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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:
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 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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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
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
Nadine Gehrke et al.
Immunity, 39(3), 482-495 (2013-09-03)
Immune sensing of DNA is critical for antiviral immunity but can also trigger autoimmune diseases such as lupus erythematosus (LE). Here we have provided evidence for the involvement of a damage-associated DNA modification in the detection of cytosolic DNA. The oxidized base
Michael J Osborne et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(10), 3877-3882 (2013-02-23)
Recognition of the methyl-7-guanosine (m(7)G) cap structure on mRNA is an essential feature of mRNA metabolism and thus gene expression. Eukaryotic translation initiation factor 4E (eIF4E) promotes translation, mRNA export, proliferation, and oncogenic transformation dependent on this cap-binding activity. eIF4E-cap
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
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