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G6264

Sigma-Aldrich

Guanosine

BioReagent, suitable for cell culture

Synonym(s):

9-(β-D-Ribofuranosyl)guanine, Guanine-9-β-D-ribofuranoside

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O5
CAS Number:
118-00-3
Molecular Weight:
283.24
Beilstein/REAXYS Number:
625911
EC Number:
204-227-8
MDL number:
MFCD00010182
UNSPSC Code:
12352205
PubChem Substance ID:
24895251
NACRES:
NA.75

biological source

synthetic

product line

BioReagent

assay

≥98%

form

powder

technique(s)

cell culture | mammalian: suitable

mp

250 °C (dec.) (lit.)

solubility

0.05 M acetic acid: 1 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

SMILES string

[H]O[H].NC1=Nc2c(ncn2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1

InChI

1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1

InChI key

NYHBQMYGNKIUIF-UUOKFMHZSA-N

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Application

Guanosine has been used:
  • as a ribonucleoside component of the basal medium to study its effects on Bacillus mojavensis′s anaerobic growth
  • as a component of the Dulbecco′s modified Eagle medium (DMEM) to culture mouse-derived embryonic stem cells
  • as a component of the nucleoside solution to culture chicken embryonic stem cells

Biochem/physiol Actions

Guanosine is a purine nucleoside that exhibits important functions in cell metabolism. It has also shown neuroprotective and neurotrophic effects in glial cells, hippocampal neurons, and pheochromocytoma cells by inducing proliferation and differentiation and also exerting anti-apoptotic effects. Guanosine acts as a therapeutic agent against several neuropathologies. It exerts its effects against sepsis-induced cognitive impairment, hepatic encephalopathy, lipopolysaccharide (LPS)-induced inflammation, ischemic injury, and azide-induced oxidative damage. Guanosine is suitable for use in cell culture applications as a precursor of guanosine monophosphate (GMP), guanosine diphosphate (GDP), guanosine triphosphate (GTP), and cyclic GMP (cGMP).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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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Jeffery T Davis et al.
Chemical Society reviews, 36(2), 296-313 (2007-02-01)
Nature's use of a simple genetic code to enable life's complex functions is an inspiration for supramolecular chemistry. DNA nucleobases carry the key information utilizing a variety of cooperative and non-covalent interactions such as hydrophobic, van der Waals, pi-pi stacking
Aditya C Bandekar et al.
Current biology : CB, 30(20), 3961-3971 (2020-09-12)
Although the major events in prokaryotic cell cycle progression are likely to be coordinated with transcriptional and metabolic changes, these processes remain poorly characterized. Unlike many rapidly growing bacteria, DNA replication and cell division are temporally resolved in mycobacteria, making
Zoran D Matović et al.
Journal of inorganic biochemistry, 121, 134-144 (2013-02-05)
Novel square-planar palladium(II) complexes with O-N-N-O-type ligands H4mda (H4mda=malamido-N,N'-diacetic acid) and H4obp (H4obp=oxamido-N,N'-di-3-propionic acid) were prepared and characterized. The ligands coordinate to the palladium(II) ion via two pairs of deprotonated ligating atoms with square chelation. A four coordinate, square-planar geometry
Zhe Li et al.
Nucleic acids research, 42(6), 4068-4079 (2013-12-29)
G-quadruplex-forming oligonucleotides containing modified nucleotide chemistries have demonstrated promising pharmaceutical potential. In this work, we systematically investigate the effects of sugar-modified guanosines on the structure and stability of a (4+0) parallel and a (3+1) hybrid G-quadruplex using over 60 modified
Jérémie Piton et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(22), 8858-8863 (2013-04-24)
The initiation of mRNA degradation often requires deprotection of its 5' end. In eukaryotes, the 5'-methylguanosine (cap) structure is principally removed by the Nudix family decapping enzyme Dcp2, yielding a 5'-monophosphorylated RNA that is a substrate for 5' exoribonucleases. In
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