58-60-6

Basic information

• Product Name: PUROMYCIN AMINONUCLEOSIDE
• Synonyms: 3’-amino-3’-deoxy-n,n-dimethyl-adenosin;6-(dimethylamino)-9-(3-amino-3-deoxy-beta-d-ribofuranosyl)purine;9-(3-amino-3-deoxy-beta-d-ribofuranosyl)-6-(dimethylamino)-9h-purine;aminonucleoside;aminonucleosidepuromycin;stylomycinaminonucleoside;PUROMYCIN AMINONUCLEOSIDE;3'-AMINO-3'-DEOXY-N6,N6-DIMETHYLADENOSINE
• CAS NO: 58-60-6
• Molecular Formula: C₁₂H₁₈N₆O₃
• Molecular Weight: 294.31
• EINECS: 200-388-3
• Mol File: 58-60-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 235℃ (Decomposition)
• Boiling Point: 436.08°C (rough estimate)
• Flash Point: >110°(230°F)
• Appearance: /
• Density: 1.2131 (rough estimate)
• Refractive Index: 1.7000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL, clear, slightly yellow
• PKA: 13.26±0.70(Predicted)
• Water Solubility: Soluble in water at 50mg/ml. May require heating
• Stability: Stable for 1 year as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 2 months.
• BRN: 93902
• CAS DataBase Reference: PUROMYCIN AMINONUCLEOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PUROMYCIN AMINONUCLEOSIDE(58-60-6)
• EPA Substance Registry System: PUROMYCIN AMINONUCLEOSIDE(58-60-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 48/22
• WGK Germany: 3
• RTECS: AU7337000
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 58-60-6(Hazardous Substances Data)

Usage

Description

Puromycin aminonucleoside (58-60-6) is the nucleoside moiety of puromycin (Cat.# 10-2100) which does not inhibit protein synthesis or induce apoptosis.1?It acts as a glomerular epithelial cell toxin2 and as such is a useful tool for producing animal models of nephropathy3,4, or puromycin aminonucleoside nephrosis (1-2.5 mg/100g rat body weight)5. Active in vivo.

Chemical Properties

White crystal

Uses

Different sources of media describe the Uses of 58-60-6 differently. You can refer to the following data:
1. Puromycin aminonucleoside is a semi-synthetic derivative of puromycin which lacks the methoxyphenylalanyl moiety. Puromycin aminonucleoside is the key intermediate in the synthesis of semi-synthetic analogues of puromycin. It does not inhibit protein synthesis or induce apoptosis, but exhibits antitumour properties. Puromycin aminonucleoside-induced nephrosis is a well-described model of human idiopathic nephrotic syndrome, suppressing integrin expression in cultured glomerular epithelial cells.
2. Puromycin Aminonucleoside is an aminonucleoside portion of the antibiotic puromycin.

Definition

ChEBI: Puromycin derivative that lacks the methoxyphenylalanyl group on the amine of the sugar ring.

Safety Profile

An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.

References

1) Chow et al. (1995), Reevaluation of the role of de novo protein synthesis in rat thymocyte apoptosis; Exp. Cell Res., 216 149 2) Krishnamurti et al. (2001), Puromycin aminonucleoside suppresses integrin expression in cultured glomerular epithelial cells; J. Am. Soc. Nephrol., 12 758 3) Egashira et al. (2006), Tryptophan-niacin metabolism in rat with puromycin aminonucleoside-induced nephrosis; Int. J. Vitam. Nutr. Res., 76 28 4) Hagiwara et al. (2006), Mitochondrial dysfunction in focal segmental glomerulosclerosis of puromycin aminonucleoside nephrosis; Kidney Int., 69 1146 5) Lowenborg et al. (2000), Glomerular function and morphology in puromycin aminonucleoside nephropathy in rats; Nephrol. Dial. Transplant, 15 1547

