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HomeProduct name listISOXANTHOPTERIN

ISOXANTHOPTERIN

Synonym(s):2-Amino-4,7-dihydroxy-1,3,5,8-tetraazanaphthalene;2-Amino-4,7-dihydroxypteridine;2-Amino-4,7-pteridinediol

  • CAS NO.:529-69-1
  • Empirical Formula: C6H5N5O2
  • Molecular Weight: 179.14
  • MDL number: MFCD00006696
  • EINECS: 208-469-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-25 18:01:24
ISOXANTHOPTERIN Structural

What is ISOXANTHOPTERIN?

Chemical properties

Off-white powder

The Uses of ISOXANTHOPTERIN

Isoxanthopterin is a substrate for the enzyme isoxanthopterin deaminase.

What are the applications of Application

Isoxanthopterin is an oxidation product of pterin via xanthine oxidase

Definition

ChEBI: 2-aminopteridine-4,7-diol is a dihydroxypteridine.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 4450, 1953 DOI: 10.1021/ja01114a016

Biological Activity

isoxanthopterin interferes with rna and dna synthesis.isoxanthopterin, a natural intermediate in the pteridine pathway, plays critical roles in pigmentation and cell division.

in vitro

isoxanthopterin was identified as a pteridine of wide natural occurrence and was reported to exerts an inhibitory action on the synthesis of ribosomal rna, possibly soluble rna and on dna in developing eggs of the milkweed bug oncopeltus fasciatus. such effects were measured by partially incubating dechorionated eggs in a solution containing isoxanthopterin and radioactive uridine or thymidine, and then testing the incorporation of the isotope into ribosomal rna or dna. the detailed mechanism of this inhibition had been discussed, and the tentative conclusion was agreed that it was due to an interaction between the pteridine and the nucleic acid (most probably dna) [1].

in vivo

previous animal study showed that rats with inherited retinal dystrophy appeared to differ from healthy rats by an elevated isoxanthopterin excretion in urine. rcs rats responded to feeding of monapterin with an increase of isoxanthopterin excretion. this phenomenon supported the idea that the rcs rat had an increased xanthinoxidase activity compared with healthy rats [2].

Purification Methods

Purify it by repeated precipitation from alkaline solution with acid (preferably AcOH or formic acid), filter, wash well with H2O, then EtOH and dry at 100o. The purity is checked by paper chromatography [RF 0.15 (n-BuOH/AcOH/H2O, 4:1:1); 0.33 (3% aqueous NH4OH). [Goto et al. Arch Biochem Biophys 111 8 1965.] [For biochemistry see Blakley Biochemistry of Folic Acid and Related Pteridines North Holland Publ Co, Amsterdam 1969.] [Beilstein 26 III/IV 3999.]

References

[1] lagowski, j. m. and forrest, h.s. interaction in vitro between isoxanthopterin and dna. proceedings of the national academy of sciences of the united states of america 58(4), 1541-1547 (1967).
[2] g. cremer-bartels, h. gerding, l. hanneken and k. krause. isoxanthopterin excretion of rats with inherited retinal dystrophy. pteridines vol. 2, 1990, pp. 103 -105.

Properties of ISOXANTHOPTERIN

Melting point: >300 °C
Density  2.17±0.1 g/cm3(Predicted)
storage temp.  room temp
solubility  DMSO (Very Slightly)
form  powder
pka 11.32±0.20(Predicted)
color  off-white
BRN  181594

Safety information for ISOXANTHOPTERIN

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P362:Take off contaminated clothing and wash before reuse.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for ISOXANTHOPTERIN

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