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I4125

Sigma-Aldrich

Inosine

≥99% (HPLC)

Synonym(s):

(−)-Inosine, Hypoxanthine 9-β-D-ribofuranoside

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About This Item

Empirical Formula (Hill Notation):
C10H12N4O5
CAS Number:
58-63-9
Molecular Weight:
268.23
Beilstein:
624896
EC Number:
200-390-4
MDL number:
MFCD00066770
UNSPSC Code:
41106305
PubChem Substance ID:
24896051
NACRES:
NA.51

Quality Level

200

Assay

≥99% (HPLC)

mp

222-226 °C (dec.) (lit.)

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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General description

Inosine is a non-canonical nucleotide majorly present as monophosphate. It has ability to base pair with deoxythymidine, deoxyadenosine and deoxyguanosine. Incorporation of inosine in place of guanine modulates translational events. Inosine has antioxidant, anti-inflammatory and neuroprotective functionality. Inosine is prescribed as a therapeutic supplement for nerve injury, inflammation and oxidative stress. It modulates biological processes through adenosine receptors. Its enhances neurite outgrowth in depressive disorders via adenosine receptors. Inosine is also used for treating sepsis in infections.

Application

Inosine has been used:
  • as a medium supplement in nucleotide rescue experiments in pancreatic cancer cell lines.
  • as a component in holidic (synthetic) medium and in larval two-choice preference assay.
  • as a reference standard in mass spectroscopy.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Inosine induces context-dependent recoding and translational stalling
Licht K, et al.
Nucleic Acids Research (2018)
Oral administration of inosine produces antidepressant-like effects in mice
Muto J, et al.
Scientific Reports, 4, 4199-4199 (2014)
Inosine-a Multifunctional Treatment for Complications of Neurologic Injury
Doyle C, et al.
Cellular Physiology and Biochemistry, 49(6), 2293-2303 (2018)
Inosine in DNA and RNA
Alseth I, et al.
Current Opinion in Genetics & Development, 26, 116-123 (2014)
Inosine reduces systemic inflammation and improves survival in septic shock induced by cecal ligation and puncture
Liaudet L, et al.
American Journal of Respiratory and Critical Care Medicine, 164(7), 1213-1220 (2001)
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