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Inosine

 

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Inosine



 
 
Inosine is a nucleoside
Nucleoside

Nucleosides are glycosylamines consisting of a nucleobase bound to a ribose or deoxyribose sugar. Examples of these include cytidine, uridine, adenosine, guanosine, thymidine and inosine....
 that is formed when hypoxanthine
Hypoxanthine

Hypoxanthine is a naturally occurring purine derivative. It is occasionally found as a constituent of nucleic acids where it is present in the anticodon of tRNA in the form of its nucleoside inosine....
 is attached to a ribose
Ribose

Ribose, primarily occurring as D-ribose, is an organic compound that occurs widely in nature. It is an aldopentose, that is a monosaccharide containing five carbon atoms that, in its acyclic form, has an aldehyde functional group at one end....
 ring (also known as a ribofuranose
Ribofuranose

Ribofuranose is the biochemical name for the 5-carbon sugar commonly known as ribose when having the furan ring structure....
) via a ß-N9-glycosidic bond
Glycosidic bond

In chemistry, a glycosidic bond is a certain type of functional group that joins a carbohydrate molecule to another, which may be another carbohydrate....
.

Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pair
Wobble base pair

A wobble base pair is a G-U and I-U / I-A / I-C pair fundamental in RNA secondary structure. Its thermodynamic stability is comparable to that of the Base pair....
s.

Knowledge of inosine metabolism has led to advances in immunotherapy
Immunotherapy

Immunotherapy, in medicine, refers to an array of treatment strategies based upon the concept of modulating the immune system to achieve a Prophylaxis and/or Immunosuppressive therapy goal....
 in recent decades. Inosine monophosphate is oxidised by the enzyme inosine monophosphate dehydrogenase yielding xanthosine monophosphate, a key precursor in purine
Purine

Purine is a heterocyclic compound aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature....
 metabolism.






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Encyclopedia


Inosine is a nucleoside
Nucleoside

Nucleosides are glycosylamines consisting of a nucleobase bound to a ribose or deoxyribose sugar. Examples of these include cytidine, uridine, adenosine, guanosine, thymidine and inosine....
 that is formed when hypoxanthine
Hypoxanthine

Hypoxanthine is a naturally occurring purine derivative. It is occasionally found as a constituent of nucleic acids where it is present in the anticodon of tRNA in the form of its nucleoside inosine....
 is attached to a ribose
Ribose

Ribose, primarily occurring as D-ribose, is an organic compound that occurs widely in nature. It is an aldopentose, that is a monosaccharide containing five carbon atoms that, in its acyclic form, has an aldehyde functional group at one end....
 ring (also known as a ribofuranose
Ribofuranose

Ribofuranose is the biochemical name for the 5-carbon sugar commonly known as ribose when having the furan ring structure....
) via a ß-N9-glycosidic bond
Glycosidic bond

In chemistry, a glycosidic bond is a certain type of functional group that joins a carbohydrate molecule to another, which may be another carbohydrate....
.

Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pair
Wobble base pair

A wobble base pair is a G-U and I-U / I-A / I-C pair fundamental in RNA secondary structure. Its thermodynamic stability is comparable to that of the Base pair....
s.

Knowledge of inosine metabolism has led to advances in immunotherapy
Immunotherapy

Immunotherapy, in medicine, refers to an array of treatment strategies based upon the concept of modulating the immune system to achieve a Prophylaxis and/or Immunosuppressive therapy goal....
 in recent decades. Inosine monophosphate is oxidised by the enzyme inosine monophosphate dehydrogenase yielding xanthosine monophosphate, a key precursor in purine
Purine

Purine is a heterocyclic compound aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature....
 metabolism. Mycophenolate mofetil is an anti-metabolite, anti-proliferative drug, used in the treatment of a variety of autoimmune diseases including Wegener's granulomatosis
Wegener's granulomatosis

Wegener's granulomatosis is a form of vasculitis that affects the lungs, kidneys and other organs. Due to its end-organ damage, it can be a serious disease that requires long-term immune suppression....
. The uptake of purine by actively dividing B cell
B cell

B cells are lymphocytes that play a large role in the humoral immunity . The principal functions of B cells are to make antibody against antigens, perform the role of Antigen Presenting Cells and eventually develop into memory B cells after activation by antigen interaction....
s can exceed 8 times that of normal body cells and therefore this set of white cells (which cannot operate purine salvage pathways) is selectively targeted by the purine deficiency resulting from IMD inhibition.

