13389-16-7

Basic information

• Product Name: 8-AMino-Inosine
• Synonyms: 8-AMino-Inosine
• CAS NO: 13389-16-7
• Molecular Formula: C10H13N5O5
• Molecular Weight: 283.24072
• Product Categories: Nucleotides, Bases & Related Reagents
• Mol File: 13389-16-7.mol

Chemical Properties

• Boiling Point: 764.5°Cat760mmHg
• Flash Point: 416.2°C
• Appearance: /
• Density: 2.25g/cm³
• Vapor Pressure: 1.42E-24mmHg at 25°C
• Refractive Index: 1.955
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Water (Slightly)
• CAS DataBase Reference: 8-AMino-Inosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-AMino-Inosine(13389-16-7)
• EPA Substance Registry System: 8-AMino-Inosine(13389-16-7)

Safety Data

• Hazardous Substances Data: 13389-16-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Amino-Inosine is used as a chemotherapeutic agent for the treatment of leukemia, functioning through the cytodestruction of neoplastic cells.
Used in Neuroprotection:
8-Amino-Inosine is used as a neuroprotective agent to treat stroke patients, aiming to restore neural function and promote recovery.

InChI:InChI=1/C10H13N5O5/c11-10-14-4-7(12-2-13-8(4)19)15(10)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H2,11,14)(H,12,13,19)

Upstream product

• 97551-56-9 8-azidoinosine 

Relevant articles and documents

Discovery of a Novel Inhibitor of Human Purine Nucleoside Phosphorylase by a Simple Hydrophilic Interaction Liquid Chromatography Enzymatic Assay

Human purine nucleoside phosphorylase (HsPNP) belongs to the purine salvage pathway of nucleic acids. Genetic deficiency of this enzyme triggers apoptosis of activated T-cells due to the accumulation of deoxyguanosine triphosphate (dGTP). Therefore, potential chemotherapeutic applications of human PNP inhibitors include the treatment of T-cell leukemia, autoimmune diseases and transplant tissue rejection. In this report, we present the discovery of novel HsPNP inhibitors by coupling experimental and computational tools. A simple, inexpensive, direct and non-radioactive enzymatic assay coupled to hydrophilic interaction liquid chromatography and UV detection (LC-UV using HILIC as elution mode) was developed for screening HsPNP inhibitors. Enzymatic activity was assessed by monitoring the phosphorolysis of inosine (Ino) to hypoxanthine (Hpx) by LC-UV. A small library of 6- and 8-substituted nucleosides was synthesized and screened. The inhibition potency of the most promising compound, 8-aminoinosine (4), was quantified through Ki and IC50 determinations. The effect of HsPNP inhibition was also evaluated in vitro through the study of cytotoxicity on human T-cell leukemia cells (CCRF-CEM). Docking studies were also carried out for the most potent compound, allowing further insights into the inhibitor interaction at the HsPNP active site. This study provides both new tools and a new lead for developing novel HsPNP inhibitors.

Purine and 8-Substituted Purine Arabinofuranosyl and Ribofuranosyl Nucleoside Derivatives as Potential Inducers of the Differentiation of the Friend Erythroleuukemia

Several antimetabolites have been demonstrated to have the capacity to initiate differentiation in vitro of a variety of leukemic cell lines.To explore the structural requirements for this activity, a series of purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells. 9-(β-D-Arabinofuranosyl)hypoxanthine and 6-(hydroxyamino)-9-(β-D-arabinofuranosyl)purine were effective inducers of maturation, producing 82percent and 74percent benzidine-positive cells, a measure of the number of cells synthesizing hemoglobin. 6-Mercapto-9-(β-D-ribofuranosyl)purine and 6-(methylmercapto)-9-(β-D-ribofuranosyl)purine and their corresponding β-D-arabinofuranosyl derivatives were also effective initiators of maturation, causing approximately 50percent of the cell population to assume a differentiated phenotype.