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, also known as Puromycin aminonucleoside (58-60-6), is the nucleoside moiety of the antibiotic puromycin. It is a semi-synthetic derivative of puromycin, which lacks the methoxyphenylalanyl moiety. PUROMYCIN AMINONUCLEOSIDE does not inhibit protein synthesis or induce apoptosis but exhibits antitumor properties. Puromycin Aminonucleoside is a white crystalline substance and is used as a key intermediate in the synthesis of semi-synthetic analogues of puromycin. It is also known to act as a glomerular epithelial cell toxin, making it a useful tool for producing animal models of nephropathy.

Uses

1. Used in Pharmaceutical Industry:
Puromycin Aminonucleoside is used as a key intermediate for the synthesis of semi-synthetic analogues of puromycin. Its role in the development of new drugs is crucial, as it helps in creating variations of the original antibiotic with potentially improved properties or targeted applications.
2. Used in Research and Development:
Puromycin Aminonucleoside is used as a research tool for producing animal models of nephropathy and puromycin aminonucleoside nephrosis. This application aids in understanding the pathophysiology of kidney diseases and contributes to the development of novel therapeutic strategies for treating such conditions.
3. Used in Antitumor Applications:
Puromycin Aminonucleoside exhibits antitumor properties, making it a potential candidate for cancer research and drug development. Its unique mechanism of action, which does not involve inhibiting protein synthesis or inducing apoptosis, may offer new insights into cancer biology and the development of targeted therapies.
4. Used in Cell Biology:
As a glomerular epithelial cell toxin, Puromycin Aminonucleoside is used to study the effects of this compound on cell function and integrity. This application can provide valuable information on cellular processes and the potential use of Puromycin Aminonucleoside in modulating cellular responses in various disease states.

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

• 72-94-6 3'-acetylamino-N⁶,N⁶-dimethyl-3'-deoxy-adenosine 
• 108989-12-4 3'-amino-N⁶,N⁶-dimethyl-2-methylsulfanyl-3'-deoxy-adenosine 
• 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 
• 101014-71-5 (1Ξ)-3-acetylamino-O,O'-dibenzoyl-1-(6-chloro-purin-9-yl)-D-1,4-anhydro-3-deoxy-ribitol 
• 1681-11-4 dimethyl-(2-methylsulfanyl-7⁽⁹⁾H-purin-6-yl)-amine 
• 178883-28-8 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-pent-4-ynyl ester 
• 178883-35-7 2,2-Dimethyl-propionic acid (2S,3S)-3-(2,2,2-trifluoro-acetylamino)-2,3-dihydro-furan-2-ylmethyl ester 
• 178883-31-3 2,2-Dimethyl-propionic acid (2S,3S)-2-hydroxy-3-(2,2,2-trifluoro-acetylamino)-pent-4-ynyl ester 
• 178883-34-6 2,2-Dimethyl-propionic acid (2S,3S)-3-acetylamino-2,3-dihydro-furan-2-ylmethyl ester 
• 178883-30-2 2,2-Dimethyl-propionic acid (2S,3S)-3-acetylamino-2-hydroxy-pent-4-ynyl ester 
• 178883-29-9 2,2-Dimethyl-propionic acid (2S,3S)-3-amino-2-hydroxy-pent-4-ynyl ester 
• 178963-32-1 (3S,4S)-3-azido-1-pentyne-4,5-diol 
• 749200-34-8 9-(3-azido-3-deoxy-β-D-ribofuranosyl)-6-(1,2,4-triazol-4-yl)purine 

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 
• 106021-34-5 C₄₉H₇₁N₁₅O₁₁S 
• 76381-71-0 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 
• 76381-72-1 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 
• 148077-16-1 sparsopuromycin 
• 76381-68-5 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 

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.