GUANOSINE

Guanosine is a purine nucleoside, in which the guanine attached to the C1 carbon of a ribose (ribofuranose) ring via a β-N9-glycosidic bond. 
Guanosine phosphorylated derivatives include GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate), and GTP (guanosine triphosphate).
These guanosine derivatives are very important in various biochemical processes, such as synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction.

CAS Number: 118-00-3
EC Number: 204-227-8
IUPAC Name: 2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,9-dihydro-6H-purin-6-one
Chemical Formula: C10H13N5O5

Other names: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one, 2-Amino-9-(β-D-ribofuranosyl)-3,9-dihydro-6H-purin-6-on, MFCD00010182, 2-amino-Inosine, Guanosine, 2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,9-dihydro-6H-purin-6-one, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-β-D-ribofuranosyl-, 9-(β-D-Ribofuranosyl)guanine, guanine riboside, Inosine,2-amino, 2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one, 2-Amino-9-(β-D-ribofuranosyl)-9H-purin-6-ol, EINECS 204-227-8, 9-β-D-ribofuranosyl-Guanine, 2-Amino-9-(β-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-on, vernine, 2H-purin-6-ol, 3,9-dihydro-2-imino-9-β-D-ribofuranosyl-, USAF CB-11, Guanine-9-β-D-ribofuranoside, Guanosin, Guanosine Hydrate, Guanine, 9-β-D-ribofuranosyl-, 2-Amino-9-β-D-ribofuranosyl-9H-purine-6(1H)-one, 9-β-D-ribofuranosylguanine, 9H-purin-6-ol, 2-amino-9-β-D-ribofuranosyl-, 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one, Guanozin, guanosine, 118-00-3, guanine riboside, vernine, Guanozin, USAF CB-11, Guanosin, Inosine, 2-amino-, L-GUANOSINE, Vernine (VAN), 9-beta-D-Ribofuranosylguanine, Guanine-9-beta-D-ribofuranoside, beta-D-Ribofuranoside, guanine-9, Guanine, 9-beta-D-ribofuranosyl-, 2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-one, Inosine, 2-amino- (VAN), Ribofuranoside, guanine-9, beta-D-, 2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one, GUANINE-9:BETA-D-RIBOFURANOSIDE, Guo, DL-Guanosine, AI3-52065, MFCD00010182, NSC 19994, 9-beta-D-ribofuranosyl-guanine, 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one, Guanine, 9-beta-D-ribofuranosyl- (VAN), UNII-12133JR80S, CHEBI:16750, GR, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-beta-D-ribofuranosyl-, 9-(beta-D-Ribofuranosyl)guanine, 26578-09-6, Guanosine, Anhydrous, 12133JR80S, 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one, 2-AMINO-9-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-6,9-DIHYDRO-1H-PURIN-6-ONE, 2-amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one, EINECS 204-227-8, 9-.beta.-D-ribofuranosylguanine, Ribonucleoside, Guanine, 9.beta.-d-ribofuranosyl-, .beta.-D-Ribofuranoside, guanine-9, 3h-guanosine, 2-amino-Inosine, 1odj, 2fqx, 9-B-D-RIBOFURANOSYLGUANINE, [3H]-guanosine, Inosine, 2-amino, guanosine-1-15N, guanosine-2-13C, guanosine-3-15N, guanosine-8-13C, guanosine-9-15N, guanosine-N-15N-, guanosine-1'-13C, Guanosine, >=98%, ST057098, guanosine-N,1-15N2, bmse000091, bmse001018, Epitope ID:141493, 9-b-D-ribofuranosyl-Guanine, SCHEMBL21217, 2(3H)-Imino-9-.beta.-D-ribofuranosyl-9H-purin-6(1H)-one, b-D-Ribofuranoside guanine-9, 9-beta-D-ribofuranosyl guanine, CHEMBL375655, GTPL4567, SGCUT00093, 9-bet.-D-Ribofuranosyl-guanine, Guanine-9-ss--D-ribofuranoside, SCHEMBL12212184, 9-(ss--D-Ribofuranosyl)guanine, Guanine-9-bet.-D-ribofuranoside, DTXSID00893055, guanosine-2-13C-N,1-15N2, 9-beta-delta-ribofuranosyl-Guanine, Guanine-9-.beta.-D-ribofuranoside, GUANOSINE ULTRA PURE 100G, 197227-95-5, beta-delta-Ribofuranoside guanine-9, Guanosine, >=97.0% (HPLC), HY-N0097, STR04471, to_000053, ZINC1550030, BBL033925, BDBM50366814, guanosine-2-13C-N,1,3-15N3, s2439, STK801927, AKOS005622500, AKOS007930368, AKOS015896931, AKOS032949764, AM83933, CCG-267277, CS-W020018, DB02857, MCULE-2959607047, Ribofuranoside, guanine-9, .beta.-D-, 9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-aminohydropurin -6-one, NCGC00142496-01, NCGC00142496-02, I890, DB-029875, G0171, Guanosine, Vetec(TM) reagent grade, >=98%, C00387, Guanosine, suitable for cell culture, BioReagent, A818517, Q422462, Q-201301, 2-Amino-9-bet.-D-ribofuranosyl-9H-purine-6-(1H)-one, 2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one, 2-Amino-9-.beta.-D-ribofuranosyl-9-H-purine-6(1H)-one, 2-Amino-1,9-dihydro-9.beta.-d-ribofuranosyl-6H-purin-6-one, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-beta-D-ribofuranosyl, 2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-.beta.-D-ribofuranosyl-, 2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one (Guanosine), (2R,3R,4S,5R)-2-(2-amino-6-hydroxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, 2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purin-6-one, 103654-69-9, 103654-70-2, 146849-94-7, 197227-93-3, 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one, 202933-46-8, 244769-87-7, 247226-75-1, 250586-91-5, 250586-97-1, 30747-23-0,

Guanosine is thought to have neuroprotective properties. 
Guanosine can reduce neuroinflammation, oxidative stress, and excitotoxicity, as well as exerting trophic effects in neuronal and glial cells. 
Guanosine is shown to be protective in central nervous system diseases including ischemic stroke, Alzheimer’s disease, Parkinson’s disease, spinal cord injury, nociception, and depression. 
Guanosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism.

