1375073-99-6

Basic information

• Product Name: 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine
• Synonyms: 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine
• CAS NO: 1375073-99-6
• Molecular Weight: 583.637
• Mol File: 1375073-99-6.mol

Chemical Properties

• CAS DataBase Reference: 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine(1375073-99-6)
• EPA Substance Registry System: 6′-(R)-methyl-5-O-(5-amino-5,6-dideoxy-β-D-allofuranosyl)-1-N-[(S)-4-amino-2-hydroxy-butanoyl]-paromamine(1375073-99-6)

Safety Data

• Hazardous Substances Data: 1375073-99-6(Hazardous Substances Data)

Upstream product

• 1375073-92-9 6′-(R)-methyl-5-O-(5-azido-5,6-dideoxy-2,3-O-dibenzoyl-β-D-allofuranosyl)-3′,4′,6′,6-tetra-O-acetyl-2′,3-diazido-1-N-[(S)-4-azido-2-O-acetyl-butanoyl]paromamine 
• 1356827-06-9 C₂₂H₁₉Cl₃N₄O₆ 
• 1375073-77-0 3',4',6',6-tetra-O-acetyl-2',3-diazido-1-N-[(S)-4-azido-2-O-acetyl-butanoyl]-6'-(R)-methyl-paromamine 
• 1356826-94-2 4-methylphenyl 2,3-O-1-methylethylidene-1-thio-β-D-ribopentodialdo-1,4-furanoside 
• 1131610-84-8 p-tolyl 1-thio-β-D-ribofuranoside 
• 1375073-82-7 C₁₃H₁₇N₃O₃S 
• 1356827-02-5 4-methylphenyl 5-azido-5,6-dideoxy-2,3-O-1-methylethylidene-1-thio-β-D-allofuranoside 
• 1356826-99-7 4-methylphenyl 6-deoxy-5-O-tosyl-2,3-O-1-methylethylidene-1-thio-α-L-allofuranoside 
• 1356826-96-4 4-methylphenyl 6-deoxy-2,3-O-1-methylethylidene-1-thio-α-L-allofuranoside 

Relevant articles and documents

Increased selectivity toward cytoplasmic versus mitochondrial ribosome confers improved efficiency of synthetic aminoglycosides in fixing damaged genes: A strategy for treatment of genetic diseases caused by nonsense mutations

Compelling evidence is now available that gentamicin and Geneticin (G418) can induce the mammalian ribosome to suppress disease-causing nonsense mutations and partially restore the expression of functional proteins. However, toxicity and relative lack of efficacy at subtoxic doses limit the use of gentamicin for suppression therapy. Although G418 exhibits the strongest activity, it is very cytotoxic even at low doses. We describe here the first systematic development of the novel aminoglycoside (S)-11 exhibiting similar in vitro and ex vivo activity to that of G418, while its cell toxicity is significantly lower than those of gentamicin and G418. Using a series of biochemical assays, we provide proof of principle that antibacterial activity and toxicity of aminoglycosides can be dissected from their suppression activity. The data further indicate that the increased specificity toward cytoplasmic ribosome correlates with the increased activity and that the decreased specificity toward mitochondrial ribosome confers the lowered cytotoxicity.

AMINOGLYCOSIDES AND USES THEREOF IN TREATING GENETIC DISORDERS

A new class of pseudo-trisaccharide aminoglycosides having an alkyl group at the 5'' position, exhibiting efficient stop codon mutation readthrough activity, low cytotoxicity and high selectivity towards eukaryotic translation systems are provided. Also provided are pharmaceutical compositions containing the same, and uses thereof in the treatment of genetic disorders, as well as processes of preparing these aminoglycosides. The disclosed aminoglycosides can be represented by the general formula I: formula I or a pharmaceutically acceptable salt thereof, wherein R1 is selected from the group consisting of alkyl, cycloalkyl and aryl; and all other variables and features are as described in the specification.