1390-73-4

Basic information

• Product Name: (1S,2S,3R,4S,6R)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-D-glucopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside
• CAS NO: 1390-73-4
• Molecular Formula: C₂₃H₄₅N₅O₁₄
• Molecular Weight: 615.6285
• Mol File: 1390-73-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 939.8°C at 760 mmHg
• Flash Point: 522.2°C
• Density: 1.64g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: (1S,2S,3R,4S,6R)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-D-glucopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,4S,6R)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-D-glucopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside(1390-73-4)
• EPA Substance Registry System: (1S,2S,3R,4S,6R)-4,6-diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-D-glucopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside(1390-73-4)

Safety Data

• Hazardous Substances Data: 1390-73-4(Hazardous Substances Data)

Usage

Description

(1S,2S,3R,4S,6R)-4,6-diamino-2-[3-O-(2,6-diamino-2,6-dideoxy-D-glucopyranosyl)-beta-D-ribofuranosyl]oxy-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside is a complex molecule that contains several amino and sugar groups. It is a derivative of the antibiotic drug gentamicin and belongs to the aminoglycoside class of antibiotics.

Uses

Used in Pharmaceutical Industry:
(1S,2S,3R,4S,6R)-4,6-diamino-2-[3-O-(2,6-diamino-2,6-dideoxy-D-glucopyranosyl)-beta-D-ribofuranosyl]oxy-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside is used as an antibiotic for its broad-spectrum activity against many types of bacteria. Its unique structure allows it to bind to the bacterial ribosome and interfere with protein synthesis, ultimately leading to bacterial cell death. However, its clinical use is often limited due to potential toxicity and the development of bacterial resistance.

Relevant articles and documents

Synthesis of multifunctional PAMAM-aminoglycoside conjugates with enhanced transfection efficiency

The development of multifunctional vectors for efficient and safe gene delivery is one of the major challenges for scientists working in the gene therapy field. In this context, we have designed a novel type of aminoglycoside-rich dendrimers with a defined structure based on polyamidoamine (PAMAM) in order to develop efficient, nontoxic gene delivery vehicles. Three different conjugates, i.e., PAMAM G4-neamine, -paromomycin, and -neomycin, were synthesized and characterized by nuclear magnetic resonance (NMR) and MALDI analysis. The conjugates were found to self-assemble electrostatically with plasmid DNA, and unlike neamine conjugate, each at its optimum showed increased gene delivery potency compared to PAMAM G4 dendrimer in three different cell lines, along with negligible cytotoxicity. These results all disclosed aminoglycosides as suitable functionalities for tailoring safe and efficient multifunctional gene delivery vectors.

Dehydroxylation of aminosugars

Dehydroxylation of aminoglycoside antibiotics is carried out by halogenation of phosphorylated aminoglycoside antibiotics followed by reduction of thus halogenated antibiotics. The dehydroxylation process is entirely new and gives the final product in a high yield. The resulting deoxyaminoglycoside antibiotics are effective against microorganisms including aminoglycoside antiobiotics-resistant microorganisms.