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Hypoxanthine

CAS# 68-94-0

Hypoxanthine

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Chemical structure

Hypoxanthine

3D structure

Chemical Properties of Hypoxanthine

Cas No. 68-94-0 SDF Download SDF
PubChem ID 790 Appearance Powder
Formula C5H4N4O M.Wt 136.11
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility DMSO : 10 mg/mL (73.47 mM; Need ultrasonic)
Chemical Name 3,7-dihydropurin-6-one
SMILES C1=NC2=C(N1)C(=O)N=CN2
Standard InChIKey FDGQSTZJBFJUBT-UHFFFAOYSA-N
Standard InChI InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Hypoxanthine

Them porcine follicular fluid.

Biological Activity of Hypoxanthine

DescriptionHypoxanthine, a purine derivative, is a potential free radical generator and could be used as an indicator of hypoxia.Hypoxanthine inhibits mouse oocyte maturation, it plays a role in vivo in maintaining meiotic arrest.
In vitro

The effect of hypoxanthine on mouse oocyte growth and development in vitro: maintenance of meiotic arrest and gonadotropin-induced oocyte maturation.[Pubmed: 3100361]

Dev Biol. 1987 Feb;119(2):313-21.

The concentration of Hypoxanthine in mouse follicular fluid has been estimated to be 2-4 mM, and although this concentration maintains meiotic arrest in fully grown mouse oocytes in vitro, oocyte maturation in vivo is not induced by a decrease in the concentration of this purine in follicular fluid (J. J. Eppig, P. F. Ward-Bailey, and D. L. Coleman, Biol. Reprod. 33, 1041-1049, 1985).
METHODS AND RESULTS:
In the present study, the effect of 2 mM Hypoxanthine on oocyte growth and development in vitro was assessed and the ability of gonadotropins to stimulate oocyte maturation in the continued presence of Hypoxanthine was determined. Oocyte-granulosa cell complexes were isolated from 10- to 11-day-old mice and cultured in the presence or absence of 2 mM Hypoxanthine. Oocytes from 10- to 11-day-old mice are in mid-growth phase and, without further development, are incompetent of undergoing meiotic maturation. During a 12-day culture period the granulosa cell-enclosed oocytes approximately doubled in size and, regardless of the presence or absence of Hypoxanthine, 50-70% developed competence to undergo germinal vesicle breakdown (GVBD). Hypoxanthine promoted the continued association of oocytes with their companion granulosa cells during the 12-day culture period, and therefore had a beneficial effect on oocyte development. Most of the oocytes that acquired GVBD competence in the absence of Hypoxanthine underwent spontaneous GVBD. In contrast, 95% of the GVBD-competent oocytes were maintained in meiotic arrest by Hypoxanthine. Following withdrawal of the Hypoxanthine after the 12-day culture, 75% of the GVBD-competent oocytes underwent GVBD.
CONCLUSIONS:
These results show that Hypoxanthine, and/or its metabolites, maintains meiotic arrest in oocytes that grow and acquire GVBD competence in vitro. Follicle-stimulating hormone (FSH), but not luteinizing hormone or human chorionic gonadotropin, induced oocyte GVBD in the continued presence of Hypoxanthine. FSH stimulated oocyte maturation at a significantly (P less than 0.01) higher frequency than coculture of the granulosa cell-denuded oocytes with granulosa cells in the continued presence of Hypoxanthine. FSH did not induce the maturation of denuded oocytes cocultured with granulosa cells.

In vivo

Hypoxanthine is the principal inhibitor of murine oocyte maturation in a low molecular weight fraction of porcine follicular fluid.[Reference: WebLink]

Proceedings of the National Academy of Sciences of the United States of America, 1985, 82(2):454-8.

Studies were carried out to identify and quantify the porcine follicular fluid (PFF) component(s) responsible for inhibition of murine oocyte maturation.
METHODS AND RESULTS:
A low molecular weight fraction of PFF (less than 1000) was prepared by dialysis and used in all experiments. This PFF fraction contained an inhibitor(s) of mouse oocyte maturation that absorbed maximally in the ultraviolet (UV) range at 250-260 nm. When the PFF fraction was charcoal-extracted, significant loss of absorbance at 250, 260, and 280 nm resulted, which corresponded to loss of inhibitory activity. Four major components of PFF were separated by ion-exchange chromatography and characterized according to their UV spectral characteristics and inhibitory activity. When individual fractions demonstrating identical spectra were pooled and analyzed by high-performance liquid chromatography, the first pooled fraction (A) was found to be impure, but adenine comprised 80% of the UV-absorbing material. Fractions B, C, and D were characterized as pure uracil, Hypoxanthine, and 7-methylinosine, respectively. The concentrations of these compounds in PFF were estimated to be 0.06 mM adenine, 0.44 mM uracil, 1.41 mM Hypoxanthine, and 0.19 mM 7-methylinosine. Comparison of the potencies of commercial preparations of these compounds established that Hypoxanthine is the major inhibitory component of the low molecular weight PFF fraction. Moreover, a commercial preparation of Hypoxanthine mimicked the action of PFF on mouse oocyte maturation in that it produced a transient inhibition of oocyte maturation that was significantly potentiated by follicle-stimulating hormone and dibutyryl cyclic adenosine monophosphate. When the inhibitory efficacies of purine and pyrimidine bases and nucleosides were compared, their relative potencies in decreasing order were purine bases greater than purine nucleosides greater than pyrimidine bases = pyrimidine nucleosides.
CONCLUSIONS:
We conclude that Hypoxanthine is the predominant low molecular weight component of PFF that inhibits mouse oocyte maturation but that other purines/pyrimidines may also play a role in vivo in maintaining meiotic arrest.