Reactions

Adenine
Adenine

Adenine is a nucleobase with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate and the cofactor s nicotinamide adenine dinucleotide and flavin adenine dinucleotide , and Protein biosynthesis, as a chemical component of DNA and RNA....
 is converted to adenosine
Adenosine

Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule moiety via a ?-N9-glycosidic bond....
 or IMP, either of which in turn is converted into inosine (I), which pairs with Adenine (A), cytosine
Cytosine

Cytosine is one of the five main bases found in DNA and RNA. It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached ....
 (C) and uracil
Uracil

Uracil is a common and naturally occurring pyrimidine derivative. Originally discovered in 1900, it was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring, sperm, and wheat germ....
 (U).

Purine nucleoside phosphorylase
Purine nucleoside phosphorylase

Purine nucleoside phosphorylase is an enzyme involved in Purine#Metabolism. PNP metabolizes adenosine into adenine, inosine into hypoxanthine, and guanosine into guanine, in each case creating ribose phosphate....
 intraconverts inosine and hypoxanthine
Hypoxanthine

Hypoxanthine is a naturally occurring purine derivative. It is occasionally found as a constituent of nucleic acids where it is present in the anticodon of tRNA in the form of its nucleoside inosine....
.

Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements.

Clinical significance

It was tried in the seventies in eastern countries for improving athletic performance. Nevertheless the clinical trials for this purpose showed no improvement.

Nowadays, it has been shown that inosine has neuroprotective properties. It has been proposed for spinal cord injury; because it improves axonal rewiring, and for administration after stroke
Stroke

A stroke is the rapidly developing loss of brain function due to a disturbance in the blood supply to the brain. According to the National Stroke Association, a "stroke" occurs when a blood clot blocks and artery or a blood vessel breaks, interrupting blood flow to an area of the brain....
, because observation has shown that axonal re-wiring is encouraged.

It is currently in phase II trials for multiple sclerosis
Multiple sclerosis

Multiple sclerosis is an autoimmune disease in which the immune system attacks the central nervous system, leading to demyelinating disease. Disease onset usually occurs in young adults, and it is more common in females....
 (MS). It produces uric acid after ingestion, which is a natural antioxidant and a peroxynitrite
Peroxynitrite

Peroxynitrite is the anion with the formula ONOO-. It is an unstable "valence isomer" of nitrate, NO3-, which has the same formula but a different structure....
 scavenger, which can suggest possible benefit in multiple sclerosis (peroxynitrite has been correlated with the axons degeneration).

Alseres Pharmaceuticals (named Boston Life Sciences when patent was granted) patented the treatment for stroke and is currently investigating the drug in the MS setting.

In the Anatomical Therapeutic Chemical Classification System
Anatomical Therapeutic Chemical Classification System

The Anatomical Therapeutic Chemical Classification System is used for the taxonomic classification of Medications. It is controlled by the World Health Organization Collaborating Centre for Drug Statistics Methodology, and was first published in 1976....
, it is classified as an antiviral
Antiviral

Antiviral may refer to:*Antiviral drug*Antiviral protein *Antivirus software*Antiviral Therapy, an academic journal...
.

Biotechnology

When designing primer
Primer (molecular biology)

A primer is a strand of nucleic acid that serves as a starting point for DNA replication. They are required because the enzymes that catalyze replication, DNA polymerases, can only add new nucleotides to an existing strand of DNA....
s for polymerase chain reaction
Polymerase chain reaction

The polymerase chain reaction is a technique widely used in molecular biology. It derives its name from one of its key components, a DNA polymerase used to amplify a piece of DNA by in vitro enzyme DNA replication....
, inosine is useful in that it will indiscriminately pair with adenine, thymine, or cytosine. This allows for design of primers that span a single nucleotide polymorphism
Single nucleotide polymorphism

A single-nucleotide polymorphism is a DNA sequence variation occurring when a single nucleotide — adenine, thymine, cytosine, or guanine — in the genome differs between members of a species ....
, without the polymorphism disrupting the primer's annealing efficiency.

Fitness

Despite a lack of clinical evidence that it improves muscle development, inosine remains an ingredient in some fitness supplements.

See also


  • Inosine monophosphate dehydrogenase


External links