
• 1558055-04-1 4,5-dimethoxy-2-nitrobenzyloxycarbonylpuromycin 
• 111210-69-6 O-methyl-N-phthaloyl-(S)-tyrosyl chloride 
• 60-18-4 L-tyrosine 
• 17554-34-6 (2S)-2-[(benzyloxycarbonyl)amino]-3-(4-methoxyphenyl)propanoic acid 
• 1164-16-5 Z-L-Tyr-OH 
• 58-60-6 3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine 
• 384334-58-1 2,2,2-Trifluoro-N-[(2S,3S,4R,5R)-4-hydroxy-2-hydroxymethyl-5-(6-[1,2,4]triazol-4-yl-purin-9-yl)-tetrahydro-furan-3-yl]-acetamide 
• 749200-34-8 9-(3-azido-3-deoxy-β-D-ribofuranosyl)-6-(1,2,4-triazol-4-yl)purine 
• 384334-64-9 9-(3-azido-3-deoxy-β-D-ribofuranosyl)-6-(dimethylamino)purine 
• 58699-62-0 3'-Azido-3'-deoxyadenosine 
• 125084-69-7 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine 
• 125127-12-0 (3aR,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-3-benzyl-4-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuro[3,4-d]oxazol-2(3H)-one 
• 125084-68-6 9-<3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine 

Downstream Products

• 57183-05-8 tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate 
• 151967-82-7 [(S)-1-[(2S,3S,4R,5R)-5-(6-Dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylcarbamoyl]-2-(4-methoxy-phenyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 1477500-67-6 C₄₈H₅₈N₉O₉P 
• 1477500-65-4 C₃₉H₄₁N₇O₈ 
• 1477500-63-2 C₆₀H₅₉N₇O₁₀ 
• 151967-83-8 [(S)-1-[(2S,3S,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-3-ylcarbamoyl]-2-(4-methoxy-phenyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 

Relevant articles and documents

Radiosynthesis of Carbon-11 Labeled Puromycin as a Potential PET Candidate for Imaging Protein Synthesis in Vivo

In order to address the limitations associated with the present range of PET radiotracers used for imaging protein synthesis in vivo we have synthesized a candidate PET radiotracer based on Puromycin (3, PURO), a protein synthesis inhibitor. The desmethylPURO 9 precursor for radiolabeling with carbon-11 radioisotope was synthesized in two steps employing EDC/HOBt amide coupling in overall 76% yield. Optimal conditions for radiolabeling were then established via methylation/deprotection sequence. Under these conditions as determined by NMR analysis 9 showed partial stability (ca. 80%) under acidic conditions. Limited evidence of stereochemical stability of 3 was also found. The radiolabeling of intermediate [11C]12 was accomplished with up to 57% conversion from [11C]iodomethane. An automated method was then developed for high radioactivity radiosynthesis to produce [11C]3 ([11C]PURO) in 16 ± 6% (n = 3) decay corrected radiochemical yields.

Design of photocaged puromycin for nascent polypeptide release and spatiotemporal monitoring of translation

The antibiotic puromycin, which inhibits protein translation, is used in a broad range of biochemical applications. The synthesis, characterization, and biological applications of NVOC-puromycin, a photocaged derivative that is activated by UV illumination, are presented. The caged compound had no effect either on prokaryotic or eukaryotic translation or on the viability of HEK 293 cells. Furthermore, no significant release of ribosome-bound polypeptide chains was detected invitro. Upon illumination, cytotoxic activity, invitro translation inhibition, and polypeptide release triggered by the uncaging of NVOC-puromycin were equivalent to those of the commercial compound. The quantum yield of photolysis was determined to be 1.1±0.2 % and the NVOC-puromycin was applied to the detection of newly translated proteins with remarkable spatiotemporal resolution by using two-photon laser excitation, puromycin immunohistochemistry, and imaging in rat hippocampal neurons. On like a light: The antibiotic puromycin (green) is a translation inhibitor that triggers the release of the nascent polypeptide chain (red) from the ribosome (yellow) and it is used in a number of applications. A photocaged puromycin derivative, NVOC-puromycin, was synthesized and characterized. Both functional recovery upon UV illumination and biological inactivity invitro and invivo were demonstrated.

Syntheses of puromycin from adenosine and 7-deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair

Protection (05′) of 2′,3′-anhydroadenosine with tert-butyldiphenylsilyl chloride and epoxide opening with dimethylboron bromide gave the 3′-bromo-3′-deoxy xylo isomer which was treated with benzylisocyanate to give the 2′-O-(N-benzylcarbamoyl) derivative. Ring closure gave the oxazolidinone, and successive deprotection concluded an efficient route to 3′-amino-3′-deoxyadenosine. Analogous treatment ofthe antibiotic tubercidin {7-deazaadenosine; 4-amino-7-(β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine} gave 3′-amino-3′-deoxytubercidin. Trifluoroacetylation of the 3′-amino function, elaboration of the heterocyclic amino group into a (1,2,4-triazol-4-yl) ring with N,N′-bis-[(dimethylamino)methylene]hydrazine, and nucleophilic aromatic substitution with dimethylamine gave puromycin aminonucleoside [9-(3-amino-3-deoxy-β-D-ribofuranosyl)-6-(dimethylamino)purine] and its 7-deaza analogue. Aminoacylation [BOC-(4-methoxy-L-phenylalanine)] and deprotection gave puromycin and 7-deazapuromycin. Most reactions gave high yields at or below ambient temperature. Equivalent inhibition of protein biosynthesis in a rabbit reticulocyte system and parallel growth inhibition of several bacteria were observed with the 7-aza/deaza pair. Replacement of N7 in the purine ring of puromycin by "CH" has no apparent effect on biological activity.