Protocol of Hypoxanthine

Kinase Assay

Hypoxanthine as an Indicator of Hypoxia: Its Role in Health and Disease through Free Radical Production[Reference: WebLink]

Pediatric Research, 1988, 23(2):143-50.

Hypoxia is a common insult during the perinatal and neonatal period. New a n d better ways t o evaluate hypoxia are needed.
METHODS AND RESULTS:
In 1975 we demonstrated high concentrations of the purine metab- olite Hypoxanthine in umbilical cord plasma after intrauterine hypoxia a n d proposed that Hypoxanthine could be used as a n indicator of hypoxia (1). Since then a large number of studies have been published dealing with different aspects of hypoxan- thine in hypoxia.

Hypoxanthine Dilution Calculator

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Hypoxanthine Molarity Calculator

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Preparing Stock Solutions of Hypoxanthine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 7.347 mL 36.735 mL 73.47 mL 146.94 mL 183.675 mL
5 mM 1.4694 mL 7.347 mL 14.694 mL 29.388 mL 36.735 mL
10 mM 0.7347 mL 3.6735 mL 7.347 mL 14.694 mL 18.3675 mL
50 mM 0.1469 mL 0.7347 mL 1.4694 mL 2.9388 mL 3.6735 mL
100 mM 0.0735 mL 0.3673 mL 0.7347 mL 1.4694 mL 1.8367 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Hypoxanthine

The effect of hypoxanthine on mouse oocyte growth and development in vitro: maintenance of meiotic arrest and gonadotropin-induced oocyte maturation.[Pubmed:3100361]

Dev Biol. 1987 Feb;119(2):313-21.

The concentration of Hypoxanthine in mouse follicular fluid has been estimated to be 2-4 mM, and although this concentration maintains meiotic arrest in fully grown mouse oocytes in vitro, oocyte maturation in vivo is not induced by a decrease in the concentration of this purine in follicular fluid (J. J. Eppig, P. F. Ward-Bailey, and D. L. Coleman, Biol. Reprod. 33, 1041-1049, 1985). In the present study, the effect of 2 mM Hypoxanthine on oocyte growth and development in vitro was assessed and the ability of gonadotropins to stimulate oocyte maturation in the continued presence of Hypoxanthine was determined. Oocyte-granulosa cell complexes were isolated from 10- to 11-day-old mice and cultured in the presence or absence of 2 mM Hypoxanthine. Oocytes from 10- to 11-day-old mice are in mid-growth phase and, without further development, are incompetent of undergoing meiotic maturation. During a 12-day culture period the granulosa cell-enclosed oocytes approximately doubled in size and, regardless of the presence or absence of Hypoxanthine, 50-70% developed competence to undergo germinal vesicle breakdown (GVBD). Hypoxanthine promoted the continued association of oocytes with their companion granulosa cells during the 12-day culture period, and therefore had a beneficial effect on oocyte development. Most of the oocytes that acquired GVBD competence in the absence of Hypoxanthine underwent spontaneous GVBD. In contrast, 95% of the GVBD-competent oocytes were maintained in meiotic arrest by Hypoxanthine. Following withdrawal of the Hypoxanthine after the 12-day culture, 75% of the GVBD-competent oocytes underwent GVBD. These results show that Hypoxanthine, and/or its metabolites, maintains meiotic arrest in oocytes that grow and acquire GVBD competence in vitro. Follicle-stimulating hormone (FSH), but not luteinizing hormone or human chorionic gonadotropin, induced oocyte GVBD in the continued presence of Hypoxanthine. FSH stimulated oocyte maturation at a significantly (P less than 0.01) higher frequency than coculture of the granulosa cell-denuded oocytes with granulosa cells in the continued presence of Hypoxanthine. FSH did not induce the maturation of denuded oocytes cocultured with granulosa cells.(ABSTRACT TRUNCATED AT 400 WORDS)

Description

Hypoxanthine, a purine derivative, is a potential free radical generator and could be used as an indicator of hypoxia.

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