GUANOSINE
Guanosine is a purine nucleoside formed from a beta-N9-glycosidic bond between guanine and a ribose ring and is essential for metabolism.
Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP), which are important in various biochemical processes.
Guanosine is thought to have neuroprotective properties, reducing neuroinflammation, oxidative stress, and excitotoxicity, and has shown protective effects in models of CNS diseases like ischemic stroke and Parkinson's disease.
CAS Number: 118-00-3
EC Number: 204-227-8
Molecular Formula: C10H13N5O5
Formula Weight: 283.2
Synonyms: guanosine, 118-00-3, guanine riboside, vernine, Guanozin, USAF CB-11, Guanosin, Inosine, 2-amino-, Vernine (VAN), Guanine-9-beta-D-ribofuranoside, DL-Guanosine, 9-beta-D-Ribofuranosylguanine, 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, 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), 9-(beta-D-Ribofuranosyl)guanine, CHEBI:16750, GR, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-beta-D-ribofuranosyl-, 26578-09-6, Guanosine, Anhydrous, 12133JR80S, 2-AMINO-9-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-6,9-DIHYDRO-1H-PURIN-6-ONE, 85-30-3, 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)tetrahydrofuran-2-yl)-3H-purin-6(9H)-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, NSC-19994, 2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one (Guanosine), UNII-12133JR80S, 2-amino-Inosine, 1odj, 2fqx, 9-B-D-RIBOFURANOSYLGUANINE, [3H]-guanosine, Inosine, 2-amino, Guanosine, >=98%, ST057098, GUANOSINE [MI], GUANOSINE [INCI], bmse000091, bmse001018, Epitope ID:141493, GUANOSINE [MART.], GUANOSINE [WHO-DD], 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, GUANOSINE [USP IMPURITY], SCHEMBL12212184, 9-(ss--D-Ribofuranosyl)guanine, Guanine-9-bet.-D-ribofuranoside, DTXSID00893055, 9-beta-delta-ribofuranosyl-Guanine, Guanine-9-.beta.-D-ribofuranoside, GUANOSINE ULTRA PURE 100G, beta-delta-Ribofuranoside guanine-9, Guanosine, >=97.0% (HPLC), HY-N0097, STR04471, to_000053, ZINC1550030, BBL033925, BDBM50366814, s2439, STK801927, AKOS005622500, AKOS007930368, AKOS015896931, AKOS032949764, AM83933, CCG-267277, CS-W020018, DB02857, 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, 30747-23-0, ADENOSINE IMPURITY H [EP IMPURITY], DB-029875, G0171, Guanosine, Vetec(TM) reagent grade, >=98%, C00387, EN300-204342, Guanosine, suitable for cell culture, BioReagent, A818517, Q422462, Q-201301, 2-Amino-9-bet.-D-ribofuranosyl-9H-purine-6-(1H)-one, Z1741979723, 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, 2-AMINO-9-.BETA.-D-RIBOFURANOSYL-9H-PURINE-6(1H)-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, (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, 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxy-methyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one, 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one, 2(3H)-imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-one, 2-amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one, 2-amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one, 9-β-D-ribofuranosyl-guanine, Guanine riboside, Guanine-9-β-D-ribofuranoside, Guanosin, Guanosine, guanosine, Guo
Guanosine is an aromatic organic molecule and a purine nucleoside.
Guanosine can be phosphorylated to become guanosine monophosphate (CGMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate.
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.
Guanosine is a purine nucleoside formed from a beta-N9-glycosidic bond between guanine and a ribose ring and is essential for metabolism.
Guanosine is a purine nucleoside in which guanine is attached to ribofuranose via a beta-N(9)-glycosidic bond.
Guanosine has a role as a fundamental metabolite.
Guanosine is a purines D-ribonucleoside and a member of guanosines.
Guanosine is functionally related to a guanine.
Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond.
Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate) which are factors in signal transduction pathways.
Guanosine is a purine nucleoside thought to have neuroprotective properties.
Guanosine is released in the brain under physiological conditions and even more during pathological events, reducing neuroinflammation, oxidative stress, and excitotoxicity, as well as exerting trophic effects in neuronal and glial cells.
In agreement, guanosine was shown to be protective in several in vitro and/or in vivo experimental models of central nervous system (CNS) diseases including ischemic stroke, Alzheimer’s disease, Parkinson’s disease, spinal cord injury, nociception, and depression.
The mechanisms underlying the neurobiological properties of guanosine seem to involve the activation of several intracellular signaling pathways and a close interaction with the adenosinergic system, with a consequent stimulation of neuroprotective and regenerative processes in the CNS.