Guanosine is an aromatic organic molecule and a purine nucleoside. 
Guanosine is present in the cerebrospinal fluid, intestinal cells, blood-brain barrier and in brain microvessels.

Guanosine is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond.

A purine nucleoside, guanine linked by Guanosine N9 nitrogen to the C1 carbon of ribose. 
Guanosine is a component of ribonucleic acid and Guanosine nucleotides play important roles in metabolism.

Guanosine (DL-Guanosine) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond.
Guanosine possesses anti-HSV activity.

Guanosine (symbol G or Guo) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. 
Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP). 

These forms play important roles in various biochemical processes such as synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction (cGMP). 
When guanine is attached by Guanosine N9 nitrogen to the C1 carbon of a deoxyribose ring Guanosine is known as deoxyguanosine.

Physical and chemical properties
Guanosine is a white, crystalline powder with no odor and mild saline taste.
Guanosine is very soluble in acetic acid, slightly soluble in water, insoluble in ethanol, diethyl ether, benzene and chloroform.

Pharmacology and Biochemistry of Guanosine:

Human Metabolite Information:

Tissue Locations:
Placenta
Prostate

Cellular Locations:
Extracellular
Lysosome
Mitochondria

Metabolite Pathways:
Adenine phosphoribosyltransferase deficiency (APRT)
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria

Azathioprine Action Pathway
Gout or Kelley-Seegmiller Syndrome
Lesch-Nyhan Syndrome (LNS)
Mercaptopurine Action Pathway
Mitochondrial DNA depletion syndrome

Biochem/physiol Actions of Guanosine:
Guanosine nucleoside elicits cellular effect as the guanine-based purinergic system. 
Guanosine modulates glutamate uptake by glutamate transporters. 

Guanosine may have neuroprotective functionality in central nervous system disorders. 
Guanosine promotes neurite arborization, outgrowth, proliferation and differentiation. 
Administration of guanosine replenished GTP and elicits protective function in renal ischemic injury.

Purification Methods of Guanosine:
Guanosine crystallises from water as a dihydrate. 
Dry Guanosine at 110o.

Functions of Guanosine:
Guanosine is required for an RNA splicing reaction in mRNA, when a "self-splicing" intron removes itself from the mRNA message by cutting at both ends, re-ligating, and leaving just the exons on either side to be translated into protein.

Application of Guanosine:
For use in cell culture applications as a precursor of GMP, GDP, GTP and cGMP.

Guanosine has been used:
As a reference standard for the analysis of glucosinolates by high-performance liquid chromatography with diode-array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI/MS)
As a component of Mouse Embryonic Fibroblasts (MEFs) culture

As a standard for the detection of residual RNA contaminant in oil palm plant genome samples by HPLC
For use in cell culture applications as a precursor of GMP, GDP, GTP and cGMP.

Guanosine is a purine nucleoside that upon sequential phosphoylation (kinases) forms GTP which is used by RNA polymerases to synthesis RNA(s). 
GTP is also important in a wide range of GTPase-dependent cell signaling processes. 
Guanosine is used in selective matricies such a guanosine gels (G-gels) for use in capillary electrophoresis chiral selection and other applications.

Sources of Guanosine:
Guanosine can be found in pancreas, clover, coffee plant, and pollen of pines.

Uses of Guanosine:
The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are structurally similar to guanosine.
Guanosine was also used to make regadenoson.

A constituent of nucleic acids.

Opacifying    
Skin conditioning
Skin-conditioning agent - miscellaneous

Potential Uses of Guanosine:
Biological additives

Use Classification of Guanosine:
Cosmetics - Opacifying; Skin conditioning

Handling and storage of Guanosine:

Precautions for safe handling:
Provide appropriate exhaust ventilation at places where dust is formed.

Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Store in cool place.

Safety Information of Guanosine:

Storage Class Code:
6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK: WGK 3

Personal Protective Equipment:
Dust mask type N95 (US), Eyeshields, Gloves

First aid measures of Guanosine:

If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.

In case of skin contact:
Wash off with soap and plenty of water.

In case of eye contact:
Flush eyes with water as a precaution.

If swallowed:
Never give anything by mouth to an unconscious person. 
Rinse mouth with water.

Indication of any immediate medical attention and special treatment needed:
No data available

Firefighting measures of Guanosine:

Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Special hazards arising from the substance or mixture:
Carbon oxides, Nitrogen oxides (NOx)
Combustible.

Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
 
Further information:
No data available

Accidental release measures of Guanosine:

Personal precautions, protective equipment and emergency procedures:
Avoid dust formation. 
Avoid breathing vapours, mist or gas.

Environmental precautions:
No special environmental precautions required.

Methods and materials for containment and cleaning up:
Sweep up and shovel. 

Molecular Weight: 283.24
XLogP3: -1.9
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 7

Rotatable Bond Count: 2
Exact Mass: 283.09166853
Monoisotopic Mass: 283.09166853
Topological Polar Surface Area: 155 Ų

Heavy Atom Count: 20
Complexity: 446
Defined Atom Stereocenter Count: 4
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes