57470
Inosine
crystallized, ≥99.0% (HPLC)
Synonym(s):
(−)-Inosine, Hypoxanthine 9-β-D-ribofuranoside
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About This Item
Empirical Formula (Hill Notation):
C10H12N4O5
CAS Number:
Molecular Weight:
268.23
EC Number:
200-390-4
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
624896
assay
≥99.0% (HPLC)
optical activity
[α]20/D −76±2°, c = 1% in 0.1 M NaOH
quality
crystallized
ign. residue
≤0.05%
mp
222-226 °C (dec.) (lit.)
solubility
H2O: soluble 50 mg/mL, clear, colorless
SMILES string
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3C(=O)NC=Nc23
InChI
1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
InChI key
UGQMRVRMYYASKQ-KQYNXXCUSA-N
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Application
Inosine was used in a study to understand the protective effect of adenosine that is mediated by inosine in rat astrocyte cultures subjected to combined glucose-oxygen deprivation. It was used as a supplement in a medium to obtain fully differentiated human colonic surface-like cells in a study. The product was used to study the effects of inosine on left ventricular contractile force, circumflex blood flow, heart rate, and arterial pressure in mongrel dogs. It was used to study the anti-inflammatory effects of inosine in human monocytes, neutrophils and epithelial cells in vitro.
Biochem/physiol Actions
Inosine is a potent stimulator of nerve growth factor (NGF) induced neurite outgrowth. The elevated levels of inosine in brain following injury are associated with the increased expression proteins related to axonal regeneration and growth. Mice given inosine demonstrated enhanced recovery of fine motor control following ischemic brain damage. Inosine may be used in studies of the process A-to-I RNA editing.
Inosine is an endogenous purine nucleoside, which is formed during the breakdown of adenosine by adenosine deaminase. Upon metabolic stress or from the sympathetic nervous system, inosine is released into the extracellular space from cells. In murine experimental system, inosine is shown to exert immunomodulatory, anti-inflammatory and anti-shock effects.
Storage Class
13 - Non Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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S E Haun et al.
Journal of neurochemistry, 67(5), 2051-2059 (1996-11-01)
Preliminary evidence suggests adenosine, a neuromodulator, has neuroprotective properties during cerebral ischemia. It is unclear, however, if adenosine has glioprotective effects. We studied the effect of adenosine on cellular injury in astroglial cultures subjected to combined glucose-oxygen deprivation. Adenosine (100-1,000
C E Jones et al.
The American journal of physiology, 233(4), H438-H443 (1977-10-11)
Effects of inosine on left ventricular contractile force, circumflex blood flow, heart rate, and arterial pressure were investigated in mongrel dogs. Infusion of 50 ml of 10, 25, or 50 mM inosine into the right atrium over 5 min produced
A Marton et al.
International journal of molecular medicine, 8(6), 617-621 (2001-11-17)
Inosine is an endogenous purine, which has been recently shown to exert immunomodulatory, anti-inflammatory and anti-shock effects in rodent experimental systems. Some of these actions may be related to partial adenosine receptor agonistic effects. It has not been investigated previously
A Panja et al.
Journal of immunology (Baltimore, Md. : 1950), 161(7), 3675-3684 (1998-10-06)
Products of an activated immune system may affect cells within the immune system as well as nonlymphoid cells in the local environment. Given the immunologically activated state of the intestinal tract, it is conceivable that locally produced cytokines could regulate
Yukti Choudhury et al.
The Journal of clinical investigation, 122(11), 4059-4076 (2012-10-25)
In the human brain, microRNAs (miRNAs) from the microRNA-376 (miR-376) cluster undergo programmed "seed" sequence modifications by adenosine-to-inosine (A-to-I) editing. Emerging evidence suggests a link between impaired A-to-I editing and cancer, particularly in high-grade gliomas. We hypothesized that disruption of
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