Within this context, the present review will provide an overview of the current literature on the effects of guanosine in the CNS.
The elucidation of the complex signaling events underlying the biochemical and cellular effects of this nucleoside may further establish guanosine as a potential therapeutic target for the treatment of several neuropathologies.
A nucleoside is a nucleobase with a five-carbon sugar (either ribose or deoxyribose).
Guanosine is a glycoside formed from the hydrolysis of nucleic acid.
A purine nucleoside is one in which the nucleobase is a purine, such as guanine in guanosine.
Guanosine is a nucleoside consisting of guanine and ribose sugar linked by β-N9-glycosidic bond.
When a phosphate group is covalently attached to the sugar, Guanosine forms a nucleotide.
An example of a nucleotide wherein three phosphate groups are attached to guanosine is guanosine triphosphate (GTP), one of the building blocks of RNA synthesis.
Guanosine (G), also known as 2-amino-inosine, belongs to the class of organic compounds known as purine nucleosides.
Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl sugar moiety.
Guanosine consists of a guanine base attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond.
Guanosine is a white, crystalline powder with no odor and mild saline taste.
Guanosine is very soluble in acetic acid, and slightly soluble in water, but insoluble in ethanol, diethyl ether, benzene, and chloroform.
Guanosine exists in all living species, ranging from bacteria to plants to humans.
High levels of guanosine can be found in clovers, coffee plants, and the pollen of pines.
Guanosine has been detected, but not quantified in, several different foods, such as leeks, garlic, chicory roots, green bell peppers, and black-eyed peas.
Guanosine plays an important role in various biochemical processes including the synthesis of nucleic acids such as RNA and intracellular signal transduction (cGMP).
The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are both structurally similar to guanosine.
Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP).
In humans, guanosine is involved in intracellular signalling through the adenosine receptors A1R and A2AR.
Evidence from rodent and cell models has shown a number of important neurotrophic and neuroprotective effects of guanosine.
In particular, Guanosine is effective in preventing deleterious consequences of seizures, spinal cord injury, pain, mood disorders and aging-related diseases, such as ischemia, Parkinson‚ Äôs and Alzheimer‚ Äôs diseases.
Studies with rodent models of Parkinson‚Äôs disease have shown that guanosine decreases neuronal apoptotic cell death and increases dopaminergic neurons at substantia nigra pars compacta, accompanied by an improvement of motor symptoms in Parkinson‚ Äôs disease.
Guanosine promotes neurite arborization, outgrowth, proliferation and differentiation.
Systemic administration of guanosine for eight weeks (8 mg/kg) has been shown to stimulate neuroprogenitors proliferation in the subventricular zone (SVZ) in a mouse model of Parkinsonism .
The effect of guanosine treatment is accompanied by an increased number of fibroblast growth factor (FGF-2)-positive cells which is an important regulator of neuroprogenitor/stem cell proliferation, survival and differentiation.
Guanosine prevents reactive oxygen species (ROS) generation and cell death in hippocampal slices subjected to the oxygen/glucose deprivation.
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.
Applications of Guanosine:
Guanosine has been used:
Guanosine is 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)
Guanosine is used as a component of Mouse Embryonic Fibroblasts (MEFs) culture
Guanosine is used as a standard for the detection of residual RNA contaminant in oil palm plant genome samples by HPLC
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.
Biological Functions of Guanosine:
Guanosine, just as the other nucleosides, can give rise to nucleotides.
When phosphorylated by kinases, the nucleoside is converted into a nucleotide.
Thus, a nucleotide is a nucleoside with a phosphate group.
Guanosine can form guanosine monophosphate (GMP, i.e. guanosine with a single phosphate group), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP, i.e. guanosine with two phosphate groups), and guanosine triphosphate (GTP, i.e. guanosine with three phosphate groups).
GTP, in particular, is one of the building blocks for the formation of RNA.
Structurally, guanine is attached to the C-1 of the ribose while the phosphate moiety is attached to the C-5 of the ribose.
Apart from nucleic acid synthesis, they are also involved in other biochemical processes, e.g. protein synthesis, photosynthesis, muscle contraction, and intracellular signal transduction (cGMP).
Sources of Guanosine:
Guanosine can be found in pancreas, clover, coffee plant, and pollen of pines.
Physical and Chemical Properties of Guanosine:
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.
Characteristics of Guanosine:
Guanosine is found in all living organisms as a structural component of RNA.
The chemical formula is C10H13N5O5.
Guanosine molar mass is 283.241 g/mol.
Guanosine dissolves readily in acetic acid and slightly soluble in water.
Guanosine is not soluble though in ethanol, benzene, and chloroform.
Pharmacology and Biochemistry of Guanosine:
Tissue Locations:
Placenta
Prostate
Cellular Locations:
Extracellular
Lysosome
Mitochondria
Common Biological Reactions of Guanosine:
Nucleosides such as guanosine can be produced by de novo synthesis pathways in the liver.
Nevertheless, they may also be obtained from the diet.
When the diet contains nucleotides, the body digests them by nucleotidases to produce nucleosides and phosphates.
Nucleosides are degraded into their subcomponents (i.e. nucleobases and sugar) by the action of nucleosidases in the lumen of the digestive tract.
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.
Guanosine vs. Deoxyguanosine:
Nucleosides may be classified into ribonucleosides or deoxyribonucleosides, depending on the sugar component.
Guanosine is a ribonucleoside due to Guanosine ribose sugar.
In contrast, deoxyguanosine is a deoxyribonucleoside for having a sugar component that is deoxyribose.
Deoxyguanosine differs from guanosine by having a hydroxyl group replaced by hydrogen at the 2′ position of the sugar moiety.
In deoxyguanosine, the N9 nitrogen of guanine is attached to the C-1 of deoxirobose ring.
Deoxyguanosine pairs up with deoxycytidine in DNA whereas guanosine pairs with cytidine in RNA.
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
Storage Conditions
Short term exposure (up to 1 week cumulative) to ambient temperature possible.
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.
Keep in suitable, closed containers for disposal.
Identifiers of Guanosine:
CAS Number: 118-00-3
ChEBI: CHEBI:16750
ChEMBL: ChEMBL375655
ChemSpider: 6544
DrugBank: DB02857
ECHA InfoCard: 100.003.844
IUPHAR/BPS: 4567
KEGG: C00387
MeSH: Guanosine
PubChem CID: 765
UNII: 12133JR80S
CompTox Dashboard (EPA): DTXSID00893055
InChI:
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
Key: NYHBQMYGNKIUIF-UUOKFMHZSA-N
InChI=1/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
Key: NYHBQMYGNKIUIF-UUOKFMHZBU
SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
CAS Number: 118-00-3
Molecular Weight: 283.24
Beilstein: 625911
EC Number: 204-227-8
MDL number: MFCD00010182
PubChem Substance ID: 24895268
Synonym(s): 9-(β-D-Ribofuranosyl)guanine, Guanine-9-β-D-ribofuranoside
Empirical Formula (Hill Notation): C10H13N5O5
Molecular Weight: 283.24
Formula: C10H13N5O5
CAS No.: 118-00-3
Shipping: Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)
Smiles: C1=NC2=C(N1C3C(C(C(O3)CO)O)O)N=C(NC2=O)N
Shipping: shipped on gel packs
Shelf Life: 12 months after date of delivery
Molecular Formula: C10H15N5O11P2 (free acid)
Molecular Weight: 443.20 g/mol (free acid)
Exact Mass: 443.02 g/mol (free acid)
Purity: ≥ 95 % (HPLC)
Form: solution in water
Color: colorless to slightly yellow
Concentration: 10 mM - 11 mM
pH: 7.5 ±0.5
Spectroscopic Properties: λmax 252 nm, ε 13.7 L mmol-1 cm-1 (Tris-HCl pH 7.5)
CAS Number: 118-00-3
NSC: 19994
Molecular Formula: C10H13N5O5
Formula Weight: 283.2
Purity: ≥98%
DMSO: 30 mg/ml
DMSO:PBS (pH 7.2) (1:5): 0.16 mg/ml
λmax: 254 nm
SMILES: O[C@H]1[C@@H](O)[C@H](N2C=NC3=C2NC(N)=NC3=O)O[C@@H]1CO
InChi Code: 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
Properties of Guanosine:
Chemical formula: C10H13N5O5
Molar mass: 283.241
Appearance: white, crystalline powder
Odor: odorless
Melting point: 239 (decomposes)
Magnetic susceptibility (χ): -149.1·10−6 cm3/mol
Biological source: microbial
Quality Level: 100
Assay: ≥98%
Form: powder
mp: 250 °C (dec.) (lit.)
Solubility: formic acid:water (1:1): 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow
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
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
Formal Charge: 0
Complexity: 446
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Names of Guanosine:
IUPAC name:
Guanosine
Preferred IUPAC name:
2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,9-dihydro-6H-purin-6-one
Other name:
Guanine riboside
