Description
Hypoxanthine is a naturally occurring purine derivative and intermediate in the synthesis of uric acid. It is elevated in the spinal fluid of patients with Lesch-Nyhan syndrome, a metabolic disorder whose symptoms include cerebral palsy, cognitive deficits, motor dysfunction, self-mutilation, and hyperuricemia. Injection of hypoxanthine (10 μM) increases succinate dehydrogenase and complex II activities and decreases cytochrome c oxidase activity, resulting in neuroenergetic impairment, ATP depletion, and cellular apoptosis in rat striatum. It is also used to induce hyperuricemia in mice for use in the development of hypouricemic agents.
Chemical Properties
White to off-white powder
Uses
Hypoxanthine is a nutrient additive for a variety of cell culture applications involving bacterial, parasite (
Plasmodium falciparum) and animal cells. Hypoxanthine is a component of selection media used in hybridoma technologies.
Uses
A naturally occurring purine derivative. Pharmaceuticals, Intermediates & Fine Chemicals
Uses
Hypoxanthine, is used as a marker for energy perturbation in hypoxia/ ischemia. The compound has been used in studies as in indicator, along with uric acid and allantoin , of in vivo free radical reactions. It has been also used in DNA studies to investigate the destabilizing effect it has on DNA duplexes containing hypoxanthine as a base, in a gas phase versus a liquid phase. Hypoxanthine has also been used in studies along with 8-oxoguanine nucleotides to investigate their interaction with human DNA pol (DNA polymerase alpha) and DNA polymerase I from Bacillus stearothermophilus. It is also used as a pharmaceutical intermediate.
Definition
ChEBI: A purine nucleobase that consists of purine bearing an oxo substituent at position 6.
General Description
Hypoxanthine (6-hydroxypurine), a purine derivative is a naturally occurring compound. It is the deaminated form of adenine and a breakdown product of adenosine monophosphate (AMP).
Biochem/physiol Actions
Hypoxanthineis capable of stimulating cell death. It can also induce reactive oxygen species (ROS). It results in endothelial dysfunction via apoptosis, stimulated by oxidative stress.
Safety Profile
Moderately toxic by
intraperitoneal route. An experimental
teratogen. When heated to decomposition it
emits toxic fumes of Nox
Purification Methods
Crystallise it from hot water and dry it at 105o. [Beilstein 26 II 252, 26 III/IV 2081.]
References
[1] HELENA BIASIBETTI-BRENDLER. Hypoxanthine Induces Neuroenergetic Impairment and Cell Death in Striatum of Young Adult Wistar Rats.[J]. Molecular Neurobiology, 2018, 55 5: 4098-4106. DOI:
10.1007/s12035-017-0634-z[2] TIANQIAO YONG . Actions of water extract from Cordyceps militaris in hyperuricemic mice induced by potassium oxonate combined with hypoxanthine[J]. Journal of ethnopharmacology, 2016, 194: Pages 403-411. DOI:
10.1016/j.jep.2016.10.001
