1037515-73-3

Basic information

• Product Name: 1,3,6',3”-tetra-azido-kanamycin A
• Synonyms: 1,3,6',3”-tetra-azido-kanamycin A
• CAS NO: 1037515-73-3
• Molecular Weight: 588.494
• Mol File: 1037515-73-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3,6',3”-tetra-azido-kanamycin A(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,6',3”-tetra-azido-kanamycin A(1037515-73-3)
• EPA Substance Registry System: 1,3,6',3”-tetra-azido-kanamycin A(1037515-73-3)

Safety Data

• Hazardous Substances Data: 1037515-73-3(Hazardous Substances Data)

Upstream product

• 59-01-8 kanamycin A 
• 3847-27-6 Kanamycin A sulfate 
• 1147358-80-2 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A 
• 3855-45-6 triflic azide 

Downstream Products

• 1147358-80-2 2',3',4',2'',4'',6''-O-hexaacetyl-1,3,6',3''-tetraazido-kanamycin A 
• 1147358-84-6 1,3,6',3''-tetraazido-5,2',4'',6''-di-O-benzylidenekanamycin A 
• 1147358-86-8 C₂₅H₃₂N₁₂O₁₁ 
• 1147358-88-0 1,3,6',3''-tetraazido-5,2',4'',6''-di-O-benzylidene-3',4',2''-tri-O-benzylkanamycin A 
• 1416341-86-0 1,3,6',3''-tetraazido-3',4',2''-tri-O-benzylkanamycin A 
• 1416341-87-1 1,3,6',3''-tetraazido-4'',6''-O-benzylidene-3',4',2''-tri-O-benzylkanamycin A 
• 1416341-88-2 1,3,6',3''-tetraazido-4'',6''-O-benzylidene-3',4',2''-tri-O-benzyl-5,2'-O-methylenekanamycin A 
• 1416341-91-7 1,3,6',3''-tetraazido-4'',6''-O-benzylidene-3',4',2''-tri-O-benzyl-5,2'-di-O-allylkanamycin A 
• 1416341-92-8 1,3,6',3''-tetraazido-4'',6''-O-benzylidene-3',4',2''-tri-O-benzyl-5,2'-O-(but-2-en-1,4-diyl)kanamycin A 
• 1416341-93-9 1,3,6',3''-tetraazido-5,2',4'',6''-di-O-benzylidene-3',4',2''-tri-O-p-methoxybenzylkanamycin A 
• 1416341-94-0 C₄₂H₅₂N₁₂O₁₄ 
• 1416341-95-1 1,3,6',3''-tetraazido-4'',6''-O-benzylidene-3',4',2''-tri-O-p-methoxybenzylkanamycin A 
• 1416341-96-2 1,3,6',3''-tetraazido-4'',6''-O-benzylidene-3',4',2''-tri-O-p-methoxybenzyl-5,2'-di-O-allylkanamycin A 
• 1416341-97-3 1,3,6',3''-tetraazido-4'',6''-O-benzylidene-3',4',2''-tri-O-p-methoxybenzyl-5,2'-O-(but-2-en-1,4-diyl)kanamycin A 

Relevant articles and documents

Inhibition of Connexin Hemichannels by New Amphiphilic Aminoglycosides without Antibiotic Activity

Connexins hemichannels (HCs) from adjacent cells form gap junctional channels that mediate cell-to-cell communication. Abnormal opening of free undocked HCs can produce cell damage and participate in the mechanism of disorders such as cardiac infarct, stroke, deafness, skin diseases, and cataracts. Therefore, inhibitors of connexin HCs have great pharmacological potential. Antibiotic aminoglycosides (AGs) have been recently identified as connexin HC inhibitors, but their antibiotic effect is an issue for the treatment of disorders where infections do not play a role. Herein, we synthesized and tested several amphiphilic AGs without antibiotic effect for their inhibition against connexin HCs, using a newly developed cell-based bacterial growth complementation assay. Several leads with superior potency than the parent compound, kanamycin A, were identified. Unlike traditional AGs, these amphiphilic AGs are not bactericidal and are not toxic to mammalian cells, making them better than traditional AGs as HC inhibitors for clinical use and other applications.

Effects of 5-O-Ribosylation of Aminoglycosides on Antimicrobial Activity and Selective Perturbation of Bacterial Translation

We studied six pairs of aminoglycosides and their corresponding ribosylated derivatives synthesized by attaching a β-O-linked ribofuranose to the 5-OH of the deoxystreptamine ring of the parent pseudo-oligosaccharide antibiotic. Ribosylation of the 4,6-disubstituted 2-deoxystreptamine aminoglycoside kanamycin B led to improved selectivity for inhibition of prokaryotic relative to cytosolic eukaryotic in vitro translation. For the pseudodisaccharide aminoglycoside scaffolds neamine and nebramine, ribosylated derivatives were both more potent antimicrobials and more selective to inhibition of prokaryotic translation. On the basis of the results of this study, we suggest that modification of the 5-OH position of the streptamine ring of other natural or semisynthetic pseudodisaccharide aminoglycoside scaffolds containing an equatorial amine at the 2′ sugar position with a β-O-linked ribofuranose is a promising avenue for the development of novel aminoglycoside antibiotics with improved efficacy and reduced toxicity.

Structure-based design of highly crowded ribostamycin/kanamycin hybrids as a new family of antibiotics

Sugar sugar! The synthesis and evaluation of ribostamycin/kanamycin hybrids incorporating a highly crowded trisubstituted aminocyclitol unit that should provide maximum complementation with the RNA receptor are reported (see picture). Analysis shows that the existing conflicts between the different sugar rings can be significantly alleviated by a simple chemical modification, leading to an improvement in activity. (Figure Presented)