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

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

• 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 
• 72-94-6 3'-acetylamino-N⁶,N⁶-dimethyl-3'-deoxy-adenosine 
• 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 
• 125084-69-7 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine 
• 101014-71-5 (1Ξ)-3-acetylamino-O,O'-dibenzoyl-1-(6-chloro-purin-9-yl)-D-1,4-anhydro-3-deoxy-ribitol 
• 178883-28-8 2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-hydroxy-pent-4-ynyl ester 
• 178883-34-6 2,2-Dimethyl-propionic acid (2S,3S)-3-acetylamino-2,3-dihydro-furan-2-ylmethyl 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 
• 125084-68-6 9-<3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine 
• 125084-70-0 9-<2,3-anhydro-5-O-<(tert-butyl)diphenylsilyl>-β-D-ribofuranosyl>adenine 
• 125084-71-1 9-[3-(benzylamino)-3-N,2-O-carbonyl-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.

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.

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.

Asymmetric synthesis of nucleosides via molybdenum-catalyzed alkynol cycloisomerization coupled with stereoselective glycosylations of deoxyfuranose glycals and 3-amidofuranose glycals

Deoxygenated furanose glycals were efficiently prepared by molybdenum pentacarbonyl-catalyzed cycloisomerization of alkynyl alcohols, which were easily prepared in chiral nonracemic form by short synthetic sequences featuring asymmetric epoxidations of commercially available allylic alcohols. The cycloisomerization reaction was demonstrated to be compatible with ester and amide functional groups. A 2,3-dideoxyfuranose glycal was stereoselectively converted into the anti-AIDS β-nucleoside stavudine (2',3'-didehydro-2',3'-dideoxythymidine, d4T) and the antiviral 3'-deoxy-β-nucleoside cordycepin. The anchimeric and hydrogen-bond-directing effects of 3-amido-2,3-dideoxyfuranose glycals were exploited in a novel and highly stereoselective synthesis strategy for a variety of biologically active 3'-amino-2',3'-dideoxy- and 3'-amino-3'-deoxy-β-nucleosides, including puromycin aminonucleoside. In addition, the mechanism of the molybdenum-catalyzed alkynol cycloisomerization reaction has been studied. Evidence is presented which indicates that cyclic molybdenum carbene anions are catalytic intermediates in these cyclizations.

Polyamine biosynthesis inhibitors

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