Upstream product

• 124-40-3 dimethyl amine 
• 6044-48-0 (1R)-O,O'-dibenzoyl-1-(6-chloro-purin-9-yl)-3-phthalimido-D-1,4-anhydro-3-deoxy-ribitol 
• 108989-12-4 3'-amino-N⁶,N⁶-dimethyl-2-methylsulfanyl-3'-deoxy-adenosine 
• 72-94-6 3'-acetylamino-N⁶,N⁶-dimethyl-3'-deoxy-adenosine 
• 178883-52-8 2,2-Dimethyl-propionic acid (2S,3R,4R,5R)-4-acetoxy-5-(6-dimethylamino-purin-9-yl)-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-furan-2-ylmethyl ester 
• 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 
• 384334-64-9 9-(3-azido-3-deoxy-β-D-ribofuranosyl)-6-(dimethylamino)purine 
• 36913-17-4 4-benzylamino-2-(6-dimethylamino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol 
• 934011-54-8 9-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]-N⁶,N⁶-dimethyladenine 
• 934011-52-6 9-[2-O-(N-benzylcarbamoyl)-3,5-O-sulfinyl-β-D-xylofuranosyl]-N⁶,N⁶-dimethyladenine 
• 669055-52-1 9-(β-D-xylofuranosyl)-N⁶,N⁶-dimethyladenine 
• 669055-54-3 9-(3,5-O-sulfinyl-β-D-xylofuranosyl)-N⁶,N⁶-dimethyladenine 
• 68044-56-4 3'-Trifluoracetamido-3'-desoxyadenosin 
• 67313-10-4 9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine 

Downstream Products

• 99672-42-1 N⁶,N⁶-dimethyl-3'-phthalimido-3'-deoxy-adenosine 
• 13347-33-6 O^2'_,O5'-diacetyl-3'-acetylamino-N⁶,N⁶-dimethyl-3'-deoxy-adenosine 
• 112718-09-9 3'-benzyloxycarbonylamino-N⁶,N⁶-dimethyl-3'-deoxy-adenosine 
• 76381-68-5 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 
• 148077-16-1 sparsopuromycin 
• 76381-72-1 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 
• 76381-71-0 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 
• 106021-34-5 C₄₉H₇₁N₁₅O₁₁S 
• 57182-86-2 6-dimethylamino-9-[3'-(O-methyl) (2S)-N-benzyloxycarbonyltyrosinylamino-3'-deoxy-β-D-ribofuranosyl]purine 
• 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 
• 833447-70-4 3'-amino-3'-deoxy-3'-(L-2-acetoxy-3-phenylpropionyl)-N⁶,N⁶-dimethyladenosine 

Relevant articles and documents

A simple and efficient synthesis of puromycin, 2,2′-anhydro- pyrimidine nucleosides, cytidines and 2′,3′-anhydroadenosine from 3′,5′-O-sulfinyl xylo-nucleosides

Synthesis of antibiotics, puromycin and 3 ′-amino-3 ′-deoxy-N 6 ,N 6 -dimethyladenosine 11 was achieved by utilizing the cyclic sulfite 6a of the xylo -3 ′,5 ′-dihydroxy group as a new protective group. The key synthetic step is the deprotection of the sulfite moiety through the intramolecular cyclization of 2-α-carbamate 7 . In a similar manner, 2,2 ′-anhydro-pyrimidine nucleosides 15 , ribo -cytidines 17 and 2 ′,3 ′-anhydroadenosine 14 were prepared in high yields from the corresponding sulfites 4 , 5 , and 6b , respectively. Copyright Taylor & Francis Group, LLC.

Nucleic acid analog with amide linkage and method of making that analog

The present invention relates to a nucleic acid analog having the formula: STR1 where R is a compound selected from a group consisting of hydrogen, a hydroxyl group, a hydrophilic group or a hydrophobic group, n is greater than or equal to 2, and Base is uracil, adenine, guanine, cytosine, thymine or hypoxanthine, with Bases in the analog being the same or different. Further, the present invention relates to a processes for making and using the analog.

Polyamine biosynthesis inhibitors

A compound having the formula: STR1 wherein R is STR2 wherein R' is hydrogen or aminopropyl and salts thereof.